N-(tert-butoxycarbonyl)-L-isoleucyl-glycine-nitrile | 225122-26-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(tert-butoxycarbonyl)-L-isoleucyl-glycine-nitrile
• 英文别名: tert-butyl N-[(2S,3S)-1-(cyanomethylamino)-3-methyl-1-oxopentan-2-yl]carbamate
• CAS: 225122-26-9
• 化学式: C₁₃H₂₃N₃O₃
• 分子量: 269.344
• InChiKey: HNTBSHVGXMFKKB-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  91.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-L-isoleucyl-glycine-nitrile 在 盐酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 6.0h， 生成 (2S)-1-(1,1-dioxobenzo[d]isothiazol-3-yl)-pyrrolidine-2-carboxylic acid [(1S,2S)-1-(cyanomethylcarbamoyl)-2-methylbutyl]amide
  参考文献：
  名称：

  Synthesis and in vitro evaluation of pseudosaccharinamine derivatives as potential elastase inhibitors

  摘要：

  Pseudosaccharinamine derivatives were evaluated for elastase inhibitory activity. Ester derivatives of pseudosaccharinamine displayed reversible and high inhibition of human leukocyte elastase (HLE) as compared to porcine pancreatic elastase (PPE). Cyanomethyl (2S,3S)-2-(1,1-dioxobenzo[d]isothiazol-3-ylamino)-3-methylpentanoate was found to inhibit HLE at K-i = 0.8 mu M. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.057
• 作为产物：
  描述：

  Boc-Ile-O-COOiBu 、 氨基乙腈盐酸盐 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 N-(tert-butoxycarbonyl)-L-isoleucyl-glycine-nitrile
  参考文献：
  名称：

  Synthesis and in vitro evaluation of pseudosaccharinamine derivatives as potential elastase inhibitors

  摘要：

  Pseudosaccharinamine derivatives were evaluated for elastase inhibitory activity. Ester derivatives of pseudosaccharinamine displayed reversible and high inhibition of human leukocyte elastase (HLE) as compared to porcine pancreatic elastase (PPE). Cyanomethyl (2S,3S)-2-(1,1-dioxobenzo[d]isothiazol-3-ylamino)-3-methylpentanoate was found to inhibit HLE at K-i = 0.8 mu M. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.057

文献信息

• Interaction of Papain-like Cysteine Proteases with Dipeptide-Derived Nitriles
  作者：Reik Löser、Klaus Schilling、Elke Dimmig、Michael Gütschow

  DOI：10.1021/jm050686b

  日期：2005.12.1

  were introduced, and systematic fluorine, bromine, and phenyl scans for phenylalanine in the P2 position were performed. Moreover, the N-terminal protection was varied. Kinetic investigations were carried out with cathepsin L, S, and K as well as papain. Changes in the backbone structure of the parent N-(tert-butoxycarbonyl)-phenylalanyl-glycine-nitrile (16), such as the introduction of an R-configured

  制备一系列44个在P2位具有各种氨基酸和在P1位具有甘氨酸的二肽腈，并将其评估为半胱氨酸蛋白酶的抑制剂。关于P2-S2相互作用对酶抑制剂复合物形成的重要贡献，重点是将结构多样性引入P2侧链。引入了非蛋白氨基酸，并进行了系统的氟，溴和苯基扫描，以检测P2位置的苯丙氨酸。而且，N-末端保护是多种多样的。使用组织蛋白酶L，S和K以及木瓜蛋白酶进行动力学研究。母体N-（叔丁氧羰基）-苯丙氨酰基-甘氨酸-腈的骨架结构变化（16），例如将R构型的氨基酸或氮杂氨基酸引入P2以及P1氮的甲基化，会导致亲和力的急剧下降。示例性地，16的氰基被醛或甲基酮官能团取代。关于靶酶的底物特异性，讨论了构效关系。
• Synthesis and in vitro evaluation of pseudosaccharinamine derivatives as potential elastase inhibitors
  作者：Haridas Rode、Stefanie Koerbe、Anita Besch、Karen Methling、Jutta Loose、Hans-Hartwig Otto

  DOI：10.1016/j.bmc.2005.11.057

  日期：2006.4

  Pseudosaccharinamine derivatives were evaluated for elastase inhibitory activity. Ester derivatives of pseudosaccharinamine displayed reversible and high inhibition of human leukocyte elastase (HLE) as compared to porcine pancreatic elastase (PPE). Cyanomethyl (2S,3S)-2-(1,1-dioxobenzo[d]isothiazol-3-ylamino)-3-methylpentanoate was found to inhibit HLE at K-i = 0.8 mu M. (c) 2005 Elsevier Ltd. All rights reserved.