methyl N-Cbz-β-alanylsulfonamide | 117290-25-2

• 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: methyl N-Cbz-β-alanylsulfonamide
• 英文别名: benzyl N-[3-(methanesulfonamido)-3-oxopropyl]carbamate
• CAS: 117290-25-2
• 化学式: C₁₂H₁₆N₂O₅S
• 分子量: 300.335
• InChiKey: JTYPIZNQEIFDRR-UHFFFAOYSA-N

物化性质

• 熔点：
  126.5-127 °C
• 密度：
  1.319±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl N-Cbz-β-alanylsulfonamide 在 氢溴酸 、 溶剂黄146 作用下， 反应 0.33h， 以71%的产率得到methyl β-alanylsulfonamide hydrobromide
  参考文献：
  名称：

  WO2007/35964

  摘要：

  公开号：
• 作为产物：
  描述：

  N-CBZ-beta-丙氨酸 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 生成 methyl N-Cbz-β-alanylsulfonamide
  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

• Convenient procedure for the preparation of alkyl and aryl substituted N-(aminoalkylacyl)sulfonamides
  作者：James T. Drummond、Graham Johnson

  DOI：10.1016/s0040-4039(00)82009-2

  日期：1988.1

  A convenient synthesis of N-(aminoalkylacyl)sulfonamides from CBZ potected glycine, β-alanine and GABA is described.

  描述了从CBZ提取的甘氨酸，β-丙氨酸和GABA方便地合成N-（氨基烷基酰基）磺酰胺的方法。
• A guanidinium group is an effective mimic of the tertiary carbocation formed by isopentenyl diphosphate isomerase
  作者：Zaile Zhuang、Muze Li、Martin E. Tanner

  DOI：10.1016/j.bmcl.2022.128971

  日期：2022.11

  Type I isopentenyl diphosphate isomerase is a metal-dependent enzyme that generates a tertiary carbocation intermediate during catalysis. This study describes an inhibitor (2-guanidinoethyl(dihydroxyphosphorylmethyl)phosphinate) of the isomerase that bears a guanidinium as a carbocation mimic and a phosphinylphosphonate as a non-hydrolyzable metal binding functionality. Inhibition kinetics show that

  I 型异戊烯二磷酸异构酶是一种金属依赖性酶，在催化过程中产生叔碳正离子中间体。该研究描述了异构酶的抑制剂（2-胍基乙基（二羟基磷酰甲基）次膦酸盐），它带有胍盐作为碳阳离子模拟物和膦酰膦酸盐作为不可水解的金属结合功能。抑制动力学表明该化合物以竞争方式发挥作用，K i值为 129 nM ( K M,IPP / K i = 27)。带有叔铵作为碳阳离子模拟物的类似抑制剂的效力要低 50 倍，这表明平面胍是一种更有效的碳阳离子模拟物。带有酰化甲磺酰胺或异羟肟酸酯基团代替焦磷酸盐的抑制剂在毫摩尔浓度下抑制酶，表明异构酶对结合中间体的二磷酸盐部分具有高度特异性。
• DRUMMOND, JAMES T.;JOHNSON, GRAHAM, TETRAHEDRON LETT., 29,(1988) N 14, 1653-1656
  作者：DRUMMOND, JAMES T.、JOHNSON, GRAHAM

  DOI：——

  日期：——