Methyl 5-(4-bromophenyl)-3-(chlorosulfonyl)thiophene-2-carboxylate | 1375472-72-2

• 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-(chlorosulfonyl)thiophene-2-carboxylate
• 英文别名: methyl 5-(4-bromophenyl)-3-chlorosulfonylthiophene-2-carboxylate
• CAS: 1375472-72-2
• 化学式: C₁₂H₈BrClO₄S₂
• mdl: MFCD21602785
• 分子量: 395.682
• InChiKey: SQJGGPLJCVNWCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  97.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 5-(4-bromophenyl)-3-(chlorosulfonyl)thiophene-2-carboxylate 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 lithium aluminium tetrahydride 、 四溴化碳 、 氨 、 sodium hydride 、 三苯基膦 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2-(5-(4-(1-benzyl-1H-pyrazol-4-yl)phenyl)-1,1-dioxidothieno[2,3-d]isothiazol-2(3H)-yl)butanoate
  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 、 copper(l) chloride 作用下， 以 水 、 溶剂黄146 为溶剂， 以81%的产率得到Methyl 5-(4-bromophenyl)-3-(chlorosulfonyl)thiophene-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.