124623-50-3Relevant articles and documents
Synthetic Study of the Highly Potent and Selective Anti-platelet Activating Factor Thiazolidin-4-one Agents and related Compounds
Tanabe, Yoo,Yamamoto, Hitomi,Murakami, Masanari,Yanagi, Kazunori,Kubota, Yoshino,et al.
, p. 935 - 948 (2007/10/02)
Stereoselective cyclo-condensation of α-sulfanylcarboxylic acids (or esters) 6 with N-methylarylimines 7 afforded the title compounds, 2-arylthiazolidin-4-ones, some of which exhibit highly potent anti-PAF activity.The reaction without added catalyst gave predominantly cis products, however, when titanium(IV) isopropoxide was added as catalyst trans products were predominantly formed.Allylation of 3-methyl-2-(3-pyridyl)thiazolidin-4-one 22 with allyl bromide using lithium amides gave the trans-5-allyl-2-(3-pyridyl)thiazolidin-4-one 23 with good selectivity.To study the stereostructure-activity relationship, the four optically active isomers of 3,5-dimethyl-2-(3-pyridyl)thiazolidin-4-one 4 and 5-(4-chlorophenyl)-3-methyl-2-(3-pyridyl)thiazolidin-4-one 5 were synthesized.The absolute configurations of compounds 4 and 5 were determined by X-ray analyses and 1H NMR measurements.Epimerization of the 5-position of compounds 4 and 5 was found to be effected by bases with high regioselectivity (>99percent), which was checked by a cross-over experiment using several optically active compounds.
STEREOSELECTIVE SYNTHESIS OF ANTI-PAF ACTIVE THIAZOLIDIN-4-ONES VIA CYCLO-CONDENSATION OF ALKYL α-MERCAPTOCARBOXYLATES WITH ARYLIMINES
Tanabe, Yoo,Kubota, Yoshi-no,Sanemitsu, Yuzuru,Itaya, Nobushige,Suzukamo, Gohfu
, p. 383 - 386 (2007/10/02)
Two distinctive methods for the synthesis of cis- and trans-2,5-disubstituted thiazolidin-4-ones via stereoselective cyclo-condensation between α-mercaptocarboxylic esters and arylimines have been developed.With the new reaction used as the key step, two sets of optically active anti-PAF active thiazolidin-4-ones were synthesized.
