(rac)-N-(2-aminocyclohexyl)-5-dimethylaminonaphthalene-1-sulfonamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (rac)-N-(2-aminocyclohexyl)-5-dimethylaminonaphthalene-1-sulfonamide
• 英文别名: (2-aminocyclohexyl)-5-(dimethylamino)naphthalene-1-sulfonamide；N-[(1R,2R)-2-aminocyclohexyl]-5-(dimethylamino)naphthalene-1-sulfonamide
• 化学式: C₁₈H₂₅N₃O₂S
• 分子量: 347.481
• InChiKey: HDKMSDKWFAVSCL-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cis-dichlorobis(dimethylsulfoxide)platinum(II) 、 (rac)-N-(2-aminocyclohexyl)-5-dimethylaminonaphthalene-1-sulfonamide 以 甲醇 为溶剂， 反应 72.0h， 生成 (dimethyl(oxo)-l6-sulfaneyl)(((1S,2S)-2-((5-(dimethylamino)naphthalene)-1-sulfonamido)cyclohexyl)amino)platinum(IV) chloride
  参考文献：
  名称：

  Evaluation of novel trans-sulfonamide platinum complexes against tumor cell lines

  摘要：

  Platinum-based drugs, mainly cisplatin, are employed for the treatment of solid malignancies. However, cisplatin treatment often results in the development of chemoresistance, leading to therapeutic failure. Here, the antitumor activity of different trans-sulfonamide platinum complexes in a panel of human cell lines is presented. The cytotoxicity profiles and cell cycle analyses of these platinum sulfonamide complexes were different from those of cisplatin. These studies showed that complex 2b with cyclohexyldiamine and dansyl moieties had the best antitumoral activities. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.022
• 作为产物：
  描述：

  丹酰氯 、 trans-1,2-Diaminocyclohexane 以 二氯甲烷 为溶剂， 反应 10.0h， 以91%的产率得到(rac)-N-(2-aminocyclohexyl)-5-dimethylaminonaphthalene-1-sulfonamide
  参考文献：
  名称：

  Expanding the synthesis of new trans-sulfonamide platinum complexes: Cytotoxicity, SAR, fluorescent cell assays and stability studies

  摘要：

  In this manuscript, we describe the synthesis of new trans-N-sulfonamide platinum complexes and their antiproliferative activity (GI(50), mu M) in human solid tumors cells. The structure activity relationships (SAR), with different new synthesized complexes by variation in ligand, halogen and also in the stereochemistry of the ligand, has been studied. Solubility and stability studies have also been carried out as well as fluorescent cell assays in order to clarify the final target in the tumor cells. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2013.01.013

文献信息

• Expanding the synthesis of new trans-sulfonamide platinum complexes: Cytotoxicity, SAR, fluorescent cell assays and stability studies
  作者：Virginia del Solar、Adolfo Quiñones-Lombraña、Silvia Cabrera、José M. Padrón、Carla Ríos-Luci、Amparo Alvarez-Valdés、Carmen Navarro-Ranninger、José Alemán

  DOI：10.1016/j.jinorgbio.2013.01.013

  日期：2013.10

  In this manuscript, we describe the synthesis of new trans-N-sulfonamide platinum complexes and their antiproliferative activity (GI(50), mu M) in human solid tumors cells. The structure activity relationships (SAR), with different new synthesized complexes by variation in ligand, halogen and also in the stereochemistry of the ligand, has been studied. Solubility and stability studies have also been carried out as well as fluorescent cell assays in order to clarify the final target in the tumor cells. (C) 2013 Elsevier Inc. All rights reserved.
• Evaluation of novel trans-sulfonamide platinum complexes against tumor cell lines
  作者：Carlos Pérez、C. Vanesa Díaz-García、Alba Agudo-López、Virginia del Solar、Silvia Cabrera、M. Teresa Agulló-Ortuño、Carmen Navarro-Ranninger、José Alemán、José A. López-Martín

  DOI：10.1016/j.ejmech.2014.02.022

  日期：2014.4

  Platinum-based drugs, mainly cisplatin, are employed for the treatment of solid malignancies. However, cisplatin treatment often results in the development of chemoresistance, leading to therapeutic failure. Here, the antitumor activity of different trans-sulfonamide platinum complexes in a panel of human cell lines is presented. The cytotoxicity profiles and cell cycle analyses of these platinum sulfonamide complexes were different from those of cisplatin. These studies showed that complex 2b with cyclohexyldiamine and dansyl moieties had the best antitumoral activities. (C) 2014 Elsevier Masson SAS. All rights reserved.