Structure-based organic synthesis of unnatural aeruginosin hybrids as potent inhibitors of thrombin

S Hanessian, K Ersmark, X Wang, JR Del Valle…

Index: Hanessian, Stephen; Ersmark, Karolina; Wang, Xiaotian; Del Valle, Juan R.; Blomberg, Niklas; Xue, Yafeng; Fjellstroem, Ola Bioorganic and Medicinal Chemistry Letters, 2007 , vol. 17, # 12 p. 3480 - 3485

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Citation Number: 32

Abstract

Based on X-ray crystallographic data of complexes of chlorodysinosin A with the enzyme thrombin, a series of analogs were synthesized varying the nature of the P1, P2, and P3 pharmacophoric sites and the central octahydroindole carboxyamide core. In general, introduction of a hydrophobic substituent on the d-leucine amide residue dramatically improved the inhibition of the enzyme. This is rationalized based on a better fit of the P3 ...

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