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Synthesis and biological activity of some new 3‐and 6‐substituted coumarin amino acid derivatives. Part I
Author(s) -
ElNaggar A. M.,
Ahmed F. S. M.,
ElSalam A. M. Abd,
Radi M. A.,
Latif M. S. A.
Publication year - 1981
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570180627
Subject(s) - chemistry , dipeptide , coumarin , tosyl , thionyl chloride , organic chemistry , carbodiimide , antimicrobial , chloride , amino acid , biochemistry
The synthesis of 6‐nitrocouarrain‐3‐CO‐amino acids and their corresponding methyl esters (II‐XVII) and some dipeptide methyl esters (XVIII‐XXVI) are described. 6‐( N ‐Tosyl‐ or N ‐phthalylaminoacyl)aminocoumarin‐3‐carboxylic acid methyl esters (XXXIV‐XL) and 3‐( N ‐phthalyl‐ or N ‐tosylaminoacytyaminocoumarins (XLV‐LVI) have been prepared via the carbodiimide and acid chloride methods. Hydrazinolysis of 3‐ or 6‐( N ‐phthalylaminoacyl)aminocoumarin derivatives in tetraline gave the corresponding 3‐ and 6‐(aminoacyl)aminocoumarins and the carboxylic acid hydrazides (XLI‐LVIII), respectively. 3‐( N ‐Tosyl‐L‐Val‐L‐Leu‐)aminocoumarin (LIX) was synthesized via the azide method. Twenty four of various substituted 3‐ and 6‐aminoacylcoumarin derivatives were found to possess specific antimicrobial activities towards different microorganisms.