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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.