Boc-Ile-NHCH₂C₆H₅ | 154128-82-2

• 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: Boc-Ile-NHCH₂C₆H₅
• 英文别名: N-(tert-butoxycarbonyl)-L-Isoleucine benzylamide；tert-butyl N-[(2S,3S)-1-(benzylamino)-3-methyl-1-oxopentan-2-yl]carbamate
• CAS: 154128-82-2
• 化学式: C₁₈H₂₈N₂O₃
• 分子量: 320.432
• InChiKey: SJOCKYYJKSNVRA-ZFWWWQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Boc-Ile-NHCH₂C₆H₅ 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Development of Potent Inhibitors of Botulinum Neurotoxin Type B

  摘要：

  Botulinum neurotoxins are the most potent toxins known to date. They are zinc-metalloproteases able to cleave selectively an essential component of neurotransmitter exocytosis, causing the syndrome of botulism characterized by a flaccid paralysis. There is a great interest in designing antagonists of the action of these toxins. One way is to inhibit their catalytic activity. In this study, we report the design of such inhibitors directed toward BoNT/B. A study of the S-1 subsite specificity, using several beta-amino thiols, has shown that this subsite prefers a p-carboxybenzyl moiety. The specificity of the S-1' and S-2' subsites was studied using two libraries of pseudotripeptides containing the S-1 synthon derived from the best beta-amino thiol tested. Finally, a selection of various non natural amino acids for the recognition of the "prime" domain led to the most potent inhibitor of BoNT/B described to date with a K-i value of 20 nM.

  DOI：

  10.1021/jm0300680
• 作为产物：
  描述：

  L-异亮氨酸 在 sodium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 42.5h， 生成 Boc-Ile-NHCH₂C₆H₅
  参考文献：
  名称：

  双重保护的氨基酸衍生物作为新型抗结核药。

  摘要：

  结核病是一种传染病，发病率高，耐药率不断上升。为了开发新的抗结核药，合成了35种化合物，其中大多数带有氨基甲酸酯和对映体纯氨基酸部分。评估了这些化合物对结核分枝杆菌菌株的活性（ATCC 27294）和对成纤维细胞MRC-5细胞的细胞毒性（ATCC CCL-171）。所制备的三种衍生物具有良好的抗菌抑制作用，其中两种具有中等的细胞毒性。亲脂性似乎在细胞生长活性中起着至关重要的作用，对于具有较高logP的衍生物而言，其效果最佳。

  DOI：

  10.1111/cbdd.13315

文献信息

• Dual‐protected amino acid derivatives as new antitubercular agents
  作者：Pedro P. Castro、Débora L. Campos、Fernando R. Pavan、Giovanni W. Amarante

  DOI：10.1111/cbdd.13315

  日期：2018.8

  drug-resistant rates. In an attempt to develop new antitubercular agents, 35 compounds were synthesized, most of them bearing a carbamate and enantiopure amino acid moiety. These compounds had their activity evaluated toward a Mycobacterium tuberculosis strain (ATCC 27294) and cytotoxicity against fibroblast MRC-5 cells (ATCC CCL-171). Three of the prepared derivatives presented a good antimicrobial inhibition

  结核病是一种传染病，发病率高，耐药率不断上升。为了开发新的抗结核药，合成了35种化合物，其中大多数带有氨基甲酸酯和对映体纯氨基酸部分。评估了这些化合物对结核分枝杆菌菌株的活性（ATCC 27294）和对成纤维细胞MRC-5细胞的细胞毒性（ATCC CCL-171）。所制备的三种衍生物具有良好的抗菌抑制作用，其中两种具有中等的细胞毒性。亲脂性似乎在细胞生长活性中起着至关重要的作用，对于具有较高logP的衍生物而言，其效果最佳。
• 2-oxoethyl derivatives as immunosuppressants
  申请人：Miles Inc.

  公开号：US05686424A1

  公开（公告）日：1997-11-11

  A class of compounds that suppress human T-lymphocyte proliferation is disclosed. The active compounds essentially contain at least the following structure: ##STR1##

  本发明揭示了一类抑制人类T淋巴细胞增殖的化合物。活性化合物基本上包含至少以下结构：##STR1##
• 2-Oxoethyl derivatives as immunosuppressants
  申请人：Bayer Corporation

  公开号：EP0564924A2

  公开（公告）日：1993-10-13

  A class of compounds which suppress human T-lymphocyte proliferation is disclosed. The active compounds essentially contain at least the following structure:

  本研究公开了一类可抑制人类 T 淋巴细胞增殖的化合物。这些活性化合物基本上至少包含以下结构：
• Benzylamide antagonists of protease activated receptor 2 with anti-inflammatory activity
  作者：Mei-Kwan Yau、Ligong Liu、Junxian Lim、Rink-Jan Lohman、Adam J. Cotterell、Jacky Y. Suen、David A. Vesey、Robert C. Reid、David P. Fairlie

  DOI：10.1016/j.bmcl.2015.12.048

  日期：2016.2

  Activation of protease activated receptor 2 (PAR2) has been implicated in inflammatory and metabolic disorders and its inhibition may yield novel therapeutics. Here, we report a series of PAR2 antagonists based on C-terminal capping of 5-isoxazolyl-L-cyclohexylalanine-L-isoleucine, with benzylamine analogues being effective new PAR2 antagonists. 5-Isoxazolyl-L-cyclohexylalanine-L-isoleucine-2-methoxy-benzylamine (10) inhibited PAR2-, but not PAR1-, induced release of Ca2+ (IC50 0.5 mu M) in human colon cells, IL-6 and TNF alpha secretion (IC50 1-5 mu M) from human kidney cells, and was anti-inflammatory in acute rat paw inflammation (ED50 5 mg/kg sc). These findings show that new benzylamide antagonists of PAR2 have anti-inflammatory activity. (C) 2015 Elsevier Ltd. All rights reserved.
• US5686424A
  申请人：——

  公开号：US5686424A

  公开（公告）日：1997-11-11