199330-92-2Relevant academic research and scientific papers
Methyl ester of the bioactive metabolite of thromboxane A2 receptor antagonist ON-579
Sato, Masakazu,Matsumoto, Keita,Kawashima, Yutaka,Tomisawa, Kazuyuki
, p. 982 - 984 (1998)
The title compound, methyl (RS)-{4-[2-(4-chlorophenyl-sulfonylamino)ethylsulfinyl]-2,6-difluorophenoxy} acetate, C17H16ClF2NO6S2, crystallizes in space group P21/c. In the crystal, the enan
Asymmetric synthesis of the sulfoxide metabolite of ON-579 by the Kagan protocol
Sato, Masakazu,Manaka, Akira,Kawashima, Yutaka,Tomisawa, Kazuyuki,Iwata, Chuzo
, p. 2451 - 2454 (2007/10/03)
A synthesis of both enantiomers of bio-active metabolite of 0N-579; 4-[2-(4-chlorophenyl- sulfonylamino)-ethylsulfinyl]-2,6-difluorophnoxyacetic acid was accomplished by the asymmetric oxidation of 0N-579 methyl-ester followed by hydrolysis. Difference in TXA2 receptor antagonizing activity was noted for the enantiomers in an U46619-induced rabbit platelet aggregation inhibitory activity.
Synthesis and evaluation of novel fluorinated sulotroban-related sulfonamide derivatives as thromboxane A2 receptor antagonists
Sato,Kawashima,Goto,Yamane,Chiba,Jinno,Satake,Iwata
, p. 403 - 414 (2007/10/02)
A series of sulotroban-related arylsulfonamide derivatives possessing a fluorinated phenoxyacetic acid moiety was synthesized and tested for TXA2 antagonizing ability on U-46619-induced platelet aggregation of rabbit platelet-rich plasma. Introduction of one or more fluorine atoms to the phenoxyacetic acid moiety increased this activity. The most potent compound among these compounds was 10c, which was 40-fold more potent (IC50 3.4 x 10-7 M) than sulotroban. 10c exhibited high activity (ID50 0.14 mg/kg) against a D-46619-induced acute thrombocytopenia model in mice when orally administrated. These findings and those of radioligand binding assays with various ligands showed 10c to be a potent and selective systemic TXA2 receptor antagonist.
