ethyl 1-(4-bromophenyl)-1H-pyrazole-3-carboxylate | 19532-36-6

• 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-bromophenyl)-1H-pyrazole-3-carboxylate
• 英文别名: Ethyl 1-(4-bromophenyl)pyrazole-3-carboxylate
• CAS: 19532-36-6
• 化学式: C₁₂H₁₁BrN₂O₂
• 分子量: 295.136
• InChiKey: WZMLCZCUOIANEL-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-bromophenyl)-1H-pyrazole-3-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以73%的产率得到1-(4-bromophenyl)-1H-pyrazole-3-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 8.0h， 生成 ethyl 1-(4-bromophenyl)-1H-pyrazole-3-carboxylate 、 ethyl 1-(4-bromophenyl)-1H-pyrazole-5-carboxylate
  参考文献：
  名称：

  HETEROCYCLIC COMPOUNDS USEFUL IN THE TREATMENT OF DISEASE

  摘要：

  描述了异环化合物，这些化合物是溶血磷脂酸受体配体，可用于治疗溶血磷脂酸受体依赖性疾病和状况，包括但不限于涉及纤维化的疾病，如心脏、肾脏、肝脏和肺的纤维化以及硬化病；炎症性疾病，如糖尿病肾病和炎症性肠病；眼病，如涉及视网膜变性的疾病；神经疾病，如瘙痒和疼痛。这些化合物的非限制性例子包括(RS)-3-环丙基-2-{4-[3-甲基-4((R)-1-苯基-乙氧羰基氨基)-异恶唑-5-基]-苄氧基}-丙酸和(R)-1-(4′-{5-[1-(2-氯-苯基)-乙氧羰基氨基]-4-氟-吡唑-1-基}-2-氟-联苯-4-基)-环丙烷甲酸。

  公开号：

  US20160024031A1

文献信息

• HETEROCYCLIC COMPOUNDS USEFUL IN THE TREATMENT OF DISEASE
  申请人：EPIGEN BIOSCIENCES, INC.

  公开号：US20160024031A1

  公开（公告）日：2016-01-28

  Heterocyclic compounds are described that are lysophosphatidic acid receptor ligands that are useful in the treatment of lysophosphatidic acid receptor-dependent diseases and conditions, including but not limited to diseases involving fibrosis, such as fibrosis of the heart, kidney, liver and lung, and scleroderma; inflammatory diseases such as diabetic nephropathy and inflammatory bowel disease; ocular diseases such as diseases involving retinal degeneration; nerve diseases such as pruritus and pain. Non-limiting examples of those compounds include (RS)-3-Cyclopropyl-2-4-[3-methyl-4((R)-1-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-benzyloxy}-propionic acid and (R)-1-(4′-5-[1-(2-Chloro-phenyl)-ethoxycarbonylamino]-4-fluoro-pyrazol-1-yl}-2-fluoro-biphenyl-4-yl)-cyclopropanecarboxylic acid.

  描述了异环化合物，这些化合物是溶血磷脂酸受体配体，可用于治疗溶血磷脂酸受体依赖性疾病和状况，包括但不限于涉及纤维化的疾病，如心脏、肾脏、肝脏和肺的纤维化以及硬化病；炎症性疾病，如糖尿病肾病和炎症性肠病；眼病，如涉及视网膜变性的疾病；神经疾病，如瘙痒和疼痛。这些化合物的非限制性例子包括(RS)-3-环丙基-2-4-[3-甲基-4((R)-1-苯基-乙氧羰基氨基)-异恶唑-5-基]-苄氧基}-丙酸和(R)-1-(4′-5-[1-(2-氯-苯基)-乙氧羰基氨基]-4-氟-吡唑-1-基}-2-氟-联苯-4-基)-环丙烷甲酸。
• [EN] LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DES RÉCEPTEURS D'ACIDE LYSOPHOSPHATIDIQUE
  申请人：INTERMUNE INC

  公开号：WO2013025733A1

  公开（公告）日：2013-02-21

  Compounds, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or diagnose diseases, disorders, or conditions associated with one or more of the lysophosphatidic acid receptors are provided.

  提供了化合物、制备这种化合物的方法、包含这种化合物的药物组合物和药物，以及使用这种化合物治疗、预防或诊断与一种或多种赖氨酸磷脂酸受体相关的疾病、紊乱或状况的方法。
• Heterocyclic compounds useful in the treatment of disease
  申请人：EPIGEN BIOSCIENCES, INC.

  公开号：US10000459B2

  公开（公告）日：2018-06-19

  Heterocyclic compounds are described that are lysophosphatidic acid receptor ligands that are useful in the treatment of lysophosphatidic acid receptor-dependent diseases and conditions, including but not limited to diseases involving fibrosis, such as fibrosis of the heart, kidney, liver and lung, and scleroderma; inflammatory diseases such as diabetic nephropathy and inflammatory bowel disease; ocular diseases such as diseases involving retinal degeneration; nerve diseases such as pruritus and pain. Non-limiting examples of those compounds include (RS)-3-Cyclopropyl-2-4-[3-methyl-4-((R)-1-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-benzyloxy}-propionic acid and (R)-1-(4′-5-[1-(2-Chloro-phenyl)-ethoxycarbonylamino]-4-fluoro-pyrazol-1-yl}-2-fluoro-biphenyl-4-yl)-cyclopropanecarboxylic acid.

  所述杂环化合物是溶血磷脂酸受体配体，可用于治疗溶血磷脂酸受体依赖性疾病和病症，包括但不限于涉及纤维化的疾病，如心脏、肾脏、肝脏和肺部纤维化以及硬皮病；炎症性疾病，如糖尿病肾病和炎症性肠病；眼部疾病，如涉及视网膜变性的疾病；神经疾病，如瘙痒和疼痛。这些化合物的非限制性实例包括 (RS)-3-Cyclopropyl-2-4-[3-methyl-4-((R)-1-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-benzyloxy}- 丙酸和 (R)-3-Cyclopropyl-2-4-[3-methyl-4-((R)-1-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-benzyloxy}- 丙酸。丙酸和(R)-1-(4′-5-[1-(2-氯苯基)-乙氧羰基氨基]-4-氟吡唑-1-基}-2-氟联苯-4-基)-环丙烷羧酸。
• LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS
  申请人：Buckman Brad O.

  公开号：US20130072449A1

  公开（公告）日：2013-03-21

  Compounds, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or diagnose diseases, disorders, or conditions associated with one or more of the lysophosphatidic acid receptors are provided.
• Heterocyclic Compounds Useful In The Treatment of Disease
  申请人：EPIGEN BIOSCIENCES, INC.

  公开号：US20180297962A1

  公开（公告）日：2018-10-18

  Heterocyclic compounds are described that are lysophosphatidic acid receptor ligands that are useful in the treatment of lysophosphatidic acid receptor-dependent diseases and conditions, including but not limited to diseases involving fibrosis, such as fibrosis of the heart, kidney, liver and lung, and scleroderma; inflammatory diseases such as diabetic nephropathy and nonalcoholic steatohepatitis (NASH); ocular diseases such as diseases involving retinal degeneration; nerve diseases such as pruritus and pain.