5-(carbobenzyloxyamino)valeronitrile | 328400-62-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(carbobenzyloxyamino)valeronitrile
• 英文别名: Carbobenzyloxyaminovaleronitrile；benzyl (4-cyanobutyl)carbamate；benzyl N-(4-cyanobutyl)carbamate
• CAS: 328400-62-0
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: AUZGFQWBYPTUAU-UHFFFAOYSA-N

物化性质

• 沸点：
  437.4±38.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(carbobenzyloxyamino)valeronitrile 在 palladium on activated charcoal sodium azide 、 氢气 、 三乙胺盐酸盐 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 24.0h， 生成 (tetrazolyl-5)1 amino-4 butane
  参考文献：
  名称：

  New substrates and inhibitors of γ-aminobutyric acid aminotransferase containing bioisosteres of the carboxylic acid group: Design, synthesis, and biological activity

  摘要：

  A series of potential substrates of gamma-aminobutyric acid aminotransferase (GABA-AT) with lipophilic bioisosteres of the carboxylic acid group (2-7) were synthesized and tested. Most of the synthesized compounds showed substrate activities with GABA-AT; 1H-tetrazole-5-propanamine (6) was the best of those tested. The potential time-dependent inhibitor of GABA-AT, 1H-tetrazole-5-(alpha-vinyl-propanamine) (8), was designed based on the structures of 6 and the antiepilepsy drug vigabatrin (4-amino-hex-5-enoic acid, 1). The synthesized compound 8 showed time-dependent inhibition of GABA-AT, but its potency is lower than that of vigabatrin. Methylation of the tetrazole group in 8 resulted in loss of time-dependent activity, suggesting that the tetrazole ring, the carboxylate bioisostere, exists in its deprotonated form in the enzyme active site. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.067
• 作为产物：
  描述：

  5-溴戊腈 在 sodium hydroxide 、 sodium azide 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 为溶剂， 反应 39.0h， 生成 5-(carbobenzyloxyamino)valeronitrile
  参考文献：
  名称：

  New substrates and inhibitors of γ-aminobutyric acid aminotransferase containing bioisosteres of the carboxylic acid group: Design, synthesis, and biological activity

  摘要：

  A series of potential substrates of gamma-aminobutyric acid aminotransferase (GABA-AT) with lipophilic bioisosteres of the carboxylic acid group (2-7) were synthesized and tested. Most of the synthesized compounds showed substrate activities with GABA-AT; 1H-tetrazole-5-propanamine (6) was the best of those tested. The potential time-dependent inhibitor of GABA-AT, 1H-tetrazole-5-(alpha-vinyl-propanamine) (8), was designed based on the structures of 6 and the antiepilepsy drug vigabatrin (4-amino-hex-5-enoic acid, 1). The synthesized compound 8 showed time-dependent inhibition of GABA-AT, but its potency is lower than that of vigabatrin. Methylation of the tetrazole group in 8 resulted in loss of time-dependent activity, suggesting that the tetrazole ring, the carboxylate bioisostere, exists in its deprotonated form in the enzyme active site. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.067

文献信息

• DRUG CONJUGATES AND METHODS OF DESIGNING THE SAME
  申请人：Brenner, Sydney

  公开号：EP1212096A2

  公开（公告）日：2002-06-12
• [EN] DRUG CONJUGATES AND METHODS OF DESIGNING THE SAME<br/>[FR] CONJUGUES DE MEDICAMENTS ET LEURS PROCEDES DE PREPARATION
  申请人：BRENNER SYDNEY

  公开号：WO2001013958A2

  公开（公告）日：2001-03-01

  The invention relates to drug conjugates and methods of their design. One embodiment of the invention is directed to a method of designing vector-linker-pharmacophore ('VLP') conjugates that is generally applicable to a wide variety of vectors, linkers, and pharmacophores. The invention also encompasses a method of improving the delivery of a pharmacophore to a patient, as well as a method of improving the therapeutic efficacy of a pharmacophore and a method of decreasing the toxicity of a pharmacophore. A method of increasing the concentration of a pharmacophore in a cell is further encompassed by the invention.
• New substrates and inhibitors of γ-aminobutyric acid aminotransferase containing bioisosteres of the carboxylic acid group: Design, synthesis, and biological activity
  作者：Hai Yuan、Richard B. Silverman

  DOI：10.1016/j.bmc.2005.09.067

  日期：2006.3

  A series of potential substrates of gamma-aminobutyric acid aminotransferase (GABA-AT) with lipophilic bioisosteres of the carboxylic acid group (2-7) were synthesized and tested. Most of the synthesized compounds showed substrate activities with GABA-AT; 1H-tetrazole-5-propanamine (6) was the best of those tested. The potential time-dependent inhibitor of GABA-AT, 1H-tetrazole-5-(alpha-vinyl-propanamine) (8), was designed based on the structures of 6 and the antiepilepsy drug vigabatrin (4-amino-hex-5-enoic acid, 1). The synthesized compound 8 showed time-dependent inhibition of GABA-AT, but its potency is lower than that of vigabatrin. Methylation of the tetrazole group in 8 resulted in loss of time-dependent activity, suggesting that the tetrazole ring, the carboxylate bioisostere, exists in its deprotonated form in the enzyme active site. (c) 2005 Elsevier Ltd. All rights reserved.