5-amino-1-phenyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid | 1093253-92-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-amino-1-phenyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid
• 英文别名: 5-Amino-1-phenyl-3-(trifluoromethyl)pyrazole-4-carboxylic acid
• CAS: 1093253-92-9
• 化学式: C₁₁H₈F₃N₃O₂
• 分子量: 271.199
• InChiKey: UODDIBVQYOPYRA-UHFFFAOYSA-N

物化性质

• 熔点：
  215-216 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• 沸点：
  416.8±45.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  81.1
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-amino-1-phenyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid 反应 1.0h， 以30%的产率得到2-苯基-5-三氟甲基-2H-吡唑-3-胺
  参考文献：
  名称：

  Synthesis and induction of G0–G1 phase arrest with apoptosis of 3,5-dimethyl-6-phenyl-8-(trifluoromethyl)-5,6-dihydropyrazolo[3,4-f][1,2,3,5]tetrazepin-4(3H)-one

  摘要：

  The multistep synthesis of 3,5-dimethyl-6-phenyl-8-(trifluoromethyl)-5,6-dihydropyrazolo [3,4-f][1,2,3,5]tetrazepin-4(3H)-one 15 has been carried out. The compound showed antiproliferative and apoptotic effects against K562, K562-R (imatinib mesilate resistant), HL60 and multidrug resistant (MDR) HL60 cell lines. Compound 15 showed a pro-apoptotic activity against HL60 and K562 resistant cell lines markedly higher than etoposide and busulfan, respectively. Flow cytometry studies carried out on K562 cells allowed to establish that 15 induces G0-G1 phase arrest followed by apoptosis. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.01.007
• 作为产物：
  描述：

  methyl 5-amino-1-phenyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate 在 氢氧化钾 、 水 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以78%的产率得到5-amino-1-phenyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid
  参考文献：
  名称：

  Synthesis and induction of G0–G1 phase arrest with apoptosis of 3,5-dimethyl-6-phenyl-8-(trifluoromethyl)-5,6-dihydropyrazolo[3,4-f][1,2,3,5]tetrazepin-4(3H)-one

  摘要：

  The multistep synthesis of 3,5-dimethyl-6-phenyl-8-(trifluoromethyl)-5,6-dihydropyrazolo [3,4-f][1,2,3,5]tetrazepin-4(3H)-one 15 has been carried out. The compound showed antiproliferative and apoptotic effects against K562, K562-R (imatinib mesilate resistant), HL60 and multidrug resistant (MDR) HL60 cell lines. Compound 15 showed a pro-apoptotic activity against HL60 and K562 resistant cell lines markedly higher than etoposide and busulfan, respectively. Flow cytometry studies carried out on K562 cells allowed to establish that 15 induces G0-G1 phase arrest followed by apoptosis. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.01.007

文献信息

• PROCEDURE FOR THE DECARBOXYLATION OF 3,5-BIS(HALOALKYL)-PYRAZOLE-4-CARBOXYLIC ACID DERIVATIVES
  申请人：BAYER CROPSCIENCE AG

  公开号：US20150225350A1

  公开（公告）日：2015-08-13

  A new process for the preparation of 3,5-bis(haloalkyl)-pyrazole derivatives of the general formula (I) is described, resulting from the reaction of 3,5-bis(haloalkyl)-pyrazole-4-carboxylic acid derivatives of the general formula (Ha) with a copper compound and a base at elevated temperature wherein R 1 is selected from H, C 1-12 -alkyl, C 3-8 -cycloalkyl, C 6-18 -aryl, C 7-19 -arylalkyl or C 7-19 -alkylaryl, CH 2 CN, CH 2 CX 3 , CH 2 COOH, CH 2 COO(C 1-12 )-alkyl, and X is independently of each other F, Cl, Br, I; R 2 and R 3 are selected independently of each other from C 1 -C 6 -haloalkyl.

  本文描述了一种制备通式（I）的3,5-双（卤代烷基）-吡唑衍生物的新工艺，该工艺是通过在升高温度下将通式（Ha）的3,5-双（卤代烷基）-吡唑-4-羧酸衍生物与铜化合物和碱反应而得到的。其中，R1从H、C1-12-烷基、C3-8-环烷基、C6-18-芳基、C7-19-芳基烷基或C7-19-烷基芳基、CH2CN、CH2CX3、CH2COOH、CH2COO（C1-12）-烷基中选择，X独立选择为F、Cl、Br、I；R2和R3独立选择为C1-C6-卤代烷基。
• US9145370B2
  申请人：——

  公开号：US9145370B2

  公开（公告）日：2015-09-29
• Synthesis and induction of G0–G1 phase arrest with apoptosis of 3,5-dimethyl-6-phenyl-8-(trifluoromethyl)-5,6-dihydropyrazolo[3,4-f][1,2,3,5]tetrazepin-4(3H)-one
  作者：Benedetta Maggio、Demetrio Raffa、Maria Valeria Raimondi、Stella Cascioferro、Fabiana Plescia、Manlio Tolomeo、Eleonora Barbusca、Giuliana Cannizzo、Salvatrice Mancuso、Giuseppe Daidone

  DOI：10.1016/j.ejmech.2008.01.007

  日期：2008.11

  The multistep synthesis of 3,5-dimethyl-6-phenyl-8-(trifluoromethyl)-5,6-dihydropyrazolo [3,4-f][1,2,3,5]tetrazepin-4(3H)-one 15 has been carried out. The compound showed antiproliferative and apoptotic effects against K562, K562-R (imatinib mesilate resistant), HL60 and multidrug resistant (MDR) HL60 cell lines. Compound 15 showed a pro-apoptotic activity against HL60 and K562 resistant cell lines markedly higher than etoposide and busulfan, respectively. Flow cytometry studies carried out on K562 cells allowed to establish that 15 induces G0-G1 phase arrest followed by apoptosis. (C) 2008 Elsevier Masson SAS. All rights reserved.