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

• 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 hydrazide
• 英文别名: (S)-7-tosyl-1,4-dithia-7-azaspiro[4.4]nonane-8-carbohydrazide；(8S)-7-(4-methylphenyl)sulfonyl-1,4-dithia-7-azaspiro[4.4]nonane-8-carbohydrazide
• 化学式: C₁₄H₁₉N₃O₃S₃
• 分子量: 373.521
• InChiKey: KKDAXBNRYRMJPP-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 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：
  152
• 氢给体数：
  2
• 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 hydrazide 、 苯乙酰氯 在 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 6.08h， 以75.7%的产率得到2-(7-p-toluenesulfonyl-1,4-dithia-7-azaspiro[4,4]nonane-8-formyl)phenylacetohydrazide
  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：

  7-p-toluenesulfonyl-1,4-dithia-7-azaspiro[4,4]nonane-8-carboxylic acid methyl ester 在 一水合肼 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以80%的产率得到7-p-toluenesulfonyl-1,4-dithia-7-azaspiro[4,4]nonane-8-carboxylic acid hydrazide
  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

• Design, synthesis and anti-HIV-1 evaluation of hydrazide-based peptidomimetics as selective gelatinase inhibitors
  作者：Liang Yang、Ping Wang、Ji-Feng Wu、Liu-Meng Yang、Rui-Rui Wang、Wei Pang、Yong-Gang Li、Yue-Mao Shen、Yong-Tang Zheng、Xun Li

  DOI：10.1016/j.bmc.2016.03.043

  日期：2016.5

  the target compounds were also submitted to the preliminary in vitro anti-HIV-1 evaluation. It resulted that gelatinase inhibition really has positive correlation with anti-HIV-1 activity, especially compounds 4m and 7h, which gave enhanced gelatinase inhibition in comparison with the positive control LY52, and also decent anti-HIV-1 potencies. The FlexX docking results provided a straightforward insight

  随着我们对明胶酶抑制剂研究的不断开展，设计，合成并测试了一系列带有喹喔啉酮以及螺杂环骨架的含酰肼的拟肽衍生物，并对其体外酶抑制作用进行了测定。结果表明，与ICN相比，喹喔啉酮（I和II系列）和1,4-二硫杂-7-氮杂螺[4,4]壬烷酰肼拟肽（III系列）对明胶酶A的选择性均显着高于APN 50值在微摩尔范围内。在这里简要讨论了结构与活动的关系。已有证据证明明胶酶抑制作用可能归因于HIV-1感染的治疗，所有目标化合物也都提交了体外抗HIV-1初步评估。结果表明，明胶酶抑制作用确实与抗HIV-1活性呈正相关，尤其是化合物4m和7h与阳性对照LY52相比，它具有更强的明胶酶抑制作用，并且还具有不错的抗HIV-1效能。FlexX对接结果提供了对抑制剂和明胶酶之间结合模式的直接了解，以及对APN上对明胶酶的选择性抑制。总的来说，我们的研究鼓励有效的明胶酶抑制剂可用于开发抗HIV-1药物。另外，化合物
• 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.