E7

A4
DA

4
4D
Paper / Subject Code: 87611 / Medicinal Chemistry- III

BC

5F
D9
48

E7
A4
DA

CD
AB

4D
5F
D9
48

AB
B0

E7
A4
CD
AB

D
16

5F
D9
48

B
0
FC

A4
Time:3Hrs Marks:75

DA

D
B

AB
16

BC
7B

D9
Q.I. Answer the following Multiple Choice Questions. Select the most appropriate

8
B0
FC

B4
FB

DA

D
option for each statement. 20M

A
16

BC
B

9
A
25

DD
7

B0
C

B4
FB

DA
D4

BF
Sr No Questions Options

BC
A
5
74

C1

48
B7
2
1 Identify the following structure a Amoxicillin

A
D4

B
FE

BF

B
5F

D
16
b Ampicillin

0A
4
45

8
B7
2
7

FC

B4
c Cloxacillin

A
4

6B
FE
9A

5F

D
B

0A
d Penicillin V

1
5
DD

48
7
2
7

C
4

FB
D4

6B
FE
9A

BF

B
BC

0A
5
4

C1
45
DD

7
42
7

B
DA

6B
E
9A

F
4D

5F
C

5F

1
48

AB

7
2
E7

C
A4

B
CD

D4

B
AB

F
5F
D

5F

16
2 Hammett constant is a measure of a Lipophilicity of substituent

7B
9

4
48

DD
B0

2
E7

FC
4

FB
DA
b Log P of substituent

D4
9A
AB
16

7B
25
c Steric effect of substituent

4
45
8

D
B0
FC

7
4

FB
DA

CD

D4
E
9A
AB

d Electronic effect of substituent

16

5F
7B

25
74
-lactam ring in cephalosporin is fused
8

AB

D
3 a Dihydrothiazine ring
B0
FC

A4
4
FB

CD

D4
FE
B

8D
6

with
7B

9
A
25

C1

74
45
B

DD
0

B4
FB

b Dihydrothiazole ring
DA
D4

FE
9A
BF

16

BC
A
25

Dihydrothiadiazine ring
4

45
8

D
7

0
E7

4
B

DA
D4

CD
6B

9A
F

AB

d Dihydrothiadiazole ring
F
5F

B
25
4

48

AB

DD
7

4 Azithromycin consists of a a 16-membered lactone ring

B0
E7

C
A4

FB
D4

BF

AB
5F

8D
b 15 membered lactam ring
16

BC
D9

5
74

7
42

B0
FC
A4

c B415 membered lactone ring

B
CD

DA
FE

4D

5F

16
B
D9

0A
d 14 membered lactam ring
45
AB

48
7
2
E7

C
B
CD

6B
9A

5 Conjugated trione system of tetracycline a 2.8-3.4

BF

AB
4D

5F
8D

5F

C1
AB

DD

has a pka of
B7
2

B0
E7
A4
B4

D4

BF
5F

b 7.2-7.8
8D

BC

16
D9
0A

4
45

B7
2
7

FC

c 9.1-97
B4

DA

CD
6B

D4
E
9A

5F
5F

7B
A

d 5.5-6.5
C1

4
8

AB

DD
B0

42
7
4
B4

FB

Water soluble artemisinin derivative used Artemether

FE

6 a
A

4D
D
16

BC

9
A

25
5

as antimalarial agent is
48

DD
B0
FC

E7
4
A

D4
9A
AB

b dihydroartemisinin
8D
16

BC

F
7B

74
45
D
B0
FC

c Arteether
B4
FB

CD

FE
9A
8D
6
7B

d Artesunate
A
5

C1

45
B

D
42

B0

4
FB

7 Structure of tripartite prodrug is a Drug-Linker-Carrier

CD

9A
BF

D
16

A
25

b Linker-Drug-Carrier
8

DD
B7

B0
FC

B4

DA
D4

c Linker-Carrier-Drug
5F

16

BC
7B

0A
74

48
42

d Drug-Linker-Drug
FC
FB

DA
B
E

AB
4D
5F

16

8 Chloramphenicol activity resides in a L-threo isomer

7B
25

48
0
E7

FC
A4

FB

b L-erythro isomer
D4

AB
5F

16
7B
25

c D-erythro isomer
74

B0
FC
A4

FB
D4
E

d D-Threo isomer
5F

16
B
D9

25
74

9 Example of an aminoglycoside is a Capreomycin

FC
4

FB
CD

D4
E
9A

b Clindamycin
5F

7B
25
74
AB

DD

c Kanamycin
FB
D4
E
9A
BC

5F

d Clarithromycin
25
74
DD

4
A

D4
E
9A
8D

BC

5F

74
DD

4
4

26537 Page 1 of 5
FE
9A
AB

8D

BC

45
D
B0

CD

9A
AB

8D

AB

DD
0

B4

BFC16B0AB48DABCDD9A45FE74D425FB7
6B
 B0 AB A4 42 C1
AB 5F 5 6B
4
CD
D9 E 74
FB
7B 0A
6B 8D
0 A BC
A4 D4
25 FC B4
8D
AB 5F FB 16
4 8D
DD E7
4D 7B B0
A
AB
A 9A FC B4 CD
BC 4 5F 42
5F 16 8D D9
B4 E A4

17
16
15
14
13
12
11
DD 74 B7 B0 AB 10
8D 9A BF A CD 5F
A 4
D4 B4 E7

26537
BC 5F 25 C1
6 8 DA D9 4
DD E FB B0 A4 D4
is

74 7B 25

of
9A AB BC 5F
D4 FC E7 FB
AB 4 5F 25 16 48
D
DD
9A 4 7B
CD
D E74
FB B0 AB 45
D4
25 FC
9A D4 7B
FC A B4 CD FE FB 16
B0
4 5F 25 16 8D AB D9 74 7B
DD E74
FB B0 A 48 A4 D4
25 FC
9A B
7B A 5F F
BC DA 16
D4 FC 4 E7 B 7 B0 DD

infection caused by
45 25 16 8D 9A 4D BF AB BC
FE
74
FB
7 B A 45 42 C1 48 DD
D4 B FC
0A
B4
BC F 5 FB 6 D 9A
DD E7 7 B0 AB 45
25 8 B C

Identify the following drug

Identify the following drug

16
B D A 9 A 4D
F AB FE
FB
7B 0 B 45F 4 2 C 4 8
DD 74
AB 5F 16 9A
FC CD
D E 7 B 7 B 0
DA
B 4
D4
16 48 4 A 5 25
DA 9A
4
D4 BF
C B 4
CD FE
7
FB
B0 B 2 8 D

-------------- is an example of NNRTI

5 1 4 7B

2-methyl imidazole and nitric acid are

5F

starting materials used for synthesis of

AB CD FE 6B DA 9A D4
B FC

Following drug is useful in treatment of

D 7 7 0 B 2

combinatorial chemistry. Which means?

48 4 B A 45 5
C 16
Heterocyclic ring present in pyrazinamide

DA 9A D4 B4 FE FB

Prontosil on metabolism leads to formation

2 FC DD 7 7 B0
BC 45
F 5F 16 8D 9 4 D B AB

Page 2 of 5
4 FC

c
c
c
c
c
c
c

A4

Solid phase synthesis is frequently used in a

a
a
a
a
a
a
a

d
b
d
b
d
b
d
b
d
b
d
b
d
b

DD E7 B7 B0 AB 2 48
9A 4D BF AB 5F 5F 16
42 C 4
CD
D E 7 B7 B 0
DA
45
FE 5F 16 8 DA 9A 4 D4 BF AB
74 B7 B0 B 4 5F 2 5F C 16 48

HIV
BF AB
HSV
CD DA

BFC16B0AB48DABCDD9A45FE74D425FB7
VZV
D4 E7 B0 H1N1
25 C1 48 D 4D
B7 BC

Sulfone
AB
pyridine

9A BF D
pyrazine

6B DA
linezolid

FB 42 48
45 C1
pyridazine

7B 0A 5 D
pyrimidine

BC F 6
cycloserine

Didanosine
Zidovudine

Delavirdine
Furosemide

Miconazole

Lamivudine
clindamycin

Itraconazole
FB
capreomycin

FC B4 DD E7 B0 AB
7

Sulfisoxazole
Ketoconazole
nitrofurantoin

Sulfanilamide
4 A

Sulfacetamide
B

Metronidazole
8D 9
Paper / Subject Code: 87611 / Medicinal Chemistry- III

16

without solvent
A4 D4 FC B4 CD
chloramphenicol

B0 AB
5F 2 5F 16 8 D9
Diloxanide furoate

AB B DA
48
CD
D E 7 B 7 0 B
A4
DA 9A 4 D4 BF A B4 CD
45 2 C 1 8

Reactions are carried out

BC 5F D9
DD FE B 6B DA A4
74 7B 0A BC 5F
9A
45
D4 F C1 B48 D E7
25 D9
FE FB 6B DA A4
74 7B 0A BC 5F
D4 F C B4 D E7
25 1 6B 8D D9 4D
FB
7B 0A A BC
A4 4
5F
FC B 48 DD E7
16
B D A 9A 4D
 E7
A4
DA

4
4D
Paper / Subject Code: 87611 / Medicinal Chemistry- III

BC

5F
D9
48

E7
A4
DA

CD
AB

4D
5F
D9
48

AB
B0

E7
A4
CD
AB

D
16

5F
D9
48

B
0
FC

A4
b Reagents and reactants are

DA

D
B

AB
16

BC
7B

D9
attached to a solid phase

8
B0
FC

B4
FB

DA

D
support

A
16

BC
B

9
A
25
c Reagents are used in the solid

DD
7

B0
C

B4
FB

DA
D4

BF
phase

BC
A
5
74

C1

48
B7
2
Molecules are constructed on a

0
d

A
D4

B
FE

BF

B
5F

D
16
solid phase support

0A
4
45

8
B7
2
7

FC

B4
18 Characteristic side effect associated with a phototoxicity

A
4

6B
FE
9A

5F

D
B

0A
Sparfloxacin is

1
5
DD

48
7
2
7

C
4

FB
D4

6B
FE
9A
b nephrotoxicity

BF

B
BC

0A
5
4

C1
45
DD
c hepatotoxicity

7
42
7

B
DA

6B
E
9A

F
4D

5F
d neurotoxicity
C

5F

1
48

AB

7
2
E7

C
A4
19 4-[(4-aminobenzene)sulfonyl]aniline is the a sulfanilamide

B
CD

D4

B
AB

F
5F
D

5F

16
7B
9
IUPAC name of

4
48

DD
B0

2
E7

FC
4

FB
DA

D4
b dapsone

9A
AB
16

7B
25
4
45
8

sulfacetamide
B

D
c
B0
FC

7
4

FB
DA

CD

D4
E
9A
AB

d sulfapyridine
16

5F
7B

25
74
8

AB

D
B0
FC

20 Target enzyme of Terbinafine is a Squalene epoxidase

A4
4
FB

CD

D4
FE
B

8D
6
7B

9
b
A

Lanosterol-14-demethylase
25

C1

74
45
B

DD
0

B4
FB

DA
D4

FE
9A
Lanosterol-14-reductase
BF

16

BC
A
25
4

45
8

D
d Squalene dehydrogenase
7

0
E7

4
B

DA
D4

CD
6B

9A
F

AB
F
5F

B
25
4

48

AB

DD
7

B0
E7

C
A4

FB
D4

Q.II Attempt ANY TWO of the following. Draw structures wherever required. 20M
BF

AB
5F

8D
16

BC
D9

5
74

7
42

B0
FC
A4

Q1. B4
B
CD

DA
FE

4D

5F

16
B
D9

0A
45
AB

48
a. With reference to the structure, answer the following questions 4M
7
2
E7

C
B
CD

6B
9A

BF

AB
4D

5F
8D

5F

C1
AB

DD

B7
2

B0
E7
A4
B4

D4

BF
5F
8D

BC

16
D9
0A

4
45

B7
2
7

FC
B4

DA

CD
6B

D4
E
9A

5F
5F

7B
A
C1

4
8

AB

DD
B0

42
7
4
B4

FB
FE
A

4D
D
16

BC

9
A

25
5
48

DD
B0
FC

E7
4
A

D4
9A
AB

8D
16

BC

F
7B

i) Give the generic name of the above drug.

74
45
D
B0
FC

B4
FB

CD

FE
9A

ii) Draw the structure of the salt form of the above drug.
8D
6
7B

A
5

C1

45
B

D
42

B0

4
FB

Above drug can be given by …………. route. Justify.

A

CD

iii)
9A
BF

D
16

A
25

DD
B7

B0
FC

iv) Explain one modification done to improve its penicillinase resistance.

B4

DA
D4

5F

16

BC
7B

0A
74

48
42

FC
FB

DA
B
E

AB
4D
5F

16
7B

b. Explain the structural features and mechanism of action of aminoglycosides. 4M

25

48
0
E7

FC
A4

FB
D4

c. Explain the structural modifications done to improve the acid stability and bioavailability
AB
5F

16
7B
25
74

of macrolides. 2M
B0
FC
A4

FB
D4
E
5F

16
B
D9

25
74

FC
4

FB
CD

D4

Q2.
E
9A

5F

7B
25
74

a. Explain the development of cephalosporins with the help of structural features. Comment
AB

DD

FB
D4
E
9A

on the advantages of each generation. 4M

BC

5F

25
74
DD

b. Clavulanic acid is given in combination with amoxicillin. Justify. 4M

4
A

D4
E
9A
8D

BC

5F

74
DD

4
4

26537 Page 3 of 5
FE
9A
AB

8D

BC

45
D
B0

CD

9A
AB

8D

AB

DD
0

B4

BFC16B0AB48DABCDD9A45FE74D425FB7
6B
 E7
A4
DA

4
4D
Paper / Subject Code: 87611 / Medicinal Chemistry- III

BC

5F
D9
48

E7
A4
DA

CD
AB

4D
5F
D9
48

AB
B0

E7
A4
CD
AB

D
16

5F
D9
48

B
0
FC

A4
DA

D
B

AB
16

BC
7B

D9
c. What are bioprecursor prodrugs? 2M

8
B0
FC

B4
FB

DA

A
16

BC
B

9
A
25
Q. 3.

DD
7

B0
C

B4
FB

DA
D4

BF
a. With reference to the structure, answer the following questions 4M

BC
A
5
74

C1

48
B7
2

A
D4

B
FE

BF

B
5F

D
16

0A
4
45

8
B7
2
7

FC

B4

A
4

6B
FE
9A

5F

D
B

0A
4

1
5
DD

48
7
2
7

C
4

FB
D4

6B
FE
9A

BF

B
BC

0A
5
4

C1
45
DD

7
42
7

B
DA

6B
E
9A

F
4D

5F
C

5F

1
48

AB

7
2
E7

C
A4

B
CD

D4

B
AB

F
5F
i) Identify the chemical class and generic name of the drug.
D

5F

16
7B
9

4
48

DD
B0

2
E7

FC
4
ii) Classify the above drug based on its duration of ation.

FB
DA

D4
9A
AB
16

7B
iii) Draw the structure of any salt form of the drug.

25
4
45
8

D
B0
FC

7
4

FB
iv) What will happen if amide group of the drug is replaced by nitrile? DA

CD

D4
E
9A
AB
16

5F
7B

25
74
8

AB

D
B0
FC

A4
4
FB

CD

D4
FE
B

b. i) Explain the acid catalyzed degradation of cephalosporins with the help of suitable 8D
6
7B

9
A
25

C1

74
45
B

DD
reaction. 2M
0

B4
FB

DA
D4

FE
9A
BF

ii) Draw the structure and use of any monobactam. 2M

16

BC
A
25
4

45
8

D
7

0
E7

4
B

DA
D4

CD
6B

9A
F

AB
F
5F

c. Draw the structure of Pyrimethamine. Why is it given in combination with sulfadoxine?2M

25
4

48

AB

DD
7

B0
E7

C
A4

FB
D4

BF

AB
5F

8D
16

BC
D9

5
74

Q. III Attempt any seven out of given nine questions. 35M

7
42

B0
FC
A4

B4
B
CD

DA
FE

4D

5F

16
B
D9

Q1. Give the synthetic scheme for synthesis of Isoniazid. Depict the metabolism of Isoniazid.
0A
45
AB

48
7
2
E7

C
B
CD

5M
6B
9A

BF

AB
4D

5F
8D

5F

Q2. With reference to the following scaffold, answer the following questions: 5M
C1
AB

DD

B7
2

B0
E7
A4
B4

D4

BF
5F
8D

BC

16
D9
0A

4
45

B7
2
7

FC
B4

DA

CD
6B

D4
E
9A

5F
5F

7B
A
C1

4
8

AB

DD
B0

42
7
4
B4

FB
FE
A

4D
D
16

BC

9
A

25
5
48

DD
B0
FC

E7
4
A

D4
9A
AB

8D
16

BC

F
7B

74
45
D
B0
FC

B4
FB

CD

FE
9A
8D
6
7B

A
5

C1

45
B

D
42

B0

4
FB

CD

9A
BF

D
16

A
25

DD
B7

B0
FC

a) Name the above scaffold and identify the target of action.

B4

DA
D4

5F

16

BC
7B

b) Identify the drug with R1 = cyclopropyl, R5 = amino, R7 = 2,6-dimethyl-4-piperazinyl, R8 =

0A
74

48
42

FC
FB

DA

Fluoro.
B
E

AB
4D
5F

16
7B
25

c) Highlight the part of the drug involved in binding to the target protein.
48
0
E7

FC
A4

FB
D4

d) Presence of small alkyl group at position 1 dictates the spectrum of activity. State whether
AB
5F

16
7B
25
74

the statement is true or false. Justify.

B0
FC
A4

FB
D4
E
5F

16
B
D9

25
74

FC
4

Q3. Explain with the help of suitable reactions the activation of acyclovir required for its
FB
CD

D4
E
9A

5F

7B

action. Name the enzyme inhibited by acyclovir. 5M

25
74
AB

DD

FB
D4
E
9A
BC

5F

25

Q4. a) Give the synthetic scheme for synthesis of Miconazole 3M

74
DD

4
A

D4
E
9A
8D

BC

5F

74
DD

4
4

26537 Page 4 of 5
FE
9A
AB

8D

BC

45
D
B0

CD

9A
AB

8D

AB

DD
0

B4

BFC16B0AB48DABCDD9A45FE74D425FB7
6B
 B0 AB A4 42 C1
AB 5F 5 6B
4
CD
D9 E 74
FB
7B 0A
6B 8D
0 A BC
A4 D4
25 FC B4
8D
AB 5F FB 16
4 8D
DD E7
4D 7B B0
A
AB
A 9A FC B4 CD
BC 4 5F 42
5F 16 8D D9
B4 DD E74 B7 B0 AB A4
8D 9A BF A CD 5F
A 4
D4 B4 E7

26537
C1 8 4

nucleus.
BC 5F 25 D9
DD E FB 6 B0 DA A4 D4
9A 74 7B AB BC 5F 25
D4 FC E7 FB
AB 4 5F 25 16 48
D
DD
9A 4 7B Drug
CD
D E74
FB B0 AB 45
D4
25 FC
9A D4 7B A CD FE FB 16

2. Sulfadiazine
4 FC B4 B0
1. Sulfapyridine
5F 25 16 AB 8D D9 74 7B

4. Sulfamethizole
E FB A D4 FC

b) Explain ADEPT.
B0 A4

3. Sulfamethizine
DD 48
Q5. Match the following:

74 7B A 5F BC 25 16

5. Sulfamethoxazole
9A D4 B F B
DA
45 FC
25 16 4 8D
E7
4D 7 B0
AB BC DD
FE FB B A 9A BF DD
74 7 45 42 C1 48
D4 B FC
0A
B4
BC F 5 FB 6 D 9A
DD E7 7 B0 AB 45
25 16 8D 9 4D B AB C
FB B A A 4 4 F C 4 DD FE
7B 0 AB B 5F 2 5F 16 8 9A 74
FC CD
D E 7 B 7 B 0
DA
B 4
D4
16 48 4 A 5 25
DA 9A
4
D4 BF
C B 4
CD FE
7
FB
B0
AB B 5 2 5F 1 8 D 9A 4 7B
CD FE B 6B DA D4 FC
D 7 0 B 2
b) Give the structure and use of Rimantadine.

48 4 7 A 45 5
Structure

DA 9A D4 B FC B4 C FE FB 16

b) Give the structure of any one mutual prodrug.

BC 45 2 8D
DD
9 7 4 7B
B0
F 5F 16 D AB

Page 5 of 5
DD E7 B7 B0 AB A4
5F 42 FC 48
9A 4D BF AB 5F 16
42 C 4
CD
D E 7 B7 B 0
DA
45
FE 5F 16 8 DA 9A 4 D4 BF AB

Q.7. a) Give the synthetic scheme for synthesis of mebendazole

74 B7 B0
AB B 4 5F 2 5F C 16 48
BF CD DA

BFC16B0AB48DABCDD9A45FE74D425FB7
D4 E7 B0
25 C1 48 D 9A 4D
B7
BF AB BC
FB 6B DA
45 42 C1 48 D
7B
FC
0A
B4
BC F 5 FB 6 D
DD E7 7 B0 AB
4 A
ii)Pyridine

8D 9 B
Paper / Subject Code: 87611 / Medicinal Chemistry- III

16 CD
iv)Isoxazole

A4 D4 FC B4
B0
AB
AB
5F 2 5F 16 8 D9
48
CD
D E 7 B 7 B 0
DA
B
A4
DA 9A 4 D4 BF A B4 CD
C
iii) 1,3,4-thiadiazole

BC 45 2 5F 1 8 D9
DD FE B 6B DA
Q6. a) Give the structure, generic name and use of drug containing 1,4-naphtho quinone
A4
74 7B 0A BC 5F
9A F B
i)Unsubsituted Pyrimidine

D4 D
Heterocyclic ring present

v) 4,6-dimethyl pyrimidine

E7

Q.8. Name two computer aided drug design techniques. Explain molecular docking in detail.

Q.9 What is solid phase synthesis? Elaborate on the linkers used in solid phase synthesis.5M
45 C1 48

5M
2M
3M
2M
5M
2M

25
3M

D9
FE FB 6B DA A4
74 7B 0A BC 5F
D4 F C B4 D E7
25 1 6B 8D D9 4D
FB
7B 0A A BC
A4 4
5F
FC B 48 DD E7
16
B D A 9A 4D