ethyl 1-(4-chlorophenyl)-1H-pyrazole-5-carboxylate | 115342-27-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1-(4-chlorophenyl)-1H-pyrazole-5-carboxylate
• 英文别名: ethyl 2-(4-chlorophenyl)pyrazole-3-carboxylate
• CAS: 115342-27-3
• 化学式: C₁₂H₁₁ClN₂O₂
• 分子量: 250.685
• InChiKey: BGZKFHIXTAWHLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  ethyl 1-(4-chlorophenyl)-1H-pyrazole-5-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以77%的产率得到1–(4-chlorophenyl)-1H-pyrazole-5-carboxylic acid
  参考文献：
  名称：

  Discovery of novel fragments inhibiting O-acetylserine sulphhydrylase by combining scaffold hopping and ligand–based drug design

  摘要：

  Several bacteria rely on the reductive sulphur assimilation pathway, absent in mammals, to synthesise cysteine. Reduction of virulence and decrease in antibiotic resistance have already been associated with mutations on the genes that codify cysteine biosynthetic enzymes. Therefore, inhibition of cysteine biosynthesis has emerged as a promising strategy to find new potential agents for the treatment of bacterial infection. Following our previous efforts to explore OASS inhibition and to expand and diversify our library, a scaffold hopping approach was carried out, with the aim of identifying a novel fragment for further development. This novel chemical tool, endowed with favourable pharmacological characteristics, was successfully developed, and a preliminary Structure-Activity Relationship investigation was carried out.

  DOI：

  10.1080/14756366.2018.1512596
• 作为产物：
  描述：

  丙酮酸乙酯 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 ethyl 1-(4-chlorophenyl)pyrazole-3-carboxylate 、 ethyl 1-(4-chlorophenyl)-1H-pyrazole-5-carboxylate
  参考文献：
  名称：

  Discovery of novel fragments inhibiting O-acetylserine sulphhydrylase by combining scaffold hopping and ligand–based drug design

  摘要：

  Several bacteria rely on the reductive sulphur assimilation pathway, absent in mammals, to synthesise cysteine. Reduction of virulence and decrease in antibiotic resistance have already been associated with mutations on the genes that codify cysteine biosynthetic enzymes. Therefore, inhibition of cysteine biosynthesis has emerged as a promising strategy to find new potential agents for the treatment of bacterial infection. Following our previous efforts to explore OASS inhibition and to expand and diversify our library, a scaffold hopping approach was carried out, with the aim of identifying a novel fragment for further development. This novel chemical tool, endowed with favourable pharmacological characteristics, was successfully developed, and a preliminary Structure-Activity Relationship investigation was carried out.

  DOI：

  10.1080/14756366.2018.1512596

文献信息

• Process Research, Development, and Pilot-Plant Preparation of Clofencet, a Novel Wheat Hybridizing Agent:  Lewis Acid-Catalyzed Reaction of Ethyl Diazoacetate with 4-Chlorophenyl Hydrazonoacetaldehyde
  作者：Jerry D. Clark、Jerald D. Heise、Ajit S. Shah、James C. Peterson、Shine K. Chou、Jeffrey Levine、Achilles M. Karakas、Yinong Ma、Kin-Yin Ng、Lefteris Patelis、John R. Springer、Don R. Stano、Richard H. Wettach、Gerard A. Dutra

  DOI：10.1021/op034123q

  日期：2004.3.1

  effective manner, and the Lewis acid-catalyzed reaction of 28 with hydrazonoacetaldehyde 29, affording β-ketoester 30. The synthesis is completed via propionylation of 30, acid-catalyzed cyclization of 31 to pyridazinecarboxylic acid ester 32, followed by saponification and isolation of carboxylic acid 9. The results and challenges of eight pilot-plant runs are reported. The baseline process developed produced

  描述了针对化学研究和开发替代合成方法的研究，该合成方法是氯芬塞 (1) 的倒数第二个中间体，一种新型小麦杂交剂。详细的逆合成分析以及从可行性研究中获得的结果，导致了替代工艺的成功开发。新路线的主要特点是安全有效地制备规模化重氮乙酸乙酯（28）的方法，以及 28 与肼基乙醛 29 的路易斯酸催化反应，得到 β-酮酯 30。 合成完成通过 30 的丙酰化、31 的酸催化环化为哒嗪羧酸酯 32，然后皂化和分离羧酸 9。报告了 8 个中试工厂运行的结果和挑战。
• ARYL GPR120 RECEPTOR AGONISTS AND USES THEREOF
  申请人：Ma Jingyuan

  公开号：US20100216827A1

  公开（公告）日：2010-08-26

  Aryl GPR120 agonists are provided. These compounds are useful for the treatment of metabolic diseases, including Type II diabetes and diseases associated with poor glycemic control.

  提供了芳基GPR120激动剂。这些化合物对于治疗代谢性疾病，包括II型糖尿病和与糖代谢控制不良有关的疾病非常有用。
• Aryl gpr120 receptor agonists and uses thereof
  申请人：Camabay Therapeutics, Inc.

  公开号：EP2690095A1

  公开（公告）日：2014-01-29

  Aryl GPR120 agonists are provided. These compounds are useful for the treatment of metabolic diseases, including Type II diabetes and diseases associated with poor glycemic control.

  提供了芳基 GPR120 激动剂。这些化合物可用于治疗代谢性疾病，包括 II 型糖尿病和与血糖控制不良有关的疾病。
• [EN] ARYL GPR120 RECEPTOR AGONISTS AND USES THEREOF<br/>[FR] AGONISTES DE RÉCEPTEUR GPR120 ARYL ET UTILISATIONS DE CEUX-CI
  申请人：METABOLEX INC

  公开号：WO2010048207A3

  公开（公告）日：2010-06-17