3-(4-Bromo-2-fluoro-benzyl)-5,6,7,8-tetrahydro-1H-benzo[4,5]thieno[2,3-d]pyrimidine-2,4-dione | 122185-77-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 3-(4-Bromo-2-fluoro-benzyl)-5,6,7,8-tetrahydro-1H-benzo[4,5]thieno[2,3-d]pyrimidine-2,4-dione
• 英文别名: 3-[(4-bromo-2-fluorophenyl)methyl]-5,6,7,8-tetrahydro-1H-[1]benzothiolo[2,3-d]pyrimidine-2,4-dione
• CAS: 122185-77-7
• 化学式: C₁₇H₁₄BrFN₂O₂S
• 分子量: 409.279
• InChiKey: WTBUGARUJCQMJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-Bromo-2-fluoro-benzyl)-5,6,7,8-tetrahydro-1H-benzo[4,5]thieno[2,3-d]pyrimidine-2,4-dione 在 盐酸 、 sodium hydride 作用下， 以 溶剂黄146 为溶剂， 反应 28.0h， 生成 [3-(4-Bromo-2-fluoro-benzyl)-2,4-dioxo-3,4,5,6,7,8-hexahydro-2H-benzo[4,5]thieno[2,3-d]pyrimidin-1-yl]-acetic acid
  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：

  2-[3-(4-Bromo-2-fluoro-benzyl)-ureido]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 3-(4-Bromo-2-fluoro-benzyl)-5,6,7,8-tetrahydro-1H-benzo[4,5]thieno[2,3-d]pyrimidine-2,4-dione
  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

• Ogawva K., Yamawaki I., Matsusita Y. I., Nomura N., Kador P. F., Kinoshit+, Eur. I. Med. Chem, 28 (1993) N 10, S 769-781
  作者：Ogawva K., Yamawaki I., Matsusita Y. I., Nomura N., Kador P. F., Kinoshit+

  DOI：——

  日期：——