N-benzyl-3-(N-Boc)aminobutanamide | 144403-09-8

• 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-benzyl-3-(N-Boc)aminobutanamide
• 英文别名: Boc-_χAbu-BZA；tert-butyl N-[4-(benzylamino)-4-oxobutyl]carbamate
• CAS: 144403-09-8
• 化学式: C₁₆H₂₄N₂O₃
• 分子量: 292.378
• InChiKey: SDFCYKFTSGSOPG-UHFFFAOYSA-N

物化性质

• 沸点：
  501.9±43.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  N-benzyl-3-(N-Boc)aminobutanamide 在 盐酸 、 甲醇 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 4''-O-(((benzyl)amino)-4-oxobutyl)carbamoylazithromycin 11,12-cyclic carbonate
  参考文献：
  名称：

  Synthesis and antibacterial activity of novel 11,12-cyclic carbonate azithromycin 4″-O-carbamate derivatives

  摘要：

  设计、合成了系列新颖的11,12-环碳酸酯阿奇霉素4'-O-氨基甲酸酯衍生物，并评价了它们的体外抗菌活性。化合物7b和7d对两种红霉素耐药的肺炎链球菌（分别为erm基因和erm及mef基因编码的耐药性）效果最佳（0.5和0.5µg·ml-1）。化合物7a、7e和7g对红霉素敏感菌株（如金黄色葡萄球菌和酿脓链球菌）显示出显著的强大活性。这些结果表明，将延长芳基烷基氨基甲酰基引入C-4"位可显著增强对erm基因或erm和mef基因编码的红霉素耐药细菌的活性。

  DOI：

  10.1038/ja.2009.108
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 34.0h， 生成 N-benzyl-3-(N-Boc)aminobutanamide
  参考文献：
  名称：

  Synthesis and antibacterial activity of novel 11,12-cyclic carbonate azithromycin 4″-O-carbamate derivatives

  摘要：

  设计、合成了系列新颖的11,12-环碳酸酯阿奇霉素4'-O-氨基甲酸酯衍生物，并评价了它们的体外抗菌活性。化合物7b和7d对两种红霉素耐药的肺炎链球菌（分别为erm基因和erm及mef基因编码的耐药性）效果最佳（0.5和0.5µg·ml-1）。化合物7a、7e和7g对红霉素敏感菌株（如金黄色葡萄球菌和酿脓链球菌）显示出显著的强大活性。这些结果表明，将延长芳基烷基氨基甲酰基引入C-4"位可显著增强对erm基因或erm和mef基因编码的红霉素耐药细菌的活性。

  DOI：

  10.1038/ja.2009.108

文献信息

• [EN] BORONIC ACID CATALYSTS AND METHODS OF USE THEREOF FOR ACTIVATION AND TRANSFORMATION OF CARBOXYLIC ACIDS<br/>[FR] CATALYSEURS À BASE D'ACIDE BORONIQUE ET PROCÉDÉS D'UTILISATION ASSOCIÉS POUR L'ACTIVATION ET LA TRANSFORMATION D'ACIDES CARBOXYLIQUES
  申请人：UNIV ALBERTA

  公开号：WO2012109749A1

  公开（公告）日：2012-08-23

  The present application provides methods and catalysts for activation of carboxylic acids for organic reactions. In particular, methods are disclosed for direct nucleophilic addition reactions, such as, amidation reactions with amines, cycloadditions, and conjugate additions, using boronic acid catalysts of formula I, II or III: Also included are novel boronic acid catalysts of formula IV, V and III:

  本申请提供了用于活化羧酸进行有机反应的方法和催化剂。具体而言，揭示了用于直接亲核加成反应的方法，例如与胺的酰胺化反应，环加成和共轭加成，使用式I、II或III的硼酸催化剂：还包括式IV、V和III的新型硼酸催化剂：
• A new powerful method for the transformation of lactams into ω-amino-carboxamides under high pressure conditions
  作者：Hiyoshizo Kotsuki、Mitsuhiro Iwasaki、Hitoshi Nishizawa

  DOI：10.1016/s0040-4039(00)61241-8

  日期：1992.8

  High-pressure reaction of N-Boc-lactams with amines provides an efficient entry to ω-N-Boc-amino-carboxamide derivatives.

  的高压反应Ñ与胺-Boc内酰胺提供了一种有效条目ω- Ñ -Boc氨基羧酰胺衍生物。
• Identification of Multiple Structurally Distinct, Nonpeptidic Small Molecule Inhibitors of Protein Arginine Deiminase 3 Using a Substrate-Based Fragment Method
  作者：Haya Jamali、Hasan A. Khan、Joseph R. Stringer、Somenath Chowdhury、Jonathan A. Ellman

  DOI：10.1021/jacs.5b00095

  日期：2015.3.18

  The protein arginine deiminases (PADs) are a family of enzymes that catalyze the post-translational hydrolytic deimination of arginine residues. Four different enzymologically active PAD subtypes have been characterized and exhibit tissue-specific expression and association with a number of different diseases. In this Article we describe the development of an approach for the reliable discovery of low molecular weight, nonpeptidic fragment substrates of the PADs that then can be optimized and converted to mechanism-based irreversible PAD inhibitors. The approach is demonstrated by the development of potent and selective inhibitors of PAD3, a PAD subtype implicated in the neurodegenerative response to spinal cord injury. Multiple structurally distinct inhibitors were identified with the most potent inhibitors having >10,000 min(-1) M-1 k(inact)/K-I values and >= 10-fold selectivity for PAD3 over PADs 1, 2, and 4.
• Synthesis and antibacterial evaluation of novel clarithromycin derivatives with C-4″ elongated arylalkyl groups against macrolide-resistant strains
  作者：Shutao Ma、Bo Jiao、Yongjing Ju、Manjie Zheng、Ruixin Ma、Lin Liu、Ling Zhang、Xuecui Shen、Chenchen Ma、Ya Meng、Hui Wang、Yunkun Qi、Xiaodong Ma、Wenping Cui

  DOI：10.1016/j.ejmech.2010.11.035

  日期：2011.2

  Novel clarithromycin derivatives with C-4 '' elongated arylalkyl groups were designed, synthesized and evaluated to probe the effect of different lengths of their C-4 '' side chains on the activity against resistant bacterial strains. These derivatives had excellent activity against erythromycin-susceptible Streptococcus pneumoniae, Streptococcus aureus or Streptococcus pyogenes and some of them exhibited greatly improved activity against erythromycin-resistant strains. Compounds 18 and 16, which had the C-4 '' elongated arylalkyl groups with eight atoms from the 4 ''-oxygen atom to the terminal benzene ring, were the most effective against S. pneumoniae expressing the erm gene and the erm and me! genes. In contrast, the most potent compounds 3, 5, 9,17 and 18 against S. pneumoniae expressing the mef gene had C-4 '' elongated arylalkyl groups with three to eight atoms between the 4 ''-oxygen atom and the terminal aromatic ring. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Synthesis and antibacterial activity of novel 11,12-cyclic carbonate azithromycin 4″-O-carbamate derivatives
  作者：Chenchen Ma、Zhaopeng Liu、Hualong Song、Rentao Jiang、Fawen He、Shutao Ma

  DOI：10.1038/ja.2009.108

  日期：2010.1

  A series of novel 11,12-cyclic carbonate azithromycin 4″-O-carbamate derivatives were designed, synthesized and evaluated for their in vitro antibacterial activities. Compounds 7b and 7d were the most effective (0.5 and 0.5 μg ml−1) against two strains of erythromycin-resistant Streptococcus pneumoniae whose resistance was encoded by the erm gene and the erm and mef genes, respectively. Compounds 7a, 7e and 7g showed significantly potent activity against erythromycin-susceptible strains such as Staphylococcus aureus and S. pyogenes. These results suggest that the introduction of the prolonged arylalkylcarbamoyl group to the C-4″ position can dramatically enhance the activity against erythromycin-resistant bacteria encoded by the erm gene or the erm and mef genes.

  设计、合成了系列新颖的11,12-环碳酸酯阿奇霉素4'-O-氨基甲酸酯衍生物，并评价了它们的体外抗菌活性。化合物7b和7d对两种红霉素耐药的肺炎链球菌（分别为erm基因和erm及mef基因编码的耐药性）效果最佳（0.5和0.5µg·ml-1）。化合物7a、7e和7g对红霉素敏感菌株（如金黄色葡萄球菌和酿脓链球菌）显示出显著的强大活性。这些结果表明，将延长芳基烷基氨基甲酰基引入C-4"位可显著增强对erm基因或erm和mef基因编码的红霉素耐药细菌的活性。