TQX-173
Chemical Name: 7-Chloro-4-oxo-8-(4H-1,2,4-triazol-4-yl)-4,5-dihydro[1,2,4]triazolo[1,5-a]quinoxaline-2-carboxylic acid
CAS No. 308137-55-5
项目整合开发状态: Biological Testing
项目研究机构: Universit?degli Studi di Firenze (Originator)
合成路线:Diazotization of substituted aniline (I) followed by reaction with ethyl 2-chloro-3-oxobutanoate (II) in MeOH yields hydrazono chloroacetate derivative (III),which is converted into oxamidrazonate (IV) by means of NH3 (gas).Treatment of derivative (IV) with ethyloxalyl chloride (V) affords ethoxalyl derivative (VI),which is then heated until cyclization occurs,providing derivative (VII).Reduction of triazole dicarboxylate (VII) with iron in HOAc gives tricyclic compound (VIII),which is nitrated by means of HNO3 to afford nitro derivative (IX).Reduction of the nitro group of (IX) by means of iron in HOAc provides the corresponding 8-amino derivative (X),which is treated with diformylhydrazine and trimethylsilyl chloride (TMSCl) in pyridine to furnish ethyl carboxylate (XI).Finally,saponification of (XI) with NaOH in EtOH gives the desired compound.
📌 参考资料/链接：
参考文献标题:7-Chloro-4,5-dihydro-8-(1,2,4-triazol-4-yl)-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates as novel highly selective AMPA receptor antagonists
文献作者:Catarzi,D.; Colotta,V.; Varano,F.; Cecchi,L.; Filacchioni,G.; Galli,A.; Costagli,C.; Carl? V.
参考来源:J Med Chem 2000,43(21),3824
📄 详细内容
合成路线:Diazotization of substituted aniline (I) followed by reaction with ethyl 2-chloro-3-oxobutanoate (II) in MeOH yields hydrazono chloroacetate derivative (III),which is converted into oxamidrazonate (IV) by means of NH3 (gas).Treatment of derivative (IV) with ethyloxalyl chloride (V) affords ethoxalyl derivative (VI),which is then heated until cyclization occurs,providing derivative (VII).Reduction of triazole dicarboxylate (VII) with iron in HOAc gives tricyclic compound (VIII),which is nitrated by means of HNO3 to afford nitro derivative (IX).Reduction of the nitro group of (IX) by means of iron in HOAc provides the corresponding 8-amino derivative (X),which is treated with diformylhydrazine and trimethylsilyl chloride (TMSCl) in pyridine to furnish ethyl carboxylate (XI).Finally,saponification of (XI) with NaOH in EtOH gives the desired compound.
参考文献标题:4,5-Dihydro-1,2,4-triazolo[1,5-a]quinoxalin-4-ones: Excitatory amino acid antagonists with combined glycine/NMDA and AMPA receptor affinity
文献作者:Catarzi,D.; Colotta,V.; Varano,F.; Cecchi,L.; Filacchioni,G.; Galli,A.; Costagl,C.
参考来源:J Med Chem 1999,42(13),2478