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Chemotherapeutic agents, XXI: Synthesis of π‐deficient pyrimidines as leishmanicides
Author(s) -
Ram Vishnu J.
Publication year - 1991
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.2503241103
Subject(s) - thiourea , chemistry , ethyl cyanoacetate , alkylation , halogenation , nucleophilic substitution , thiouracil , substitution (logic) , medicinal chemistry , stereochemistry , organic chemistry , malononitrile , catalysis , biology , thyroid , computer science , programming language , endocrinology
Synthesis of 5‐cyano‐6‐(3‐pyridyl)‐2‐thiouracil (1) has been described from 3‐pyridinecarboxaldehyde, thiourea, and ethyl cyanoacetate. Alkylation of 1 with mono‐ and dihaloalkanes under different conditions, provided 2a,b, 3a,b , and 4a‐i . Halogenation of 4g with POCl 3 yielded 5 which underwent nucleophilic substitution with amines to give 6a‐g . Fusion of 4a with aromatic and heterocyclic amines at 160°C gave the substitution products 7a‐c . Some of the compounds were screened for antileishmanial activity but only one of them ( 6d ) demonstrated very significant activity.