(Z)-3-[([2,2']Bithiophenyl-5-ylmethyl)-carbamoyl]-acrylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: (Z)-3-[([2,2']Bithiophenyl-5-ylmethyl)-carbamoyl]-acrylic acid
• 英文别名: (Z)-4-oxo-4-[(5-thiophen-2-ylthiophen-2-yl)methylamino]but-2-enoic acid
• 化学式: C₁₃H₁₁NO₃S₂
• 分子量: 293.367
• InChiKey: CPPSMHJHOJPYOG-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-aminosulfonylphenyl)benzylamine 、 (Z)-3-[([2,2']Bithiophenyl-5-ylmethyl)-carbamoyl]-acrylic acid 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (Z)-But-2-enedioic acid ([2,2']bithiophenyl-5-ylmethyl)-amide (2'-sulfamoyl-biphenyl-4-ylmethyl)-amide
  参考文献：
  名称：

  Novel cyclopentane dicarboxamide sodium channel blockers as a potential treatment for chronic pain

  摘要：

  A series of new voltage-gated sodium channel blockers were prepared based on the screening lead succinic diamide BPBTS. Replacement of the succinimide linker with the more rigid cyclic 1,2-trans-diamide linker was well tolerated. N-Methylation on the biphenylsulfonamide side of the amide moiety significantly reduced the clearance rate in rat pharmacokinetic studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.002
• 作为产物：
  描述：

  2,2'-联二噻吩 在 正丁基锂 、 Zn(N3)2-2 pyr 、 二苯基磷酸 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (Z)-3-[([2,2']Bithiophenyl-5-ylmethyl)-carbamoyl]-acrylic acid
  参考文献：
  名称：

  Novel cyclopentane dicarboxamide sodium channel blockers as a potential treatment for chronic pain

  摘要：

  A series of new voltage-gated sodium channel blockers were prepared based on the screening lead succinic diamide BPBTS. Replacement of the succinimide linker with the more rigid cyclic 1,2-trans-diamide linker was well tolerated. N-Methylation on the biphenylsulfonamide side of the amide moiety significantly reduced the clearance rate in rat pharmacokinetic studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.002

文献信息

• Novel cyclopentane dicarboxamide sodium channel blockers as a potential treatment for chronic pain
  作者：Pengchang P. Shao、Dong Ok、Michael H. Fisher、Maria L. Garcia、Gregory J. Kaczorowski、Chunshi Li、Kathryn A. Lyons、William J. Martin、Peter T. Meinke、Birgit T. Priest、McHardy M. Smith、Matthew J. Wyvratt、Feng Ye、William H. Parsons

  DOI：10.1016/j.bmcl.2005.02.002

  日期：2005.4

  A series of new voltage-gated sodium channel blockers were prepared based on the screening lead succinic diamide BPBTS. Replacement of the succinimide linker with the more rigid cyclic 1,2-trans-diamide linker was well tolerated. N-Methylation on the biphenylsulfonamide side of the amide moiety significantly reduced the clearance rate in rat pharmacokinetic studies. (c) 2005 Elsevier Ltd. All rights reserved.