4-(2-chlorophenyl)methyl-1-(2H)-phthalazinone | 888494-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-(2-chlorophenyl)methyl-1-(2H)-phthalazinone
• 英文别名: 4-(2-chlorobenzyl)phthalazin-1(2H)-one；4-[(2-chlorophenyl)methyl]-2H-phthalazin-1-one
• CAS: 888494-47-1
• 化学式: C₁₅H₁₁ClN₂O
• 分子量: 270.718
• InChiKey: NXXMGRASOYMKFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-chlorophenyl)methyl-1-(2H)-phthalazinone 、 3-溴丙烯 在 potassium carbonate 作用下， 生成 2-Allyl-4-(2-chloro-benzyl)-2H-phthalazin-1-one
  参考文献：
  名称：

  Vasorelaxant activity of phthalazinones and related compounds

  摘要：

  Several series of dihydrostilbenamide, imidazo[2,1-a]isoindole, pyrimido[2,1-a]isoindole and phthalazinone derivatives were obtained and their vasorelaxant activity was measured on isolated rat aorta rings pre-contracted with phenylephrine (10(-5) M). Some phthalazinones attained, practically, the total relaxation of the organ at micromolar concentrations. For the most potent compound 9h (EC50 = 0.43 mu M) the affinities for alpha(1A), alpha(1B) and alpha(1D) adrenergic sub-receptors were determined. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.02.003
• 作为产物：
  描述：

  (2Z) 2-(1-(2-chlorophenyl)methylene)benzofuran-3(2H)-one 在 肼 作用下， 以93%的产率得到4-(2-chlorophenyl)methyl-1-(2H)-phthalazinone
  参考文献：
  名称：

  Anti-HIV activity of stilbene-related heterocyclic compounds

  摘要：

  Viral transcription has not been routinely targeted in the development of new antiviral drugs. This crucial step of the viral cycle depends on the concerted action of cellular and viral proteins such as NF-kappa B and Tat. In the present study, stilbene-related heterocyclic compounds including benzalphthalide, phthalazinone, imidazoindole and pyrimidoisoindole derivatives are tested for their anti-HIV activity. Original assays based on recombinant viruses were used to evaluate HIV replication inhibition and stably transfected cell lines were used to evaluate inhibition of Tat and NF-kappa B proteins. Some of the stilbene-related heterocyclic compounds analysed displayed anti-HIV activity through interference with NF-kappa B and Tat function. Moreover, compounds inhibiting both targets displayed a stronger activity on viral replication. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.087

文献信息

• Design and synthesis of 4-benzyl-1-(2H)-phthalazinone derivatives as novel androgen receptor antagonists
  作者：Kazumi Inoue、Ko Urushibara、Misae Kanai、Kei Yura、Shinya Fujii、Mari Ishigami-Yuasa、Yuichi Hashimoto、Shuichi Mori、Emiko Kawachi、Mio Matsumura、Tomoya Hirano、Hiroyuki Kagechika、Aya Tanatani

  DOI：10.1016/j.ejmech.2015.08.002

  日期：2015.9

  differentiation, growth, and maintenance of male reproductive organs, and also has effects on hair and skin. In this paper, we report the synthesis of nonsteroidal AR antagonists having a 4-benzyl-1-(2H)-phthalazinone skeleton. Among the synthesized compounds, 11c with two ortho-substituents on the phenyl group potently inhibited SC-3 cell proliferation (IC50: 0.18 μM) and showed high wt AR-binding affinity

  雄激素受体（AR）在多种生理功能（包括男性生殖器官的分化，生长和维持）中起着重要作用，并且对头发和皮肤也有影响。在本文中，我们报告了具有4-苄基-1-（2 H）-酞嗪酮骨架的非甾体类AR拮抗剂的合成。在合成的化合物中，在苯基上带有两个邻位取代基的11c可以有效抑制SC-3细胞增殖（IC 50：0.18μM），并表现出与羟基氟他胺相当的高AR结合亲和力（IC 50：10.9μM）。 （3）。化合物11c还抑制了含有T877A突变的AR的LNCaP细胞的增殖。与AR配体结合域对11c的对接研究表明，苄基对拮抗作用很重要。这些酞嗪酮衍生物可用于研究AR拮抗剂的潜在临床应用。
• Anti-HIV activity of stilbene-related heterocyclic compounds
  作者：Luis M. Bedoya、Esther del Olmo、Rocío Sancho、Bianca Barboza、Manuela Beltrán、Ana E. García-Cadenas、Sonsoles Sánchez-Palomino、José L. López-Pérez、Eduardo Muñoz、Arturo San Feliciano、José Alcamí

  DOI：10.1016/j.bmcl.2006.04.087

  日期：2006.8

  Viral transcription has not been routinely targeted in the development of new antiviral drugs. This crucial step of the viral cycle depends on the concerted action of cellular and viral proteins such as NF-kappa B and Tat. In the present study, stilbene-related heterocyclic compounds including benzalphthalide, phthalazinone, imidazoindole and pyrimidoisoindole derivatives are tested for their anti-HIV activity. Original assays based on recombinant viruses were used to evaluate HIV replication inhibition and stably transfected cell lines were used to evaluate inhibition of Tat and NF-kappa B proteins. Some of the stilbene-related heterocyclic compounds analysed displayed anti-HIV activity through interference with NF-kappa B and Tat function. Moreover, compounds inhibiting both targets displayed a stronger activity on viral replication. (c) 2006 Elsevier Ltd. All rights reserved.
• Vasorelaxant activity of phthalazinones and related compounds
  作者：Esther del Olmo、Bianca Barboza、Ma Inés Ybarra、José Luis López-Pérez、Rosalía Carrón、Ma Angeles Sevilla、Cinthia Boselli、Arturo San Feliciano

  DOI：10.1016/j.bmcl.2006.02.003

  日期：2006.5

  Several series of dihydrostilbenamide, imidazo[2,1-a]isoindole, pyrimido[2,1-a]isoindole and phthalazinone derivatives were obtained and their vasorelaxant activity was measured on isolated rat aorta rings pre-contracted with phenylephrine (10(-5) M). Some phthalazinones attained, practically, the total relaxation of the organ at micromolar concentrations. For the most potent compound 9h (EC50 = 0.43 mu M) the affinities for alpha(1A), alpha(1B) and alpha(1D) adrenergic sub-receptors were determined. (C) 2006 Elsevier Ltd. All rights reserved.