4-bromo-3-carboxymethoxy-5-(4-methanesulfonylamino-phenyl)-thiophene-2-carboxylic acid | 864132-92-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-bromo-3-carboxymethoxy-5-(4-methanesulfonylamino-phenyl)-thiophene-2-carboxylic acid
• 英文别名: 4-Bromo-3-(carboxymethoxy)-5-(4-methanesulfonamidophenyl)thiophene-2-carboxylic acid；4-bromo-3-(carboxymethoxy)-5-[4-(methanesulfonamido)phenyl]thiophene-2-carboxylic acid
• CAS: 864132-92-3
• 化学式: C₁₄H₁₂BrNO₇S₂
• 分子量: 450.288
• InChiKey: CCHCWRCPQOYXJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  167
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-bromo-3-carboxymethoxy-5-(4-methanesulfonylamino-phenyl)-thiophene-2-carboxylic acid 、 alkaline earth salt of/the/ methylsulfuric acid 在 三乙胺 、 lithium hydroxide 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 生成 4-bromo-5-[4-(2-carboxy-acetylamino)-phenyl]-3-carboxymethoxy-thiophene-2-carboxylic acid
  参考文献：
  名称：

  Monocyclic thiophenes as protein tyrosine phosphatase 1B inhibitors: Capturing interactions with Asp48

  摘要：

  A series of monocyclic thiophenes was designed and synthesized as PTP1B inhibitors. Guided by X-ray co-crystal structural information and computational modeling, rational design led to key interactions with Asp48 and improved inhibitory potency against PTP1B.

  DOI：

  10.1016/j.bmcl.2006.06.051
• 作为产物：
  描述：

  5-(4-amino-phenyl)-4-bromo-3-methoxycarbonylmethoxy-thiophene-2-carboxylic acid methyl ester 在 lithium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4-bromo-3-carboxymethoxy-5-(4-methanesulfonylamino-phenyl)-thiophene-2-carboxylic acid
  参考文献：
  名称：

  Monocyclic thiophenes as protein tyrosine phosphatase 1B inhibitors: Capturing interactions with Asp48

  摘要：

  A series of monocyclic thiophenes was designed and synthesized as PTP1B inhibitors. Guided by X-ray co-crystal structural information and computational modeling, rational design led to key interactions with Asp48 and improved inhibitory potency against PTP1B.

  DOI：

  10.1016/j.bmcl.2006.06.051

文献信息

• Inhibitors of protein tyrosine phosphatase 1B
  申请人：Lee Jinbo

  公开号：US20050203087A1

  公开（公告）日：2005-09-15

  Protein tyrosine phosphatases (PTPases) such as PTP1B can play a role in regulating a wide variety of cellular responses such as insulin signaling. Substituted thiophene compounds such as, for example, 2-carboxyl, 3-carboxymethoxy, 5-aryl substituted thiophenes, can inhibit PTP1B and thereby induce greater insulin sensitivity. Accordingly, PTP1B inhibition can provide an alternate treatment for PTPase-mediated disorders such as diabetes.

  蛋白酪氨酸磷酸酶（PTPases）如PTP1B可以在调节多种细胞反应中发挥作用，例如胰岛素信号传导。取代噻吩化合物，例如2-羧基、3-羧甲氧基、5-芳基取代的噻吩，可以抑制PTP1B，从而增加胰岛素敏感性。因此，PTP1B抑制可以作为PTPase介导的疾病（如糖尿病）的替代治疗方法。
• US7521473B2
  申请人：——

  公开号：US7521473B2

  公开（公告）日：2009-04-21
• [EN] INHIBITORS OF PROTEIN TYROSINE PHOSPHATASE 1B<br/>[FR] INHIBITEURS DE LA PROTEINE TYROSINE PHOSPHATASE 1B
  申请人：WYETH CORP

  公开号：WO2005081954A2

  公开（公告）日：2005-09-09

  Protein tyrosine phosphatases (PTPases) such as PTP1B can play a role in regulating a wide variety of cellular responses such as insulin signaling. Substituted thiophene compounds such as, for example, 2-carboxyl, 3-carboxymethoxy, 5-aryl substituted thiophenes, can inhibit PTPIB and thereby induce greater insulin sensitivity. Accordingly, PTP1B inhibition can provide an alternate treatment for PTPase-mediated disorders such as diabetes.
• Monocyclic thiophenes as protein tyrosine phosphatase 1B inhibitors: Capturing interactions with Asp48
  作者：Zhao-Kui Wan、Jinbo Lee、Weixin Xu、David V. Erbe、Diane Joseph-McCarthy、Bruce C. Follows、Yan-Ling Zhang

  DOI：10.1016/j.bmcl.2006.06.051

  日期：2006.9

  A series of monocyclic thiophenes was designed and synthesized as PTP1B inhibitors. Guided by X-ray co-crystal structural information and computational modeling, rational design led to key interactions with Asp48 and improved inhibitory potency against PTP1B.