trans-4-[(4-bromobenzenesulfonyl)aminomethyl]cyclohexanecarboxylic acid | 674819-27-3

• 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: trans-4-[(4-bromobenzenesulfonyl)aminomethyl]cyclohexanecarboxylic acid
• 英文别名: 4-[(4-bromobenzenesulfonylamino)methyl]cyclohexanecarboxylic acid
• CAS: 674819-27-3
• 化学式: C₁₄H₁₈BrNO₄S
• 分子量: 376.271
• InChiKey: OEXAASQOHMSUSV-XYPYZODXSA-N

物化性质

• 沸点：
  527.7±56.0 °C(Predicted)
• 密度：
  1.499±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.47
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-吡啶甲酰肼 、 trans-4-[(4-bromobenzenesulfonyl)aminomethyl]cyclohexanecarboxylic acid 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成
  参考文献：
  名称：

  Galiano, Silvia; Erviti, Oihana; Perez, Silvia, Arzneimittel-Forschung/Drug Research, 2005, vol. 55, # 2, p. 81 - 85

  摘要：

  DOI：
• 作为产物：
  描述：

  tranexamic acid 、 4-溴苯磺酰氯 在 sodium carbonate 作用下， 以 水 为溶剂， 以91%的产率得到trans-4-[(4-bromobenzenesulfonyl)aminomethyl]cyclohexanecarboxylic acid
  参考文献：
  名称：

  氨甲环酸新磺酰胺衍生物分子间相互作用的合成与描述

  摘要：

  摘要 氨甲环酸（4-氨基甲基-环己烷甲酸）与磺酰氯反应生成结构相关的四种磺酰胺衍生物，采用简单环保的方法来检测它们的三维行为和范德华相互作用。分子以不同的可能性结晶，因为它是/在其 O 和 N 原子烷基化后/与共分子一起。所有分子均在单斜晶系中结晶，空间群为P 2 1 / n 、P 2 1 / c 和P 2 1 / a 。X 射线研究表明，分子通过不同种类的氢键相互作用使自身稳定。分子通过 O-H⋯O 氢键连接形成反转二聚体，通过 N-H⋯O 相互作用进一步连接。N和O原子被烷基化的分子表现出非经典相互作用并产生中心对称的R 2 2 (24)环基序。共结晶的主体和客体分子通过 O-H⋯O 相互作用相互连接以产生不同的环基序。借助 ToposPro 软件，对与所考虑结构中的分子堆积和氢键网络相对应的底层网络的拓扑结构进行了分析。

  DOI：

  10.1016/j.molstruc.2015.09.022

文献信息

• Synthesis of new thiophene and benzo[b]thiophene hydrazide derivatives as human NPY Y5 antagonists
  作者：Silvia Galiano、Oihana Erviti、Silvia Pérez、Antonio Moreno、Laura Juanenea、Ignacio Aldana、Antonio Monge

  DOI：10.1016/j.bmcl.2003.11.070

  日期：2004.2

  Neuropeptide Y is one of the most potent appetite stimulating hormones known. Novel thiophene and benzo[b]thiophene hydrazide derivatives were synthetized and evaluated biologically as NPY Y(1) and Y(5) receptor subtype antagonists. They were found to have nanomolar binding affinities for human NPY Y(5) receptor, obtaining the lead compound, trans-N-4-[N'-(thiophene-2-carbonyl)hydrazinocarbonyl]cy

  神经肽Y是已知的最有效的食欲刺激激素之一。合成了新型噻吩和苯并[b]噻吩酰肼衍生物，并将其作为NPY Y（1）和Y（5）受体亚型拮抗剂进行生物学评估。他们发现它们对人NPY Y（5）受体具有纳摩尔结合亲和力，从而获得了先导化合物反式N-4- [N'-（噻吩-2-羰基）肼基羰基]环己基甲基-4-溴苯磺酰胺hY（5）受体的7.70 nM IC（50）。
• Synthesis and evaluation of new hydrazide derivatives as neuropeptide Y Y5 receptor antagonists for the treatment of obesity
  作者：Laura Juanenea、Silvia Galiano、Oihana Erviti、Antonio Moreno、Silvia Pérez、Ignacio Aldana、Antonio Monge

  DOI：10.1016/j.bmc.2004.06.023

  日期：2004.9

  NPY is the most potent orexigenic agent known to man, with NPY Y1 and NPY Y5 being the receptor subtypes that are most likely responsible for centrally-mediated NPY-induced feeding responses. Based on the aforementioned, novel hydrazide derivatives were prepared for the purpose of searching new NPY Y5 receptor antagonists. Many of the compounds exhibited nanomolar binding affinity for this receptor, affording trans-N-4-[N'-(3,4-dichlorophenyl)hydrazinocarbonyl]cyclohexylmethyl}-4-fluorobenzenesulfonamide, which showed the best activity (IC50=0.43 nM). (C) 2004 Published by Elsevier Ltd.
• Synthesis and evaluation of new arylsulfonamidomethylcyclohexyl derivatives as human neuropeptide Y Y5 receptor antagonists for the treatment of obesity
  作者：Antonio Moreno、Silvia Pérez、Silvia Galiano、Laura Juanenea、Oihana Erviti、Carmen Frígola、Ignacio Aldana、Antonio Monge

  DOI：10.1016/j.ejmech.2003.10.001

  日期：2004.1

  NPY is the most potent orexigenic peptide identified up to now. Stimulation of food intake is measured by the Y-1 and Y-5 receptor subtypes. In this study, the synthesis and evaluation of new arylsulfonamidomethylcyclohexyl derivatives are described as potential selective antagonists of the human NPY Y-5 receptor. The SAR of these series was examined and the amide derivatives were the compounds that showed the best activities. trans-N-4-[(Quinolin-3-yl)aminocarbonyl]cyclohexylmethyl}-2,4-dichlorobenzenesulfonamide (42) bound to the human neuropeptide Y Y-5 receptor with a 2 nM IC50. (C) 2003 Elsevier SAS. All rights reserved.
• Combining NMR and molecular modelling in a drug delivery context: investigation of the multi-mode inclusion of a new NPY-5 antagonist bromobenzenesulfonamide into β-cyclodextrin
  作者：Gloria Uccello-Barretta、Federica Balzano、Giuseppe Sicoli、Carmen Frı́glola、Ignacio Aldana、Antonio Monge、Donatella Paolino、Salvatore Guccione

  DOI：10.1016/j.bmc.2003.10.033

  日期：2004.1

  NMR spectroscopic and molecular modelling methods have been employed to describe the complexation of trans-N-4-[N'-(4-chlorobenzoyl)hydrazinocarbonyl]cyclohexylmethyl-4-bromobenzenesulfonamide, a new chemotype of NPY-5 antagonist, and beta-cyclodextrin, revealing the coexistence of two different kinds of 1:1 complexes where conformational changes of the guest compound with respect to the free state are also detected (C) 2003 Elsevier Ltd. All rights reserved.