2,4-bis(4-bromophenyl)-2,7-dimethyl-2,3-dihydro-1H-benzo[b][1,4]diazepine

• 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: 2,4-bis(4-bromophenyl)-2,7-dimethyl-2,3-dihydro-1H-benzo[b][1,4]diazepine
• 英文别名: 2,4-bis(4-bromophenyl)-2,3-dihydro-2,7-dimethyl-1H-1,5-benzodiazepine；2,4-Bis(4-bromophenyl)-2,7-dimethyl-1,3-dihydro-1,5-benzodiazepine
• 化学式: C₂₃H₂₀Br₂N₂
• 分子量: 484.233
• InChiKey: MOKVMCQJYVGRRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4-溴苯基)乙炔 、 3,4-二氨基甲苯 在 mercuric triflate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2,4-bis(4-bromophenyl)-2,7-dimethyl-2,3-dihydro-1H-benzo[b][1,4]diazepine 、 2,4-bis(4-bromophenyl)-2,3-dihydro-2,8-dimethyl-1H-1,5-benzodiazepine
  参考文献：
  名称：

  Terminal alkynes as keto-methyl equivalent toward one pot synthesis of 1,5-benzodiazepine derivatives under catalysis of Hg(OTf)2

  摘要：

  Mercuric triflate catalyzes the reaction between 1,2-diaminobenzene and terminal alkynes to afford 2,4-disubstituted 2-methyl-2,3-dihydro-1H-benzo[b][1,4]diazepine in an excellent yield. The terminal alkynes function as a source of keto-methyl equivalent. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.036

文献信息

• A green and sustainable approach for the synthesis of 1,5-benzodiazepines and spirooxindoles in one-pot using a MIL-101(Cr) metal–organic framework as a reusable catalyst
  作者：Fillip Kumar Sarkar、Ajay Gupta、Ramen Jamatia、Jasha Momo H. Anal、Amarta Kumar Pal

  DOI：10.1039/d1nj03176g

  日期：——

  MIL-101(Cr) has been efficiently utilized for the synthesis of biologically relevant heterocycles such as 1,5-benzodiazepines and spirooxindoles in one-pot. MIL-101(Cr) was prepared via a solvothermal method and characterized by FT-IR, PXRD, SEM, TEM, EDX, and ICP-OES analysis. Thermogravimetric analysis (TGA) described its high thermal stability. Low catalyst loading, easy separation, reusability, and high

  金属-有机骨架 MIL-101(Cr) 已被有效地用于合成生物相关的杂环，如 1,5-苯二氮卓类和螺环吲哚。MIL-101(Cr) 是通过溶剂热法制备的，并通过 FT-IR、PXRD、SEM、TEM、EDX 和 ICP-OES 分析进行表征。热重分析 (TGA) 描述了其高热稳定性。低催化剂负载、易于分离、可重复使用和高产率是该协议的一些显着特点。无溶剂反应条件 (SFRC) 或水作为溶剂是绿色和可持续工艺开发领域的一些额外优势。
• Synthesis and inhibition studies towards the discovery of benzodiazepines as potential antimalarial compounds
  作者：Drista Sharma、Abhishek Pareek、Hemant Arya、Rani Soni、Praveen Rai、Akhil Agrawal、Surendra Nimesh、Diwakar Kumar、Srinivasarao Yaragorla、Tarun Kumar Bhatt

  DOI：10.1016/j.exppara.2022.108411

  日期：2022.12

  apicoplast in the survival of the parasite. In this study, we present the rational design strategy employing sustainable catalysis for the synthesis of benzodiazepine (BDZ) conformers followed by their biological evaluation as prospective inhibitors against the potential target of the IPP pathway, 1-deoxy-D-xylulose-5-phosphatereductoisomerase (DXR). The study reported the inhibitory profile of 8c and 6d

  基于靶标的针对顶端质体（一种非常重要的细胞器）的治疗方法的发现是一个压倒一切的观点。MEP 通路是一种经认可的药物靶标，可深入了解顶端体在寄生虫生存中的重要性。在这项研究中，我们提出了采用可持续催化合成苯并二氮卓 (BDZ) 构象异构体的合理设计策略，然后将其作为针对 IPP 途径潜在靶标 1-脱氧-D-木酮糖-5-磷酸还原异构酶的前瞻性抑制剂进行生物学评估(DXR)。该研究报告了 8c 和 6d 对寄生虫发育红细胞阶段唯一药物靶标的典型步骤的抑制作用。
• Insuasty, Braulio; Abonia, Rodrigo; Quiroga, Jairo, Journal of Heterocyclic Chemistry, 1993, vol. 30, # 1, p. 229 - 231
  作者：Insuasty, Braulio、Abonia, Rodrigo、Quiroga, Jairo、Meier, Herbert

  DOI：——

  日期：——
• Quiroga, J.; Insuasty, B.; Abonia, R., Journal of Heterocyclic Chemistry, 1994, vol. 31, # 4, p. 813 - 818
  作者：Quiroga, J.、Insuasty, B.、Abonia, R.、Baumann, W.

  DOI：——

  日期：——
• Terminal alkynes as keto-methyl equivalent toward one pot synthesis of 1,5-benzodiazepine derivatives under catalysis of Hg(OTf)2
  作者：Gourhari Maiti、Utpal Kayal、Rajiv Karmakar、Rudraksha N. Bhattacharya

  DOI：10.1016/j.tetlet.2012.01.036

  日期：2012.3

  Mercuric triflate catalyzes the reaction between 1,2-diaminobenzene and terminal alkynes to afford 2,4-disubstituted 2-methyl-2,3-dihydro-1H-benzo[b][1,4]diazepine in an excellent yield. The terminal alkynes function as a source of keto-methyl equivalent. (C) 2012 Elsevier Ltd. All rights reserved.