6-氯-3-羟基苯并[b]噻吩-2-羧酸甲酯 | 33851-22-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 6-氯-3-羟基苯并[b]噻吩-2-羧酸甲酯
• 英文名称: 6-chloro-3-hydroxybenzo[b]thiophene-2-carboxylic acid methyl ester
• 英文别名: methyl 6-chloro-3-hydroxybenzo[b]thiophene-2-carboxylate；6-Chloro-3-hydroxy-benzo[b]thiophene-2-carboxylic acid methyl ester；methyl 6-chloro-3-hydroxy-1-benzothiophene-2-carboxylate
• CAS: 33851-22-8
• 化学式: C₁₀H₇ClO₃S
• mdl: MFCD00052504
• 分子量: 242.683
• InChiKey: KCZUOINFDZHETR-UHFFFAOYSA-N

物化性质

• 熔点：
  146-148°C

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 安全说明：
  S26,S37/39
• 危险类别码：
  R20/21/22,R36/37/38

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	6-chloro-3-hydroxybenzo[b]thiophene-2-carboxylic acid	1393803-55-8	C9H5ClO3S	228.656
  ——	6-chloro-3-(3-cyanopropoxy)-benzo[b]thiophene-2-carboxylic acid methyl ester	——	C14H12ClNO3S	309.773
  ——	3-tert-butoxycarbonylmethoxy-6-chlorobenzo[b]thiophene-2-carboxylic acid methyl ester	863904-17-0	C16H17ClO5S	356.827
  ——	3-(1-carboxy-ethoxy)-6-chloro-benzo[b]thiophene-2-carboxylic acid	863904-27-2	C12H9ClO5S	300.719
  ——	methyl 6-chloro-3-trifluoromethanesulfonyloxybenzo[b]thiophene-2-carboxylate	892128-19-7	C11H6ClF3O5S2	374.746
  ——	6-chloro-3-hydroxybenzo[b]thiophene-2-carbohydrazide	1393803-57-0	C9H7ClN2O2S	242.686
  ——	6-chloro-3-hydroxy-N'-(propan-2-ylidene)benzo[b]thiophene-2-carbohydrazide	1393803-58-1	C12H11ClN2O2S	282.751

反应信息

• 作为反应物：
  描述：

  6-氯-3-羟基苯并[b]噻吩-2-羧酸甲酯 在 hydrazine hydrate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 6-chloro-3-hydroxy-N'-(propan-2-ylidene)benzo[b]thiophene-2-carbohydrazide
  参考文献：
  名称：

  Efficient synthesis and 5-LOX/COX-inhibitory activity of some 3-hydroxybenzo[b]thiophene-2-carboxylic acid derivatives

  摘要：

  A series of 3-hydroxybenzo[b]thiophene-2-carboxylic acid derivatives has been prepared and subsequently evaluated with regards to the inhibition of 5-LOX/COX. Structure optimization furnished derivatives with promising in vitro activity as dual 5-LOX/COX inhibitors with submicromolar IC50 values for inhibition of 5-LOX and COX-1, respectively. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.012
• 作为产物：
  描述：

  4-氯-2-硝基苯甲酸 在 硫酸 、 lithium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-氯-3-羟基苯并[b]噻吩-2-羧酸甲酯
  参考文献：
  名称：

  Efficient synthesis and 5-LOX/COX-inhibitory activity of some 3-hydroxybenzo[b]thiophene-2-carboxylic acid derivatives

  摘要：

  A series of 3-hydroxybenzo[b]thiophene-2-carboxylic acid derivatives has been prepared and subsequently evaluated with regards to the inhibition of 5-LOX/COX. Structure optimization furnished derivatives with promising in vitro activity as dual 5-LOX/COX inhibitors with submicromolar IC50 values for inhibition of 5-LOX and COX-1, respectively. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.012

文献信息

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

  公开号：US20050203081A1

  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 bicyclic fused-thiophene compounds can inhibit PTP1B and thereby induce greater insulin sensitivity. Accordingly, PTP1B inhibition can provide an alternate treatment for PTPase-mediated disorders such as diabetes.

  蛋白质酪氨酸磷酸酶（PTPases），如PTP1B，在调节广泛的细胞反应，如胰岛素信号传导中发挥作用。取代的并环融合噻吩化合物可以抑制PTP1B，从而增加胰岛素敏感性。因此，PTP1B的抑制可以提供一种治疗PTPase介导的疾病，如糖尿病的替代方法。
• 1,3-substitued cycloalkyl derivatives having acidic, mostly heterocyclic groups; processes for their preparation and their use as pharmaceuticals
  申请人：Aventis Pharma Deutschland GmbH

  公开号：US20040209932A1

  公开（公告）日：2004-10-21

  The invention relates to 1,3-substituted cycloalkyl derivatives having acidic, mostly heterocyclic groups and to their physiologically acceptable salts and physiologically functional derivatives. What is described are compounds of the formula I, 1 in which the radicals are as defined, and their physiologically acceptable salts and processes for their preparation. The compounds are suitable for the treatment and/or prevention of disorders of fatty acid metabolism and glucose utilization disorders as well as of disorders in which insulin resistence is involved.

  本发明涉及具有酸性、大多数是杂环基团的1,3-取代环烷衍生物及其生理上可接受的盐和生理上功能衍生物。所描述的是式I中的化合物，其中基团如定义所示，以及它们的生理上可接受的盐和制备它们的过程。这些化合物适用于治疗和/或预防脂肪酸代谢障碍和葡萄糖利用障碍以及胰岛素抵抗涉及的疾病。
• Inhibitors of Protein Tyrosine Phosphatase 1B
  申请人：Lee Jinbo

  公开号：US20090048286A1

  公开（公告）日：2009-02-19

  Protein tyrosine phosphatases (PTPases) such as PTP1B can play a role in regulating a wide variety of cellular responses such as insulin signaling. Substituted bicyclic fused-thiophene compounds 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可以在调节各种细胞响应（如胰岛素信号传导）方面发挥作用。取代的双环融合噻吩化合物可以抑制PTP1B，从而增强胰岛素敏感性。因此，PTP1B的抑制可以提供PTPase介导的疾病（如糖尿病）的另一种治疗方法。
• 1,3-SUBSTITUTED CYCLOALKYL DERIVATIVES HAVING ACIDIC, MOSTLY HETEROCYCLIC GROUPS, PROCESSES FOR THEIR PREPARATION AND THEIR USE AS PHARMACEUTICALS
  申请人：Goerlitzer Jochen

  公开号：US20080249126A1

  公开（公告）日：2008-10-09

  The invention relates to 1,3-substituted cycloalkyl derivatives having acidic, mostly heterocyclic groups and to their physiologically acceptable salts and physiologically functional derivatives. What is described are compounds of the formula I, in which the radicals are as defined, and their physiologically acceptable salts and processes for their preparation. The compounds are suitable for the treatment and/or prevention of disorders of fatty acid metabolism and glucose utilization disorders as well as of disorders in which insulin resistance is involved.

  本发明涉及具有酸性、大多数为杂环基团的1,3-取代环烷衍生物及其生理上可接受的盐和生理上功能性衍生物。所描述的是式I的化合物，其中基团如定义所述，以及它们的生理上可接受的盐和制备它们的方法。这些化合物适用于治疗和/或预防脂肪酸代谢紊乱和葡萄糖利用紊乱以及涉及胰岛素抵抗的紊乱。
• Bicyclic and tricyclic thiophenes as protein tyrosine phosphatase 1B inhibitors
  作者：A.F. Moretto、S.J. Kirincich、W.X. Xu、M.J. Smith、Z.-K. Wan、D.P. Wilson、B.C. Follows、E. Binnun、D. Joseph-McCarthy、K. Foreman、D.V. Erbe、Y.L. Zhang、S.K. Tam、S.Y. Tam、J. Lee

  DOI：10.1016/j.bmc.2005.11.005

  日期：2006.4

  A novel pyridothiophene inhibitor of PTP1B was discovered by rational screening of phosphotyrosine mimics at high micromolar concentrations. The potency of this lead compound has been improved significantly by medicinal chemistry guided by X-ray crystallography and molecular modeling. Excellent consistency has been observed between structure-activity relationships and structural information from PTP1B-inhibitor complexes.