(R)-2-(5-bromothiophen-2-ylsulfonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid | 1312952-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (R)-2-(5-bromothiophen-2-ylsulfonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
• 英文别名: (3R)-2-(5-bromothiophen-2-yl)sulfonyl-3,4-dihydro-1H-isoquinoline-3-carboxylic acid
• CAS: 1312952-27-4
• 化学式: C₁₄H₁₂BrNO₄S₂
• 分子量: 402.29
• InChiKey: JTERQFNDXRJFFJ-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-2-(5-bromothiophen-2-ylsulfonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 在 N-甲基吗啉 、 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.67h， 生成 (3R)-2-(5-((4-butylphenyl)ethynyl)thiophen-2-ylsulfonyl)-N-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
  参考文献：
  名称：

  Synthesis and biological evaluation in U87MG glioma cells of (ethynylthiophene)sulfonamido-based hydroxamates as matrix metalloproteinase inhibitors

  摘要：

  Matrix metalloproteinases (MMPs) are important factors in gliomas since these enzymes facilitate invasion into the surrounding brain and participate in neovascularization. In particular, the gelatinases (MMP-2 and MMP-9), and more recently MMP-25, have been shown to be highly expressed in gliomas and have been associated with disease progression. Thus, inhibition of these MMPs may represent a promising non-cytotoxic approach to glioma treatment. We report herein the synthesis and biological evaluation of a series of 4-butylphenyl(ethynylthiophene)sulfonamido-based hydroxamates. Among the new compounds tested, a promising derivative, 5a, was identified, which exhibits nanomolar inhibition of MMP-2, MMP-9, and MMP-25, but weak inhibitory activity toward other members of the MMP family. This compound also exhibited anti-invasive activity of U87MG glioblastoma cells at nanomolar concentrations, without affecting cell viability. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.033
• 作为产物：
  描述：

  5-溴噻吩-2-磺酰氯 、 (R)-(+)-1,2,3,4-四氢异喹啉-3-羧酸 在 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以71%的产率得到(R)-2-(5-bromothiophen-2-ylsulfonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological evaluation in U87MG glioma cells of (ethynylthiophene)sulfonamido-based hydroxamates as matrix metalloproteinase inhibitors

  摘要：

  Matrix metalloproteinases (MMPs) are important factors in gliomas since these enzymes facilitate invasion into the surrounding brain and participate in neovascularization. In particular, the gelatinases (MMP-2 and MMP-9), and more recently MMP-25, have been shown to be highly expressed in gliomas and have been associated with disease progression. Thus, inhibition of these MMPs may represent a promising non-cytotoxic approach to glioma treatment. We report herein the synthesis and biological evaluation of a series of 4-butylphenyl(ethynylthiophene)sulfonamido-based hydroxamates. Among the new compounds tested, a promising derivative, 5a, was identified, which exhibits nanomolar inhibition of MMP-2, MMP-9, and MMP-25, but weak inhibitory activity toward other members of the MMP family. This compound also exhibited anti-invasive activity of U87MG glioblastoma cells at nanomolar concentrations, without affecting cell viability. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.033