Premium
Synthesis and activity of four ( N , N ‐dimethylamino)benzamide nonsteroidal anti‐inflammatory drugs based on thiazole and thiazoline
Author(s) -
Lynch Daniel E.,
Hayer Ravinder,
Beddows Samantha,
Howdle Joy,
Thake C. Douglas
Publication year - 2006
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.5570430130
Subject(s) - benzamide , chemistry , thiazoline , adduct , benzoic acid , thiazole , hydrochloride , infrared spectroscopy , crystal structure , nuclear magnetic resonance spectroscopy , stereochemistry , spectroscopy , medicinal chemistry , crystallography , organic chemistry , physics , quantum mechanics
Four compounds derived from 2‐aminothiazole and 2‐amino‐2‐thiazoline were prepared by coupling the respective bases with the acid chlorides of either 3‐ or 4‐( N , N ‐dimethylamino)benzoic acid. Products were identified using infrared spectroscopy, 1 H NMR spectroscopy and electrospray mass spectroscopy and in two cases by single‐crystal X‐ray diffraction. Of the four, N ‐(thiazol‐2‐yl)‐3‐( N , N ‐dimethylamino)‐benzamide (1), N ‐(thiazolin‐2‐yl)‐4‐( N , N ‐dimethylamino)benzamide (2), N ‐(thiazolin‐2‐yl)‐3‐( N , N ‐dimethylamino) benzamide (3) and N ‐(thiazolin‐2‐yl)‐4‐( N , N ‐dimethylamino)benzamide (4), the hydrochloride salts of compounds 3 and 4 showed anti‐inflammatory activity across a concentration range of 10 −2 −5 × 10 −4 M while 3 (at a concentration of 10 −5 M ) was found to have no adverse effect on myocardial function. The X‐ray crystal structure of 2 and the 1:1 adduct structure of 3 with 3‐( N , N ‐dimethylamino)benzoic acid are reported.