Medicinal Chemical Studies on Antiplasmin Drugs. III. 4-Aminomethylcyclohexanecarboxylic Acid and Its Derivatives having a Methyl Group
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概要
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To investigate the structure-activity relationship between two isomers of 4-aminomethylcyclohexanecarboxylic acid (AMCHA) in connection with their antiplasmin activity, their conformations in H_2O were simply estimated on the basis of conformational free energy (-⊿G°). The nuclear magnetic resonance spectra of both isomers of 4-tertbutylcyclohexylmethylamine hydrochloride and of cyclohexylmethylamine hydrochloride gave a value of -⊿G°=1.4 kcal/mol for the N^^+H_3CH_2-group. The biologically active trans AMCHA in H_2O exists, as in its crystal structure, largely in the equatorial N^^+H_3CH_2-equatorial COO-form, while about 79% of cis AMCHA exists as the axial N^^+H_3CH_2-equatorial COO-form, in contrast to the crystal structures of its hydrohalides. Further, 1-Me AMCHA, 4-Me AMCHA and 4-(1-aminoethyl) cyclohexanecarboxylic acid were synthesized. The stereoisomers of these compounds were separated and the configurations of the isomers were determined. No compound showed a more potent antiplasmin activity than trans AMCHA.
- 公益社団法人日本薬学会の論文
- 1979-11-25
著者
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磯田 純郎
Research Institute, Daiichi Pharmaceutical Co., Ltd.,
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磯田 純郎
Research Institute Daiichi Seiyaku Co. Ltd.
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平田 三四司
Research Institute, Daiichi Seiyaku Co., Ltd.
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平田 三四司
Research Institute Daiichi Seiyaku Co. Ltd.
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