6-bromohexanoic acid N,N-bis(4-methoxycarbonylphenyl)amide | 875210-91-6

• 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: 6-bromohexanoic acid N,N-bis(4-methoxycarbonylphenyl)amide
• 英文别名: 6-bromohexanecarbonic acid-N,N-bis(4-methoxycarbonylphenyl)amide；6-bromohexanoic acid-N,N-bis(4-methoxycarbonylphenyl)amide；methyl 4-[N-(6-bromohexanoyl)-4-methoxycarbonylanilino]benzoate
• CAS: 875210-91-6
• 化学式: C₂₂H₂₄BrNO₅
• 分子量: 462.34
• InChiKey: PYDMLMYFGAFGIO-UHFFFAOYSA-N

物化性质

• 熔点：
  133-135 °C(Solv: methanol (67-56-1))
• 沸点：
  632.6±50.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-bromohexanoic acid N,N-bis(4-methoxycarbonylphenyl)amide 在 硼烷四氢呋喃络合物 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 环己酮 为溶剂， 反应 6.0h， 生成 4-[N-(6-(3,5-bis(decyloxy)phenoxy)hexyl)-N-(4-(methoxycarbonyl)phenyl)amino]benzoic acid methyl ester
  参考文献：
  名称：

  A Novel Class of Potent Nonglycosidic and Nonpeptidic Pan-Selectin Inhibitors

  摘要：

  An early step of the inflammatory response, the rolling of leukocytes on activated endothelial cells, is mediated by selectin/carbohydrate interactions. The tetrasaccharide sialy Lewis(x) is a ligand for E-, P-, and L-selectin and therefore serves as a lead structure for the development of analogues. A combination of synthesis and structure-based design allowed rapid optimization. The current lead 2a was evaluated in our E-selectin cell flow chamber assay where it proved to inhibit rolling and adhesion with an IC50 of 28 +/- 7 mu M. The assays used are predictive for the in vivo efficacy of test compounds as shown for 2a in a proteose peptone induced peritonitis model of acute inflammation in mice.

  DOI：

  10.1021/jm060468y
• 作为产物：
  描述：

  4-乙酰氨基苯甲酸甲酯 在 potassium phosphate 、 copper(l) iodide 、 (1S,2S)-(+)-1,2-环己二胺 、 sodium hydride 作用下， 以 二丁醚 为溶剂， 反应 12.5h， 生成 6-bromohexanoic acid N,N-bis(4-methoxycarbonylphenyl)amide
  参考文献：
  名称：

  A Novel Class of Potent Nonglycosidic and Nonpeptidic Pan-Selectin Inhibitors

  摘要：

  An early step of the inflammatory response, the rolling of leukocytes on activated endothelial cells, is mediated by selectin/carbohydrate interactions. The tetrasaccharide sialy Lewis(x) is a ligand for E-, P-, and L-selectin and therefore serves as a lead structure for the development of analogues. A combination of synthesis and structure-based design allowed rapid optimization. The current lead 2a was evaluated in our E-selectin cell flow chamber assay where it proved to inhibit rolling and adhesion with an IC50 of 28 +/- 7 mu M. The assays used are predictive for the in vivo efficacy of test compounds as shown for 2a in a proteose peptone induced peritonitis model of acute inflammation in mice.

  DOI：

  10.1021/jm060468y

文献信息

• [DE] NICHTGLYKOSIDISCHE UND NICHTPEPTIDISCHE SELEKTININHIBITOREN UND DEREN VRWENDUNG<br/>[EN] NON-GLYCOSIDIC AND NON-PEPTIDIC SELECT INHIBITORS, AND THE USE THEREOF<br/>[FR] INHIBITEURS DE LA SELECTINE NON GLYCOSIDIQUES ET NON PEPTIDIQUES ET LEUR UTILISATION
  申请人：UNIV MAINZ JOHANNES GUTENBERG

  公开号：WO2006010598A1

  公开（公告）日：2006-02-02

  Es wird eine Klasse nichtglykosidischer und nichtpeptidischer Selektininhibitoren mit niedrigem Molekulargewicht nach der allgemeinen Formel (1) beschrieben, sowie Verfahren zu ihrer Herstellung. Es handelt sich dabei um eine Klasse untoxischer, in vivo anti-inflammatorisch wirksamer Selektininhibitoren, welche nicht die Nachteile der glykosidischen Inhibitorkomplexe aufweist und zudem in vitro potenter ist, als der bekannte Wirkstoff Bimosiamose. Es werden weiterhin die Verbindungen enthaltende Arzneimittel und deren Verwendung bei der Behandlung von Erkrankungen beschrieben.

  根据通用公式（1），描述了一类低分子量的非糖苷和非肽类选择性抑制剂，以及它们的制备方法。这是一类无毒、体内抗炎有效的选择性抑制剂，不具有糖苷抑制剂复合物的缺点，并且在体外比已知药物Bimosiamose更强效。还描述了含有这些化合物的药物及其在治疗疾病中的用途。
• Non-Glycosidic and Non-Peptidic Select Inhibitors, and the Use Thereof
  申请人：Dannhardt Gerd

  公开号：US20070276036A1

  公开（公告）日：2007-11-29

  A new class of non-glycosidic and non-peptidic inhibitors of selectins with low molecular weight according to the general formula 1 is described, as well as methods for their production. These compounds represent a new class of non-toxic, in vivo anti-inflammatory effective inhibitors of selectins, and do not exhibit the disadvantages of the glycosidic inhibitor complexes, and are furthermore more potent in vitro, compared to the known drug bimosiamose. Furthermore, medicaments containing the compounds and their uses in the treatment of diseases are described.

  本文介绍了一种新型非糖基和非肽基选择素抑制剂，其分子量低，符合一般公式1，以及其生产方法。这些化合物代表了一类新型的无毒、体内抗炎有效的选择素抑制剂，并且不具有糖基抑制剂复合物的缺点，此外，在体外方面比已知的药物bimosiamose更具有潜力。此外，本文还介绍了含有这些化合物的药物及其在治疗疾病方面的用途。
• Non-glycosidic and non-peptidic inhibitors of selectin, and the use thereof
  申请人：Johannes Gutenberg-Universität Mainz

  公开号：US07485742B2

  公开（公告）日：2009-02-03

  A new class of non-glycosidic and non-peptidic inhibitors of selectins with low molecular weight according to the general formula 1 is described, as well as methods for their production. These compounds represent a new class of non-toxic, in vivo anti-inflammatory effective inhibitors of selectins, and do not exhibit the disadvantages of the glycosidic inhibitor complexes, and are furthermore more potent in vitro, compared to the known drug bimosiamose. Furthermore, medicaments containing the compounds and their uses in the treatment of diseases are described.

  本文介绍了一种新型非糖苷和非肽类低分子量选择素抑制剂，其通用式为1，并介绍了它们的生产方法。这些化合物代表了一类新型的无毒、体内抗炎有效的选择素抑制剂，并且不具有糖苷抑制剂复合物的缺点，而且在体外比已知药物bimosiamose更具有更强的效力。此外，本文还介绍了含有这些化合物的药物以及它们在治疗疾病中的用途。
• US7485742B2
  申请人：——

  公开号：US7485742B2

  公开（公告）日：2009-02-03
• A Novel Class of Potent Nonglycosidic and Nonpeptidic Pan-Selectin Inhibitors
  作者：Holger K. Ulbrich、Andreas Luxenburger、Philip Prech、Einar E. Eriksson、Oliver Soehnlein、Pierre Rotzius、Lennart Lindbom、Gerd Dannhardt

  DOI：10.1021/jm060468y

  日期：2006.10.1

  An early step of the inflammatory response, the rolling of leukocytes on activated endothelial cells, is mediated by selectin/carbohydrate interactions. The tetrasaccharide sialy Lewis(x) is a ligand for E-, P-, and L-selectin and therefore serves as a lead structure for the development of analogues. A combination of synthesis and structure-based design allowed rapid optimization. The current lead 2a was evaluated in our E-selectin cell flow chamber assay where it proved to inhibit rolling and adhesion with an IC50 of 28 +/- 7 mu M. The assays used are predictive for the in vivo efficacy of test compounds as shown for 2a in a proteose peptone induced peritonitis model of acute inflammation in mice.