3-phenyl-6-p-toluidinopyridazine | 350984-86-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-phenyl-6-p-toluidinopyridazine
• 英文别名: N-(4-methylphenyl)-6-phenylpyridazin-3-amine
• CAS: 350984-86-0
• 化学式: C₁₇H₁₅N₃
• 分子量: 261.326
• InChiKey: ZPLVSSDWNAIHQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯化铑(三水) 、 3-phenyl-6-p-toluidinopyridazine 以 乙二醇甲醚 为溶剂， 以37%的产率得到(3-phenyl-6-p-toluidinopyridazinato)2rhodium(III) chloride hydrate
  参考文献：
  名称：

  Cyclometallation of 3-phenyl-6-p-toluidinopyridazine forming a six-membered auracycle and a five-membered palladacycle certified by X-ray analysis

  摘要：

  3-Phenyl-6-p-toluidinopyridazine (abbreviated as Hptp) was prepared as an ambidentate substrate of cyclometallation. Sodium tetrachloroaurate(III), gold(III) bromide, lithium tetrachloropalladate(II), and rhodium(III) chloride cyclometallated Hptp to give [Au(ptp)Cl-2], [Au(ptp)Br-2] [Pd(ptp)Cl], and [Rh(ptp)(2)Cl], respectively. These complexes and [Pd(ptp)Cl(PBu3)] (PBu3 = tri-n-butylphosphine) were characterized spectroscopically. The square-planar structures of [Au(ptp)Br-2]. (CH3)(2)SO and [Pd(ptp)Cl(PBu3)]. CH3OH were determined by X-ray analysis. Cycloauration preferred forming a six-membered metallacycle while cyclopalladation and cyclorhodation formed five-membered metallacycles. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0277-5387(01)00912-3
• 作为产物：
  描述：

  乙烷,三氯氟- 在 bis-triphenylphosphine-palladium(II) chloride 、 水 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 1.5h， 生成 3-phenyl-6-p-toluidinopyridazine
  参考文献：
  名称：

  Synthesis and biological activity of aminophthalazines and aminopyridazines as novel inhibitors of PGE2 production in cells

  摘要：

  This Letter reports the synthesis and biological evaluation of a collection of aminophthalazines as a novel class of compounds capable of reducing production of PGE(2) in HCA-7 human adenocarcinoma cells. A total of 28 analogs were synthesized, assayed for PGE2 reduction, and selected active compounds were evaluated for inhibitory activity against COX-2 in a cell free assay. Compound 2xxiv (R-1 = H, R-2 = p-CH3O) exhibited the most potent activity in cells (EC50 = 0.02 mu M) and minimal inhibition of COX-2 activity (3% at 5 mu M). Furthermore, the anti-tumor activity of analog 2vii was analyzed in xenograft mouse models exhibiting good anti-cancer activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.030

文献信息

• Synthesis and biological activity of aminophthalazines and aminopyridazines as novel inhibitors of PGE2 production in cells
  作者：Federico Medda、Earlphia Sells、Hui-Hua Chang、Justin Dietrich、Shashi Chappeta、Breland Smith、Vijay Gokhale、Emmanuelle J. Meuillet、Christopher Hulme

  DOI：10.1016/j.bmcl.2012.11.030

  日期：2013.1

  This Letter reports the synthesis and biological evaluation of a collection of aminophthalazines as a novel class of compounds capable of reducing production of PGE(2) in HCA-7 human adenocarcinoma cells. A total of 28 analogs were synthesized, assayed for PGE2 reduction, and selected active compounds were evaluated for inhibitory activity against COX-2 in a cell free assay. Compound 2xxiv (R-1 = H, R-2 = p-CH3O) exhibited the most potent activity in cells (EC50 = 0.02 mu M) and minimal inhibition of COX-2 activity (3% at 5 mu M). Furthermore, the anti-tumor activity of analog 2vii was analyzed in xenograft mouse models exhibiting good anti-cancer activity. (C) 2012 Elsevier Ltd. All rights reserved.
• Cyclometallation of 3-phenyl-6-p-toluidinopyridazine forming a six-membered auracycle and a five-membered palladacycle certified by X-ray analysis
  作者：Matsuo Nonoyama、Kiyohiko Nakajima、Kiyoko Nonoyama

  DOI：10.1016/s0277-5387(01)00912-3

  日期：2001.11

  3-Phenyl-6-p-toluidinopyridazine (abbreviated as Hptp) was prepared as an ambidentate substrate of cyclometallation. Sodium tetrachloroaurate(III), gold(III) bromide, lithium tetrachloropalladate(II), and rhodium(III) chloride cyclometallated Hptp to give [Au(ptp)Cl-2], [Au(ptp)Br-2] [Pd(ptp)Cl], and [Rh(ptp)(2)Cl], respectively. These complexes and [Pd(ptp)Cl(PBu3)] (PBu3 = tri-n-butylphosphine) were characterized spectroscopically. The square-planar structures of [Au(ptp)Br-2]. (CH3)(2)SO and [Pd(ptp)Cl(PBu3)]. CH3OH were determined by X-ray analysis. Cycloauration preferred forming a six-membered metallacycle while cyclopalladation and cyclorhodation formed five-membered metallacycles. (C) 2001 Published by Elsevier Science Ltd.