4-(2-溴乙氧基)苯磺酰胺 | 125174-28-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(2-溴乙氧基)苯磺酰胺
• 英文名称: 4-(2-bromo-ethoxy)-benzenesulfonamide
• 英文别名: 4-(2-Bromoethoxy)benzenesulfonamide
• CAS: 125174-28-9
• 化学式: C₈H₁₀BrNO₃S
• mdl: MFCD07329990
• 分子量: 280.142
• InChiKey: CYGFGUSYYFANTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-溴乙氧基)苯磺酰胺 在 sodium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 24.17h， 生成 1-cyclohexyl-3-[4-(2-piperidin-1-ylethoxy)benzene]sulfonylurea
  参考文献：
  名称：

  Novel sulfonylurea derivatives as H3 receptor antagonists. Preliminary SAR studies

  摘要：

  The combination of antagonism at histamine H-3 receptor and the stimulation of insulin secretion have been proposed as an approach to new dual therapeutic agents for the treatment of type 2 diabetes mellitus associated with obesity. We have designed and synthesized a new series of non-imidazole derivatives, based on a basic amine ring connected through an alkyl spacer of variable length to a phenoxysulfonylurea moiety. These compounds were initially evaluated for histamine H-3 receptor binding affinities, suggesting that a propoxy chain linker between the amine and the core ring could be essential for optimal binding affinity. Compound 56, 1-(naphthalen-1-yl)-3-[(p-(3-pyrrolidin-1-ylpropoxy) benzene)]sulfonylurea exhibited the best H-3 antagonism affinity. However, since all these derivatives failed to block K-ATP channels, the link of these two related moieties should not be considered a good pharmacophore for obtaining new dual H-3 antagonists with insulinotropic activity, suggesting the necessity to propose a new chemical hybrid prototype. (C)2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.049
• 作为产物：
  描述：

  4-(2-溴乙氧基)苯磺酰氯 在 氨 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以78%的产率得到4-(2-溴乙氧基)苯磺酰胺
  参考文献：
  名称：

  Novel sulfonylurea derivatives as H3 receptor antagonists. Preliminary SAR studies

  摘要：

  The combination of antagonism at histamine H-3 receptor and the stimulation of insulin secretion have been proposed as an approach to new dual therapeutic agents for the treatment of type 2 diabetes mellitus associated with obesity. We have designed and synthesized a new series of non-imidazole derivatives, based on a basic amine ring connected through an alkyl spacer of variable length to a phenoxysulfonylurea moiety. These compounds were initially evaluated for histamine H-3 receptor binding affinities, suggesting that a propoxy chain linker between the amine and the core ring could be essential for optimal binding affinity. Compound 56, 1-(naphthalen-1-yl)-3-[(p-(3-pyrrolidin-1-ylpropoxy) benzene)]sulfonylurea exhibited the best H-3 antagonism affinity. However, since all these derivatives failed to block K-ATP channels, the link of these two related moieties should not be considered a good pharmacophore for obtaining new dual H-3 antagonists with insulinotropic activity, suggesting the necessity to propose a new chemical hybrid prototype. (C)2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.049

文献信息

• Prospective computational design and in vitro bio-analytical tests of new chemical entities as potential selective CYP17A1 lyase inhibitors
  作者：N.J. Gumede、W. Nxumalo、K. Bisetty、L. Escuder Gilabert、M.J. Medina-Hernandez、S. Sagrado

  DOI：10.1016/j.bioorg.2019.103462

  日期：2020.1

  resistant prostate cancer (mCRPC) patients. The selective CYP17A1 inhibition of 17,20-lyase route has emerged as a novel strategy. Such inhibition blocks the production of androgens everywhere they are found in the body. In this work, a three dimensional-quantitative structure activity relationship (3D-QSAR) pharmacophore model is developed on a diverse set of non-steroidal inhibitors of CYP17A1 enzyme

  前列腺癌（PCa）进入第4阶段的发展和进展是主要在老年男性中遇到的主要问题。PCa细胞的生长受到雄激素和雄激素受体（AR）的刺激。因此，近年来已经探索了诸如阻断雄激素合成和抑制AR结合的治疗策略。但是，最近批准的药物（或处于临床阶段）未能提高该转移cast割抵抗性前列腺癌（mCRPC）患者的预期存活率。CYP17A1选择性抑制17,20-裂合酶途径已成为一种新的策略。这种抑制作用会阻止在人体各处发现的雄激素的产生。在这项工作中，在一组不同的CYP17A1酶非甾体抑制剂上建立了三维定量结构活性关系（3D-QSAR）药效团模型。选择高活性化合物以定义六点药效基团假说，其独特的几何排列符合以下描述：两个氢键受体（A），两个氢键供体（D）和两个芳环（R）。QSAR模型显示出足够的预测统计量。3D-QSAR模型进一步用于数据库虚拟筛选潜在的抑制命中结构。密度泛函理论（DFT）优化提供了解释命中物反应
• Quinazoline derivatives and applications thereof
  申请人：Suntory Limited

  公开号：US05814631A1

  公开（公告）日：1998-09-29

  A chymase inhibitor containing as its effective ingredient a quinazoline derivative, or a pharmaceutically acceptable salt thereof, having the formula (1): ##STR1## and a pharmaceutical preparation for the prevention of cardiac and circulatory system diseases derived from abnormal exacerbation of Ang II production containing the same as its effective ingredient.

  一种含有喹唑啉衍生物或其药学上可接受的盐作为有效成分的chymase抑制剂，其化学式为（1）： ##STR1## 以及一种以该化合物作为有效成分的预防心脏和循环系统疾病的制药制剂，该疾病是由于Ang II产生异常恶化引起的。
• QUINAZOLINE DERIVATIVES AND USE THEREOF
  申请人：SUNTORY LIMITED

  公开号：EP0795548A1

  公开（公告）日：1997-09-17

  A chymase inhibitor containing as its effective ingredient a quinazoline derivative, or a pharmaceutically acceptable salt thereof, having the formula (1): and a pharmaceutical preparation for the prevention of cardiac and circulatory system diseases derived from abnormal exacerbation of Ang II production containing the same as its effective ingredient.

  一种糜蛋白酶抑制剂，其有效成分含有式（1）的喹唑啉衍生物或其药学上可接受的盐： 以及一种用于预防因血管紧张素 II 生成异常增加而引起的心脏和循环系统疾病的药物制剂，其有效成分也包含上述成分。
• Selective class III antiarrhythmic agents. 1. Bis(arylalkyl)amines
  作者：Peter E. Cross、John E. Arrowsmith、Geoffrey N. Thomas、Michael Gwilt、Roger A. Burges、Alan J. Higgins

  DOI：10.1021/jm00166a011

  日期：1990.4

  A series of bis(arylalkyl)amines is described and their effects on prolonging effective refractory period in isolated cardiac tissue listed. Most compounds prolonged the cardiac action potential without significantly altering the maximum rate of depolarization and may be defined as selective class III antiarrhythmic agents. It was found that a particularly advantageous structural feature was to have a methanesulfonamido moiety on both of the aryl rings. Thus, compound 16 [1-(4-methanesulfonamidophenoxy)2-[N-(4-methanesulfonamidophene thyl)-N- methylamine]ethane] was selected for further investigations. The compound is highly potent and selective class III agent which acts by blockade of cardiac potassium channels.
• CROSS, PETER E.;ARROWSMITH, JOHN E.;THOMAS, GEOFFREY N.;GWILT, MICHAEL;BU+, J. MED. CHEM., 33,(1990) N, C. 1151-1155
  作者：CROSS, PETER E.、ARROWSMITH, JOHN E.、THOMAS, GEOFFREY N.、GWILT, MICHAEL、BU+

  DOI：——

  日期：——