(S)-(1-hydroxycarbamoyl-3-methyl-butyl)-carbamic acid benzyl ester | 66179-55-3

• 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: (S)-(1-hydroxycarbamoyl-3-methyl-butyl)-carbamic acid benzyl ester
• 英文别名: Cbz-L-Leu-NHOH；Benzyloxycarbonylleucyl-hydroxamate；benzyl N-[(2S)-1-(hydroxyamino)-4-methyl-1-oxopentan-2-yl]carbamate
• CAS: 66179-55-3
• 化学式: C₁₄H₂₀N₂O₄
• 分子量: 280.324
• InChiKey: REYWRBIAVGFTAA-LBPRGKRZSA-N

物化性质

• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-苯丙氨酸甲酯 、 (S)-(1-hydroxycarbamoyl-3-methyl-butyl)-carbamic acid benzyl ester 在 碘 作用下， 以 二甲基亚砜 为溶剂， 以90%的产率得到N-(benzyloxycarbonyl)-L-leucyl-L-phenylalanine methyl ester
  参考文献：
  名称：

  Iodine-Mediated Oxidative Coupling of Hydroxamic Acids with Amines towards a New Peptide-Bond Formation

  摘要：

  An efficient and straightforward approach for the coupling of N-protected hydroxamic acids with an amino component in the presence of iodine is delineated. The reaction is mediated by the formation of unstable but reactive acyl nitroso intermediates. The peptide hydroxamic acids were found to be useful substrates in coupling reactions.

  DOI：

  10.1055/s-0035-1560266
• 作为产物：
  描述：

  (S)-(-)-2-异氰酰基-4-甲基戊酸甲酯 在 羟胺钾盐 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (S)-(1-hydroxycarbamoyl-3-methyl-butyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  新型氨基酸脲基衍生物作为氨肽酶N / CD13抑制剂的设计，合成和生物学评估

  摘要：

  合成了一系列氨基酸脲基衍生物作为氨肽酶N（APN / CD13）抑制剂，并对其APN抑制活性和抗癌作用进行了评估。结果表明，这些氨基酸脲基衍生物中的大多数对APN表现出良好的抑制作用，其中一些优于Bestatin。活性最高的化合物12j（IC 50  = 1.1μM，与Bestatin IC 50  = 8.1μM相比）不仅具有更好的APN抑制活性和对癌细胞的抗增殖作用，而且与人癌细胞侵袭相比具有显着的阻断作用阳性对照Bestatin。这些氨基酸脲基衍生物可能会在将来开发为用于癌症化学疗法的新型APN抑制剂。

  DOI：

  10.1016/j.bmc.2012.04.035

文献信息

• Solid Phase Synthesis of Hydroxamic Acids
  作者：Sharon M. Dankwardt

  DOI：10.1055/s-1998-1774

  日期：1998.7

  The solid phase synthesis of hydroxamic acids is presented. Carboxylic acid ester linked, polymer-supported CBZ-protected amino acids were displaced from the resin with aqueous hydroxylamine to provide the corresponding hydroxamic acids.

  羟肟酸的固相合成方法如下。首先，将带有酯键的聚合物支持的CBZ保护氨基酸从树脂上释放下来，然后用水合羟胺处理，生成相应的羟肟酸。
• A Novel, Simple and Practical Protocol for N-Protected-α-Amino Hydroxamic Acids
  作者：G. Vidyasagar Reddy

  DOI：10.1080/00397919908085996

  日期：1999.10

  A facile single step methodology for the preparation of N-Protected-alpha-amino hydroxamic acids from readily accessible N-protected oxazolidinones using hydroxylamine hydrochloride and triethylamine is described.
• An application of triflic anhydride as an acid activator: Synthesis of Nα-protected amino hydroxamic acids
  作者：Eti Chetankumar、Srinivasulu Chinthaginjala、Vommina V Sureshbabu

  DOI：10.24820/ark.5550190.p012.173

  日期：——
• Iodine-Mediated Oxidative Coupling of Hydroxamic Acids with Amines towards a New Peptide-Bond Formation
  作者：Vommina Sureshbabu、Muniyappa Krishnamurthy、T. Vishwanatha、Nageswara Panguluri、V. Panduranga

  DOI：10.1055/s-0035-1560266

  日期：——

  An efficient and straightforward approach for the coupling of N-protected hydroxamic acids with an amino component in the presence of iodine is delineated. The reaction is mediated by the formation of unstable but reactive acyl nitroso intermediates. The peptide hydroxamic acids were found to be useful substrates in coupling reactions.
• Design, synthesis and biological evaluation of novel amino acid ureido derivatives as aminopeptidase N/CD13 inhibitors
  作者：Li Su、Yuping Jia、Lei Zhang、Yingying Xu、Hao Fang、Wenfang Xu

  DOI：10.1016/j.bmc.2012.04.035

  日期：2012.6

  A series of amino acid ureido derivatives as aminopeptidase N (APN/CD13) inhibitors were synthesized and evaluated for their APN inhibitory activities and anti-cancer effects. The results showed that most of these amino acid ureido derivatives exhibited good inhibition against APN, several of which were better than Bestatin. The most active compound 12j (IC50 = 1.1 μM, compared with Bestatin IC50 = 8

  合成了一系列氨基酸脲基衍生物作为氨肽酶N（APN / CD13）抑制剂，并对其APN抑制活性和抗癌作用进行了评估。结果表明，这些氨基酸脲基衍生物中的大多数对APN表现出良好的抑制作用，其中一些优于Bestatin。活性最高的化合物12j（IC 50  = 1.1μM，与Bestatin IC 50  = 8.1μM相比）不仅具有更好的APN抑制活性和对癌细胞的抗增殖作用，而且与人癌细胞侵袭相比具有显着的阻断作用阳性对照Bestatin。这些氨基酸脲基衍生物可能会在将来开发为用于癌症化学疗法的新型APN抑制剂。