3-Ethoxycarbonyl-1-phenyl-1,4,5,6-tetrahydro-cyclopentapyrazol | 97377-96-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-Ethoxycarbonyl-1-phenyl-1,4,5,6-tetrahydro-cyclopentapyrazol
• 英文别名: 1-phenyl-1,4,5,6-tetrahydro-cyclopentapyrazole-3-carboxylic acid ethyl ester；1-Phenyl-1,4,5,6-tetrahydro-3-cyclopentapyrazole carboxylic acid ethyl ester；ethyl 1-phenyl-1H,4H,5H,6H-cyclopenta[c]pyrazole-3-carboxylate；ethyl 1-phenyl-5,6-dihydro-4H-cyclopenta[c]pyrazole-3-carboxylate
• CAS: 97377-96-3
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: OLPOEALDWXWXKB-UHFFFAOYSA-N

物化性质

• 熔点：
  156-157 °C(Solv: ethanol (64-17-5))
• 沸点：
  418.9±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Ethoxycarbonyl-1-phenyl-1,4,5,6-tetrahydro-cyclopentapyrazol 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 1-苯基-1,4,5,6-四氢环戊并[c]吡唑-3-羧酸
  参考文献：
  名称：

  Pyrazole-4-Carboxamide (YW2065): A Therapeutic Candidate for Colorectal Cancer via Dual Activities of Wnt/β-Catenin Signaling Inhibition and AMP-Activated Protein Kinase (AMPK) Activation

  摘要：

  Dysregulation of the Wnt/beta-catenin signaling pathway has been widely recognized as a pathogenic mechanism for colorectal cancer (CRC). Although numerous Wnt inhibitors have been developed, they commonly suffer from toxicity and unintended effects. Moreover, concerns have been raised in targeting this pathway because of its critical roles in maintaining stem cells and regenerating tissues and organs. On the basis of the anthelmintic drug pyrvinium and previous lead FX1128, we have developed a compound YW2065 (1c) which demonstrated excellent anti-CRC effects in vitro and in vivo. YW2065 achieves its inhibitory activity for Wnt signaling by stabilizing Axin-1, a scaffolding protein that regulates proteasome degradation of beta-catenin. Simultaneously, YW2065 also led to the activation of the tumor suppressor AMPK, providing an additional anticancer mechanism. In addition, YW2065 showed favorable pharmacokinetic properties without obvious toxicity. The anti-CRC effect of YW2065 was highlighted by its promising efficacy in a mice xenograft model.

  DOI：

  10.1021/acs.jmedchem.9b01252
• 作为产物：
  描述：

  1-phenyl-1,3a,4,5,6,6a-hexahydro-6a-(1-pyrrolidinyl)-3-cyclopentapyrazole carboxylic acid ethyl ester 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 生成 3-Ethoxycarbonyl-1-phenyl-1,4,5,6-tetrahydro-cyclopentapyrazol
  参考文献：
  名称：

  Cyclopentapyrazole and tetrahydroindazole compounds and their use as

  摘要：

  本发明提供了新的物质组合物及其治疗应用。更具体地说，本发明包括新颖的环戊吡唑和四氢吲唑化合物，其化学式为XXX，以及它们用作抗过敏剂、抗炎剂或中间体的用途。

  公开号：

  US04851425A1

文献信息

• SMITH, HERMAN W.
  作者：SMITH, HERMAN W.

  DOI：——

  日期：——
• US4851425A
  申请人：——

  公开号：US4851425A

  公开（公告）日：1989-07-25
• [EN] CYCLOPENTAPYRAZOLE AND TETRAHYDROINDAZOLE COMPOUNDS
  申请人：——

  公开号：WO1986007357A3

  公开（公告）日：1987-04-23