3-[4-chloro-3-(trifluoromethyl)phenyl]-1-(3-hydroxypyridin-2-yl)urea | 199803-76-4

• 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: 3-[4-chloro-3-(trifluoromethyl)phenyl]-1-(3-hydroxypyridin-2-yl)urea
• 英文别名: 1-[4-Chloro-3-(trifluoromethyl)phenyl]-3-(3-hydroxypyridin-2-yl)urea
• CAS: 199803-76-4
• 化学式: C₁₃H₉ClF₃N₃O₂
• 分子量: 331.682
• InChiKey: WUMXJFOYZAORBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  74.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氨基-3-羟基吡啶 、 4-氯-3-三氟甲基异氰酸苯酯 以 1,4-二氧六环 为溶剂， 以83%的产率得到3-[4-chloro-3-(trifluoromethyl)phenyl]-1-(3-hydroxypyridin-2-yl)urea
  参考文献：
  名称：

  In vitro inhibition of translation initiation by N,N′-diarylureas—potential anti-cancer agents

  摘要：

  Symmetrical N,N'-diarylureas: 1,3-bis(3,4-dichlorophenyl)-, 1,3-bis[4-chloro-3-(trifluoromethyl)phenyl]- and 1,3-bis[3,5-bis(trifluoromethyl)phenyl]urea, were identified as potent activators of the eIF2 alpha kinase heme regulated inhibitor. They reduce the abundance of the eIF2.GTP.tRNA(i)(Met) ternary complex and inhibit cancer cell proliferation. An optimization process was undertaken to improve their solubility while preserving their biological activity. Non-symmetrical hybrid ureas were generated by combining one of the hydrophobic phenyl moieties present in the symmetrical ureas with the polar 3-hydroxy-tolyl moiety. O-alkylation of the later added potentially solubilizing charge bearing groups. The new non-symmetrical N,N'-diarylureas were characterized by ternary complex reporter gene and cell proliferation assays, demonstrating good bioactivities. A representative sample of these compounds potently induced phosphorylation of eIF2 alpha and expression of CHOP at the protein and mRNA levels. These inhibitors of translation initiation may become leads for the development of potent, non-toxic, and target specific anti-cancer agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.126

文献信息

• N,N'-DIARYLUREA COMPOUNDS AND N,N'-DIARYLTHIOUREA COMPOUNDS AS INHIBITORS OF TRANSLATION INITIATION
  申请人：Aktas Bertal Huseyin

  公开号：US20120115915A1

  公开（公告）日：2012-05-10

  Compositions and methods for inhibiting translation initiation are provided. Compositions, methods and kits for treating (1) cellular proliferative disorders, (2) non-proliferative, degenerative disorders, (3) viral infections, and/or (4) disorders associated with viral infections, using N,N′-diarylureas and/or N,N′-diarylthiourea compounds are described.

  本文提供了抑制翻译起始的组合物和方法。描述了使用N，N'-二芳基脲和/或N，N'-二芳基硫脲化合物治疗（1）细胞增生性疾病，（2）非增生性退行性疾病，（3）病毒感染和/或（4）与病毒感染相关的疾病的组合物、方法和试剂盒。
• N,N'-Diarylurea Compounds and N,N'-Diarylthiourea Compounds as Inhibitors of Translation Initiation
  申请人：President and Fellows of Harvard College

  公开号：US20160318857A1

  公开（公告）日：2016-11-03

  Compositions and methods for inhibiting translation initiation are provided. Compositions, methods and kits for treating (1) cellular proliferative disorders, (2) non-proliferative, degenerative disorders, (3) viral infections, and/or (4) disorders associated with viral infections, using N,N′-diarylureas and/or N,N′-diarylthiourea compounds are described.
• US9421211B2
  申请人：——

  公开号：US9421211B2

  公开（公告）日：2016-08-23
• US9932300B2
  申请人：——

  公开号：US9932300B2

  公开（公告）日：2018-04-03
• [EN] METHODS OF SELECTING CANCER PATIENTS FOR TREATMENT WITH N,N'-DIARYLUREA COMPOUNDS AND N,N'-DIARYLTHIOUREA COMPOUNDS<br/>[FR] PROCÉDÉS DE SÉLECTION DE PATIENTS CANCÉREUX POUR TRAITEMENT PAR DES COMPOSÉS DE N,N'-DIARYLURÉE ET DE N,N'-DIARLYTHIOURÉE
  申请人：HARVARD COLLEGE

  公开号：WO2012162025A1

  公开（公告）日：2012-11-29

  A method for identifying candidate patients for treatment of cancer with an arylurea compound or an arylthiourea compound by determination of the level of HRI expression or HRI activity in cancer cells from the individual is provided. Embodiments of the present disclosure are directed to methods of identifying cancer patients for treatment with an arylurea compound or an arylthiourea compound. According to one aspect, the term arylyurea compound includes a diarylurea compound and vice versa. According to an additional aspect, the term arylthiourea compound includes a diarylthiourea compound and vice versa.