2-(3-carboxy-acryloylamino)-4,5-dimethyl-thiophene-3-carboxylic acid ethyl ester | 295347-56-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-(3-carboxy-acryloylamino)-4,5-dimethyl-thiophene-3-carboxylic acid ethyl ester
• 英文别名: 4-[(3-ethoxycarbonyl-4,5-dimethylthiophen-2-yl)amino]-4-oxobut-2-enoic acid
• CAS: 295347-56-7
• 化学式: C₁₃H₁₅NO₅S
• 分子量: 297.332
• InChiKey: BFTZHIBQBQWJNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(3-carboxy-acryloylamino)-4,5-dimethyl-thiophene-3-carboxylic acid ethyl ester 、 N-甲硫脲 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 Ethyl 4,5-dimethyl-2-[[2-(3-methyl-2-methylimino-4-oxo-1,3-thiazolidin-5-yl)acetyl]amino]thiophene-3-carboxylate
  参考文献：
  名称：

  Identification of iminooxothiazolidines as secreted frizzled related protein-1 inhibitors

  摘要：

  Secreted frizzled related protein-1 (sFRP-1) inhibitors have the potential to be used for the treatment of osteoporosis or other bone related disorders, since the level of sFRP-1 affects osteoblast apoptosis and proliferation. From high throughput screening, we have identified a class of iminooxothiazolidines as sFRP-1 inhibitors. Structure-activity relationships were established for various regions of the scaffold along with the biochemical characterization of this class to probe selectivity, binding and ex vivo activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.085
• 作为产物：
  描述：

  马来酸酐 、 2-氨基-4,5-二甲基噻吩-3-羧酸乙酯 以 乙醚 为溶剂， 反应 10.0h， 以2-(3-Carboxy-acryloylamino)-4,5-dimethyl-thiophene-3-carboxylic acid ethyl ester (5.96 g, 72% yield) was obtained as a yellow solid by filtration的产率得到2-(3-carboxy-acryloylamino)-4,5-dimethyl-thiophene-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Iminothiazolidinone derivatives as SFRP-1 antagonists

  摘要：

  提供公式1的化合物或药学上可接受的盐，这些化合物是分泌的毛细管扭曲相关蛋白-1的抑制剂。这些化合物和含有这些化合物的组合物可用于治疗各种疾病，包括骨质疏松症。

  公开号：

  US20060270720A1

文献信息

• Identification of iminooxothiazolidines as secreted frizzled related protein-1 inhibitors
  作者：Mengxiao Shi、Barbara Stauffer、Ramesh Bhat、Julia Billiard、Helga Ponce-de-Leon、Laura Seestaller-Wehr、Shoichi Fukayama、Annamarie Mangine、Robert Moran、Girija Krishnamurthy、Peter Bodine、Ariamala Gopalsamy

  DOI：10.1016/j.bmcl.2009.09.085

  日期：2009.11

  Secreted frizzled related protein-1 (sFRP-1) inhibitors have the potential to be used for the treatment of osteoporosis or other bone related disorders, since the level of sFRP-1 affects osteoblast apoptosis and proliferation. From high throughput screening, we have identified a class of iminooxothiazolidines as sFRP-1 inhibitors. Structure-activity relationships were established for various regions of the scaffold along with the biochemical characterization of this class to probe selectivity, binding and ex vivo activity. (C) 2009 Elsevier Ltd. All rights reserved.
• Iminothiazolidinone derivatives as SFRP-1 antagonists
  申请人：Gopalsamy Ariamala

  公开号：US20060270720A1

  公开（公告）日：2006-11-30

  Compounds of Formula 1, or pharmaceutically acceptable salts thereof, are provided: which are inhibitors of secreted frizzled related protein-1. The compounds, and compositions containing the compounds, can be used to treat a variety of disorders, including osteoporosis.

  提供了化学式1的化合物或其药学上可接受的盐，它们是分泌的毛细胞周围蛋白-1的抑制剂。这些化合物和含有这些化合物的组合物可用于治疗各种疾病，包括骨质疏松症。