3-(4-bromobenzoyl)benzonitrile | 1206248-37-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-bromobenzoyl)benzonitrile
• CAS: 1206248-37-4
• 化学式: C₁₄H₈BrNO
• 分子量: 286.128
• InChiKey: UUYQLMCLVPNUBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.86
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(4-bromobenzoyl)benzonitrile 在 重铬酸吡啶 、 二异丁基氢化铝 、 caesium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.0h， 生成 (3Z,6Z)-3-(3-(4-bromobenzoyl)benzylidene)-6-((5-tert-butyl-1H-imidazol-4-yl)methylene)piperazine-2,5-dione
  参考文献：
  名称：

  Synthesis and structure–activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents

  摘要：

  KPU-105 (4), a potent anti-microtubule agent that contains a benzophenone was derived from the dike-topiperazine-type vascular disrupting agent (VDA) plinabulin 3, which displays colchicine-like tubulin depolymerization activity. To develop derivatives with more potent anti-microtubule and cytotoxic activities, we further modified the benzophenone moiety of 4. Accordingly, we obtained a 4-fluorobenzophenone derivative 16j that inhibited tumor cell growth in vitro with a subnanomolar IC50 value against HT-29 cells (IC50 = 0.5 nM). Next, the effect of 16j on mitotic spindles was evaluated in HeLa cells. Treatment with 3 nM of 16j partially disrupted the interphase microtubule network. By contrast, treatment with the same concentration of CA-4 barely affected the microtubule network, indicating that 16j exhibited more potent anti-mitotic effects than did CA-4. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.059
• 作为产物：
  描述：

  4-溴苯甲酸 在 正丁基锂 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 3-(4-bromobenzoyl)benzonitrile
  参考文献：
  名称：

  Synthesis and structure–activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents

  摘要：

  KPU-105 (4), a potent anti-microtubule agent that contains a benzophenone was derived from the dike-topiperazine-type vascular disrupting agent (VDA) plinabulin 3, which displays colchicine-like tubulin depolymerization activity. To develop derivatives with more potent anti-microtubule and cytotoxic activities, we further modified the benzophenone moiety of 4. Accordingly, we obtained a 4-fluorobenzophenone derivative 16j that inhibited tumor cell growth in vitro with a subnanomolar IC50 value against HT-29 cells (IC50 = 0.5 nM). Next, the effect of 16j on mitotic spindles was evaluated in HeLa cells. Treatment with 3 nM of 16j partially disrupted the interphase microtubule network. By contrast, treatment with the same concentration of CA-4 barely affected the microtubule network, indicating that 16j exhibited more potent anti-mitotic effects than did CA-4. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.059

文献信息

• Kinetically Controlled, Highly Chemoselective Acylation of Functionalized Grignard Reagents with Amides by N−C Cleavage
  作者：Guangchen Li、Michal Szostak

  DOI：10.1002/chem.201904678

  日期：2020.1.13

  (iPrMgCl⋅LiCl) permits excellent substrate scope with respect to both the amide and Grignard coupling partners. These reactions enable facile, operationally simple and chemoselective access to tetrahedral intermediates from amides under significantly milder conditions than chelation-controlled intermediates. This novel direct two-component coupling sets the stage for using amides as acylating reagents

  在动力学控制下，通过高度化学选择性的NC裂解，已实现了酰胺与功能化格氏试剂的直接无过渡金属酰化反应。该方法提供了通过瞬态四面体中间体快速收敛的官能化联芳基酮的途径。通用的Turbo-Grignard试剂（iPrMgCl·LiCl）促进了通过原位卤素-镁交换而直接获得功能化Grignard试剂的优点，因此，相对于酰胺和Grignard偶合剂，都具有出色的底物范围。与螯合控制的中间体相比，这些反应能够在较温和的条件下从酰胺中轻松，操作简单且化学选择性地接近酰胺的四面体中间体。
• 一种作为BTK抑制剂的化合物及其制备方法和应用
  申请人：深圳海博为药业有限公司

  公开号：CN116554102A

  公开（公告）日：2023-08-08

  本发明提供了一种作为BTK抑制剂的化合物及其制备方法和应用；该化合物具有式I所示的结构，或其互变异构体、内消旋体、外消旋体、对映异构体、非对映异构体或其混合物形式、药学上可接受的水合物、溶剂化物或盐；其中，R1选自取代或非取代的C1‑C8烷基，取代或非取代的C3‑C10环烷基，取代或非取代的C1‑C8杂烷基，取代或非取代的3至10元杂环烷基，或，取代或非取代的芳基或杂环芳基；R3选自取代或非取代的芳基，或，取代或非取代的吡啶基；A、B独立地选自C、O、N、酰胺基或S；n为0、1、2、3或4；m为0、1或2。该化合物可用作BTK蛋白质激酶抑制剂，对BTK有较强的抑制性，且具有良好的药代动力学性质及血脑屏障透过率，有很好的应用前景。