4-[(4-Fluoro-benzenesulfonylamino)-methyl]-cyclohexanecarboxylic acid | 744248-54-2

• 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: 4-[(4-Fluoro-benzenesulfonylamino)-methyl]-cyclohexanecarboxylic acid
• 英文别名: 4-(((4-fluorophenyl)sulfonamido)methyl)cyclohexane-1-carboxylic acid
• CAS: 744248-54-2
• 化学式: C₁₄H₁₈FNO₄S
• mdl: MFCD09798596
• 分子量: 315.366
• InChiKey: AISZJTPLQRGKDX-XYPYZODXSA-N

物化性质

• 沸点：
  489.2±51.0 °C(Predicted)
• 密度：
  1.319±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 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：

  4-[(4-Fluoro-benzenesulfonylamino)-methyl]-cyclohexanecarboxylic acid 在 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 44.0h， 生成 4-(((4-(4-methylpiperazin-1-yl)phenyl)sulfonamido)methyl)-N-(pyridin-3-yl)cyclohexane-1-carboxamide
  参考文献：
  名称：

  A new chemotype with promise against Trypanosoma cruzi

  摘要：

  Pyridyl benzamide 2 is a potent inhibitor of Trypanosoma cruzi, but not other protozoan parasites, and had a selectivity-index of >= 10. The initial structure-activity relationship (SAR) indicates that benzamide and sulfonamide functional groups, and N-methylpiperazine and sterically unhindered 3-pyridyl substructures are required for high activity against T. cruzi. Compound 2 and its active analogs had low to moderate metabolic stabilities in human and mouse liver microsomes.

  DOI：

  10.1016/j.bmcl.2019.126778
• 作为产物：
  描述：

  4-氟苯磺酰氯 、 tranexamic acid 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以67%的产率得到4-[(4-Fluoro-benzenesulfonylamino)-methyl]-cyclohexanecarboxylic acid
  参考文献：
  名称：

  A new chemotype with promise against Trypanosoma cruzi

  摘要：

  Pyridyl benzamide 2 is a potent inhibitor of Trypanosoma cruzi, but not other protozoan parasites, and had a selectivity-index of >= 10. The initial structure-activity relationship (SAR) indicates that benzamide and sulfonamide functional groups, and N-methylpiperazine and sterically unhindered 3-pyridyl substructures are required for high activity against T. cruzi. Compound 2 and its active analogs had low to moderate metabolic stabilities in human and mouse liver microsomes.

  DOI：

  10.1016/j.bmcl.2019.126778

文献信息

• 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.