2-(bromoacetylamino)benzonitrile | 64377-70-4

• 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: 2-(bromoacetylamino)benzonitrile
• 英文别名: 2-bromo-N-(2-cyanophenyl)acetamide；2-Bromo-N-(2-cyanophenyl)acetamid；N-(2-cyanophenyl)bromoacetamide
• CAS: 64377-70-4
• 化学式: C₉H₇BrN₂O
• 分子量: 239.071
• InChiKey: NSEJRXVQAYTDSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(bromoacetylamino)benzonitrile 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Dicationic 2-fluorenonylcarbapenems: Potent anti-MRS agents with improved solubility and pharmacokinetic properties

  摘要：

  The synthesis and biological evaluation of a series of dicationic-substituted 2-fluorenonylcarbapenems is described. This class of compounds showed enhanced water solubility while maintaining potent activity against MRS. Introduction of a beta 1--methyl substituent was found to improve pharmacokinetics. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00567-3
• 作为产物：
  描述：

  2-氨基苯甲腈 以24%的产率得到
  参考文献：
  名称：

  PEET N. P.; SUNDER S., J. HETEROCYCL. CHEM. , 1977, 14, NO 4, 561-566

  摘要：

  DOI：

文献信息

• Fragment hopping-based discovery of novel sulfinylacetamide-diarylpyrimidines (DAPYs) as HIV-1 nonnucleoside reverse transcriptase inhibitors
  作者：Sheng Han、Yali Sang、Yan Wu、Yuan Tao、Christophe Pannecouque、Erik De Clercq、Chunlin Zhuang、Fen-Er Chen

  DOI：10.1016/j.ejmech.2019.111874

  日期：2020.1

  fragment hopping approach is widely applied in drug development. A series of diarylpyrimidines (DAPYs) were obtained by hopping the thioacetamide scaffold to novel human immunodeficiency virus type 1 (HIV-1) nonnucleoside reverse transcriptase inhibitors (NNRTIs) to address the cytotoxicity issue of Etravirine and Rilpivirine. Although the new compounds (11a-l) in the first-round optimization possessed less

  片段跳跃法被广泛应用于药物开发中。通过将硫代乙酰胺支架跳至新型人类免疫缺陷病毒1型（HIV-1）非核苷逆转录酶抑制剂（NNRTIs），可以解决一系列的二芳基嘧啶（DAPYs），从而解决了依特韦林和利吡韦林的细胞毒性问题。尽管在第一轮优化中的新化合物（11a-1）具有较弱的抗病毒活性，但它们显示出低得多的细胞毒性。对硫的进一步优化导致亚磺酰基乙酰胺-DAPYs表现出改善的抗病毒活性和更高的选择性指数，尤其是对K103N突变株。最有效的化合物12a对WT的EC50值为0.0249μM，对K103N突变株的EC50值为0.0104μM，细胞毒性低（CC50> 221μM）和高选择性指数（SI WT> 8873，SI K103N> 21186）。此外，该化合物在物种间显示出良好的体外微粒体稳定性。计算研究预测了这些有效化合物与HIV-1逆转录酶的结合模型，从而为新进展提供了进一步的见识。
• Design, synthesis, and biological evaluation of aromatic tertiary amine derivatives as selective butyrylcholinesterase inhibitors for the treatment of Alzheimer's disease
  作者：Xin Lu、Nan Qin、Yijun Liu、Chenxi Du、Feng Feng、Wenyuan Liu、Yao Chen、Haopeng Sun

  DOI：10.1016/j.ejmech.2022.114729

  日期：2022.12

  strategy for AD. Previously, an aromatic tertiary amine derivative (S17–1001) was screened and validated as a selective BChE inhibitor. Structured-based molecular modification guided the synthesis of 43 analogs. Biological test of cholinesterase inhibition, in vitro blood brain barrier permeation assay, neurotoxicity assay and neuroprotective effects assay indicated two optimal compounds 17c and 19c

  丁酰胆碱酯酶（BChE）最近被认为是进展性阿尔茨海默病（AD）的生物标志物，选择性BChE抑制剂的开发引起了极大的兴趣，可能是AD的可行治疗策略。此前，一种芳香叔胺衍生物 ( S17 – 1001 ) 被筛选并验证为选择性 BChE 抑制剂。基于结构的分子修饰指导了 43 种类似物的合成。胆碱酯酶抑制生物学试验、体外血脑屏障渗透试验、神经毒性试验和神经保护作用试验表明两种最佳化合物17c和19c。两种化合物均显示选择性 BChE 抑制 ( h BChE < 20 nM,ee AChE > 10 μM），良好的 BBB 渗透性和原代细胞安全性。此外，17c可以剂量反应保护细胞免受 Aβ 1-42诱导的损伤。它还证明了17c和19c在体内测试中能够恢复认知障碍。这些数据表明，17c和19c代表了在针对 AD 的药物发现过程中进行后续跟踪的有希望的候选者。
• Synthesis and biological evaluations of sulfanyltriazoles as novel HIV-1 non-nucleoside reverse transcriptase inhibitors
  作者：Zhiwei Wang、Baogen Wu、Kelli L. Kuhen、Badry Bursulaya、Truc N. Nguyen、Deborah G. Nguyen、Yun He

  DOI：10.1016/j.bmcl.2006.05.096

  日期：2006.8

  A novel sulfanyltriazole was discovered as an HIV-1 non-nucleoside reverse transcriptase inhibitor via HTS using a cell-based assay. Chemical modifications and molecular modeling studies were carried out to establish its SAR and understand its interactions with the enzyme. These modifications led to the identification of sulfanyltriazoles with low nanomolar potency for inhibiting HIV-1 replication and promising activities against selected NNRTI resistant mutants. These novel and potent sulfanyltriazoles could serve as advanced leads for further optimization. (c) 2006 Elsevier Ltd. All rights reserved.
• THIONAPHTHALENE DERIVATIVES, METHOD OF PRODUCING THE SAME, AND ANTIALLERGIC AGENT CONTAINING THE SAME
  申请人：TEIJIN LIMITED

  公开号：EP0419676B1

  公开（公告）日：1994-12-07
• 3-Amino-2(1H)-quinolones by Cyclizaion of N-Acylated Anthranilic Acid Derivatives
  作者：Matthias Rehwald、Karl Gewald、Hans-Joachim Lankau、Klaus Unverferth

  DOI：10.3987/com-96-7700

  日期：——

  Reaction of secondary amines with the N-(iodoacetyl)anthranilic acid derivatives, 2-(iodoacetylamino)acetophenone and 2-(iodoacetylamino)benzophenone yields 3-amino-2(1H)-quinolones in two steps. Analogously heterocondensed 5-amino-6(7H)-pyrazolo[5,4-b]pyridones were prepared. Hydroxyquinolines were subjected to Cl/OH exchange to give chloroquinolines, which are convenient for consecutive reactions.