5-(3-phthalimido-4-pentenyl)-1H-tetrazole | 875932-95-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 5-(3-phthalimido-4-pentenyl)-1H-tetrazole
• 英文别名: 2-[5-(2H-tetrazol-5-yl)pent-1-en-3-yl]isoindole-1,3-dione
• CAS: 875932-95-9
• 化学式: C₁₄H₁₃N₅O₂
• 分子量: 283.29
• InChiKey: OIJFUTKXOYIQPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  91.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(3-phthalimido-4-pentenyl)-1H-tetrazole 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 1-methyl-1H-tetrazole-5-(α-vinylpropanamine)
  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：

  4-phthalimido-5-hexenenitrile 在 sodium azide 、 三乙胺盐酸盐 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以60%的产率得到5-(3-phthalimido-4-pentenyl)-1H-tetrazole
  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

• Vigabatrin bioisoteres and related methods of use
  申请人：Silverman B. Richard

  公开号：US20070105924A1

  公开（公告）日：2007-05-10

  Compounds bioisoteric to vigabatrin and related methods of use.

  复合物对维加巴林具有生物隐秘性和相关使用方法。
• WO2007/35964
  申请人：——

  公开号：——

  公开（公告）日：——