1-benzyl-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one | 174399-44-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 1-benzyl-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
• 英文别名: 1-benzyl-5-phenyl-1H-1,4-benzodiazepin-2(3H)-one；1-benzyl-5-phenyl-3H-1,4-benzodiazepin-2-one
• CAS: 174399-44-1
• 化学式: C₂₂H₁₈N₂O
• 分子量: 326.398
• InChiKey: DOIVLCMBJTUYAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one 以 乙醇 、 二氯甲烷 为溶剂， 生成 (1-benzyl-5-phenyl-1H-1,4-benzodiazepin-2(3H)-one(-H))PdCl(triphenylphosphine)
  参考文献：
  名称：

  Synthesis and Evaluation of 5-Phenyl-1H-1,4-benzodiazepin-2(3H)-one-Based Palladium Complexes as Precatalysts in C−C Bond Forming Reactions

  摘要：

  The C-H activation of C-3-unsubstituted 1,4-benzodiazepin-2(3H)-ones (LH = 2a-c) (2a 1-methyl-5-phenyl-1H-1,4-benzodiazepin-2(3H)-one, 2b = 1-benzyl-5-phenyl-1H-1,4-benzodiazepin-2(3H)-one, 2c = benzyl-2-(2,3-dihydro-2-oxo-5-phenyl-1,4-benzodiazepin-1-yl)acetate) with Na2PdCl4 afforded the insoluble palladacycles [(L)PdCl](2) 3a-c. Treatment of the latter with triphenylphosphine afforded the soluble monomeric triphenylphosphine analogues [(L)Pd(PPh3)Cl] 4a-c. 1-Methyl-3-(2-(methylthio)ethyl)-5-phenyl-1H-1,4-benzodiazepin-2(3H)-one (LH = 2d) reacted with Na2PdCl4 or with PdCl2(MeCN)(2) to afford the monomeric cis-S-N-coordinated complex 5d of the type [(LH)PdCl2]. 34(tert-Butylthio)methyl)-1-methyl-5-phenyl-1H-1,4-benzodiazepin-2(3H)-one, 2e, reacted with Pd(OAc)(2) in acetic acid and, following LiCl metathesis, yielded the monomeric cis-S-N-bound pincer palladacycle 6f. X-ray structures of 5d and 4a have been determined. 3a and 6f were found to be effective precatalysts for Suzuki coupling reactions, and 3a, 3c, and 4a were effective precatalysts in Heck couplings across a range of substrates.

  DOI：

  10.1021/om0506623
• 作为产物：
  描述：

  溴甲苯 、 1,3-二氢-5-苯基-1,4-苯并二氮杂卓-2-酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以40 %的产率得到1-benzyl-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
  参考文献：
  名称：

  基于地西泮的 GPX4 共价修饰剂诱导肝癌细胞铁死亡

  摘要：

  由于全球癌症发病率迅速上升，需要开发结构和机制独特的新化疗药物。在这里，我们报告了不可逆的硫醇反应性地西泮衍生物的鉴定，作为肝癌细胞中 GPX4 修饰剂和纳摩尔铁死亡诱导剂。

  DOI：

  10.1039/d3cc06215e

文献信息

• Synthesis and Evaluation of 5-Phenyl-1<i>H</i>-1,4-benzodiazepin-2(3<i>H</i>)-one-Based Palladium Complexes as Precatalysts in C−C Bond Forming Reactions
  作者：John Spencer、David P. Sharratt、Jairton Dupont、Adriano L. Monteiro、Vinicius I. Reis、Marcelo P. Stracke、Frank Rominger、Iain M. McDonald

  DOI：10.1021/om0506623

  日期：2005.11.1

  The C-H activation of C-3-unsubstituted 1,4-benzodiazepin-2(3H)-ones (LH = 2a-c) (2a 1-methyl-5-phenyl-1H-1,4-benzodiazepin-2(3H)-one, 2b = 1-benzyl-5-phenyl-1H-1,4-benzodiazepin-2(3H)-one, 2c = benzyl-2-(2,3-dihydro-2-oxo-5-phenyl-1,4-benzodiazepin-1-yl)acetate) with Na2PdCl4 afforded the insoluble palladacycles [(L)PdCl](2) 3a-c. Treatment of the latter with triphenylphosphine afforded the soluble monomeric triphenylphosphine analogues [(L)Pd(PPh3)Cl] 4a-c. 1-Methyl-3-(2-(methylthio)ethyl)-5-phenyl-1H-1,4-benzodiazepin-2(3H)-one (LH = 2d) reacted with Na2PdCl4 or with PdCl2(MeCN)(2) to afford the monomeric cis-S-N-coordinated complex 5d of the type [(LH)PdCl2]. 34(tert-Butylthio)methyl)-1-methyl-5-phenyl-1H-1,4-benzodiazepin-2(3H)-one, 2e, reacted with Pd(OAc)(2) in acetic acid and, following LiCl metathesis, yielded the monomeric cis-S-N-bound pincer palladacycle 6f. X-ray structures of 5d and 4a have been determined. 3a and 6f were found to be effective precatalysts for Suzuki coupling reactions, and 3a, 3c, and 4a were effective precatalysts in Heck couplings across a range of substrates.
• Diazepam-based covalent modifiers of GPX4 induce ferroptosis in liver cancer cells
  作者：Dharmendra K. Yadav、Sona Tiwari、Sathyapriya Senthil、Sai Kumari Vechalapu、Santhosh Duraisamy、Viral Rawat、Mohammed Isfahur Rahman、Shweta Khanna、Dharmaraja Allimuthu

  DOI：10.1039/d3cc06215e

  日期：——

  chemotherapeutics that are structurally and mechanistically unique is needed due to the rapid rise of the cancer incidence across the globe. Here, we report the identification of irreversible, thiol-reactive diazepam derivatives as GPX4 modifiers and nanomolar inducers of ferroptosis in liver cancer cells.

  由于全球癌症发病率迅速上升，需要开发结构和机制独特的新化疗药物。在这里，我们报告了不可逆的硫醇反应性地西泮衍生物的鉴定，作为肝癌细胞中 GPX4 修饰剂和纳摩尔铁死亡诱导剂。