4-(4-(trifluoromethyl)phenyl)-1H-pyrazole | 497946-98-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-(trifluoromethyl)phenyl)-1H-pyrazole
• 英文别名: 4-[4-(trifluoromethyl)phenyl]-1H-pyrazole
• CAS: 497946-98-2
• 化学式: C₁₀H₇F₃N₂
• 分子量: 212.174
• InChiKey: UNXSFMWWHHIALZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(-)-4-苯基-2-丁醇 、 4-(4-(trifluoromethyl)phenyl)-1H-pyrazole 在 tetrabutylammonium tetrafluoroborate 、 4-(二甲氨基)三苯基膦 作用下， 以 乙腈 为溶剂， 以71 %的产率得到
  参考文献：
  名称：

  Electrochemical Azo‐free Mitsunobu‐type Reaction

  摘要：

  The classic chemical Mitsunobu reaction suffers from the need of excess alcohol activation reagents and the generation of significant by‐products. Efforts to overcome these limitations have resulted in numerous creative solutions, but the substrate scope of these catalytic processes remains limited. Here we report an electrochemical Mitsunobu‐type reaction, which features azo‐free alcohol activation and broad substrate scope. This user‐friendly technology allows a vast collection of heterocycles as the nucleophile, which can couple with a series of chiral cyclic and acyclic alcohols in moderate to high yields and excellent ee's. This practical reaction is scalable, chemoselective, uses simple Electrasyn setup with inexpensive electrodes and requires no precaution to exclude air and moisture. The synthetic utility is further demonstrated on the structural modification of diverse bioactive natural products and pharmaceutical derivatives and its straightforward application in a multiple‐step synthesis of a drug candidate.

  DOI：

  10.1002/anie.202402878
• 作为产物：
  描述：

  3-(dimethylamino)-2-[4-(trifluoromethyl)phenyl]prop-2-enal 在 肼 作用下， 以 甲醇 为溶剂， 生成 4-(4-(trifluoromethyl)phenyl)-1H-pyrazole
  参考文献：
  名称：

  P2–P3 conformationally constrained ketoamide-based inhibitors of cathepsin K

  摘要：

  An orally bioavailable series of ketoamide-based cathepsin K inhibitors with good pharmacokinetic properties has been identified. Starting from a potent inhibitor endowed with poor drug properties, conformational constraint of the P(2)-P(3) linker and modifications to P(1') elements led to an enhancement in potency, solubility, clearance, and bioavailability. These optimized inhibitors attenuated bone resorption in a rat TPTX hypocalcemic bone resorption model.

  DOI：

  10.1016/j.bmcl.2005.05.062

文献信息

• Synthesis, anticancer activity and DNA-binding properties of novel 4-pyrazolyl-1,8-naphthalimide derivatives
  作者：Shenghui Li、Shengjie Xu、Yonghe Tang、Shan Ding、Jinchao Zhang、Shuxiang Wang、Guoqiang Zhou、Chuanqi Zhou、Xiaoliu Li

  DOI：10.1016/j.bmcl.2013.12.014

  日期：2014.1

  series of 4-pyrazolyl-1,8-naphthalimide derivatives have been designed and facilely synthesized. For anticancer activity in vitro, most of the compounds were found to be more toxic against human mammary cancer cells (MCF-7) than human cervical carcinoma cells (Hela) and human lung cancer cells (A549). Compounds 4i, 4h, 4b and 4a showed improved cytotoxic activity against MCF-7 cells over amonafide, in

  已经设计并容易地合成了一系列新颖的4-吡唑基-1，8-萘二甲酰亚胺衍生物。对于体外抗癌活性，发现大多数化合物对人乳腺癌细胞（MCF-7）的毒性比人宫颈癌细胞（Hela）和人肺癌细胞（A549）高。化合物4i，4h，4b和4a与阿莫那肽相比对MCF-7细胞表现出改善的细胞毒活性，尤其是化合物4i和4h，其对MCF-7细胞系的IC 50值分别为0.51μM和0.79μM 。4i的DNA结合特性通过紫外可见光谱，荧光和圆二色性（CD）光谱学和热变性进行了研究。结果表明，作为DNA嵌入剂的化合物4i显示出与CT-DNA的中等结合亲和力。
• [EN] ALPHA-KETOAMIDE DERIVATIVES AS CATHEPSIN K INHIBITORS<br/>[FR] DERIVES D'ALPHA-CETOAMIDE UTILISES EN TANT QU'INHIBITEURS DE LA CATHEPSINE K
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2003013518A1

  公开（公告）日：2003-02-20

  Biaryl ketoamide derivatives (I), which are useful as cathepsin K inhibitors are described herein. The described invention also includes methods of making such biaryl ketoamide derivatives as well as methods of using the same in the treatment of disorders, including osteoporosis, associated with enhanced bone turnover which can ultimately lead to fracture.

  本文描述了有用于作为蛋白酶K抑制剂的双芳基酮酰胺衍生物(I)。所述的发明还包括制备这种双芳基酮酰胺衍生物的方法，以及在治疗与增强骨转换相关的疾病，包括骨质疏松症，最终可能导致骨折的方法。
• Pyrazole compounds and methods of making and using same
  申请人：ABIDE THERAPEUTICS, INC.

  公开号：US10093630B2

  公开（公告）日：2018-10-09

  Provided herein are pyrazole compounds and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful as modulators of one or more of MAGL, ABHD6, and FAAH. Furthermore, the subject compounds and compositions are useful for the treatment of, for example, pain, solid tumors and/or obesity.

  本文提供了吡唑化合物和包含所述化合物的药物组合物。所述化合物和组合物可用作 MAGL、ABHD6 和 FAAH 中一种或多种的调节剂。此外，所述化合物和组合物还可用于治疗疼痛、实体瘤和/或肥胖症等。
• Design, synthesis, and biologic evaluation of some novel N-arylpyrazole derivatives as cytotoxic agents
  作者：Shengjie Xu、Shenghui Li、Yonghe Tang、Jinchao Zhang、Shuxiang Wang、Chuanqi Zhou、Xiaoliu Li

  DOI：10.1007/s00044-013-0552-1

  日期：2013.11

  A novel series of N-arylpyrazole derivatives (5a-5d, 7a-7c) has been designed and synthesized via aromatic substitution reaction of N-nonsubstituted pyrazoles with 4-fluoronitrobenzene in the presence of base. The structures of these compounds were established on the basis of elemental (C, H, and N) and spectral analysis (H-1 NMR, C-13 NMR, HRMS, and FT-IR). All the compounds were tested for their cytotoxic activity in vitro against four human tumor cell lines: carcinoma (Bel-7402), nasopharyngeal carcinoma (KB), immature granulocyte leukemia (HL-60), and gastrocarcinoma (BGC-823) by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. The results showed that most of the obtained compounds exhibited promising cytotoxicity against tested carcinoma cell lines with low IC50 values. The bis-pyrazole derivative 7c, bearing alkoxy group on the 5-position of phenyl ring, was the most effective one. It is inhibition of cell growth of Bel-7402 cells was 1.5-fold higher than that found for cisplatin. And, also mono-pyrazole derivatives 5a and 5b, decorated with trifluoromethyl group on the phenyl ring, displayed better cytotoxicity than that of cisplatin against Bel-7402 cell line.
• PYRAZOLE COMPOUNDS AND METHODS OF MAKING AND USING SAME
  申请人：ABIDE THERAPEUTICS, INC.

  公开号：US20170190669A1

  公开（公告）日：2017-07-06

  Provided herein are pyrazole compounds and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful as modulators of one or more of MAGL, ABHD6, and FAAH. Furthermore, the subject compounds and compositions are useful for the treatment of, for example, pain, solid tumors and/or obesity.