N-benzyl-N-[(2-napthalenyl)sulfonyl]glycine | 276695-59-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-benzyl-N-[(2-napthalenyl)sulfonyl]glycine
• 英文别名: 2-[Benzyl(naphthalen-2-ylsulfonyl)amino]acetic acid
• CAS: 276695-59-1
• 化学式: C₁₉H₁₇NO₄S
• 分子量: 355.414
• InChiKey: CLYFNRLWCJEPPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-[(2-napthalenyl)sulfonyl]glycine 在 盐酸羟胺 、 三乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 2-[Benzyl-(naphthalene-2-sulfonyl)-amino]-N-hydroxy-acetamide
  参考文献：
  名称：

  蛋白酶抑制剂-第5部分。解组织梭状芽孢杆菌胶原酶的烷基/芳基磺酰基-和芳基磺酰基-脲基/芳基脲基-甘氨酸异羟肟酸酯抑制剂。

  摘要：

  烷基/芳基磺酰基卤化物与甘氨酸反应得到一系列衍生物，其首先通过用苄基氯处理而被N-苄基化，然后在碳二亚胺衍生物存在下用羟胺转化成相应的异羟肟酸。如上所述，通过使N-苄基-甘氨酸与芳基异氰酸酯，芳基磺酰基异氰酸酯或苯甲酰基异硫氰酸酯反应，然后将它们的COOH基团转化为CONHOH部分，可获得其他衍生物。分析了这里报道的90种新化合物作为溶组织梭状芽孢杆菌胶原酶（EC 3.4.24.3）的抑制剂，这是一种锌酶，可降解天然胶原的三个螺旋区域。所制备的异羟肟酸酯衍生物的活性通常比相应的羧酸盐高100-500倍。在一系列合成异羟肟酸酯中，导致最佳抑制剂的取代模式是涉及全氟烷基磺酰基和取代的芳基磺酰基部分的那些，例如五氟苯基磺酰基，3-和4-羧基苯基磺酰基-，3-三氟甲基-苯基磺酰基或1-和2-萘基。因此，似乎与基质金属蛋白酶（MMP）异羟肟酸酯抑制剂相似，溶组织梭状芽孢杆菌胶原酶抑制剂应在P（1'）

  DOI：

  10.1016/s0223-5234(00)00127-6
• 作为产物：
  描述：

  N-benzyl-2-naphthalenesulfonamide 在 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-benzyl-N-[(2-napthalenyl)sulfonyl]glycine
  参考文献：
  名称：

  Progresses in the pursuit of aldose reductase inhibitors: The structure-based lead optimization step

  摘要：

  Aldose reductase (ALR2) is a crucial enzyme in the development of the major complications of diabetes mellitus. Very recently it has been demonstrated that the ARL2 inhibitor, fidarestat, significantly prevents inflammatory signals (TNF-alpha, LPS) that cause cancer (colon, breast, prostate and lung), metastasis, asthma, and other inflammatory diseases. Currently, fidarestat is in phase Ill clinical trial for diabetic neuropathy and was found to be safe. Thus the finding of novel, potent ARL2 inhibitors is today more than in the past in great demand as they can pave the way for a novel therapeutic approach for a number of diseases besides the diabetes. Herein, starting from the virtual screening-derived ALR2 inhibitor S12728 (1), a rational receptor-based lead optimization has been undertaken. The design and synthetic efforts here reported led to the discovery of several new compounds endowed with low micromolar/submicromolar activities. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.045

文献信息

• Progresses in the pursuit of aldose reductase inhibitors: The structure-based lead optimization step
  作者：Anna Ramunno、Sandro Cosconati、Stefania Sartini、Vita Maglio、Sara Angiuoli、Valeria La Pietra、Salvatore Di Maro、Mariateresa Giustiniano、Concettina La Motta、Federico Da Settimo、Luciana Marinelli、Ettore Novellino

  DOI：10.1016/j.ejmech.2012.02.045

  日期：2012.5

  Aldose reductase (ALR2) is a crucial enzyme in the development of the major complications of diabetes mellitus. Very recently it has been demonstrated that the ARL2 inhibitor, fidarestat, significantly prevents inflammatory signals (TNF-alpha, LPS) that cause cancer (colon, breast, prostate and lung), metastasis, asthma, and other inflammatory diseases. Currently, fidarestat is in phase Ill clinical trial for diabetic neuropathy and was found to be safe. Thus the finding of novel, potent ARL2 inhibitors is today more than in the past in great demand as they can pave the way for a novel therapeutic approach for a number of diseases besides the diabetes. Herein, starting from the virtual screening-derived ALR2 inhibitor S12728 (1), a rational receptor-based lead optimization has been undertaken. The design and synthetic efforts here reported led to the discovery of several new compounds endowed with low micromolar/submicromolar activities. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Protease inhibitors – Part 5. Alkyl/arylsulfonyl- and arylsulfonylureido-/arylureido- glycine hydroxamate inhibitors of Clostridium histolyticum collagenase
  作者：A Scozzafava

  DOI：10.1016/s0223-5234(00)00127-6

  日期：2000.3

  Reaction of alkyl/arylsulfonyl halides with glycine afforded a series of derivatives which were first N-benzylated by treatment with benzyl chloride, and then converted to the corresponding hydroxamic acids with hydroxylamine in the presence of carbodiimide derivatives. Other derivatives were obtained by reaction of N-benzyl-glycine with aryl isocyanates, arylsulfonyl isocyanates or benzoyl isothiocyanate

  烷基/芳基磺酰基卤化物与甘氨酸反应得到一系列衍生物，其首先通过用苄基氯处理而被N-苄基化，然后在碳二亚胺衍生物存在下用羟胺转化成相应的异羟肟酸。如上所述，通过使N-苄基-甘氨酸与芳基异氰酸酯，芳基磺酰基异氰酸酯或苯甲酰基异硫氰酸酯反应，然后将它们的COOH基团转化为CONHOH部分，可获得其他衍生物。分析了这里报道的90种新化合物作为溶组织梭状芽孢杆菌胶原酶（EC 3.4.24.3）的抑制剂，这是一种锌酶，可降解天然胶原的三个螺旋区域。所制备的异羟肟酸酯衍生物的活性通常比相应的羧酸盐高100-500倍。在一系列合成异羟肟酸酯中，导致最佳抑制剂的取代模式是涉及全氟烷基磺酰基和取代的芳基磺酰基部分的那些，例如五氟苯基磺酰基，3-和4-羧基苯基磺酰基-，3-三氟甲基-苯基磺酰基或1-和2-萘基。因此，似乎与基质金属蛋白酶（MMP）异羟肟酸酯抑制剂相似，溶组织梭状芽孢杆菌胶原酶抑制剂应在P（1'）