2-bromo-1-(2-chloro-4-(trifluoromethyl)phenyl)ethan-1-one | 129322-87-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-1-(2-chloro-4-(trifluoromethyl)phenyl)ethan-1-one
• 英文别名: 2-chloro-4-trifluoromethylphenacyl bromide；2'-Chloro-4'-(trifluoromethyl)phenacyl bromide；2-bromo-1-[2-chloro-4-(trifluoromethyl)phenyl]ethanone
• CAS: 129322-87-8
• 化学式: C₉H₅BrClF₃O
• 分子量: 301.49
• InChiKey: BNJSCVFMFFERGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-bromo-1-(2-chloro-4-(trifluoromethyl)phenyl)ethan-1-one 在 sodium tetrahydroborate 、 盐酸羟胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 6.0h， 生成 2-(3-amino-5-cyclopropyl-4H-1,2,4-triazol-4-yl)-1-(2-chloro-4-(trifluoromethyl)phenyl)ethanol
  参考文献：
  名称：

  Aminoazabenzimidazoles, a Novel Class of Orally Active Antimalarial Agents

  摘要：

  Whole-cell high-throughput screening of the AstraZeneca compound library against the asexual blood stage of Plasmodium falciparum (Pf) led to the identification of amino imidazoles, a robust starting point for initiating a hit-to-lead medicinal chemistry effort. Structure-activity relationship studies followed by pharmacokinetics optimization resulted in the identification of 23 as an attractive lead with good oral bioavailability. Compound 23 was found to be efficacious (ED90 of 28.6 mg.kg(-1)) in the humanized P. falciparum mouse model of malaria (Pf/SCID model). Representative compounds displayed a moderate to fast killing profile that is comparable to that of chloroquine. This series demonstrates no cross-resistance against a panel of Pf strains with mutations to known antimalarial drugs, thereby suggesting a novel mechanism of action for this chemical class.

  DOI：

  10.1021/jm500535j
• 作为产物：
  描述：

  2氯-4-三氟甲基苯乙酮 在 溴 作用下， 以 氯仿 为溶剂， 以37 %的产率得到2-bromo-1-(2-chloro-4-(trifluoromethyl)phenyl)ethan-1-one
  参考文献：
  名称：

  [EN] NITROGEN-CONTAINING HETEROCYCLIC DERIVATIVE, AND COMPOSITION AND PHARMACEUTICAL USE THEREOF
  [FR] DÉRIVÉ HÉTÉROCYCLIQUE CONTENANT DE L'AZOTE, COMPOSITION ET UTILISATION PHARMACEUTIQUE DE CELUI-CI
  [ZH] 一种含氮杂环衍生物及其组合物和药学上的应用

  摘要：

  一种通式(I)所述的化合物或者其立体异构体、氘代物、溶剂化物、前药、代谢产物、药学上可接受的盐或共晶，及其中间体，以及在AR相关疾病如癌症中的用途。 B-L-K (I)

  公开号：

  WO2024012570A1

文献信息

• Neue Fluor enthaltende und an der CH3-Gruppe gegebenenfalls halogenierte Acetophenone und deren Herstellung aus neuen Fluor enthaltenden Benzonitrilen
  申请人：BAYER AG

  公开号：EP0365914B1

  公开（公告）日：1992-07-22
• Substituierte 2-Aminothiazole
  申请人：BAYER AG

  公开号：EP0365913B1

  公开（公告）日：1993-11-18
• US5104879A
  申请人：——

  公开号：US5104879A

  公开（公告）日：1992-04-14
• US5142092A
  申请人：——

  公开号：US5142092A

  公开（公告）日：1992-08-25
• Aminoazabenzimidazoles, a Novel Class of Orally Active Antimalarial Agents
  作者：Shahul Hameed P、Murugan Chinnapattu、Gajanan Shanbag、Praveena Manjrekar、Krishna Koushik、Anandkumar Raichurkar、Vikas Patil、Sandesh Jatheendranath、Suresh S. Rudrapatna、Shubhada P. Barde、Nikhil Rautela、Disha Awasthy、Sapna Morayya、Chandan Narayan、Stefan Kavanagh、Ramanatha Saralaya、Sowmya Bharath、Pavithra Viswanath、Kakoli Mukherjee、Balachandra Bandodkar、Abhishek Srivastava、Vijender Panduga、Jitender Reddy、K. R. Prabhakar、Achyut Sinha、María Belén Jiménez-Díaz、María Santos Martínez、Iñigo Angulo-Barturen、Santiago Ferrer、Laura María Sanz、Francisco Javier Gamo、Sandra Duffy、Vicky M. Avery、Pamela A. Magistrado、Amanda K. Lukens、Dyann F. Wirth、David Waterson、V. Balasubramanian、Pravin S. Iyer、Shridhar Narayanan、Vinayak Hosagrahara、Vasan K. Sambandamurthy、Sreekanth Ramachandran

  DOI：10.1021/jm500535j

  日期：2014.7.10

  Whole-cell high-throughput screening of the AstraZeneca compound library against the asexual blood stage of Plasmodium falciparum (Pf) led to the identification of amino imidazoles, a robust starting point for initiating a hit-to-lead medicinal chemistry effort. Structure-activity relationship studies followed by pharmacokinetics optimization resulted in the identification of 23 as an attractive lead with good oral bioavailability. Compound 23 was found to be efficacious (ED90 of 28.6 mg.kg(-1)) in the humanized P. falciparum mouse model of malaria (Pf/SCID model). Representative compounds displayed a moderate to fast killing profile that is comparable to that of chloroquine. This series demonstrates no cross-resistance against a panel of Pf strains with mutations to known antimalarial drugs, thereby suggesting a novel mechanism of action for this chemical class.