(3,5-bis(trifluoromethyl)phenyl)(1-(5-chloro-2-hydroxyphenyl)-1H-1,2,3-triazol-4-yl)methanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3,5-bis(trifluoromethyl)phenyl)(1-(5-chloro-2-hydroxyphenyl)-1H-1,2,3-triazol-4-yl)methanone
• 英文别名: (3,5-bis(trifluoromethyl)phenyl)(1-(5-chloro-2-hydroxyphenyl)triazol-4-yl)methanone；YK-Ncl-240；[3,5-bis(trifluoromethyl)phenyl]-[1-(5-chloro-2-hydroxyphenyl)triazol-4-yl]methanone
• 化学式: C₁₇H₈ClF₆N₃O₂
• 分子量: 435.713
• InChiKey: ZXTHCPSJOPLMQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3,5-双三氟甲基苯甲醛 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 叔丁醇 为溶剂， 反应 2.17h， 生成 (3,5-bis(trifluoromethyl)phenyl)(1-(5-chloro-2-hydroxyphenyl)-1H-1,2,3-triazol-4-yl)methanone
  参考文献：
  名称：

  Optimization of the anti-cancer activity of the phosphatidylinositol-3 kinase pathway inhibitor PITENIN-1: switching thiourea with 1,2,3-triazole

  摘要：

  我们曾报道过 N-((3-氯-2-羟基-5-硝基苯基)氨基硫酰基)苯甲酰胺（称为 PITENIN-1）令人鼓舞的体外和体内抗癌活性。在目前的工作中，我们描述了 PIT-1 系列的结构-活性关系研究，其基础是用 1,2,3-三唑取代中央硫脲单元，从而提高肝微粒体稳定性、药物相似性和对癌细胞的毒性。

  DOI：

  10.1039/c4md00109e

文献信息

• [EN] SMALL MOLECULE INHIBITORS OF PI3-KINASE SIGNALING<br/>[FR] INHIBITEURS À PETITE MOLÉCULE DE LA SIGNALISATION PI3-KINASE
  申请人：UNIV TUFTS

  公开号：WO2014153337A3

  公开（公告）日：2014-12-31
• SMALL MOLECULE INHIBITORS OF PI3-KINASE SIGNALING
  申请人：TUFTS UNIVERSITY

  公开号：US20160297777A1

  公开（公告）日：2016-10-13

  Provided are certain 1,2,3-triazole and 1,2,3-triazole dimer analogs of DM-PIT-1 which are second-generation selective non-phosphoinositide small molecule inhibitors of phosphatidylinositol-3,4,5-trisphosphate (PIP3), including 1,2,3-triazoles represented by formula (I) where: Ar represents aryl or heteroaryl; X represents O or S; each of R a , R b , R c , and R d independently represents hydrogen, halogen, C 1 -C 10 alkyl, —OH, —CF 3 , aryl, amino, or nitro; and Ar is optionally substituted with one or more substituents independently selected from the group consisting of halogen, C 1 -C 10 alkyl, —OH, —CF 3 , amino, and nitro. Also provided are pharmaceutical compositions comprising compounds of the invention and a pharmaceutical carrier. Also provided are methods of inhibiting PIP3-mediated signaling in a cell and treating cancer using compounds of the invention.
• US9701646B2
  申请人：——

  公开号：US9701646B2

  公开（公告）日：2017-07-11
• Optimization of the anti-cancer activity of the phosphatidylinositol-3 kinase pathway inhibitor PITENIN-1: switching thiourea with 1,2,3-triazole
  作者：Yadagiri Kommagalla、Sinziana Cornea、Robert Riehle、Vladimir Torchilin、Alexei Degterev、Chepuri V. Ramana

  DOI：10.1039/c4md00109e

  日期：——

  We previously reported encouraging in vitro and in vivo anti-cancer activity of N-((3-chloro-2-hydroxy-5-nitrophenyl)carbamothioyl)benzamide (termed PITENIN-1). In the current work, we describe the structure–activity relationship study of the PIT-1 series, based on the replacement of a central thiourea unit with 1,2,3-triazole, which leads to increased liver microsomal stability, drug likeness and toxicity towards cancer cells.

  我们曾报道过 N-((3-氯-2-羟基-5-硝基苯基)氨基硫酰基)苯甲酰胺（称为 PITENIN-1）令人鼓舞的体外和体内抗癌活性。在目前的工作中，我们描述了 PIT-1 系列的结构-活性关系研究，其基础是用 1,2,3-三唑取代中央硫脲单元，从而提高肝微粒体稳定性、药物相似性和对癌细胞的毒性。