This document summarizes the synthesis of new C-2, C-3 substituted heterocyclic derivatives of L-ascorbic acid and their characterization and evaluation of bacterial activity. Specifically, it describes the multi-step synthesis of Schiff bases and 1,3-oxazepine derivatives from L-ascorbic acid, including protection of hydroxyl groups, esterification, hydrazide formation, Schiff base formation with substituted benzaldehydes, and Diels-Alder reaction with phthalic anhydride to form 1,3-oxazepines. The synthesized compounds were characterized using melting point, FTIR, and 1H NMR spectroscopy and tested for antibacterial activity against gram-positive and
Synthesis and Characterization of Schiff Base from Aromatic Amine and Aromati...ijtsrd
The synthesis of Schiff base From Aromatic Amine And Aromatic P Nitro benzaldehyde was performed by a novel method of stirring followed by the addition of p nitro benzaldehydeandm nitro aniline 0.02M . Characterization of the synthesized compounds, determination of purity and identity of the compounds using following spectroscopic and chromatographic techniques Solubility, Thin Layer Chromatographic studies, Ultra Violet studied rotational and vibrational studies FT IR studies. The compounds were investigated for their Antimicrobial activity by cup plate method. Compound1 nitro 4 1 imino,4 nitrophenyl benzene was found to be the most active according to pharmacological evaluation exhibited antimicrobial. Ms. Chetana D. Patil | Mr. Digamber N. Bhosale | Ms. Smita P. Bedis "Synthesis and Characterization of Schiff Base from Aromatic Amine and Aromatic P-Nitro Benzaldehyde" Published in International Journal of Trend in Scientific Research and Development (ijtsrd), ISSN: 2456-6470, Volume-3 | Issue-5 , August 2019, URL: https://www.ijtsrd.com/papers/ijtsrd26401.pdfPaper URL: https://www.ijtsrd.com/pharmacy/medicinal-chemistry/26401/synthesis-and-characterization-of-schiff-base-from-aromatic-amine-and-aromatic-p-nitro-benzaldehyde/ms-chetana-d-patil
IJERA (International journal of Engineering Research and Applications) is International online, ... peer reviewed journal. For more detail or submit your article, please visit www.ijera.com
A STUDY ON FORMATION OF SALYCILIC ACID FORMALDEHYDE POLYMER SAMPLEEDITOR IJCRCPS
Condensation of salicylic acid (0.02 mole) with formaldehyde (0.016 mole) in presence of aqueous 40% H2SO4.
Keywords: pipette,thermometer,spectro-photometer,conicalflakk,waterbath.
Bidentate Schiff base ligand 3-(3,4-Dihydroxy-phenyl)-2-[(4-dimethylamino-benzylidene)-amino]-2-methyl-propionic acid was prepared and characterized by spectroscopic techniques studies and elemental analysis. The Cd(II), Ni(II), Cu(II), Co(II), Cr(III),and Fe(III) of mixed-ligand complexes were structural explicate through moler conductance , [FT-IR, UV-Vis & AAS], chloride contents, , and magnetic susceptibility measurements. Octahedral geometries have been suggested for all complexes. The Schiff base and its complexes were tested against various bacterial species, two of {gram(G+) and gram(G-)} were shown weak to good activity against all bacteria.
Synthesis and Characterization of Schiff Base from Aromatic Amine and Aromati...ijtsrd
The synthesis of Schiff base From Aromatic Amine And Aromatic P Nitro benzaldehyde was performed by a novel method of stirring followed by the addition of p nitro benzaldehydeandm nitro aniline 0.02M . Characterization of the synthesized compounds, determination of purity and identity of the compounds using following spectroscopic and chromatographic techniques Solubility, Thin Layer Chromatographic studies, Ultra Violet studied rotational and vibrational studies FT IR studies. The compounds were investigated for their Antimicrobial activity by cup plate method. Compound1 nitro 4 1 imino,4 nitrophenyl benzene was found to be the most active according to pharmacological evaluation exhibited antimicrobial. Ms. Chetana D. Patil | Mr. Digamber N. Bhosale | Ms. Smita P. Bedis "Synthesis and Characterization of Schiff Base from Aromatic Amine and Aromatic P-Nitro Benzaldehyde" Published in International Journal of Trend in Scientific Research and Development (ijtsrd), ISSN: 2456-6470, Volume-3 | Issue-5 , August 2019, URL: https://www.ijtsrd.com/papers/ijtsrd26401.pdfPaper URL: https://www.ijtsrd.com/pharmacy/medicinal-chemistry/26401/synthesis-and-characterization-of-schiff-base-from-aromatic-amine-and-aromatic-p-nitro-benzaldehyde/ms-chetana-d-patil
IJERA (International journal of Engineering Research and Applications) is International online, ... peer reviewed journal. For more detail or submit your article, please visit www.ijera.com
A STUDY ON FORMATION OF SALYCILIC ACID FORMALDEHYDE POLYMER SAMPLEEDITOR IJCRCPS
Condensation of salicylic acid (0.02 mole) with formaldehyde (0.016 mole) in presence of aqueous 40% H2SO4.
Keywords: pipette,thermometer,spectro-photometer,conicalflakk,waterbath.
Bidentate Schiff base ligand 3-(3,4-Dihydroxy-phenyl)-2-[(4-dimethylamino-benzylidene)-amino]-2-methyl-propionic acid was prepared and characterized by spectroscopic techniques studies and elemental analysis. The Cd(II), Ni(II), Cu(II), Co(II), Cr(III),and Fe(III) of mixed-ligand complexes were structural explicate through moler conductance , [FT-IR, UV-Vis & AAS], chloride contents, , and magnetic susceptibility measurements. Octahedral geometries have been suggested for all complexes. The Schiff base and its complexes were tested against various bacterial species, two of {gram(G+) and gram(G-)} were shown weak to good activity against all bacteria.
New Schiff base ligand (E)-6-(2-(4-
(dimethylamino)benzylideneamino)-2-phenylacetamido)-3,3-
dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic
acid = (HL) Figure(1) was prepared via condensation of
Ampicillin and 4(dimethylamino)benzaldehyde in methanol
.Polydentate mixed ligand complexes were obtained from 1:1:2
molar ratio reactions with metal ions and HL, 2NA on reaction
with MCl2 .nH2O salt yields complexes corresponding to the
formulas [M(L)(NA)2Cl] ,where M =
Fe(II),Co(II),Ni(II),Cu(II),and Zn(II) and NA=nicotinamide.
The 1H-NMR, FT-IR, UV-Vis and elemental analysis
were used for the characterization of the ligand. The complexes
were structurally studied through AAS, FT-IR, UV-Vis,
chloride contents, conductance, and magnetic susceptibility
measurements. All complexes are non-electrolytes in DMSO
solution. Octahedral geometries have been suggested for each
of the complexes. The Schiff base ligands function as
tridentates and the deprotonated enolic form is preferred for
coordination. In order to evaluate the effect of the bactericidal
activity, these synthesized complexes, in comparison to the un
complexed Schiff base has been screened against bacterial
species, Staphy
IJERA (International journal of Engineering Research and Applications) is International online, ... peer reviewed journal. For more detail or submit your article, please visit www.ijera.com
Solvent Extraction Method for the Separation of Cerium(III) as
Cations From Aqueous Media By use 4-[N-(5-methyl isoxazol-3-
yl)benzene sulfonamide azo]-1- Naphthol Coupled With
Spectroscopic Method For Determination
Synthesis and Characterization of New Complexes of 2-(6-Methoxybenzo[d]thiazo...IOSR Journals
Abstract: The synthesis and characterization of manganese (ІІ), cobalt (ІІ), nickel (ІІ), copper (ІІ), zinc (ІІ), cadmium (ІІ) and mercury (ІІ) bidentate 2-(6-methoxybenzo[d]thiazol-2-ylamino)-2-phenyl acetonitrile ligand which was prepared from Benz aldehyde and 6-methoxybenzo[d]thiazol-2-amine in the presence of KCN and acidic medium. The complexes were synthesized by treating an ethanolic solution of the ligand with appropriate amount of metal salts [1:2] [M: L] ratio. The complexes were characterized by using metal and elemental chemical analysis, molar conductance, magnetic susceptibility measurements, FTIR , electronic spectral and mole ratio method. According to the obtained data the probable coordination geometries of manganese (ІІ), cobalt (ІІ), nickel (ІІ), copper (ІІ) zinc (ІІ), cadmium (ІІ) and mercury (ІІ) in these complexes are octahedral. All complexes were found to be non-electrolyte in absolute ethanol, and the complexes were formulated as [ML2Cl2] XH2O. Keywords: 2-(6-methoxybenzo[d]thiazol-2-ylamino)-2-phenyl acetonitrile, N2-donor, transition metals.
The IOSR Journal of Pharmacy (IOSRPHR) is an open access online & offline peer reviewed international journal, which publishes innovative research papers, reviews, mini-reviews, short communications and notes dealing with Pharmaceutical Sciences( Pharmaceutical Technology, Pharmaceutics, Biopharmaceutics, Pharmacokinetics, Pharmaceutical/Medicinal Chemistry, Computational Chemistry and Molecular Drug Design, Pharmacognosy & Phytochemistry, Pharmacology, Pharmaceutical Analysis, Pharmacy Practice, Clinical and Hospital Pharmacy, Cell Biology, Genomics and Proteomics, Pharmacogenomics, Bioinformatics and Biotechnology of Pharmaceutical Interest........more details on Aim & Scope).
All manuscripts are subject to rapid peer review. Those of high quality (not previously published and not under consideration for publication in another journal) will be published without delay.
Kinetics of Ruthenium(III) Catalyzed and Uncatalyzed Oxidation of Monoethanol...Ratnakaram Venkata Nadh
Kinetics of uncatalyzed and ruthenium(III) catalyzed oxidation of monoethanolamine by N-bromosuccinimide
(NBS) has been studied in an aqueous acetic acid medium in the presence of sodium acetate
and perchloric acid, respectively. In the uncatalyzed oxidation the kinetic orders are: the first order in NBS,
a fractional order in the substrate. The rate of the reaction increased with an increase in the sodium acetate
concentration and decreased with an increase in the perchloric acid concentration. This indicates that free
amine molecules are the reactive species. Addition of halide ions results in a decrease in the kinetic rate,
which is noteworthy. Both in absence and presence of a catalyst, a decrease in the dielectric constant of the
medium decreases the kinetic rate pointing out that these are dipole—dipole reactions. A relatively higher
oxidation state of ruthenium i.e., Ru(V) was found to be the active species in Ru(III) catalyzed reactions. A
suitable mechanism consistent with the observations has been proposed and a rate law has been derived to
explain the kinetic orders.
Synthesis, Characterization and Study of Antioxidant Activities of Some New P...IJRES Journal
A series of substituted pyrazoline derivatives 5(a-c) have been synthesized by the reaction of substituted chalcones 4(a-c) with isatinhydrazide. The starting materials, chalcones were prepared by clasien schimidt condensation of appropriate 1-hydroxy-2-acetonaphthone with substituted aldehydes in the presence of sodium hydroxide and in poly ethylene glycol (PEG-400). The structures of the synthesized compounds were confirmed by IR, 1HNMR & Mass spectral data. The synthesized compounds were screened for Antioxidant Activity by DPPH method.
New Schiff base ligand (E)-6-(2-(4-
(dimethylamino)benzylideneamino)-2-phenylacetamido)-3,3-
dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic
acid = (HL) Figure(1) was prepared via condensation of
Ampicillin and 4(dimethylamino)benzaldehyde in methanol
.Polydentate mixed ligand complexes were obtained from 1:1:2
molar ratio reactions with metal ions and HL, 2NA on reaction
with MCl2 .nH2O salt yields complexes corresponding to the
formulas [M(L)(NA)2Cl] ,where M =
Fe(II),Co(II),Ni(II),Cu(II),and Zn(II) and NA=nicotinamide.
The 1H-NMR, FT-IR, UV-Vis and elemental analysis
were used for the characterization of the ligand. The complexes
were structurally studied through AAS, FT-IR, UV-Vis,
chloride contents, conductance, and magnetic susceptibility
measurements. All complexes are non-electrolytes in DMSO
solution. Octahedral geometries have been suggested for each
of the complexes. The Schiff base ligands function as
tridentates and the deprotonated enolic form is preferred for
coordination. In order to evaluate the effect of the bactericidal
activity, these synthesized complexes, in comparison to the un
complexed Schiff base has been screened against bacterial
species, Staphy
IJERA (International journal of Engineering Research and Applications) is International online, ... peer reviewed journal. For more detail or submit your article, please visit www.ijera.com
Solvent Extraction Method for the Separation of Cerium(III) as
Cations From Aqueous Media By use 4-[N-(5-methyl isoxazol-3-
yl)benzene sulfonamide azo]-1- Naphthol Coupled With
Spectroscopic Method For Determination
Synthesis and Characterization of New Complexes of 2-(6-Methoxybenzo[d]thiazo...IOSR Journals
Abstract: The synthesis and characterization of manganese (ІІ), cobalt (ІІ), nickel (ІІ), copper (ІІ), zinc (ІІ), cadmium (ІІ) and mercury (ІІ) bidentate 2-(6-methoxybenzo[d]thiazol-2-ylamino)-2-phenyl acetonitrile ligand which was prepared from Benz aldehyde and 6-methoxybenzo[d]thiazol-2-amine in the presence of KCN and acidic medium. The complexes were synthesized by treating an ethanolic solution of the ligand with appropriate amount of metal salts [1:2] [M: L] ratio. The complexes were characterized by using metal and elemental chemical analysis, molar conductance, magnetic susceptibility measurements, FTIR , electronic spectral and mole ratio method. According to the obtained data the probable coordination geometries of manganese (ІІ), cobalt (ІІ), nickel (ІІ), copper (ІІ) zinc (ІІ), cadmium (ІІ) and mercury (ІІ) in these complexes are octahedral. All complexes were found to be non-electrolyte in absolute ethanol, and the complexes were formulated as [ML2Cl2] XH2O. Keywords: 2-(6-methoxybenzo[d]thiazol-2-ylamino)-2-phenyl acetonitrile, N2-donor, transition metals.
The IOSR Journal of Pharmacy (IOSRPHR) is an open access online & offline peer reviewed international journal, which publishes innovative research papers, reviews, mini-reviews, short communications and notes dealing with Pharmaceutical Sciences( Pharmaceutical Technology, Pharmaceutics, Biopharmaceutics, Pharmacokinetics, Pharmaceutical/Medicinal Chemistry, Computational Chemistry and Molecular Drug Design, Pharmacognosy & Phytochemistry, Pharmacology, Pharmaceutical Analysis, Pharmacy Practice, Clinical and Hospital Pharmacy, Cell Biology, Genomics and Proteomics, Pharmacogenomics, Bioinformatics and Biotechnology of Pharmaceutical Interest........more details on Aim & Scope).
All manuscripts are subject to rapid peer review. Those of high quality (not previously published and not under consideration for publication in another journal) will be published without delay.
Kinetics of Ruthenium(III) Catalyzed and Uncatalyzed Oxidation of Monoethanol...Ratnakaram Venkata Nadh
Kinetics of uncatalyzed and ruthenium(III) catalyzed oxidation of monoethanolamine by N-bromosuccinimide
(NBS) has been studied in an aqueous acetic acid medium in the presence of sodium acetate
and perchloric acid, respectively. In the uncatalyzed oxidation the kinetic orders are: the first order in NBS,
a fractional order in the substrate. The rate of the reaction increased with an increase in the sodium acetate
concentration and decreased with an increase in the perchloric acid concentration. This indicates that free
amine molecules are the reactive species. Addition of halide ions results in a decrease in the kinetic rate,
which is noteworthy. Both in absence and presence of a catalyst, a decrease in the dielectric constant of the
medium decreases the kinetic rate pointing out that these are dipole—dipole reactions. A relatively higher
oxidation state of ruthenium i.e., Ru(V) was found to be the active species in Ru(III) catalyzed reactions. A
suitable mechanism consistent with the observations has been proposed and a rate law has been derived to
explain the kinetic orders.
Synthesis, Characterization and Study of Antioxidant Activities of Some New P...IJRES Journal
A series of substituted pyrazoline derivatives 5(a-c) have been synthesized by the reaction of substituted chalcones 4(a-c) with isatinhydrazide. The starting materials, chalcones were prepared by clasien schimidt condensation of appropriate 1-hydroxy-2-acetonaphthone with substituted aldehydes in the presence of sodium hydroxide and in poly ethylene glycol (PEG-400). The structures of the synthesized compounds were confirmed by IR, 1HNMR & Mass spectral data. The synthesized compounds were screened for Antioxidant Activity by DPPH method.
A new Schiff base 4-chlorophenyl)methanimine
(6R,7R)-3-methyl-8-oxo-7-(2-phenylpropanamido)-5-thia-1-
azabicyclo[4.2.0]oct-2-ene-2-carboxylate= (HL)= C23H20
ClN3O4S) has been synthesized from β-lactam antibiotic
(cephalexin mono hydrate(CephH)=(C16H19N3O5S.H2O) and 4-
chlorobenzaldehyde . Figure(1) Metal mixed ligand complexes
of the Schiff base were prepared from chloride salt of
Fe(II),Co(II),Ni(II),Cu(II),Zn(II) and Cd (II), in 50% (v/v)
ethanol –water medium (SacH ) .in aqueous ethanol(1:1)
containing and Saccharin(C7H5NO3S) = sodium hydroxide.
Several physical tools in particular; IR, CHN, 1H NMR, 13C
NMR for ligand and melting point molar conductance, magnetic
moment. and determination the percentage of the metal in the
complexes by flame(AAS). The ligands and there metal
complexes were screened for their antimicrobial activity against
four bacteria (gram + ve) and (gram -ve) {Escherichia coli,
Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus}.
The proposed structure of the complexes using program, Chem
office 3D(2006). The general formula have been given for the
prepared mixed ligand complexes Na2[M(Sac)3(L)], M(II) = Fe
(II), Co(II) , Ni(II), Cu (II), Zn(II) , and Cd(II).
HL= C29H24 ClN3O4S, L= C29H23 ClN3O4S -.
Oxidation of 7-Methyl Sulfanyl-5-Oxo-5H-Benzothiazolo-[3, 2-A]-Pyrimidine-6-...inventionjournals
International Journal of Engineering and Science Invention (IJESI) is an international journal intended for professionals and researchers in all fields of computer science and electronics. IJESI publishes research articles and reviews within the whole field Engineering Science and Technology, new teaching methods, assessment, validation and the impact of new technologies and it will continue to provide information on the latest trends and developments in this ever-expanding subject. The publications of papers are selected through double peer reviewed to ensure originality, relevance, and readability. The articles published in our journal can be accessed online.
ABSTRACT- L-Ascorbic acid derivatives was synthesized on treatment with acetone and acetyl chloride afforded 5,6-acetal of L-ascorbic acid then benzylation of C-2 and C-3 hydroxyl groups of the lactone ring was accomplished using K2CO3 and benzyl bromide in DMF, then deblocking of the 5,6-O,O-protected derivative of L-Ascorbic acid with acetic acid and methanol gave 2,3-O,O-dibenzyl-L-Ascorbic acid. Subsequently mono-tosylation at 6 position of 2,3-O, O-dibenzyl-L-Ascorbic acid was carried out with addition of p-toluenetosylchloride (PTSC) in Pyridine and MDC solvent medium gave 2,3-O,O-dibenzyl-6-O-tosyl-L-Ascorbic acid. All the structures were characterized by 1H NMR, 13C NMR and Mass Spectroscopy.
Key-words- L-Ascorbic acid, 5,6-Acetal, Benzylation, Hydrolysis, Tosylation
The synthesis of polyoxychloropropylenepoxymethacrylate oligoesters by esterification of polyoxychloropropylenetriepoxide by methacrylic acid has been carried out. It has been established that by varying the conditions of carrying out of the reaction, one can prepare, mainly, the mono-, di- and trimethacrylic oligoesters. On the basis of epoxy diane ED-20 and synthesized polyoxychloropropylenepoxymethacrylate oligoesters as modifiers there have been prepared the self-extinction compositions, which after curing by N, N1–diaminodiphenylsulfone possess higher physical-mechanical, adhesion and heat-physical properties.
International Journal of Pharmaceutical Science Invention (IJPSI) is an international journal intended for professionals and researchers in all fields of Pahrmaceutical Science. IJPSI publishes research articles and reviews within the whole field Pharmacy and Pharmaceutical Science, new teaching methods, assessment, validation and the impact of new technologies and it will continue to provide information on the latest trends and developments in this ever-expanding subject. The publications of papers are selected through double peer reviewed to ensure originality, relevance, and readability. The articles published in our journal can be accessed online.
Targeted Intermediates of Eudesmic Acid: Synthesis and X-ray Investigationsijtsrd
it was carried out synthesis of esters and their dinitro derivatives of 3,4,5-trimethoxybenzoic (eudesmic) acid. Esterification of eudesmic acid carried out n absolute methanol or ethanol and corresponding methyl and ethyl 3,4,5-trimethoxybenzoates (2, 3) have been synthesized in good yields. It was revealed that nitration of these esters gives only dinitro products. The structure of the synthesized compounds of the methyl and ethyl 2,6-dinitro-3,4,5-trimethoxybenzoates (4, 5) was determined by X-ray diffraction analysis (XRD). In the asymmetric part of the crystal structures of 4, 5 one and two molecules are observed, respectively. In crystalline structures a flat nitro groups and carboxylic groups do not participate in the conjugation with aromatic rings. In the crystal structure of 4, an intermolecular C8-H...O9 hydrogen bond is observed, these H bonds link the molecules along the [010] axis. In the crystal structure of 5, intermolecular C9B-H...O4A and C10B-H...O8A hydrogen bonds form chains along the [011] axis. The formed chains are cross linked by the intermolecular C9B-H...O5A hydrogen bonds. Olimova M.I. | Okmanov R. Ya. | Elmuradov B. Zh."Targeted Intermediates of Eudesmic Acid: Synthesis and X-ray Investigations" Published in International Journal of Trend in Scientific Research and Development (ijtsrd), ISSN: 2456-6470, Volume-1 | Issue-6 , October 2017, URL: http://www.ijtsrd.com/papers/ijtsrd2417.pdf http://www.ijtsrd.com/chemistry/other/2417/targeted-intermediates-of-eudesmic-acid--synthesis-and-x-ray-investigations/olimova-mi
Synthesis and antimicrobial activity of some methyl (4- (benzo[d]oxazol-2-yl)...QUESTJOURNAL
ABSTRACT: In the present study, a new series of methyl (4-(benzo[d]oxazol-2-yl)phenyl) carbamodithioate amine derived from methyl (4-(benzo[d]oxazol-2-yl)phenyl) carbamodithioate (4TO1-TO6) have been synthesized by reacting the thio methyl group with different amines in presence of ethenol. The structural assessment of the compounds (TO 1- TO 6) was made on the basis of spectral data. The synthesized compounds were screened for their in vitro growth inhibiting activity against different strains of bacteria and fungi viz., Escherichia coli, Bacillus subtilis, Pseudomonas aeruginosa, S. aureus, Candida albicans and Cryptococcus neoformans were compared with standard agents such as Norfloxacin (10μg/ml) and Amphotericin B (10μg/ml) using broth dilution method. Compounds exhibit moderate to high antibacterial and antifungal activity
ER Publication,
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In this work a new prodrug polymer was
prepared with two attachment groups (amid-ester), using di
functional spacer such as ethanol amine, which could react with
polyacrylic acid producing amide group, with remain ethanol
terminal group which could react with captopril acyl chloride,
producing ester group with extended the arm substituted drug to
improve the hydrolysis and to prevent the steric effect of polymer
chains. Many advantages enhanced the prodrug of polymer. The
prepared polymers were characterized by FTIR, 1H –NMR
spectroscopies. Controlled drug release was studied in different
pH values at 37℃, using UV. Spectra with comparing with
calibration curve. The modification percentage test was studied,and swelling percentage was calculated and all physical properties were observed.
Simple Synthesis of Some Novel Polyfunctionally Derivatives of 2H-Coumarin-2-...IOSRJAC
Compound (2) was prepared from the reaction of ethyl-2-oxo-2H-coumarin-3-carboxylate (1) with ethylcyanoacetate in ethanol containing a catalytic amount of piperidine as catalyst. Compound (2) is the key intermediate for the synthesis of several series of new compounds such as ((pyrimidine, tetrazine, piperidine, oxazepine)-2H-coumarin-2-one derivatives by reaction with selected reagents such as urea, cyanoacetamide, cyanoacetohydrazide, orthoaminophenol and 5-aminotriazole.
Simple Synthesis of Some Novel Polyfunctionally Derivatives of 2H-Coumarin-2-...
iasj
1. Iraqi NaƟonal Journal of Chemistry, 2014, volume 55, 264- المجلة العراقیة الوطنیة لعلوم الكیمیاء- 2014 العدد الخامس والخمسون 274
The New C-2,C-3 Substituted Heterocyclic Derivatives of
L-Ascorbic acid: Synthesis, Characterization, and Bacterial
Activity
Muna Sameer Al-Rawi, Jumbad Hermiz Tomma and Dhuha Faruk Hussein
dr.m1967@yahoo.com Jumbadtomma@yahoo.com duhaF.Hussien@yahoo.com
Department of Chemistry , College of Education Ibn Al- HaithamUniversity of Baghdad.
(NJC)
(Received on 2/6/2014) (Accepted for publication 28/8/2014)
264
Abstract
New Schiff bases derivatives [IV]a-e is prepared via condensation of D-erythroascorbic
acid with p-substituted aldehydes in dry benzene. To obtain these
derivatives, the 5,6-O-isopropylidene-L-ascorbic acid[I] was chosen as starting material,
compound prepared from the reaction of L-ascorbic acid as starting material.
Compound[I] was prepared from the reaction of L-ascorbic acid with dry acetone in the
presence of hydrogen chloride. The esterification of hydroxyl groups at C-2 and C-3
positions with excess ofethyl α –chloroacetate in the presence of sodium acetate produce
acorresebonding ester [II] , which was condensed with hydrazine hydrate to give new
hydrazide [III] . The new Schiff bases [IV]a-e were synthesized by reaction of acid
hydrizide with different p-substituted benzaldehyde in dry benzene . The new 1,3-
oxazepine derivatives [V]a-ewere obtained by Diels-Alder reaction of Schiff bases with
phthalic anhydride in dry benzene (Scheme 1) . All the synthesized compounds have
been characterized by melting points , FTIR and 1HMNR (of some of theme)
spectroscopy. The biological activity of synthesized compounds was examined against
two types of bacteria; G(+) and G(-).
Key words : L- ascorbic acid, Hydrazied, Schiff bases, 1,3-Oxazepine.
2. Iraqi NaƟonal Journal of Chemistry, 2014, volume المجلة العراقیة الوطنیة لعلوم الكیمیاء- 2014 العدد الخامس والخمسون 55
265
الخلاصة
ارثرو حامض اسكوربیك مع الدیهایداتاروماتیة معوضة في موقع بارا D- حضرت قواعد شف جدیدة من تكاثف
L- كمادة اولیة، والذي تم تحضیره من تفاعل [I] اسكوربیك اسد -L- ایزوبروبلدین – O -6 ، . تم اختیار 5
اسكوربیك اسد كمادة اولیة مع الاسیتون الجاف في وجود كلورید الهیدروجین. تم تحویل مجامیع الهیدروكسیل في
والذي تم تكثیفه مع ، [II] بتفاعلها مع اثیل كلورواسیتات بوجود خلات الصودیوم لیعطي الاستر الجدید C- و 3 C-2
حضرت من تفاعل مركبات الهایدرازاید [IV]a-e قواعد شف الجدیدة .[III] الهایدرازین المائي لیعطي مركب الهایدرازاید
تم [V]a-e 3 – اوكسازبین الجدیدة ، مع بنزالدیهایدات المعوضة في موقع بارا في البنزین الجاف . اما مشتقات 1
الحصول علیها من تفاعل الاضافة لقواعد شف مع انهیدرید الفثالك في البنزین الجاف مع التصعید العكسي
1 للبعض HNMR وطیف FTIR (الشكل 1) . شخصت المركبات المحضرة بقیاس درجات انصهارها وبواسطة طیف
منها درست الفعالیة البایولوجیة للمركبات المحضرة ضد نوعین من البكتریا واظهرت النتائج فعالیة بایولوجیة تراوحت
Staphylococcus (G+) ,Echerichia coli (G-) بین العالیة والمتوسطة والواطئة ضد نوعین من البكتریا
3- اوكسازبین . ، الكلمات المفتاحیة: حامض الاسكوربیك ، قواعد شف، الهایدرا ا زید، 1
Introduction
L-ascorbic acid is one of the natural
antioxidant present in biological system
because of its activity to attack the free
radicals and other reactive oxygen
species, as the literatures point to the
great role which ascorbic acid plays to
prevent a number of diseases and its
importance in food industry [1,2].
Hydrazides derivatives have growing
importance because of the wide
spectrum of their biological applications
like antibacterial, antitumoral, anti-inflammatory,
antifungal and
antitubercular agents[3,4] .
Hydrazones possessing an azomethine
–NHN=CH- proton constitute
an important class of compound for new
drug development[5,6], and the imine
group played a good intermediate in the
organic synthesis of many heterocyclic
compounds, as in1, 3-Oxazepine
derivativesis[7].
1, 3-Oxazepine non-homologuos seven
member rings, that contains oxygen at
position 1 and nitrogen at position 3.
Oxazepine is used in the medical field
and has been much chemically and
biologically studied. Many workers
synthesized and studied the oxozepine
derivatives mentioned as in the
literates[8,9].
3. Iraqi NaƟonal Journal of Chemistry, 2014, volume المجلة العراقیة الوطنیة لعلوم الكیمیاء- 2014 العدد الخامس والخمسون 55
O
O
acetone
dry HCl
NH2NH2.H2O
O
O
Me
Me
X X
266
HO
HO
HO OH
[I]
[II]
[III]
[IV]
O
O
O
O
HO OH
Me
Me
O
O
O
O
O
Me
Me
O
[V]
Benzene
GAA
O
O
O
Me
O
O
X= 4-OH , 4-NO2 , 4-Cl , 4-OCH3 , 4-Br
ClCH2COOC2H5
CH3CO2Na
OCH2C OC2H5
H2NHN
O
H5C2O CH2C
O
O
O
O
OCH2C NHNH2
CH2C
H C
=NHN
O
O
O
O
OCH2C NHN =
CH2C
C C
O
O
O
O
OCH2C NHN
CH2C
C X
HC
O
C
C O
C
C
O
O
O
O
Phathalic
anhydride
X
X
O
Me
O
Me
O
Me
,
NNH
Scheme(1)
4. Iraqi NaƟonal Journal of Chemistry, 2014, volume المجلة العراقیة الوطنیة لعلوم الكیمیاء- 2014 العدد الخامس والخمسون 55
267
Experimental
MATERIALS : All the chemicals were
supplied from Merck , GCC and Aldrich
Chemicals Co. and used as received .
Techniques : FTIR spectra were
recorded using potassium bromide discs
on a Shimadzo (Ir prestige-21) FTIR
spectrophotometer .1HNMR spectra were
carried out by company : Bruker , model:
ultra shield 300 MHz , origin :
Switzerland and are reported in ppm(δ),
DMSO was used as a solvent with TMS
as an internal standard . Measurements
were made at chemistry department,
Al-albyat university , Uncorrected
melting points were determined by using
Hot-Stage, Gallen Kamp melting point
apparatus.
SYNTHESIS METHODS
Preparation of 5,6-O-isopropylidene-
L-ascorbic acid[I]:
This compound was prepared
from the reaction of L-ascorbic acid with
dry acetone in a acidic media , following
Salomonmethode [10].
Synthesis of 2,3-O-diethylacetate -5,6 –
O-isopropylidene-L-ascorbic acid[II]:
A mixture of compound [I] (0.01mole),
ethylchloroacetate (0.02mole) and
sodium acetate (0.06mole) in (10mL)
ethanol was heated under reflux for 4hrs
, then cooled and poured into water. The
resulting of a white crystals solid was
filtered off, washed with water, dried and
recrystallized by ethanol to give
compound [II]. m.p (60-62)0C, yield
87%.
Preparation of 2,3-O-dihydrazide
methylene-5,6-O-isopropylidene-L-ascorbic
acid[III]:
Compound [II] (0.01mol) was
dissolved in minimum amount of
ethanol. hydrazine hydrate(0.002 mol)
was added slowly and the mixture was
heated under reflux for 6hrs. Then the
mixture was cooled and the glow yellow
solid was filtered, and recrystallized
from petroleumether. m.p(220-
222)0C, yield 78%.
Synthesis of Schiff bases [IV]a-e
A mixture of new hydrazide
compounds [III] (0.01 mol) , p-substituted
benzaldehyde (0.02 mol) ,
dry benzene (15 mL) was refluxed for
6hrs . The solvent was evaporated under
vaccum and the residue crystallized from
chloroform. The physical data of all
Schiff bases are listed in Table (1).
Synthesis of1,3-oxazepine [V]a-e
A mixture of equimolar
amounts (0.01mol) of Schiff bases [IV]a-e
and phthalicanhydriedein dry benzene as
a solvent was refluxed for 8 hrs , the
solvent was removed and the resulting
colored crystalline solid recrystallized
from petroleum ether to obtained 1,3-
oxazipenes [IV]a-e.The physical
properties of all synthesized 1,3-
oxazepines are listed in Table (1) .
Results and Discussion
The first step employs the protection of
the hydroxyl groups at C-5 and C-6
positions in L- ascorbic acid with acetal
leading to formation compound 5,6-O-isopropylidene-
L-ascorbic acid [I] using
dry acetone in acidic media, following
Salomon[10] method. The FTIR spectrum
showed a broad stretching band in the
region (3240-3074) cm-1 for O-H
vinylic, stretching bands between (2993-
2890) cm-1 for C-H aliphatic, a stretching
band at 1751 cm-1 due to C=O of
Lactone ring, a stretching band at 1663
cm-1 for C=C and stretching bands at
(1141) cm-1 for C-O stretching .
This is followed by reaction of
the hydroxyl groups at C-2 and C-3
positions with two mole of ethyl chloro
acetate in basic media. The FTIR
spectrum for compound [II] has
confirmed the formation of compound
[II] by disappearance the bands for (O-H)
of compound [I] and exhibited
appearance of a stretching band at
(1707) cm-1 for (C=O) of the ester group.
Stretching bands are between( 2924-
2834)cm-1 for C-H aliphatic group.
Condensation of one mole of
compound [II] with two mole of
hydrazine hydrate give a new hydrazide
5. Iraqi NaƟonal Journal of Chemistry, 2014, volume المجلة العراقیة الوطنیة لعلوم الكیمیاء- 2014 العدد الخامس والخمسون 55
268
[III] ,which is characterized by its
melting point, FTIR spectrum, which
showed the following absorption bands:
C=O of amide group at (1677) cm-1,
bands in the regions (3450, 3200, 3194)
cm-1 due to asymmetric and symmetric
stretching vibration of NH , NH2 groups.
Also the spectrum showed band at
(2987-2853) cm-1 assignable to
thestretching of aliphatic (C-H).The
1HNMR spectrum (in DMSO) showed a
sharp singlet signal at δ 1.38 ppm for
protons of CH2 groups , a doublet signal
at δ 2.28ppmfor NH-NH2 protons,singlet
signal at δ 3.10ppm for three protons of
CH3acetal groups and asingle at 3.79
ppm for NH group[11].
New Schiff bases [IV]a-e are
prepared via condensation of hydrazide
compound [III] and p- substituted
benzaldehyde in dry benzene. These
Schiff bases [IV]a-e are characterized by
their melting, FTIR and 1HNMR
Spectroscopy . FTIR absorption-spectra
showedthe disappearance of absorption
bands due to NH2 and C=O groups of the
starting materials together with
appearance of new absorption stretching
band for imine C=N group.
The other data of functional
groups which are characteristics of these
compounds are given in Table 2.
The 1HNMR spectrum (in
DMSO), Figure (1) of compounds [IV]c
showed a sharp signal at δ 2.60 ppm for
protons of methylene groups and a signal
at δ 3.15ppm which could be for three
protons of CH3acetal groups, doublet of
doublets at δ( 6.57-7.41) ppm could be
attribiuted to eight aromatic protons.
Furthermore, a sharp signal for N-H
proton was absorbed at δ 8.28 ppm .
The 1,3-oxazepine derivatives
[V]a-e were obtained by Diels-Alder
reaction of Schiff bases[IV]a-e with
phthalic anhydridesin dry benzene.The
characteristic FTIR absorption bands of
these compounds, was confirmed from
the disappearance of band due to C=N of
schiff base and other peaks
characterized of cyclic anhydride of the
starting materials together, with
appearance of new bands for oxazepine
ring. All the spectral data of FTIR
spectroscopy of these compounds are
listed in Table (2).The 1HNMR spectrum
of compound [V]e (in DMSO), Figure (2)
, showed a singlet signal of N-CH proton
absorbed at δ (8.51) ppm, the aromatic
ring protons appear at the range (δ 6.90-
8.16) ppm, a singlet signals at δ(3.61)
ppm for CH3acetal groups, finally, a
singlet signal at δ (1.98) ppm that could
be attributed to the proton of CH2
groups.
6. Iraqi NaƟonal Journal of Chemistry, 2014, volume المجلة العراقیة الوطنیة لعلوم الكیمیاء- 2014 العدد الخامس والخمسون 55
Table 1: Physical properties of synthesized compounds [IV]a-e and [V]a-e
O
O
O
O
O
O
O
O
Me
OH OH
269
Comp
. No.
Nomencalture Structural Formula Molecular
Formula
M.P0C Yield% Color
[IV]a 2,3-O-bis[ (4`-hydroxy
phenyl ) semicarbazone
methylene]- 5,6-O-isopropylidene-
L-ascorbic
acid
O
Me
=NHN
O
O
O
O
Me
OCH2C NHN =
O
CH2C
OH C C OH
C26H28N4O10 198-200 78 Yellow
[IV]b 2,3-O-bis[(4`-nitro phenyl
semicarba -zone
methylene]- 5,6-O-isopropylidene-
L-ascorbic
acid
Me O
O
O
=NHN
O
O
O
Me
OCH2C NHN =
CH2C
O2N C C NO2
C26H26N6O12 118-120 75 Green-yellow
[IV]c 2,3-O-bis[(4`-
chlorophenyl)
semicarbazone
methylene]- 5,6-O-isopropylidene-
L-ascorbic
acid
Me
O
=NHN
O
O
O
O O
Me
OCH2C NHN =
CH2C
Cl C C Cl
C26H26N4O8 Cl2 106-108 72
Dark
Yellw
[IV]d 2,3-O-bis[ (4`-
methoxyphenyl )
semicarbazone
methylene]- 5,6-O-isopropylidene-
L-ascorbic
acid
Me
O
=NHN
O
O
O
O O
Me
OCH2C NHN =
CH2C
H3CO C C OCH3
C28H32N4O10 164-166 55 Orange
[IV]e 2,3-O-bis[ (4`-
bromophenyl )
semicarbazone
methylene]- 5,6-O-isopropylidene-
L-ascorbic
acid
O
Me
O
=NHN
O
O
O
O
Me
OCH2C NHN =
CH2C
Br C C Br
C26H26N4O8Br2 132-134 50 Red-brown
[V]a 2,3-O-bis[ (4`-
hydroxyphenyl) 2,3-
dihydro benz
[1,2e][1,3]oxazepine-4,7-
diones-methyl ene]- 5,6-O-isopropylidene-
L-ascorbic
acid
O
O
O
OCH2C NHN
O
CH2C
C
HC
O
C
C O
C
C
O
O
O
O
Me
NNH
C42H40N4O16 182-184 80
Pale
Orange
7. Iraqi NaƟonal Journal of Chemistry, 2014, volume المجلة العراقیة الوطنیة لعلوم الكیمیاء- 2014 العدد الخامس والخمسون 55
O
O
O
Me
NO2 NO2
O
O
O
Me
Cl Cl
O
O
270
[V]b 2,3-O-bis[ (4`-nitro
phenyl) 2,3-dihydro benz
[1,2e] [1,3] oxazepine-4,7-
diones-methylene]- 5,6-O-isopropylidene-
L-ascorbic
acid
O
O
O
OCH2C NHN
O
CH2C
C
HC
O
C
C O
C
C
O
O
O
O
Me
NNH
C42H38N6O18 124-126 82 White
[V]c 2,3-O-bis[ (4`-
chlorophenyl ) 2,3-dihydro
benz [1,2e][1,3]oxazepine-
4,7-diones-methyl ene]-
5,6-O-isopropylidene-L-ascorbic
acid
O
O
O
OCH2C NHN
O
CH2C
C
HC
O
C
C O
C
C
O
O
O
O
Me
NNH
C42H38N4O14 Cl2 176-178 75 Brown
[V]d 2,3-O-bis[ (4`-methoxy
phenyl ) 2,3-dihydro benz
[1,2e][1,3]oxazepine-4,7-
diones-methyl ene]- 5,6-O-isopropylidene-
L-ascorbic
acid
O
O
O
OCH2C NHN
O
O
CH2C
C
HC
O
C
Me
C O
C
C
O
O
O
O
H3CO
O
Me
NNH OCH3
C44H44N4O16 168-170 70
Pale
Brown
[V]e 2,3-O-bis[ (4`-
bromophenyl ) 2,3-dihydro
benz [1,2e][1,3]oxazepine-
4,7-diones-methyl ene]-
5,6-O-isopropylidene-L-ascorbic
acid
O
O
O
OCH2C NHN
O
CH2C
C
HC
O
C
Me
C O
C
C
O
O
O
O
Br
O O
Me
NNH Br
C42H38N4O14 Br2 140-142 50 Brown
9. Iraqi NaƟonal Journal of Chemistry, 2014, volume المجلة العراقیة الوطنیة لعلوم الكیمیاء- 2014 العدد الخامس والخمسون 55
272
Biological Activity
The antibacterial activity of the
synthesized compounds was performed
according to the agar diffusion
method[12]. The synthesized compounds
were tested against E.coli and Staph.
aureus. Each compound was dissolved in
DMSO to give concentration 1ppm.
The plates were then incubated at 37ᵒC
and examined after 24 hrs. The zone of
inhibition formed were measured in
millimeter and clarity as in Table 3. All
the compounds exhibit the highest or low
biological activity against both the
organisms . Most of the 1,3-oxazepin
compounds showed a high inhibition
against gram(+) becteria that could be
related to the heterocyclic ring. While
the Schiff bases compounds showed low-moderiate
activity against two types of
the bacteria gram(+) and garm (-).
Finally, the Schiff base [IV]e did not
show any biological activity towards
bacteria gram(+) and garm(-) .
Figure (1)1HNMR spectrum of compound [IV]c
10. Iraqi NaƟonal Journal of Chemistry, 2014, volume المجلة العراقیة الوطنیة لعلوم الكیمیاء- 2014 العدد الخامس والخمسون 55
273
//
Figure (2)1HNMR spectrum of compound [V]e
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