Substituted indole-2-carboxylic acid benzylidene-hydrazides and analogs as activators of caspases and inducers of apoptosis and the use thereof
a technology of benzylidenehydrazide and indole-2-carboxylic acid, which is applied in the field of substituted indole-2-carboxylic acid benzylidenehydrazide and analogs, can solve the problems of bone marrow toxicity, cancer cells lose the capacity to undergo cellular suicide, and cancer cells become cancerous, so as to prevent or ameliorate neoplasia and cancer. , to achieve th
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example 1
5-Chloro-3-methyl-indole-2-carboxylic Acid (4-Methylbenzylidene)-hydrazide
[0188] A solution of 5-chloro-3-methyl-indole-2-carboxylic acid hydrazide (13 mg, 0.054 mmol), p-tolualdehyde (6.5 mg, 0.054 mmol) in ethanol (5 mL) was refluxed for 8 h. It was evaporated in vacuo and the residue was purified by column chromatography (silica gel, EtOAc / Hexane=4:1) to give 7.8 mg (42%) of the title compound. .sup.1H NMR (CD.sub.3OD): 8.26 (s, 1H), 7.72 (d, J=8.1 Hz, 2H), 7.62 (bs, 1H), 7.39 (d, J=8.7 Hz, 1H), 7.28-7.21 (m, 3H), 2.58 (s, 3H), 2.39 (s, 3H).
example 2
5-Chloro-3-methyl-indole-2-carboxylic Acid (Benzylidene)-hydrazide
[0189] The title compound was prepared similar to Example 1. From 5-chloro-3-methyl-indole-2-carboxylic acid hydrazide (26 mg, 0.11 mmol) and benzaldehyde (11 mg, 0.11 mmol) was obtained 14 mg (39%) of the title compound. .sup.1H NMR (DMSO-d.sub.6): 11.56 (bs, 1H), 8.37 (bs, 1H), 7.73 (bs, 2H), 7.71 (bs, 1H), 7.55-7.44 (m, 3H), 7.23 (d, J=7.2 Hz, 1H), 4.40 (bs, 1H), 2.50 (s, 3H).
example 3
5-Chloro-3-methyl-indole-2-carboxylic Acid (4-Dimethylaminobenzylidene)-hy- drazide
[0190] The title compound was prepared similar to Example 1. From 5-chloro-3-methyl-indole-2-carboxylic acid hydrazide (24 mg, 0.1 mmol) and p-dimethylaminobenzaldehyde (14.9 mg, 0.1 mmol) was obtained 5 mg (21%) of the title compound. .sup.1H NMR (CD.sub.3OD): 10.9 (bs, 1H), 9.07 (bs, 1H), 8.2-6.6 (m, 6H), 3.06 (s, 6H), 2.70 (s, 3H).
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