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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:
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
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
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
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
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
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
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
PHARMAWISDOM MEDICINAL
CHEMISTRY
9 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
ANTITUBERCULAR DRUGS
CLASSIFICATION:
Based on chemical moiety
Salicylic acid derivatives
Para amino salicylic acid
Pyridine derivatives
Isonicotinic acid hydrazide
Ethionamide
Pyrazine derivatives
Pyrazinamide
Ethylene Di-amino Butanol derivatives
Ethambutol
Antibiotics
Streptomycin
Cycloserine
Rifampicin
Kanamycin
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
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
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
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
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
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
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
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
PHARMAWISDOM MEDICINAL
CHEMISTRY
18 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
ANTIMALARIAL DRUGS
CLASSIFICATION:
Based on their chemical moiety
Cinchona alkaloids
Quinine
Cinchonine
4-amino quinolines
Chloroquine
Amodiaquine
Hydroxychloroquine
8-amion quinolines
Primaquine
Pamaquine
Tafenoquine
Quinoline Methanol
Mefloquine
9-amino acridines
Quinacrine
Acridine
2,4-diamino pyrimidines
Pyrimethamine
Trimethoprim
Biguanides
Proguanil
Chlorproguanil
Sulphonamides
Sulfadoxine
Sulfamethoxazole
Tetracyclines
Tertracycline
Doxycycline
Newer drugs(Sesqui Terpene Lactones)
Artemisinin
Artesunate
Artemether
Arteether
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
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
PHARMAWISDOM MEDICINAL
CHEMISTRY
21 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
ANTINEOPLASTIC AGENTS
(ANTI CANCER DRUGS)
CLASSIFICATION: Based on chemical moiety
Alkylating agents
Nitrogen mustards
Chlorambucil
Cyclophosphamide
Melphalan
Mechlorethamine
Alkyl sulphonates
Busulfan
Aziridines
Thio-TEPA
Benzo-TEPA
Nitrosovrea
Carmustine
Lomustine
Semustine
Triazenes (Methyl Hydrazines)
Procarbazine
Dacarbazine
Anti-metabolites
Folate analogues
Methotrexate
Purine analogues
6-mercaptopurine
6-thioguanine
Pyrimidine analogues
5-fluorouracil
Floxuridine
Cytarabine
Natural products
Vinca alkaloids
Vincristine
Vinblastine
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
PHARMAWISDOM MEDICINAL
CHEMISTRY
23 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
CHLORAMBUCIL
CH2CH2CH2COOH
Conc. HNO3
CH2CH2CH2COOHO2N
Pd/SOCl2
O
CH2CH2CH2COOHN
ClH2CH2C
ClH2CH2C
4-Phenyl butyric acid
CH2CH2CH2COOHH2N
4-(4-aminophenyl)butanoic acid
4-(4-nitrophenyl)butanoic acid
CH2CH2CH2COOHN
HOH2CH2C
HOH2CH2C
Chlorambucil
POCl3
Ethylene Oxide
BUSULFAN
CH3SO2Cl
Methane sulfonyl
chloride
(2moles)
+ OH(CH2)4OH
1,4-Butanediol
CH3SO2O(CH2)4OSO2CH3
Buslulfan
Pyridine
- 2HCl
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
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
PHARMAWISDOM MEDICINAL
CHEMISTRY
26 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD
VINCA ALKALOIDS
N
H
N
OH
C2H5
H3COOC
N
H3CO
N
H
HO
OCOCH3
COOCH3
C2H5H
R
R = CHO - Vincristine
R = CH3 - Vinblastine

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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
  • 9. PHARMAWISDOM MEDICINAL CHEMISTRY 9 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD ANTITUBERCULAR DRUGS CLASSIFICATION: Based on chemical moiety Salicylic acid derivatives Para amino salicylic acid Pyridine derivatives Isonicotinic acid hydrazide Ethionamide Pyrazine derivatives Pyrazinamide Ethylene Di-amino Butanol derivatives Ethambutol Antibiotics Streptomycin Cycloserine Rifampicin Kanamycin
  • 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
  • 18. PHARMAWISDOM MEDICINAL CHEMISTRY 18 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD ANTIMALARIAL DRUGS CLASSIFICATION: Based on their chemical moiety Cinchona alkaloids Quinine Cinchonine 4-amino quinolines Chloroquine Amodiaquine Hydroxychloroquine 8-amion quinolines Primaquine Pamaquine Tafenoquine Quinoline Methanol Mefloquine 9-amino acridines Quinacrine Acridine 2,4-diamino pyrimidines Pyrimethamine Trimethoprim Biguanides Proguanil Chlorproguanil Sulphonamides Sulfadoxine Sulfamethoxazole Tetracyclines Tertracycline Doxycycline Newer drugs(Sesqui Terpene Lactones) Artemisinin Artesunate Artemether Arteether
  • 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
  • 21. PHARMAWISDOM MEDICINAL CHEMISTRY 21 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD ANTINEOPLASTIC AGENTS (ANTI CANCER DRUGS) CLASSIFICATION: Based on chemical moiety Alkylating agents Nitrogen mustards Chlorambucil Cyclophosphamide Melphalan Mechlorethamine Alkyl sulphonates Busulfan Aziridines Thio-TEPA Benzo-TEPA Nitrosovrea Carmustine Lomustine Semustine Triazenes (Methyl Hydrazines) Procarbazine Dacarbazine Anti-metabolites Folate analogues Methotrexate Purine analogues 6-mercaptopurine 6-thioguanine Pyrimidine analogues 5-fluorouracil Floxuridine Cytarabine Natural products Vinca alkaloids Vincristine Vinblastine
  • 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
  • 23. PHARMAWISDOM MEDICINAL CHEMISTRY 23 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD CHLORAMBUCIL CH2CH2CH2COOH Conc. HNO3 CH2CH2CH2COOHO2N Pd/SOCl2 O CH2CH2CH2COOHN ClH2CH2C ClH2CH2C 4-Phenyl butyric acid CH2CH2CH2COOHH2N 4-(4-aminophenyl)butanoic acid 4-(4-nitrophenyl)butanoic acid CH2CH2CH2COOHN HOH2CH2C HOH2CH2C Chlorambucil POCl3 Ethylene Oxide BUSULFAN CH3SO2Cl Methane sulfonyl chloride (2moles) + OH(CH2)4OH 1,4-Butanediol CH3SO2O(CH2)4OSO2CH3 Buslulfan Pyridine - 2HCl
  • 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
  • 26. PHARMAWISDOM MEDICINAL CHEMISTRY 26 S.SEETARAMSWAMY, Asst.Professor, CBCP, HYDERABAD VINCA ALKALOIDS N H N OH C2H5 H3COOC N H3CO N H HO OCOCH3 COOCH3 C2H5H R R = CHO - Vincristine R = CH3 - Vinblastine