5-Methyl-3-(4-trifluoromethyl-phenylamino)-1H-pyrazole-4-carboxylic acid ethyl ester | 213479-32-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-Methyl-3-(4-trifluoromethyl-phenylamino)-1H-pyrazole-4-carboxylic acid ethyl ester
• 英文别名: ethyl 5-methyl-3-[4-(trifluoromethyl)anilino]-1H-pyrazole-4-carboxylate
• CAS: 213479-32-4
• 化学式: C₁₄H₁₄F₃N₃O₂
• 分子量: 313.279
• InChiKey: IPZYLHAYKHYFGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  67
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-Methyl-3-(4-trifluoromethyl-phenylamino)-1H-pyrazole-4-carboxylic acid ethyl ester 在 水 、 三乙酰氧基硼氢化钠 、 二异丁基氢化铝 、 potassium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 二甲基亚砜 、 甲苯 为溶剂， 生成 4-[[3-methyl-6-(trifluoromethyl)-2H-pyrazolo[3,4-b]quinolin-4-yl]methyl]-1,4-oxazepane
  参考文献：
  名称：

  发现口服活性吡唑并喹啉作为有效的PDE10抑制剂可用于精神分裂症的治疗

  摘要：

  已合成了一系列吡唑并喹啉类似物，并显示出与PDE10的高亲和力结合。通过SAR研究和我们的前导优化工作，发现化合物16和27在MK-801诱导的多动症大鼠模型中具有有效的口服抗精神病活性。

  DOI：

  10.1016/j.bmcl.2011.11.023
• 作为产物：
  描述：

  在 肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 5-Methyl-3-(4-trifluoromethyl-phenylamino)-1H-pyrazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  发现口服活性吡唑并喹啉作为有效的PDE10抑制剂可用于精神分裂症的治疗

  摘要：

  已合成了一系列吡唑并喹啉类似物，并显示出与PDE10的高亲和力结合。通过SAR研究和我们的前导优化工作，发现化合物16和27在MK-801诱导的多动症大鼠模型中具有有效的口服抗精神病活性。

  DOI：

  10.1016/j.bmcl.2011.11.023

文献信息

• 3-amino-5-methyl-1H-pyrazole-4-carboxylic acids and esters thereof as anticonvulsants, muscle relaxants and anxiolytics
  申请人：A.H. ROBINS COMPANY, INCORPORATED

  公开号：EP0315433A2

  公开（公告）日：1989-05-10

  Pharmaceutical compositions which comprise a compound represented by the formula where R¹ represents a hydrogen atom, a lower alkyl group or a pharmaceutically acceptable cation; R² and R³ independently represent a hydrogen atom, a lower alkyl group, an aryl group, a cycloalkyl group, a lower alkenyl group, a 1-adamantyl group, a hetero­cyclicaminoalkyl group, a diloweralkylaminoloweralkyl group, or R² together with R³ and the adjacent nitrogen atom may form a heterocyclic ring structure; and/or a pharmaceutically acceptable acid salt thereof; the use of such compounds in medicine; and the use of such compounds in the preparation of anticonvul­sant agents, muscle relaxants and anxiolytic agents, are disclosed.

  药物组合物，其中包含由式表示的化合物 其中 R¹ 代表氢原子、低级烷基或药学上可接受的阳离子； R²和R³各自代表氢原子、低级烷基、芳基、环烷基、低级烯基、1-金刚烷基、杂环氨基烷基、稀释烷基氨基低级烷基，或R²与R³及相邻氮原子可形成杂环环结构； 和/或其药学上可接受的酸盐；公开了此类化合物在医药中的用途；以及此类化合物在制备抗惊厥剂、肌肉松弛剂和抗焦虑剂中的用途。
• Pyrazole Bioisosteres of Leflunomide as B-Cell Immunosuppressants for Xenotransplantation and Chronic Rejection:  Scope and Limitations
  作者：Christos Papageorgiou、Rainer Albert、Philipp Floersheim、Michel Lemaire、Francis Bitch、Hans-Peter Weber、Elsebeth Andersen、Valerie Hungerford、Max H. Schreier

  DOI：10.1021/jm981028c

  日期：1998.8.1

  T-cell immunosuppressant-based therapies efficiently control early graft rejection in allotransplantation settings. They fail, however, to prevent those rejection events which are mediated by transplant-induced antibody (Ab) responses such as those involved in xenograft and chronic allograft rejection. This is mainly due to their inability to block T-cell-independent Ab production against the transplanted organs. The bioactive metabolite 2(Z) of leflunomide (1) inhibits the formation of such Ab, but the drug has pharmacokinetic properties and a therapeutic window incompatible with transplantation indications. Pyrazole 3, a constrained analogue of 2(Z), was designed and shown to be conformationally and biologically similar to 2(Z). Further investigations with derivatives of 3 demonstrated that the pyrazoles had very tight structure-activity relationships, the only equipotent compound being 3o. However, in contrast to 2(Z), both 3 and 3o were inactive in vivo due to short half-life and drug concentrations lower than the in vitro obtained IC50 values, Compound 3o inhibits T-cell-independent Ab production by a different biochemical mechanism from that of 2(Z) and 3 and may therefore represent a valuable tool for the identification of new targets for B-cell inhibition.
• US4826866A
  申请人：——

  公开号：US4826866A

  公开（公告）日：1989-05-02
• US4871737A
  申请人：——

  公开号：US4871737A

  公开（公告）日：1989-10-03