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Dr. M. Geethavani, M. Pharm., PhD
Professor & HOD
Department of pharmaceutical Chemistry
BALAJI COLLEGE PHARMACY (BALA)
Sanapa Road, Rudrampeta bypass Anantapuramu.
Anantapur District, Andhra Pradesh State, INDIA - 515001
Research work
 Contents
 Title
 Introduction
 Literacture review
 Aim and objectives
 Drug profile
 Methodology
 Observation , Results and Conclusion
 References
Introduction:
 After the discovery of the first fluoroquinolone, norfloxacin
in1980 as an antibacterial agent with potent and broad
spectrum activity, several new members of this family have
emerged with enhanced activity against Gram positive and
anaerobic bacteria with improved pharmacokinetic profile.
 Much has been learned about how molecular modifications
of the core quinolone structure affect the antibacterial profile.
 The structure–activity relationship of quinolones has been the
subject of extensive review. For most of the current agents,
hydrogen at position 2, a carboxyl group at position 3 and a
keto group at position 4 in the bicyclic ring cannot be
changed without a significant loss of activity.
 Furthermore it appears that a cyclopropyl group is optimal at
C-1. Ofloxacin is an antibiotic useful for the treatment of a
number of bacterial infections.
Author
Conclusion
Gisela C.Muscia et al The multi component syntheses of 2,4-di-
aryl-quinolines and analogous polycyclic
derivatives as anti-tuberculosis agents.
Dr.D.Sriram et al 1-cyclopropyl-6-fluoro-8-methoxy-1,4-
dihydro-4-oxo-7[[N4-[30-[(4,6-
dimethylpyrimidin-2-
yl)benzenesulfonamido-4-yl]imino-10-(5-
fluoroisatinyl)]methyl]-3-methyl N1-
piperazinyl]-3-quinoline carboxylic acid
emerged as the most potent broad-
spectrum chemotherapeutic agent active
against HIV (EC50: 12.1 mg/ml), and
Mycobacterium tuberculosis (MIC: 1.22
mg/ml).
Martin et al. synthesized binuclear analogues with the
–CONH– bridge connecting the pyrazine
and benzene rings with anti-mycobacterial
activity.
Farzana et al synthesized triazolo derivatives and
evaluate for its anti-TB activity. Literature
review suggests that 4-amino-5-(pyridin-
4-yl)-4H-1, 2, 4-triazole-3-thiol can show
anti TB activity.
Aim :
To establish the methods of synthesis for the proposed derivatives
.
Objectives :
• To synthesize some novel ofloxacin derivatives by microwave
oven.
• To confirm the structure of the synthesized ofloxacin by spectral
analysis.
• To evaluate the proposed derivatives for their anti-tubercular
activities.
• To explore possible novel synthetic derivatives of ofloxacin using
potent antimycobacterial pharmacophore such as carboxamide.
• To characterize the structures of new compounds with physical
and spectral data.
• To evaluate antitubercular activity of synthesised compounds
 With reference to the need research on antimicrobials for drug resistant
pathogens, the investigation was initiated to synthesize new chemical
entity as a hit for virulent pathogens like Mycobacterium tuberculosis.
 In search of new synthetic molecules it was observed that they are
developing resistance against virulent pathogens.
 In accordance to view on obtaining less toxic and less resistant synthetic
molecules and reference to the high lipophillic scaffold of Ofloxacin
reported in the literature, the present scheme was designed to obtain
amide pharmacophore derivatives of Ofloxacin, in which it acts as a cell
wall/membrane permeability enhance for the selected pharmacophore.
 The present work is a part of this worldwide efforts to develop better
Fluoroquinolones than the available ones with respect to activity or
toxicity or resistance or all of these.
Principles Of Microwave Heating
 1.Dipole interaction
Polar ends of a molecule tend to align themselves
and oscillate in step with the oscillating electrical
field of the microwaves. Collisions and friction
between the moving molecules result in heating.
 2. Ionic conduction
It results if there are free ions or ionic species
present in the substance being heated. The electric
field generates ionic motion as the molecules try to
orient themselves to the rapidly changing field.
This causes the instantaneous super heating
Advantages
 Uniform heating occurs throughout the material
 Process speed is increased
 High efficiency of heating
 Reduction in unwanted side reaction
 Purity in final product Improve reproducibility
Environmental heat loss can be avoided
• Drug profile
OFLOXACIN STRUCTURE:
• Nomenclature : 9-fluoro-3-methyl-10-(4-methylpiperazin-
1yl)-7-oxo-3,7-
dihyro-2H-[1,4]oxazino[2,3,4-ij]quinoline-
6-carboxylic acid
• Molecular weight : 361.368 g/mole.
• Molecular formula : C18H20FN3O4.
• Solubility : Methanol, chloroform.
• Properties:
• Colour : white ,colour less needles from ethanol.
• Melting point : 250-257ºC
• Log P : -0.39
N
O
F
N
O
OH
O
N
Literature survey
Chemical synthesis and Purification
Characterization of compounds.
Screening for anti tubercular activity
Development of Structure activity relationship.
Make recommendation for further research.
Step 1
Step 2
Step 3
24-02-2024
Dept. of Pharmaceutical Chemistry 11
Ofloxacin
(0.01 mole)
Ofloxacin was treated with Thionyl chloride to get
ofloxacin chloride. Ofloxacinchloride was treated
with diff.amino acids which includes Alanine,
Histidine, Cystine, Glycine, Glutamic acid ,valine
to obtain respective carboxamide derivatives.
Subjected for microwave
irradiation(20seconds) and
subjected for vacuum
filtration.
Reaction is to
be monitored
by TLC
The final product is
tobe subjected to
purification process
Scheme:
N
F
O
OH
O
O
N
N
(E)
N
F
O O
O
N
N
(E)
Cl
S
O
C
l
2
N
F
O O
O
N
(E)
N
F
O O
O
N
N
(E)
H
N
(S)
O
O
C
y
st
in
e
N
F
O O
O
N
N
(Z)
Alanine
H
N (S)
HN N
O
HO
HN
(S)
O
OH
Histidine
NH3
Ch
lo
rin
at
ion
N
F
O O
O
N
N
H2N (S)
O
HO
O
HO
Glutamic Acid
N
F
N
N
O
O
H2N
(S)
O
OH
O
Valine
N
O
N
F
H
N
O O
N
O
HO
N
O
N
F
N
O O
H2N
(S)
O
OH
O
HO
G
l
y
c
i
n
e
Microwa
ve
Radiation
-20Sec
M
i
c
r
o
w
a
v
e
R
a
d
i
a
t
i
o
n
-
2
0
S
e
c
Microwave
Radiation -20Sec
M
i
c
r
o
w
a
v
e
R
a
d
i
a
t
i
o
n
-
2
0
S
e
c
Microwave
Radiation -20Sec
Microwave
Radiation -20Sec
M
icrowave
Radiation
-20Sec
A
s
p
a
r
t
i
c
A
c
i
d
N
IR: 3405.04 (O-H stretching ), 3133.58 (N-H stretching ), 1709.06 (C=O stretching ), 1295.27 (C-N stretching), 1126.18 (C-O
stretching ), 1050.72 (C-F stretching ).
Ofloxacin Aspartic acid
1HNMR : 6.68-7.90 (2H Fluroquinolone, 1H (4.5), 3H alkyl, ( 5.5) ( oxazine), 4H(
2.27-3.45) (Piperazine), 2H ,2.6 (Methylene), 3H( 2.85) methyl, 1H ( sec.amine)
Ofloxacin aspartic acid
Ofloxacin Aspartic acid
IR : 3413.72[O-H stretching], 3040.88[N-H stretching], 1714.89[C=O
stretching], 1290.84[C-N stretching], 959.06[C-O stretching],798.16[C-F
stretching].
Ofloxacin Valine
NMR:1H [pyridinone 8.418], 1H[Benzene-7.266], 3H[Morpholine- 3.280 -
4.277], C=O[Aliphatic-3.52], 1H[Aliphatic- 2.258] 5H [Piperazine 2.650-3.529]
1H [Piridinone 2.144], Aliphatic morpholine [1.260]Aliphatic 6H, 2CH3 Alkyl
[1.260].
Ofloxacin Valine
Ofloxacin Valine
M+1: 360.1
Standard Drug Photograph
Conclusion:
The synthetic derivatives of ofloxacin exhibited potent
Antimycobacterial activity against Mycobacterium tuberculosis
whilst the activity towards virulent pathogen was good.
 All compounds Histidine, Alanine, Valine, Aspartic acid, Glycine,
Cysteine,
Glutamic acid derivatives bearing ofloxacin carboxamide
exhibited considerable inhibition against drug resistant
Mycobacterium tuberculosis showed high potent activity when
compared to standard drug Streptomycin, pyrazinamide,
ciprofloxacin.
 Further research can be carried out on ofloxacin with amino
acids.
24-02-2024
Dept. of Pharmaceutical Chemistry 24
1. Salah, S. A. (2003). Synthesis and biological evaluation of
tetra cyclic fluoroquinalones as antibacterial and anticancer
agents. Vol. 62, pp. 293-97.
2. Akhiles Roy A.R.(1995).Synthesis and biological evaluation of
some substituted fluoroquinalones. Vol.74, pp. 458-92
3. Asif Hussain PhD, S. A. (2003). Synthesis and biological
evaluation of tetra cyclic fluoroquinalones as antibacterial and
anticancer agents. Vol. 62. pp.293-97.
4. Neu (2002) Symposium on fluoroquinalones [Journal]. - [S.l.]
: the American journal of medicine. Vol. 91. pp. 564
5. Hadi Adibi (2007)Synthesis of 7-substituted fluoroquinalones
derivatives containing triazolidine [Journal]. Vol. 34. pp. 221-23
6. Mohofad Asif (2012)A antimicrobial cancer and anti microbial
activity of tetrafluoroquinalones compounds [Journal]. - [S.l.] :
the American journal of medicine, Vol. 27. pp. 214-45
References
24-02-2024
Dept. of Pharmaceutical Chemistry 25

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Microwave Assisted Synthesis and Characterisation of Ofloxacin Carboxamide Derivatives : Multidrug Resistant Anti-Tubercular drugs

  • 1. Dr. M. Geethavani, M. Pharm., PhD Professor & HOD Department of pharmaceutical Chemistry BALAJI COLLEGE PHARMACY (BALA) Sanapa Road, Rudrampeta bypass Anantapuramu. Anantapur District, Andhra Pradesh State, INDIA - 515001 Research work
  • 2.  Contents  Title  Introduction  Literacture review  Aim and objectives  Drug profile  Methodology  Observation , Results and Conclusion  References
  • 3. Introduction:  After the discovery of the first fluoroquinolone, norfloxacin in1980 as an antibacterial agent with potent and broad spectrum activity, several new members of this family have emerged with enhanced activity against Gram positive and anaerobic bacteria with improved pharmacokinetic profile.  Much has been learned about how molecular modifications of the core quinolone structure affect the antibacterial profile.  The structure–activity relationship of quinolones has been the subject of extensive review. For most of the current agents, hydrogen at position 2, a carboxyl group at position 3 and a keto group at position 4 in the bicyclic ring cannot be changed without a significant loss of activity.  Furthermore it appears that a cyclopropyl group is optimal at C-1. Ofloxacin is an antibiotic useful for the treatment of a number of bacterial infections.
  • 4. Author Conclusion Gisela C.Muscia et al The multi component syntheses of 2,4-di- aryl-quinolines and analogous polycyclic derivatives as anti-tuberculosis agents. Dr.D.Sriram et al 1-cyclopropyl-6-fluoro-8-methoxy-1,4- dihydro-4-oxo-7[[N4-[30-[(4,6- dimethylpyrimidin-2- yl)benzenesulfonamido-4-yl]imino-10-(5- fluoroisatinyl)]methyl]-3-methyl N1- piperazinyl]-3-quinoline carboxylic acid emerged as the most potent broad- spectrum chemotherapeutic agent active against HIV (EC50: 12.1 mg/ml), and Mycobacterium tuberculosis (MIC: 1.22 mg/ml). Martin et al. synthesized binuclear analogues with the –CONH– bridge connecting the pyrazine and benzene rings with anti-mycobacterial activity. Farzana et al synthesized triazolo derivatives and evaluate for its anti-TB activity. Literature review suggests that 4-amino-5-(pyridin- 4-yl)-4H-1, 2, 4-triazole-3-thiol can show anti TB activity.
  • 5. Aim : To establish the methods of synthesis for the proposed derivatives . Objectives : • To synthesize some novel ofloxacin derivatives by microwave oven. • To confirm the structure of the synthesized ofloxacin by spectral analysis. • To evaluate the proposed derivatives for their anti-tubercular activities. • To explore possible novel synthetic derivatives of ofloxacin using potent antimycobacterial pharmacophore such as carboxamide. • To characterize the structures of new compounds with physical and spectral data. • To evaluate antitubercular activity of synthesised compounds
  • 6.  With reference to the need research on antimicrobials for drug resistant pathogens, the investigation was initiated to synthesize new chemical entity as a hit for virulent pathogens like Mycobacterium tuberculosis.  In search of new synthetic molecules it was observed that they are developing resistance against virulent pathogens.  In accordance to view on obtaining less toxic and less resistant synthetic molecules and reference to the high lipophillic scaffold of Ofloxacin reported in the literature, the present scheme was designed to obtain amide pharmacophore derivatives of Ofloxacin, in which it acts as a cell wall/membrane permeability enhance for the selected pharmacophore.  The present work is a part of this worldwide efforts to develop better Fluoroquinolones than the available ones with respect to activity or toxicity or resistance or all of these.
  • 7. Principles Of Microwave Heating  1.Dipole interaction Polar ends of a molecule tend to align themselves and oscillate in step with the oscillating electrical field of the microwaves. Collisions and friction between the moving molecules result in heating.  2. Ionic conduction It results if there are free ions or ionic species present in the substance being heated. The electric field generates ionic motion as the molecules try to orient themselves to the rapidly changing field. This causes the instantaneous super heating
  • 8. Advantages  Uniform heating occurs throughout the material  Process speed is increased  High efficiency of heating  Reduction in unwanted side reaction  Purity in final product Improve reproducibility Environmental heat loss can be avoided
  • 9. • Drug profile OFLOXACIN STRUCTURE: • Nomenclature : 9-fluoro-3-methyl-10-(4-methylpiperazin- 1yl)-7-oxo-3,7- dihyro-2H-[1,4]oxazino[2,3,4-ij]quinoline- 6-carboxylic acid • Molecular weight : 361.368 g/mole. • Molecular formula : C18H20FN3O4. • Solubility : Methanol, chloroform. • Properties: • Colour : white ,colour less needles from ethanol. • Melting point : 250-257ºC • Log P : -0.39 N O F N O OH O N
  • 10. Literature survey Chemical synthesis and Purification Characterization of compounds. Screening for anti tubercular activity Development of Structure activity relationship. Make recommendation for further research. Step 1 Step 2 Step 3
  • 12. Ofloxacin (0.01 mole) Ofloxacin was treated with Thionyl chloride to get ofloxacin chloride. Ofloxacinchloride was treated with diff.amino acids which includes Alanine, Histidine, Cystine, Glycine, Glutamic acid ,valine to obtain respective carboxamide derivatives. Subjected for microwave irradiation(20seconds) and subjected for vacuum filtration. Reaction is to be monitored by TLC The final product is tobe subjected to purification process
  • 13. Scheme: N F O OH O O N N (E) N F O O O N N (E) Cl S O C l 2 N F O O O N (E) N F O O O N N (E) H N (S) O O C y st in e N F O O O N N (Z) Alanine H N (S) HN N O HO HN (S) O OH Histidine NH3 Ch lo rin at ion N F O O O N N H2N (S) O HO O HO Glutamic Acid N F N N O O H2N (S) O OH O Valine N O N F H N O O N O HO N O N F N O O H2N (S) O OH O HO G l y c i n e Microwa ve Radiation -20Sec M i c r o w a v e R a d i a t i o n - 2 0 S e c Microwave Radiation -20Sec M i c r o w a v e R a d i a t i o n - 2 0 S e c Microwave Radiation -20Sec Microwave Radiation -20Sec M icrowave Radiation -20Sec A s p a r t i c A c i d N
  • 14. IR: 3405.04 (O-H stretching ), 3133.58 (N-H stretching ), 1709.06 (C=O stretching ), 1295.27 (C-N stretching), 1126.18 (C-O stretching ), 1050.72 (C-F stretching ). Ofloxacin Aspartic acid
  • 15. 1HNMR : 6.68-7.90 (2H Fluroquinolone, 1H (4.5), 3H alkyl, ( 5.5) ( oxazine), 4H( 2.27-3.45) (Piperazine), 2H ,2.6 (Methylene), 3H( 2.85) methyl, 1H ( sec.amine) Ofloxacin aspartic acid
  • 17. IR : 3413.72[O-H stretching], 3040.88[N-H stretching], 1714.89[C=O stretching], 1290.84[C-N stretching], 959.06[C-O stretching],798.16[C-F stretching]. Ofloxacin Valine
  • 18. NMR:1H [pyridinone 8.418], 1H[Benzene-7.266], 3H[Morpholine- 3.280 - 4.277], C=O[Aliphatic-3.52], 1H[Aliphatic- 2.258] 5H [Piperazine 2.650-3.529] 1H [Piridinone 2.144], Aliphatic morpholine [1.260]Aliphatic 6H, 2CH3 Alkyl [1.260]. Ofloxacin Valine
  • 20.
  • 22.
  • 23. Conclusion: The synthetic derivatives of ofloxacin exhibited potent Antimycobacterial activity against Mycobacterium tuberculosis whilst the activity towards virulent pathogen was good.  All compounds Histidine, Alanine, Valine, Aspartic acid, Glycine, Cysteine, Glutamic acid derivatives bearing ofloxacin carboxamide exhibited considerable inhibition against drug resistant Mycobacterium tuberculosis showed high potent activity when compared to standard drug Streptomycin, pyrazinamide, ciprofloxacin.  Further research can be carried out on ofloxacin with amino acids.
  • 24. 24-02-2024 Dept. of Pharmaceutical Chemistry 24 1. Salah, S. A. (2003). Synthesis and biological evaluation of tetra cyclic fluoroquinalones as antibacterial and anticancer agents. Vol. 62, pp. 293-97. 2. Akhiles Roy A.R.(1995).Synthesis and biological evaluation of some substituted fluoroquinalones. Vol.74, pp. 458-92 3. Asif Hussain PhD, S. A. (2003). Synthesis and biological evaluation of tetra cyclic fluoroquinalones as antibacterial and anticancer agents. Vol. 62. pp.293-97. 4. Neu (2002) Symposium on fluoroquinalones [Journal]. - [S.l.] : the American journal of medicine. Vol. 91. pp. 564 5. Hadi Adibi (2007)Synthesis of 7-substituted fluoroquinalones derivatives containing triazolidine [Journal]. Vol. 34. pp. 221-23 6. Mohofad Asif (2012)A antimicrobial cancer and anti microbial activity of tetrafluoroquinalones compounds [Journal]. - [S.l.] : the American journal of medicine, Vol. 27. pp. 214-45 References