propyl 3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate | 1226871-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: propyl 3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
• 英文别名: Propyl-3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate；propyl 3-chloro-5,6-dihydroxy-7-nitro-1-benzothiophene-2-carboxylate
• CAS: 1226871-16-4
• 化学式: C₁₂H₁₀ClNO₆S
• 分子量: 331.734
• InChiKey: CJAXPEVRJYPGMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  丙醇 、 3-氯-5,6-二羟基-7-硝基-1-苯并噻吩-2-羧酸 在 氯化亚砜 作用下， 以60%的产率得到propyl 3-chloro-5,6-dihydroxy-7-nitrobenzo[b]thiophene-2-carboxylate
  参考文献：
  名称：

  Design, synthesis and in vitro/in vivo evaluation of orally bioavailable prodrugs of a catechol-O-methyltransferase inhibitor

  摘要：

  Compound is an investigational, nanomolar inhibitor of catechol-O-methyltransferase (COMT) that suffers from poor oral bioavailability, most probably due to its low lipophilicity throughout most of the gastrointestinal tract and, to a lesser extent, its rapid systemic clearance. Several lipophilic esters were designed as prodrugs and synthesized in an attempt to optimize presystemic drug absorption. A modest twofold increase in 6-h exposure of 1 was observed with two prodrugs, compared to that of 1, after oral treatment in rats. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.057

文献信息

• Design, synthesis and in vitro/in vivo evaluation of orally bioavailable prodrugs of a catechol-O-methyltransferase inhibitor
  作者：Jarkko Rautio、Jukka Leppänen、Marko Lehtonen、Krista Laine、Mikko Koskinen、Jarmo Pystynen、Jouko Savolainen、Mikko Sairanen

  DOI：10.1016/j.bmcl.2010.02.057

  日期：2010.4

  Compound is an investigational, nanomolar inhibitor of catechol-O-methyltransferase (COMT) that suffers from poor oral bioavailability, most probably due to its low lipophilicity throughout most of the gastrointestinal tract and, to a lesser extent, its rapid systemic clearance. Several lipophilic esters were designed as prodrugs and synthesized in an attempt to optimize presystemic drug absorption. A modest twofold increase in 6-h exposure of 1 was observed with two prodrugs, compared to that of 1, after oral treatment in rats. (C) 2010 Elsevier Ltd. All rights reserved.