Methyl 5-(4-bromophenyl)-3-sulfamoylthiophene-2-carboxylate | 1428510-54-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: Methyl 5-(4-bromophenyl)-3-sulfamoylthiophene-2-carboxylate
• 英文别名: methyl 5-(4-bromophenyl)-3-sulfamoylthiophene-2-carboxylate
• CAS: 1428510-54-6
• 化学式: C₁₂H₁₀BrNO₄S₂
• 分子量: 376.252
• InChiKey: QYYHUAYDVZSNBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 5-(4-bromophenyl)-3-sulfamoylthiophene-2-carboxylate 在 lithium aluminium tetrahydride 、 四溴化碳 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Methyl 2-(5-(4-bromophenyl)-1,1-dioxothieno[2,3-d]isothiazol-2(3H)-yl)butyrate
  参考文献：
  名称：

  Design, synthesis and SAR investigation of thienosultam derivatives as ADAMTS-5 (aggrecanase-2) inhibitors

  摘要：

  A series of 1,1-dioxothieno[2,3-d]isothiazole (thienosultam) derivatives were designed and synthesized as novel ADAMTS-5 inhibitors for an investigation into a side chain of thienosultam for the S1' pocket. The resulting compounds (19 and 24) show high ADAMTS-5 inhibition and other MMP selectivity, and these compounds show good oral bioavailability. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.120
• 作为产物：
  描述：

  甲基3-氨基-5-(4-溴苯基)-2-噻吩羧酸酯 在 盐酸 、 sodium nitrate 、 二氧化硫 、 氨 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 Methyl 5-(4-bromophenyl)-3-sulfamoylthiophene-2-carboxylate
  参考文献：
  名称：

  Design, synthesis and SAR investigation of thienosultam derivatives as ADAMTS-5 (aggrecanase-2) inhibitors

  摘要：

  A series of 1,1-dioxothieno[2,3-d]isothiazole (thienosultam) derivatives were designed and synthesized as novel ADAMTS-5 inhibitors for an investigation into a side chain of thienosultam for the S1' pocket. The resulting compounds (19 and 24) show high ADAMTS-5 inhibition and other MMP selectivity, and these compounds show good oral bioavailability. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.120

文献信息

• Design, synthesis and SAR investigation of thienosultam derivatives as ADAMTS-5 (aggrecanase-2) inhibitors
  作者：Masakazu Atobe、Naomi Maekawara、Masashi Kawanishi、Hiroko Suzuki、Eiichi Tanaka、Shiro Miyoshi

  DOI：10.1016/j.bmcl.2013.01.120

  日期：2013.4

  A series of 1,1-dioxothieno[2,3-d]isothiazole (thienosultam) derivatives were designed and synthesized as novel ADAMTS-5 inhibitors for an investigation into a side chain of thienosultam for the S1' pocket. The resulting compounds (19 and 24) show high ADAMTS-5 inhibition and other MMP selectivity, and these compounds show good oral bioavailability. (C) 2013 Elsevier Ltd. All rights reserved.