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Table 1 SAR of 8-substituted protoberberine analogous against M. tuberculosis strain H 37 Rv

From: Synthesis and structure−activity relationship of 8-substituted protoberberine derivatives as a novel class of antitubercular agents

Compda

R1

R2

R3

R4

R5

R6

MICb

cLogPc

1

     

> 128

−0.77

2

     

128

−1.08

3

     

> 128

−0.77

6a

PhOCH3-p

OCH2O

OCH3

OCH3

H

32

0.35

6b

PhOCH3-m

OCH2O

OCH3

OCH3

H

16

0.35

6c

PhCH3-p

OCH2O

OCH3

OCH3

H

16

0.93

6d

1-naphthyl

OCH2O

OCH3

OCH3

H

8

1.60

6e

n-C10H21

OCH2O

OCH3

OCH3

H

2

3.29

7a

PhOCH3-p

OCH2O

H

OCH3

OCH3

4

0.35

7b

PhOCH3-m

OCH2O

H

OCH3

OCH3

2

0.35

7c

PhCH3-p

OCH2O

H

OCH3

OCH3

2

0.93

7d

PhCl-p

OCH2O

H

OCH3

OCH3

1

1.14

7e

PhCl-m

OCH2O

H

OCH3

OCH3

2

1.14

7f

1-naphthyl

OCH2O

H

OCH3

OCH3

2

1.60

7g

n-C10H21

OCH2O

H

OCH3

OCH3

0.5

3.29

7h

n-C12H25

OCH2O

H

OCH3

OCH3

1

4.35

8a

PhOCH3-p

OCH3

OCH3

OCH3

OCH3

H

16

0.04

8b

PhOCH3-m

OCH3

OCH3

OCH3

OCH3

H

16

0.04

8c

PhCH3-p

OCH3

OCH3

OCH3

OCH3

H

16

0.62

8d

1-naphthyl

OCH3

OCH3

OCH3

OCH3

H

4

1.29

8e

n-C10H21

OCH3

OCH3

OCH3

OCH3

H

1

2.98

RIF

     

0.0625

3.90

INH

     

0.0625

−1.12

  1. a: General structural formular is shown in Figure 2.
  2. b: MIC: minimum inhibitory concentration.
  3. c: Chemoffice Ultra 11.0 (Cambridge office).
  4. RIF: rifampin; INH: isoniazid.