76972-10-6Relevant academic research and scientific papers
Design and synthesis of furyl/thineyl pyrroloquinolones based on natural alkaloid perlolyrine, lead to the discovery of potent and selective PDE5 inhibitors
Zheng, Hongbo,Li, Lin,Sun, Bin,Gao, Yun,Song, Wei,Zhao, Xiaoyu,Gao, Yanhui,Xie, Zhiyu,Zhang, Nianzhao,Ji, Jianbo,Yuan, Huiqing,Lou, Hongxiang
, p. 30 - 38 (2018)
Based on perlolyrine (1), a natural alkaloid with weak PDE5 potency from the traditional Chinese aphrodisiac plant Tribulus terrestris L., a series α-substituted tetrahydro-β-carboline (THβC) derivatives were synthesized via T+BF4--mediated oxidative C–H functionalization of N-aryl THβCs with diverse potassium trifluoroborates. Following Winterfeldt oxidation afforded the corresponding furyl/thienyl pyrroloquinolones, of which 5-ethylthiophene/ethylfuran derivatives 20a–b were identified as the most potent and selective PDE5 inhibitors. Among the enantiomers, (S)-20a and (S)-20b (IC50 = 0.52 and 0.39 nM) were found to be more effective than their (R)-antipode, display favorable pharmacokinetic profiles, exert in vitro vasorelaxant effects on the isolated thoracic aorta, and exhibit in vivo efficacy in the anesthetized rabbit erectile model.
Synthesis and biological activities of novel β-carbolines as PDE5 inhibitors
Sui, Zhihua,Guan, Jihua,Macielag, Mark J.,Jiang, Weiqin,Qiu, Yuhong,Kraft, Patricia,Bhattacharjee, Sheela,John, T. Matthew,Craig, Elizabeth,Haynes-Johnson, Donna,Clancy, Joanna
, p. 761 - 765 (2007/10/03)
A series of N2-furoyl and N2pyrimidinyl β-carbolines was discovered to possess potent inhibitory activity against PDE5. During the synthesis we developed a tandem resin quenching protocol, which allowed us to synthesize large number
Pyrimidones. 2. Synthesis and Reactions of 2-Chloropyrimidines
Coppola, Gary M.,Hardtmann, Goetz E.,Huegi, Bruno S.
, p. 1479 - 1482 (2007/10/02)
The treatment of 1-alkyl-5-aryl and 1-alkyl-4,5-diaryl-2-(1H)pyrimidones with phosphorus oxychloride and phosphorus pentachloride resulted in chlorination and dealkylation to furnish 2-chloro-5-aryl (or 4,5-diaryl)pyrimidines.These chloropyrimidines were
