4-tert-butoxycarbonylamino-hex-5-enoic acid | 124099-19-0

• 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: 4-tert-butoxycarbonylamino-hex-5-enoic acid
• 英文别名: Boc-4-amino-4-vinylbutyric acid；5-Hexenoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-；4-[(2-methylpropan-2-yl)oxycarbonylamino]hex-5-enoic acid
• CAS: 124099-19-0
• 化学式: C₁₁H₁₉NO₄
• 分子量: 229.276
• InChiKey: UVHUXCMJPFOMEG-UHFFFAOYSA-N

物化性质

• 熔点：
  88.7-91.2 °C
• 沸点：
  382.1±35.0 °C(Predicted)
• 密度：
  1.078±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-tert-butoxycarbonylamino-hex-5-enoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 5.0h， 生成 1-O-linolenoyl-2-O-(4-aminobutyryl)-3-O-(4-vinyl-4-aminobutyryl)-rac-glycerol
  参考文献：
  名称：

  Synthesis, brain uptake, and pharmacological properties of a glyceryl lipid containing GABA and the GABA-T inhibitor .gamma.-vinyl-GABA

  摘要：

  1-O-Linolenoyl-2-O-(4-aminobutyryl)-3-O-(4-vinyl-4-aminobutyryl)glycerol (LGV) was synthesized as an example of a prodrug which readily penetrates the blood-brain barrier (brain penetration index 97% +/- 15%) and releases two active substances in the central nervous system (CNS): GABA (4-aminobutanoic acid) and the GABA transaminase inhibitor (GABA-T) of GABA breakdown. In vitro studies showed that the compound can inhibit GABA-T after hydrolysis by CNS esterases and that it enhanced GABAergic inhibition when applied to rat hippocampus slices. In vivo studies indicate that LGV depresses the spontaneous locomotor activity of mice. Its activity on a molar basis was some 300 times greater than that of gamma-vinyl-GABA.

  DOI：

  10.1021/jm00164a042
• 作为产物：
  描述：

  2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 、 4-氨基-5-己烯酸 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以82.6%的产率得到4-tert-butoxycarbonylamino-hex-5-enoic acid
  参考文献：
  名称：

  Design, synthesis and anticonvulsive activity of analogs of γ-vinyl GABA

  摘要：

  For the development of new anticonvulsive agents, analogs of gamma-vinyl GABA (vigabatrin) containing GABA, gamma-vinyl GABA, valproic acid, nipecotic acid or isonipecotic acid moieties were prepared and evaluated for their anticonvulsive activities. Most of the prepared compounds showed moderate anticonvulsive activities. Among them compounds 10 and 16 displayed the most potent anticonvulsive activity and a broader spectrum compared to vigabatrin.

  DOI：

  10.1016/j.farmac.2004.01.011

文献信息

• Design and synthesis of anticonvulsive agents as γ-vinyl GABA-based potential dual acting prodrugs and their biological activities
  作者：Yong-chul Kim、Long-Xuan Zhao、Tae-Hyung Kim、Sun-mi Je、Eun-kyung Kim、Heesung Choi、Whi-Gun Chae、Minsoo Park、Jongwon Choi、Yurngdong Jahng、Eung-Seok Lee

  DOI：10.1016/s0960-894x(00)00064-0

  日期：2000.4

  For the development of new anticonvulsive agents, gamma-vinyl GABA (vigabatrin) and GABA mimetics derivatives were covalently coupled as potential dual acting prodrugs and evaluated for their anticonvulsive activities. Among the prepared compounds, 11 showed the most potent anticonvulsive activity, a shorter onset time and a broader spectrum compared to vigabatrin.

  为了开发新的抗惊厥药，将γ-乙烯基GABA（维格巴林）和GABA模拟衍生物共价偶联，作为潜在的双重作用前药，并评估其抗惊厥活性。在制备的化合物中，与viGABAtrin相比，有11种化合物显示出最强的抗惊厥活性，更短的起效时间和更宽的光谱。
• JACOB, JAMES N.;HESSE, GARY W.;SHASHOUA, VICTOR E., J. MED. CHEM., 33,(1990) N, C. 733-736
  作者：JACOB, JAMES N.、HESSE, GARY W.、SHASHOUA, VICTOR E.

  DOI：——

  日期：——
• CN116621720
  申请人：——

  公开号：——

  公开（公告）日：——