5-(p-yolyl)-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole | 1342638-84-9

• 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-(p-yolyl)-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole
• 英文别名: 5-(p-tolyl)-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole；5-(4-Methylphenyl)-1-[4-(trifluoromethyl)phenyl]pyrazole
• CAS: 1342638-84-9
• 化学式: C₁₇H₁₃F₃N₂
• 分子量: 302.299
• InChiKey: ZFMIDYOVYZKCCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-[3-(4-methylphenyl)prop-2-ynylideneamino]-4-(trifluoromethyl)aniline 在 gold(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以62%的产率得到5-(p-yolyl)-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole
  参考文献：
  名称：

  Cycloisomerization of acetylenic oximes and hydrazones under gold catalysis: Synthesis and cytotoxic evaluation of isoxazoles and pyrazoles

  摘要：

  通过一种通用的环异构化方法，已经报道了取代异恶唑和吡唑的合成。金(III)氯化物促进α,β-炔基肟和α,β-炔基脒的环异构化的能力是该策略的核心。研究了一系列炔基前体，以良好的至优秀的化学收率得到了28个产物实例。选定的化合物对COLO320癌细胞系的细胞毒性潜力进行了筛选。测试化合物的IC50值在微摩尔范围内，其中最佳化合物5-(6-甲氧基萘-2-基)-3-苯基异恶唑(3h)的IC50值为38.9 μM。对于该化合物，获得了与Aurora-A激酶复合的晶体结构，揭示了其在活性位点内的结合模式，结合自由能为-9.54 kcal/mol。

  DOI：

  10.1007/s12039-015-0993-9

文献信息

• BENZISOXAZOLES
  申请人：Hoffmann-La Roche Inc.

  公开号：US20150259334A1

  公开（公告）日：2015-09-17

  The present invention relates to compounds of general formula wherein Ar 1 /Ar 2 are phenyl or a 5 or 6-membered heteroaryl; R 1 /R 2 is hydrogen, halogen, lower alkyl, CF 3 or lower alkoxy; n,m are 1 or 2; or to a pharmaceutically acceptable acid addition salt, to a racemic mixture or to its corresponding enantiomer and/or optical isomers thereof, with the exception of the compound 2,1-benzisoxazole, 3-(4-chlorophenyl)-5-(1-phenyl-1H-pyrazol-5 -yl)-. The compounds may be used for the treatment of schizophrenia, obsessive-compulsive personality disorder, major depression, bipolar disorders, anxiety disorders, normal aging, epilepsy, retinal degeneration, traumatic brain injury, spinal cord injury, post-traumatic stress disorder, panic disorder, Parkinson's disease, dementia, Alzheimer's disease, mild cognitive impairment, chemotherapy-induced cognitive dysfunction, Down syndrome, autism spectrum disorders, hearing loss, tinnitus, spinocerebellar ataxia, amyotrophic lateral sclerosis, multiple sclerosis, Huntington's disease, stroke, radiation therapy, chronic stress, abuse of neuro-active drugs, such as alcohol, opiates, methamphetamine, phencyclidine and cocaine.

  本发明涉及一般式为的化合物 其中Ar1/Ar2是苯基或5或6成员杂环基；R1/R2是氢、卤素、低碳基、CF3或低烷氧基；n，m为1或2；或其药学上可接受的酸盐、外消旋体混合物或其相应的对映异构体，但不包括化合物2,1-苯并异噁唑，3-(4-氯苯基)-5-(1-苯基-1H-吡唑-5-基)-。这些化合物可用于治疗精神分裂症、强迫性人格障碍、重度抑郁症、双相情感障碍、焦虑症、正常衰老、癫痫、视网膜退化、创伤性脑损伤、脊髓损伤、创伤后应激障碍、惊恐障碍、帕金森病、痴呆症、阿尔茨海默病、轻度认知障碍、化疗引起的认知功能障碍、唐氏综合症、自闭症谱系障碍、听力损失、耳鸣、脊髓小脑性共济失调、肌萎缩性侧索硬化症、多发性硬化症、亨廷顿病、中风、放射治疗、慢性应激、神经活性药物滥用，如酒精、鸦片类、甲基苯丙胺、邻-二氯苯基环已酮和可卡因。
• Synthesis of Pyrazoles via CuI-Mediated Electrophilic Cyclizations of α,β-Alkynic Hydrazones
  作者：Metin Zora、Arif Kivrak

  DOI：10.1021/jo201685p

  日期：2011.11.18

  Synthesis of pyrazoles via electrophilic cyclization of alpha,beta-alkynic hydrazones by copper(I) iodide is described. When treated with copper(I) iodide in the presence of triethylamine in refluxing acetonitrile, alpha,beta-alkynic hydrazones, prepared readily from hydrazines and propargyl aldehydes and ketones, undergo electrophilic cyclization to afford pyrazole derivatives in good to excellent yields. The reaction appears to be general for a variety of alpha,beta-alkynic hydrazones and tolerates the presence of aliphatic, aromatic, and ferrocenyl moieties with electron-withdrawing and electron-donating substituents.
• US9440962B2
  申请人：——

  公开号：US9440962B2

  公开（公告）日：2016-09-13