methyl (R)-4-(dimethylamino)-3-hydroxybutanoate | 145554-74-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl (R)-4-(dimethylamino)-3-hydroxybutanoate
• 英文别名: methyl (3R)-4-(dimethylamino)-3-hydroxybutanoate
• CAS: 145554-74-1
• 化学式: C₇H₁₅NO₃
• 分子量: 161.201
• InChiKey: KCRZWFZLGUAJKE-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (R)-4-(dimethylamino)-3-hydroxybutanoate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 硝基甲烷 为溶剂， 生成 Z 15
  参考文献：
  名称：

  Acylcarnitine analogues as topical, microbicidal spermicides.

  摘要：

  Acylcarnitine analogues, (+)-6-Carboxylatomethyl-2-alkyl-4,4-dimethylmorpholinium (Z-n, where n = the number of carbons in the alkyl chain), synthesized in multi-gram quantities show in vitro activities as spermicides, anti-HIV agents, and inhibitors of the growth of Candida albicans. Activity improves with increasing chain length. Compound Z-15 is a candidate for further study as a topical, microbicidal spermicide. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00423-0
• 作为产物：
  描述：

  sodium (R)-norcarnitine 、 原甲酸三甲酯 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以58%的产率得到methyl (R)-4-(dimethylamino)-3-hydroxybutanoate
  参考文献：
  名称：

  (+)-Hemipalmitoylcarnitinium strongly inhibits carnitine palmitoyltransferase-I in intact mitochondria

  摘要：

  The reaction of the methyl ester of (R)-norcarnitine with 1-bromo-2-heptadecanone produces (+)-6-[(methoxycarbonyl)methyl]-2-pentadecyl-4,4-dimethylmorpholinium bromide, 3, which hydrolyzes to (+)-6-(carboxylatomethyl)-2-pentadecyl-4,4-dimethylmorpholinium (hemipalmitoylcarnitinium, HPC) upon treatment with aqueous sodium hydroxide. Single-crystal X-ray analyses have confirmed the structures of (+)-HPC and 3. (+)-HPC inhibits carnitine palmitoyltransferase (CPT-I) activity for the forward reaction (palmitoyl-CoA + carnitine -->) in intact mitochondria from rat heart and rat liver. (+)-HPC competitively (versus carnitine) inhibits CPT-I activity in both rat heart and liver mitochondria with K(i) = 2.8 +/- 0.5 and 4.2 +/- 0.7 muM, respectively. As one of the strongest specific inhibitors of CPT-I, HPC is a potential therapeutic agent in myocardial ischemia and Type II diabetes.

  DOI：

  10.1021/jm00054a007

文献信息

• Carnitine analogues as topical, microbicidal spermicides
  申请人：Virginia Tech Intellectual Properties, Inc.

  公开号：US06656936B1

  公开（公告）日：2003-12-02

  Acylcarnitine analogues having alkyl side chains of 10 to 30 carbon atoms display excellent spermicidal and anti-HIV activity, a well as being potent inhibitors of the growth of Candida albicans.

  具有10到30个碳原子的烷基侧链的酰基肉碱类似物显示出优异的杀精和抗HIV活性，同时也是强效的白色念珠菌生长抑制剂。
• Acylcarnitine analogues as topical, microbicidal spermicides.
  作者：Prashant S. Savle、Gustavo F. Doncel、Stephen D. Bryant、M. Patricia Hubieki、R. Graham Robinette、Richard D. Gandour

  DOI：10.1016/s0960-894x(99)00423-0

  日期：1999.9

  Acylcarnitine analogues, (+)-6-Carboxylatomethyl-2-alkyl-4,4-dimethylmorpholinium (Z-n, where n = the number of carbons in the alkyl chain), synthesized in multi-gram quantities show in vitro activities as spermicides, anti-HIV agents, and inhibitors of the growth of Candida albicans. Activity improves with increasing chain length. Compound Z-15 is a candidate for further study as a topical, microbicidal spermicide. (C) 1999 Elsevier Science Ltd. All rights reserved.
• (+)-Hemipalmitoylcarnitinium strongly inhibits carnitine palmitoyltransferase-I in intact mitochondria
  作者：Richard D. Gandour、On Tai Leung、Anthony T. Greway、Rona R. Ramsay、Noirin Nic A Bhaird、Frank R. Fronczek、Bret M. Bellard、G. Kumaravel

  DOI：10.1021/jm00054a007

  日期：1993.1

  The reaction of the methyl ester of (R)-norcarnitine with 1-bromo-2-heptadecanone produces (+)-6-[(methoxycarbonyl)methyl]-2-pentadecyl-4,4-dimethylmorpholinium bromide, 3, which hydrolyzes to (+)-6-(carboxylatomethyl)-2-pentadecyl-4,4-dimethylmorpholinium (hemipalmitoylcarnitinium, HPC) upon treatment with aqueous sodium hydroxide. Single-crystal X-ray analyses have confirmed the structures of (+)-HPC and 3. (+)-HPC inhibits carnitine palmitoyltransferase (CPT-I) activity for the forward reaction (palmitoyl-CoA + carnitine -->) in intact mitochondria from rat heart and rat liver. (+)-HPC competitively (versus carnitine) inhibits CPT-I activity in both rat heart and liver mitochondria with K(i) = 2.8 +/- 0.5 and 4.2 +/- 0.7 muM, respectively. As one of the strongest specific inhibitors of CPT-I, HPC is a potential therapeutic agent in myocardial ischemia and Type II diabetes.