7-p-toluenesulfonyl-1,4-dithia-7-azaspiro[4,4]nonane-8-carboxylic acid

• 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: 7-p-toluenesulfonyl-1,4-dithia-7-azaspiro[4,4]nonane-8-carboxylic acid
• 英文别名: (8S)-7-(4-methylphenyl)sulfonyl-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid
• 化学式: C₁₄H₁₇NO₄S₃
• 分子量: 359.491
• InChiKey: YIVUZDIRWOBHSX-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-p-toluenesulfonyl-1,4-dithia-7-azaspiro[4,4]nonane-8-carboxylic acid 在 羟胺钾盐 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 32.0h， 生成 7-p-toluenesulfonyl-1,4-dithia-7-azaspiro[4,4]nonane-8-carboxylic acid hydroxyamide
  参考文献：
  名称：

  Sulphonamide 1,4-dithia-7-azaspiro[4,4]nonane derivatives as gelatinase A inhibitors

  摘要：

  Gelatinase A, a zinc-containing endopeptidase, has been shown to be an essential therapeutic target for tumor intervention owing to its participation in almost all types of solid tumors. Based on our previous work with respect to quinoxalinone peptidomimetics, a novel series of sulphonamide-containing 1,4-dithia-7-azaspiro[4,4]nonane (DAN) derivatives have been synthesized and evaluated as potential gelatinase A inhibitors hereby. The results revealed that the majority of tested compounds displayed satisfactory inhibition activity against gelatinase A. Among the tested compounds, 2b, 3a, 4a-d, 6a, 6d, 7a-d exhibited more potent gelatinase A inhibition than the positive control LY52. Furthermore, two test compounds 2b and 6a demonstrated moderate anti-proliferative in vitro and anti-metastatic activities in vivo, which might be utilized as potential leads in future chemical optimization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.016
• 作为产物：
  描述：

  对甲苯磺酰氯 、 1,4-二硫-7-氮杂螺[4,4]壬烷-8-羧酸氢溴酸盐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 10.0h， 以68.2%的产率得到7-p-toluenesulfonyl-1,4-dithia-7-azaspiro[4,4]nonane-8-carboxylic acid
  参考文献：
  名称：

  Sulphonamide 1,4-dithia-7-azaspiro[4,4]nonane derivatives as gelatinase A inhibitors

  摘要：

  Gelatinase A, a zinc-containing endopeptidase, has been shown to be an essential therapeutic target for tumor intervention owing to its participation in almost all types of solid tumors. Based on our previous work with respect to quinoxalinone peptidomimetics, a novel series of sulphonamide-containing 1,4-dithia-7-azaspiro[4,4]nonane (DAN) derivatives have been synthesized and evaluated as potential gelatinase A inhibitors hereby. The results revealed that the majority of tested compounds displayed satisfactory inhibition activity against gelatinase A. Among the tested compounds, 2b, 3a, 4a-d, 6a, 6d, 7a-d exhibited more potent gelatinase A inhibition than the positive control LY52. Furthermore, two test compounds 2b and 6a demonstrated moderate anti-proliferative in vitro and anti-metastatic activities in vivo, which might be utilized as potential leads in future chemical optimization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.016

文献信息

• Sulphonamide 1,4-dithia-7-azaspiro[4,4]nonane derivatives as gelatinase A inhibitors
  作者：Leilei Shi、Qiang Wang、Haina Wang、Hua Zhou、Yonggang Li、Xun Li

  DOI：10.1016/j.bmc.2013.10.016

  日期：2013.12

  Gelatinase A, a zinc-containing endopeptidase, has been shown to be an essential therapeutic target for tumor intervention owing to its participation in almost all types of solid tumors. Based on our previous work with respect to quinoxalinone peptidomimetics, a novel series of sulphonamide-containing 1,4-dithia-7-azaspiro[4,4]nonane (DAN) derivatives have been synthesized and evaluated as potential gelatinase A inhibitors hereby. The results revealed that the majority of tested compounds displayed satisfactory inhibition activity against gelatinase A. Among the tested compounds, 2b, 3a, 4a-d, 6a, 6d, 7a-d exhibited more potent gelatinase A inhibition than the positive control LY52. Furthermore, two test compounds 2b and 6a demonstrated moderate anti-proliferative in vitro and anti-metastatic activities in vivo, which might be utilized as potential leads in future chemical optimization. (C) 2013 Elsevier Ltd. All rights reserved.