3-Hydroxy-7-methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester | 42087-79-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3-Hydroxy-7-methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester
• 英文别名: methyl 3-hydroxy-7-methoxy-1-benzothiophene-2-carboxylate
• CAS: 42087-79-6
• 化学式: C₁₁H₁₀O₄S
• 分子量: 238.264
• InChiKey: BCNIGXNISRAYKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  84
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Hydroxy-7-methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester 在 氢氧化钾 、 potassium tert-butylate 、 N,N'-羰基二咪唑 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 14.25h， 生成 3-isopropoxy-7-methoxy-N-(1H-1,2,3,4-tetrazol-5-yl)-1-benzo[b]thiophene-2-carboxamide
  参考文献：
  名称：

  Novel benzothiophene-, benzofuran-, and naphthalenecarboxamidotetrazoles as potential antiallergy agents

  摘要：

  The synthesis and antiallergic activity of a series of novel benzothiophene-, benzofuran-, and naphthalenecarbox-amidotetrazoles are described. A number of the compounds inhibit the release of histamine from anti-IgE stimulated basophils obtained from allergic donors. Optimal inhibition is exhibited in benzothiophenes with a 3-alkoxy substituent in combination with a 5-methoxy, 6-methoxy, or a 5,6-dimethoxy group. Compounds 13c (CI-959) also inhibited respiratory burst of human neutrophils and the release of mediators from anti-IgE-stimulated human chopped lung.

  DOI：

  10.1021/jm00083a023
• 作为产物：
  描述：

  3-甲氧基-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 3-Hydroxy-7-methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester
  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

• Efficient synthesis and 5-LOX/COX-inhibitory activity of some 3-hydroxybenzo[b]thiophene-2-carboxylic acid derivatives
  作者：Finn K. Hansen、Mehdi Khankischpur、Ibrahim Tolaymat、Renata Mesaros、Gerd Dannhardt、Detlef Geffken

  DOI：10.1016/j.bmcl.2012.06.012

  日期：2012.8

  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.
• Novel benzothiophene-, benzofuran-, and naphthalenecarboxamidotetrazoles as potential antiallergy agents
  作者：David T. Connor、Wiaczeslaw A. Cetenko、Michael D. Mullican、Roderick J. Sorenson、Paul C. Unangst、Robert J. Weikert、Richard L. Adolphson、John A. Kennedy、David O. Thueson

  DOI：10.1021/jm00083a023

  日期：1992.3

  The synthesis and antiallergic activity of a series of novel benzothiophene-, benzofuran-, and naphthalenecarbox-amidotetrazoles are described. A number of the compounds inhibit the release of histamine from anti-IgE stimulated basophils obtained from allergic donors. Optimal inhibition is exhibited in benzothiophenes with a 3-alkoxy substituent in combination with a 5-methoxy, 6-methoxy, or a 5,6-dimethoxy group. Compounds 13c (CI-959) also inhibited respiratory burst of human neutrophils and the release of mediators from anti-IgE-stimulated human chopped lung.