N-(3-bromopropyl)-4-chlorobenzenesulfonamide | 161826-98-8

• 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: N-(3-bromopropyl)-4-chlorobenzenesulfonamide
• CAS: 161826-98-8
• 化学式: C₉H₁₁BrClNO₂S
• 分子量: 312.615
• InChiKey: SEVVUFXNDVQBBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-bromopropyl)-4-chlorobenzenesulfonamide 在 caesium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80.5%的产率得到1-(4-chlorobenzenesulfonyl)azetidine
  参考文献：
  名称：

  Synthesis and characterization ofN-arylsulfonylazetidines

  摘要：

  Abstractmagnified imageA convenient method for the synthesis of N‐arylsulfonyl azetidines using N‐(3‐bromopropyl)‐arylsulfonamide with cesium carbonate and potassium iodide in DMF is reported. The reaction conditions are optimized and seven N‐arylsulfonyl azetidines have been synthesized in good yield using this method. The structures of compounds 2a and 2e were determined by X‐ray crystallography.

  DOI：

  10.1002/jhet.5570450449
• 作为产物：
  描述：

  3-溴丙胺氢溴酸盐 、 4-氯苯磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到N-(3-bromopropyl)-4-chlorobenzenesulfonamide
  参考文献：
  名称：

  A Convergent Synthesis of CGS23305, A Thromboxane Synthase Inhibitor

  摘要：

  发现了 CGS23305 的聚合合成方法。吡啶醛中间体 5 的合成路线从四个步骤缩减为两个步骤。通过 N,N-二乙烯胺 6 与丙烯酸乙酯的 Miachel 加成，吡啶醛被转化为关键的吡啶醛酯中间体 7。利用多功能分子 19 进行维蒂希烯化反应，完成了碳键的组装。通过氢化和水解，从 14（6 个步骤）中得到了 CGS23305，总收率为 44%。

  DOI：

  10.1055/s-1999-3458

文献信息

• Synthesis and evaluation of tetrahydroquinolin-2(1H)-one derivatives as novel anti-pancreatic cancer agents via targeting autophagy
  作者：Qi Shen、Jie Wang、Chen-Xi Liu、Wei Cui、Lei Zhang、Yu-chao Zhang、Yue Wang、Jing Wu、Jian-Xin Li

  DOI：10.1016/j.ejmech.2019.03.013

  日期：2019.5

  strategies are urgently needed. During a project aiming at discovery of anticancer agents, we performed a structure modification on polycyclic polyprenylated acylphloroglucinols (PPAPs) skeleton, and discovered that PPAP rearranged to a tetrahydroquinolin-2(1H)-one feature. Here, series of tetrahydroquinolin-2(1H)-one derivatives were designed, synthesized and evaluated against a highly metastatic human

  胰腺癌是最致命的肿瘤之一，由于其对营养饥饿的显着耐受性，其5年生存率不到6％，因此迫切需要新的药物和治疗策略。在一个旨在发现抗癌药的项目中，我们对多环多亚丙基化酰基间苯三酚（PPAP）骨架进行了结构修饰，并发现PPAP重排为四氢喹啉2（1 H）-一个特征。在此，设计，合成和评估了一系列四氢喹啉-2（1 H）-one衍生物对高转移性人胰腺癌细胞系（PANC-1）的构效关系。其中，衍生物11k对IC表现出最强的抑制活性营养剥夺条件下4.9μM的50值。相比之下，所有这些衍生物在正常营养条件下对PANC-1细胞均显示出低细胞毒性，这表明这些衍生物似乎具有替代的肿瘤细胞死亡机制，并导致毒性更低。进一步的评估表明，在营养缺乏的条件下，11k减少了菌落的形成并诱导了PANC-1的凋亡，并呈浓度依赖性。在体内研究中，11k显着抑制了裸鼠的肿瘤发展和体重。初步机理研究表明，11k明显下调了LC3-II的表
• PREVENTIVE OR THERAPEUTIC DRUGS FOR DIABETES
  申请人：SHIONOGI & CO., LTD.

  公开号：EP1190710A1

  公开（公告）日：2002-03-27

  A composition for use as a preventive or therapeutic agent for diabetes, containing a compound of the formula (I): wherein, A is optionally substituted aryl or optionally substituted heteroaryl; B is lower alkyl, optionally substituted aryl and the like; X1 is -O-, -S-, or -N Ra- wherein Ra is hydrogen or lower alkyl; X2 is -NRbCO-, -CONRb-, -NRbCONRb-, -SO2-, -NRbSO2-, -D-, -D-O-, -D-CO-, -D-SO2-, -D-NRbCO- or -D- NRbSO2- wherein D is a divalent heterocyclic group; Rb is hydrogen or optionally substituted lower alkyl; m is an integer of 0 to 3; n is an integer of 2 to 5.

  一种用作糖尿病预防或治疗剂的组合物，含有式（I）化合物： 其中，A 是任选取代的芳基或任选取代的杂芳基；B 是低级烷基、任选取代的芳基等；X1 是-O-、-S-或-N Ra-，其中 Ra 是氢或低级烷基；X2是-NRbCO-、-CONRb-、-NRbCONRb-、-SO2-、-NRbSO2-、-D-、-D-O-、-D-CO-、-D-SO2-、-D-NRbCO-或-D- NRbSO2-，其中 D 是二价杂环基团；Rb 是氢或任选取代的低级烷基；m 是 0 至 3 的整数； n 是 2 至 5 的整数。
• Synthesis and activities of new arylsulfonamido thromboxane A2 receptor antagonists
  作者：E Sartori、F Camy、JM Teulon、F Caussade、A Virone-Oddos、A Cloarec

  DOI：10.1016/0223-5234(93)90093-t

  日期：1993.1

  New benzoic, benzeneacetic and thiazole-4-acetic acids bearing an arylsulfonamido alkyl or alkylhetero side chain were synthesized and tested in vitro for affinity for human platelet thromboxane A2 receptors and inhibition of U46619-induced rat aortic ring contraction. Influence of substitution patterns, chain length and presence of heteroatoms were studied and compounds within a 30 nmol range for inhibition of U46619-induced contractions were found. One of the most potent, 2-[(4-chloro-benzenesulfonylamino-ethyl)thio] thiazole-4-acetic acid (VII-4) was orally active (1 mg/kg), as evidenced by the inhibition of U46619-induced platelet aggregation in guinea pigs, ex vivo.
• In silico identification, design and synthesis of novel piperazine-based antiviral agents targeting the hepatitis C virus helicase
  作者：Marcella Bassetto、Pieter Leyssen、Johan Neyts、Mark M. Yerukhimovich、David N. Frick、Matthew Courtney-Smith、Andrea Brancale

  DOI：10.1016/j.ejmech.2016.10.043

  日期：2017.1

  A structure-based virtual screening of commercial compounds was carried out on the HCV NS3 helicase structure, with the aim to identify novel inhibitors of HCV replication. Among a selection of 13 commercial structures, one compound was found to inhibit the subgenomic HCV replicon in the low micromolar range. Different series of new piperazine-based analogues were designed and synthesised, and among them, several novel structures exhibited antiviral activity in the HCV replicon assay. Some of the new compounds were also found to inhibit HCV NS3 helicase function in vitro, and one directly bound NS3 with a dissociation constant of 570 +/- 270 nM. (C) 2016 Elsevier Masson SAS. All rights reserved.
• EP1190710
  申请人：——

  公开号：——

  公开（公告）日：——