Classification and Synthesis of Sulpha drugs, Anti Viral Drugs, Anti Fungal Agents, Anti Tubercular Agents, Anti leprotic Agents, Antiamoebic Agents, Anthelmintics, Anti Malarial Drugs, Anti cancer Drugs
Sulfonamide (also called sulphonamide, sulfa drugs or sulpha drugs) is the basis of several groups of drugs. The original antibacterial sulfonamides are synthetic antimicrobial agents that contain the sulfonamide group.
Sulfonamide (also called sulphonamide, sulfa drugs or sulpha drugs) is the basis of several groups of drugs. The original antibacterial sulfonamides are synthetic antimicrobial agents that contain the sulfonamide group.
Tetracyclines are Octahydro napthacene derivatives which are bacteriostatic potent broad spectrum antibiotics and are the most widely prescribed form of antibiotic after penicillins.
TETRA means = four
CYCL means = hydrocarbon rings
INE means = derivation.
Tetracyclines are introduced 50 years ago as potent broad spectrum antibiotics.
They are biosynthesized form acetic acid and propionic acid units in microorganisms.
Tetracyclines,Biological sources,History,Sturctures,SAR,Mechanism of action,Spectrum of activity,Important structural units and the three acidity constants in the tetracycline molucule,amphoteric nature,epimerisation, chelation with metals,toxicity and uses.
Natural compounds from the bark of the cinchona tree, most notably quinine was observed to exhibit antimalarial activity.
Until the development of synthetic derivatives (ie. 4-aminoquinoline antimalarials), quinine continued to be the first choice to treat malaria.
Quinine is associated with side effects such as diarrhœa.
4-aminoquinoline antimalarials such as amodiaquine and chloroquine largely replaced quinine because of reduced unpleasant side effects.
The life cycle of the parasite and the immunological defence mechanisms against the parasite are complex.
Part of the parasite’s life cycle involves invasion of red blood cells (erythrocytes).
The haemoglobin within the red blood cell is broken down by the parasite and is used as a source of amino acids.
The 4-aminoquinolines act at the erythrocytic stage of the parasite.
Doxycycline is a compound used in prophylaxis against plasmodial parasites.
Other compounds associated with treating malaria include halofantrine and lumefantrine, often used in combination with other drugs.
Malignancy is most familiar as a characterization of cancer.Chemotherapy is a category of cancer treatment that uses one or more anti-cancer drugs as part of a standardized chemotherapy regimen
Aminoglycosides(medicinal chemistry by p.ravisankar)Dr. Ravi Sankar
Aminoglycosides,Aminocyclitols,Source,Structures of streptomycin,Dihydrostreptomycin,A mention of other aminoglycoside antibiotics,Acid hydrolysis,Mechanism of action,SAR,Dihydrostreptomycin and its importance,therapeutic uses, toxicity.
Mitsunubu reaction had been synthesised by Japanese scientist OYO Mitsunbu.
It involves the Conversion of primary, Secondary alcohol into the ester group.
It follows SN2 mechanism.
Tetracyclines are Octahydro napthacene derivatives which are bacteriostatic potent broad spectrum antibiotics and are the most widely prescribed form of antibiotic after penicillins.
TETRA means = four
CYCL means = hydrocarbon rings
INE means = derivation.
Tetracyclines are introduced 50 years ago as potent broad spectrum antibiotics.
They are biosynthesized form acetic acid and propionic acid units in microorganisms.
Tetracyclines,Biological sources,History,Sturctures,SAR,Mechanism of action,Spectrum of activity,Important structural units and the three acidity constants in the tetracycline molucule,amphoteric nature,epimerisation, chelation with metals,toxicity and uses.
Natural compounds from the bark of the cinchona tree, most notably quinine was observed to exhibit antimalarial activity.
Until the development of synthetic derivatives (ie. 4-aminoquinoline antimalarials), quinine continued to be the first choice to treat malaria.
Quinine is associated with side effects such as diarrhœa.
4-aminoquinoline antimalarials such as amodiaquine and chloroquine largely replaced quinine because of reduced unpleasant side effects.
The life cycle of the parasite and the immunological defence mechanisms against the parasite are complex.
Part of the parasite’s life cycle involves invasion of red blood cells (erythrocytes).
The haemoglobin within the red blood cell is broken down by the parasite and is used as a source of amino acids.
The 4-aminoquinolines act at the erythrocytic stage of the parasite.
Doxycycline is a compound used in prophylaxis against plasmodial parasites.
Other compounds associated with treating malaria include halofantrine and lumefantrine, often used in combination with other drugs.
Malignancy is most familiar as a characterization of cancer.Chemotherapy is a category of cancer treatment that uses one or more anti-cancer drugs as part of a standardized chemotherapy regimen
Aminoglycosides(medicinal chemistry by p.ravisankar)Dr. Ravi Sankar
Aminoglycosides,Aminocyclitols,Source,Structures of streptomycin,Dihydrostreptomycin,A mention of other aminoglycoside antibiotics,Acid hydrolysis,Mechanism of action,SAR,Dihydrostreptomycin and its importance,therapeutic uses, toxicity.
Mitsunubu reaction had been synthesised by Japanese scientist OYO Mitsunbu.
It involves the Conversion of primary, Secondary alcohol into the ester group.
It follows SN2 mechanism.
Sulphonamides are the first effective chemotherapeutic agents used for bacterial infection in humans. Sulfonamides have a wide range of pharmacological activities such as Oral hypoglycemic, antileprotic, anti epileptic, anti-hypertensive, anti-bacterial, anti-protozoal, anti-fungal, anti retroviral, anti cancer, antiinflammatory, and used as diuretic. This review consists of a discussion on the various pharmacological effects of sulfonamides
In vitro enzyme inhibition studies on new sulfonamide derivatives of 4-tosyl ...Jing Zang
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Classifications and Synthesis of Chemotherapeutic Drugs
1. PHARMAWISDOM MEDICINAL
CHEMISTRY
1 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
SULFONAMIDES
German bacteriologist and pathologist who was awarded the 1939 Nobel Prize for Physiology or
Medicine for his discovery (announced in 1932) of the antibacterial effects of Prontosil, the first
of the sulfonamide drugs.
They act as antimicrobial agents by inhibiting bacterial growth and activity and commonly called
sulfa drugs.
Chemically, it is a molecule containing the sulfonamido (sulfanilamide, SO2NH2)
functional group attached to aniline.
Structurally related to p-amino benzoic acid (PABA).
This group is also present in other non-antibacterial compounds like
-Sulphonureas
-Benzothiazids
-Furosemide
-Acetazolamide
MOA of SULFONAMIDE:
2. PHARMAWISDOM MEDICINAL
CHEMISTRY
2 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
CLASSIFICATION:
Orally absorbable agents
Short acting (6-9hrs.)-
Sulfadiazine
Sulfacytine
Sulfamethizole
Sulfisoxazole
Intermediate acting (10-12hrs.)-
Sulfamethaxazole
Sulfamoxole
Long acting (7days)-
Sulfadoxine
Sulfamethopyrazine
Orally non absorbable agents
Sulfasalazine
Olsalazine
Topical agents
Silver sulfadiazine
Sulfacetamide
Mafenide
Some Important Structures:
N
H
NS
O
O
H2N
Sulphapyridine
N
H
N S
O
O
N N
COOH
OH
Sulfasalazine
N
N
H
NS
O
O
H2N
Sulfadiazine
H
NS
O
O
H2N
Sulfamethoxazole
N
O CH3
H
NS
O
O
H2N
Sulfisoxazole
O
N
CH3H3C
3. PHARMAWISDOM MEDICINAL
CHEMISTRY
3 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
SAR of SULFONAMIDES
SH2N
O
O
NH R
4
3 2
1
p-Amino group
Aromatic ring
Sulfanilamide group
N1
-Substitution group
The amino & Sulphonyl groups on the benzene ring are essential & should be in 1,4-
position
Replacement of Aromatic ring by other ring systems or the introduction of additional
substituents on it decreases or abolish activity.
Exchange of the -SO2NH group by –CO-NH reduce the activity.
Substitution of Aromatic Heterocyclic nuclei at N1
- yields highly potent compounds.
N1
–Di substitution in general leads to inactive.
GENERAL SYNTHASIS OF SULFONAMIDE
NHCOCH3
4-acetamidobenzene -
sulfonyl chloride
Benzene Nitrobenzene
NO2 NH2
NHCOCH3
SO2Cl
NHCOCH3
SO2NH2
NH2
SO2NH2
Aniline Acetanilide
4-acetamidobenzene -
sulfonamide
Sulfonamide
HNO3
H2SO4
Sn/HCl (CH3CO)2O
CH3COOH
ClSO3H
NH3
H2O/HCl
4. PHARMAWISDOM MEDICINAL
CHEMISTRY
4 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
SULPHADIAZINE
NHCOCH3
SO2Cl
NHCOCH3
SO2NH
N
N
NH2
SO2NH
N
N
H2O/H+
Sulphadiazine
2-amino pyridine
N
N
H2N
4-acetamidobenzene -
1-sulfonyl chloride
Hydrolysis
SULFASALAZINE
N
H
N S
O
O
NH2
Sulphapyridine
N
H
N S
O
O
N N+
Cl-
OH
COOH
N
H
N S
O
O
N N
COOH
OH
NaNO2/HCl
Diazotisation
Diazonium salt
Salicyclic acid
Coupling
Sulfasalazine
5. PHARMAWISDOM MEDICINAL
CHEMISTRY
5 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
TRIMETHOPRIM
CH2OHH3CO
H3CO
H3CO
H2
CH3CO
H3CO
H3CO
H2N C
NH
NH2
Guanidine
3,4,5-Trimethoxy
benzaldehyde
H2C
C
C
N
N
malononitrile
C
HC
N
NH2
H2
CH3CO
H3CO
H3CO
N
N
NH2
H2N
NH3
Trimethoprim
6. PHARMAWISDOM MEDICINAL
CHEMISTRY
6 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
ANTIVIRAL DRUGS
Antiviral drugs are a class of medication used specifically for treating viral infections.
CLASSIFICATION
Based on their chemical structure
1. Purine Analogs:
Acyclovir
Vidarabin (Herpes)
Zidovudine (HIV)
2. Pyrimidine Analogs
Iodoxuridine
Trifluridine (herpes)
3. Thio-semi carbazone
Methisazone
4. Adamantine amines
Amantadine
Rimantadine
ACYCLOVIR
N
N
OH
H2N
C6H5COOCH2CH2OCH2Cl
-HCl
NaOH/H2O/H
-C6H5COOH
2-amino-6-hydroxy
purine
N
H
N
N
N
OH
H2N N
N
H2C O CH2
CH2OCC6H5
O
N
N
OH
H2N N
N
H2C O CH2
CH2HOAcyclovir
7. PHARMAWISDOM MEDICINAL
CHEMISTRY
7 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
ZIDOVUDINE
N
HN
O
CH3
O
O
CH2OH
OH
N
HN
O
CH3
O
O
CH2OH
OSO2CH3
N
HN
O
CH3
O
O
CH2OH
N3
Zidovudine
LiN3
DMF
(Dimethyl formide)
CH3SO2Cl
-HCl
8. PHARMAWISDOM MEDICINAL
CHEMISTRY
8 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
ANTIFUNGAL DRUGS
CLASSIFICATION: Based on chemical structure
Polyenes(antibiotics): Amphotericin-B
Azoles
Triazoles: fluconazole, itraconazole
Imidazole’s: clotrimazole, ketoconazole
Fluorinated pyrimidine derivatives: 5-flurocytosine
Acid and their salts: benzoic acid, salicylic acid.
Natural products: griseofulvin
FLUCONAZOLE
F
F
C
O
CH2CH2Cl
2,4-difluorobenzyl
ethalene chloride
N
N
H
N
-HCl
(1,2,4-Triazole)
F
F
C
O
CH2CH2
formation
alkoxide
F
F
C
H2C
H2C
O
N
N
N
H
(1,2,4-Triazole)
F
F
C
OH
H2
C N
N
N
N C
H2
Fluconazole
N
N
N
N
N
N
N
N
10. PHARMAWISDOM MEDICINAL
CHEMISTRY
10 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
ISONIAZID
N
CH3
Oxidation
4-methyl pyridine
N
C OHO
N
C NHNH2O
Isoniazide
H2N NH2
Hydrazine
-H2O
ETHAMBUTOL
CH3CH2CH NO2
CH2OH
Reduction CH3CH2CH NH2
CH2OH
2-Nitro-1-butanol 2-amino butanol
CH3CH2CH NH2
CH2OH
(2 moles)
ClCH2CH2Cl
ethylene dichloride -2HCl
CH3CH2CH
H
N
CH2OH
H2
C
Ethambutol
H2
C CHCH2CH3
CH2OH
11. PHARMAWISDOM MEDICINAL
CHEMISTRY
11 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
ANTILEPROSY DRUGS
CLASSIFICATION:
SULFONES
Dapsone
Thiosemi carbazones
Amithiazone
Phenazines
Clofazimine
Antibiotics
Rifampicin (rifampin)
DAPSONE
2
H2SO4
Condensation
S
O
O
S
O
O
O2N NO2
HNO3/H2SO4
Nitration
4-4'-dinitrophenyl sulfone
Sn/HCl
Reduction
S
O
O
H2N NH2
Benzene
(2 Moles)
DAPSONE
12. PHARMAWISDOM MEDICINAL
CHEMISTRY
12 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
CLOFAZIMINE
NH
NH2
Cl
4-Chlorophenyl-O-Phenylenediamine
+
NH2
N
H
Cl
N
N
H
Cl
NH2
+
Cl-
N
H
N
N
H
Cl
NCH(CH3)2
FeCl3
Isopropyl amine
NH2CH(CH3)2
Clofazimine
13. PHARMAWISDOM MEDICINAL
CHEMISTRY
13 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
ANTIAMEBIC DRUGS
CLASSIFICATION:
Based on chemical moiety
Alkaloids
E.g. emetine
Nitroimidazoles
E.g. metronidazole, tinidazole
8-hydroxy quinolones
E.g. iodoquinol, chloroquine
Antibiotics
E.g. Bacitracin, oxytetracylin
Miscellaneous
E.g.diloxanide furoate
METRANIDAZOLE
H2N CH2CH2
1,2-diamino ethane
CH3CN / Zn
Catalytic
hydrogination
N
N
H
CH3
2-methyl-imidazole
HNO3/H2
N
N
H
CH3O2N
ClCH2CH2OH
reflux
2-chloroethanol
2-methyl-5-nitro imidazole
N
N CH3O2N
CH2CH2OH
Metrandazole
NH2
14. PHARMAWISDOM MEDICINAL
CHEMISTRY
14 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
DILOXANIDE FUROATE
NHCH3
OH
+ OHC C
Cl
Cl
Cl
+ NaCN
N
OH
H3C CCl
O
N
O
H3C CCHCl2
O
Diloxanide furoate
N-methyl amine
phenol
O
C Cl
O
C
O
O
NaOH
Furoyl
NaOH
15. PHARMAWISDOM MEDICINAL
CHEMISTRY
15 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
ANTIHELMINTHIC DRUGS
CLASSIFICATION:
Chlorinated derivatives
Tetrachloro ethane
Benzimidazole derivatives
Mebendazole
Albendazole
Thibendazole
Piperzine derivatives
Diethyl carbamazine
Heterocyclic derivatives
Pyrantal pamoate
Amides
Niclosamide
Natural products
Avermectins
Nilbemycin
DIETHYL CARBAMAZINE
HN NH + Cl C
O
N
C2H5
C2H5
Piperzine diethyl carbamoyl
chloride
HN N
CH3Cl
Chloromethane
Diethyl carbamazine
C
O
N
C2H5
C2H5
N N C
O
N
C2H5
C2H5
H3C
-HCl
-HCl
16. PHARMAWISDOM MEDICINAL
CHEMISTRY
16 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
ALBENDAZOLE
H
N
NO2HS
C
O
CH3
+
2-nitro-4-mercapto
acetanilide
BrCH2CH2CH3
-HBr
H
N
NO2H3CH2CH2CS
C
O
CH3
Red/hydrolysis
SnCl2
NH2
NH2H3CH2CH2CS
Methyl urea
H3CH2CH2CS
Acylation
CH3COOH
Albendazole
n-propyl bromide
N
H
N
NH2
H3CH2CH2CS N
H
N
N
H
C CH3
O
N
H
O
H2N
CH3
-CH3NH2
17. PHARMAWISDOM MEDICINAL
CHEMISTRY
17 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
PYRANTEL PAMOATE
N
N
CH3
S
H
HOOC OH
H2
C
HO COOH
Pyrantel
pamoate(pamoic acid)
pyrantel pamoate
S CHO
+
CN
H2
C COOH
Thiophene-2-
carboxaldehyde cyano acetic acid
knoevenagel
reaction S C
H
CHCN
CH3OH/HCl
S C
H
CHC
NH
O
NH2CH2CHCHNHCH
2
N-methyl propylene
1,3-diamine
S C
H
C
H
N
N
CH3
Pyrantel
19. PHARMAWISDOM MEDICINAL
CHEMISTRY
19 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
CHLOROQUINE
N
Cl
Cl
4,7-dichloroquinoline
+
CH3CH(CH2)3N
NH2
C2H5
C2H5
Phenol
condensation
N
NHCH(CH2)3N
Cl
CH3
C2H5
C2H54-amino-1-diethylamino
pentane
Chloroquine
PRIMAQUINE
N
H3CO
NO2
Reduction
Sn/HCl
BrCH(CH2)3Br
CH3
N
H3CO
NHCH(CH2)3Br
CH3
NH3
N
H3CO
NHCH(CH2)3NH2
CH3
6-methoxy-8-nitroquinoline
N
H3CO
NH2
8-amino-6-methoxy quinoline
Primaquine
1,4-dibromopentane
20. PHARMAWISDOM MEDICINAL
CHEMISTRY
20 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
PYRIMETHAMINE
CH2Cl
Cl
KCN
CH2CN
Cl
CH3CH2COC2H5
O C
Cl
C C2H5
CN OH
HC
Cl
C C2H5
CN O
(Enol form)(Keto form)
CH3Cl
C C C2H5
CN OCH3
H2N C NH2
NH
Guanide
N
N
H2N
C2H5
NH2Cl
Pyrimethamine Cl
1-chloro-4-
(chloromethyl)
benzene
Ethyl propionate
P h a r m a w i s d o m . b l o g s p o t . i n
NORFLAXACIN CIPROFLOXACIN
HN N
F
COOH
CH3
O
HN N
F
N
COOH
O
22. PHARMAWISDOM MEDICINAL
CHEMISTRY
22 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
Antibiotics
Actinomycin-D
Bleomycin
Mitomycin
Some Structures of ANTI-CANCER DRUGS
CH2CH2CH2COOHN
ClH2CH2C
ClH2CH2C
Chlorambucil
CH3SO2O(CH2)4OSO2CH3
Buslulfan
ClCH2CH2N C NHCH2CH2Cl
O
N O
Carmustine
P
S
NN
N
Thio-TEPA
C
H2
C
H
N
H
NH3C
O
NH CH
CH3
CH3
Procarbazine
N
N
SH
N
H
N
Mercaptopurine
HN
N
H
F
O
O
5-Fluoro uracil
N
CH3
C
O
H
N CH
COOH
CH2
CH2
COOH
H2
C
N
N
N
N
NH2
H2N
Methotrexate
24. PHARMAWISDOM MEDICINAL
CHEMISTRY
24 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
CARMUSTINE
NH
+
COCl2
Aziridine
(2moles)
N C N
O
2HCl ClCH2CH2NH C NHCH2CH2Cl
O
1,3-bis-2-chloroethyl urea
NaNO2
HCOOH
ClCH2CH2N C NHCH2CH2Cl
O
N O
Carmustine
Phosgene
-2HCl
di(aziridin-1-yl)methanone
5-FLUROURACIL
N
H
HN
O
O
Uracil
CF3OF
Fluoroxy trifluro
methane HN
N
H
F
O
O
5-Fluoro uracil
Fluorination
25. PHARMAWISDOM MEDICINAL
CHEMISTRY
25 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
6-MERCAPTOPURINE
HN
N
O
N
H
N
Hypoxanthine
POCl3
N
N
SCN
N
H
NN
N
Cl
N
H
N
Pyridine
6-chloro purine
NaSCN
-NaCl
N
N
SH
N
H
N
Mercaptopurine
H2O
METHOTREAXATE (AMETHOPTERIN)
N
N
NH2
NH2
NH2H2N
2,4,5,6-Tetra amino
pyrimidine
+ BrCH2CHCHO
Br
2,3-dibromo
propionaldehyde
+
HN
CH3
C
O
H
N CH
COOH
CH2
CH2
COOHMethyl amino benzoyl
glutamate
lime water
NaOH
CH3COOH
N
CH3
C
O
H
N CH
COOH
CH2
CH2
COOH
H2
C
N
N
N
N
NH2
H2N
Cyclization
Dehydration
-2HBr/H2O
Methotrexate