3-[3-(4-Bromo-2-fluoro-benzyl)-ureido]-5-chloro-benzo[b]thiophene-2-carboxylic acid methyl ester | 1026318-01-3

• 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: 3-[3-(4-Bromo-2-fluoro-benzyl)-ureido]-5-chloro-benzo[b]thiophene-2-carboxylic acid methyl ester
• 英文别名: Methyl 3-[(4-bromo-2-fluorophenyl)methylcarbamoylamino]-5-chloro-1-benzothiophene-2-carboxylate
• CAS: 1026318-01-3
• 化学式: C₁₈H₁₃BrClFN₂O₃S
• 分子量: 471.734
• InChiKey: FEDVSKRAHXYATG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  95.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[3-(4-Bromo-2-fluoro-benzyl)-ureido]-5-chloro-benzo[b]thiophene-2-carboxylic acid methyl ester 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 [3-(4-Bromo-2-fluoro-benzyl)-8-chloro-2,4-dioxo-3,4-dihydro-2H-benzo[4,5]thieno[3,2-d]pyrimidin-1-yl]-acetic acid ethyl ester
  参考文献：
  名称：

  Syntheses of substituted 2,4-dioxo-thienopyrimidin-1-acetic acids and their evaluation as aldose reductase inhibitors

  摘要：

  A series of 2,4-dioxo-thieno[2,3-d], [3,2-d] and [3,4-d]pyrimidin-1-acetic acids (2) with a benzyl moiety at the N-3 position were prepared and tested in vitro for aldose reductase inhibitory activity against partially purified enzyme from rat lens. Some of these compounds were also evaluated for inhibition of sorbitol accumulation in the sciatic nerve or lens of streptozotocin-induced diabetic rats in vivo. Among the synthesized compounds, several showed potent aldose reductase inhibitory activity with IC50s in the 10(-8) M range. Particularly, the potencies of non-substituted thieno- (2a and 2aa), 5-methylthieno- (2c), 5,6-dimethylthieno-(2g), 6-isopropylthieno- (2j and 2k), 6-chlorothienopyrimidine (2q) and benzothienopyrimidine (2ac) analogs were approximately equipotent to FK-366 (1A) and Ponalrestat (1B) as references. Although most compounds were inactive in vivo, 2 compounds, 2k and 2q, possessed moderate in vivo activity.

  DOI：

  10.1016/0223-5234(93)90112-r
• 作为产物：
  描述：

  4-溴-2-氟苄胺 、 3-amino-5-chlorobenzo[b]thiophene-2-carboxylic acid methyl ester 、 氯甲酸三氯甲酯 生成 3-[3-(4-Bromo-2-fluoro-benzyl)-ureido]-5-chloro-benzo[b]thiophene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Syntheses of substituted 2,4-dioxo-thienopyrimidin-1-acetic acids and their evaluation as aldose reductase inhibitors

  摘要：

  A series of 2,4-dioxo-thieno[2,3-d], [3,2-d] and [3,4-d]pyrimidin-1-acetic acids (2) with a benzyl moiety at the N-3 position were prepared and tested in vitro for aldose reductase inhibitory activity against partially purified enzyme from rat lens. Some of these compounds were also evaluated for inhibition of sorbitol accumulation in the sciatic nerve or lens of streptozotocin-induced diabetic rats in vivo. Among the synthesized compounds, several showed potent aldose reductase inhibitory activity with IC50s in the 10(-8) M range. Particularly, the potencies of non-substituted thieno- (2a and 2aa), 5-methylthieno- (2c), 5,6-dimethylthieno-(2g), 6-isopropylthieno- (2j and 2k), 6-chlorothienopyrimidine (2q) and benzothienopyrimidine (2ac) analogs were approximately equipotent to FK-366 (1A) and Ponalrestat (1B) as references. Although most compounds were inactive in vivo, 2 compounds, 2k and 2q, possessed moderate in vivo activity.

  DOI：

  10.1016/0223-5234(93)90112-r

文献信息

• Syntheses of substituted 2,4-dioxo-thienopyrimidin-1-acetic acids and their evaluation as aldose reductase inhibitors
  作者：K Ogawva、I Yamawaki、YI Matsusita、N Nomura、PF Kador、JH Kinoshita

  DOI：10.1016/0223-5234(93)90112-r

  日期：1993.1

  A series of 2,4-dioxo-thieno[2,3-d], [3,2-d] and [3,4-d]pyrimidin-1-acetic acids (2) with a benzyl moiety at the N-3 position were prepared and tested in vitro for aldose reductase inhibitory activity against partially purified enzyme from rat lens. Some of these compounds were also evaluated for inhibition of sorbitol accumulation in the sciatic nerve or lens of streptozotocin-induced diabetic rats in vivo. Among the synthesized compounds, several showed potent aldose reductase inhibitory activity with IC50s in the 10(-8) M range. Particularly, the potencies of non-substituted thieno- (2a and 2aa), 5-methylthieno- (2c), 5,6-dimethylthieno-(2g), 6-isopropylthieno- (2j and 2k), 6-chlorothienopyrimidine (2q) and benzothienopyrimidine (2ac) analogs were approximately equipotent to FK-366 (1A) and Ponalrestat (1B) as references. Although most compounds were inactive in vivo, 2 compounds, 2k and 2q, possessed moderate in vivo activity.