119383-00-5Relevant articles and documents
STRUCTURE-ACTIVITY RELATIONSHIP OF OPTICALLY ACTIVE 2-(3-PYRIDYL)THIAZOLIDIN-4-ONES AS A PAF ANTAGONIST
Tanabe, Y.,Suzukamo, G.,Komuro, Y.,Imanishi, N.,Morooka, S.,et al.
, p. 379 - 382 (1991)
Two sets of optically active 5-substituted-2-(3-pyridyl)thiazolidin-4-ones, highly potent and selective antagonists of platelet activation factor (PAF), displayed apparently different anti-PAF activities between their enantiomers, wherein these activities depend markedly on the absolute configuration of the 2-position in the thiazolidin-4-ones.
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.
Highly stereoselective synthesis of the anti-platelet activating factor, 4-thiazolidinones, using silyl derivatives of 2-mercaptoalkanoic acids
Tanabe,Okumura,Nagaosa,Murakami
, p. 1467 - 1472 (2007/10/02)
The cyclo-condensation of silyl 2-mercaptoalkanoates and arylmethyleneamines proceeded with high stereoselectivity to give alternatively both the cis- and trans-2,5-disubstituted 4-thiazolidinones, some of which are known as anti-platelet activating factor-active drugs. The use of the piperidine catalyst and no catalyst showed very high cis-stereoselectivity (cis/trans=10/1-50/1) during the reaction. On the other hand, the trans-selective reaction was promoted by Ti(O-i-Bu)4 and Al(O-s-Bu)3 catalysts (cis/trans=1/8-1/25). Both reactions were conducted with higher cis- and trans-selectivities as compared with those of the alkyl 2-mercaptoalkanoates under mild conditions. The cyclo-condensation using trimethylsilyl 2-(trimethylsilylthio)propionate and methyl 2-(trialkylsilylthio)propionates proceeded by the action of a catalytic amount (0.02 molar amount) of tetrabutylammonium fluoride with moderate cis-selectivity.
Direct enantiomeric separation of platelet-activating factor receptor antagonist SM-10661 by ligand-exchange high-performance liquid chromatography with a copper (II) N,S-dioctyl-D-penicillamine complex.
Okamoto,Ueda,Takahashi,Nakazawa,Doi
, p. 1740 - 1741 (2007/10/02)
The enantiomeric separation of SM-10661, a platelet activating factor receptor antagonist, was investigated by HPLC using ligand-exchange chiral stationary phases. The stereoisomers of SM-10661 could all be separated by ligand-exchange HPLC with a Cu(II) N,S-dioctyl-D-penicillamine complex (Sumichiral OA-5000). The mechanism for the resolution includes the involvement of hydrophobic interactions between SM-10661 and Cu(II) D-penicillamine.
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.
