hemibenzoylcarnitinium | 141661-40-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: hemibenzoylcarnitinium
• CAS: 141661-40-7
• 化学式: C₁₄H₂₀NO₄*Cl
• 分子量: 301.77
• InChiKey: SZVPHTRVPOHNPP-QMDUSEKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.21
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  sodium (R)-norcarnitine 在 盐酸 作用下， 以 异丙醇 为溶剂， 反应 96.0h， 生成 hemibenzoylcarnitinium
  参考文献：
  名称：

  Syntheses, structures, and enzymatic evaluations of hemiacylcarnitiniums, a new class of carnitine acyltransferase inhibitors

  摘要：

  The syntheses of (2S,6R)-6-(carboxymethyl)-2-hydroxy-2,4,4-trimethylmorpholinium chloride (hemiacetylcarnitinium, HAC), (2S,6R)-6-(carboxymethyl)-2-ethyl-2-hydroxy-4,4-dimethylmorpholinium bromide (hemipropanoylcarnitinium, HPrC), and (2S,6R)-6-(carboxymethyl)-2-hydroxy-4,4-dimethyl-2-phenylmorpholinium chloride monohydrate (hemibenzoylcarnitinium, HBC) are described. The crystal structure of HAC is reported and compared with crystal structures of HPrC, HBC, carnitine.HCl, acetylcarnitine.HCl, and acetylcarnitine.HCl.H2O. HAC, HPrC, and HBC inhibit carnitine acetyltransferase (CAT) activity from multiple biological sources. The best inhibitor, HAC, has K(i) of 69 +/- 5-mu-M with rat liver peroxisomal CAT. HAC binds more strongly than the natural substrate (and isomer), acetylcarnitine. HAC also strongly inhibits, K(i) = 92 +/- 14-mu-M, CAT from rat heart mitochondria. HPrC inhibits pigeon breast CAT with a K(i) of 200 +/- 30-mu-M. HBC inhibits pigeon breast CAT, rat heart mitochondrial CAT, rat liver mitochondrial CAT, and rat liver peroxisomal carnitine octanoyltransferase (COT), with values of K(i) of 3500 +/- 500, 2400 +/- 70,1670 +/- 70, and 1100 +/- 100-mu-M, respectively. Racemic 6-(carboxymethyl)-2-hydroxy-2-pentadecyl-4,4-dimethylmorpholinium bromide (hemipalmitoylcarnitinium, HPC) strongly inhibits (K(i) = 2 +/- 0.3-mu-M) beef liver mitochondrial CPT(i). In summary, hemiacylcarnitiniums show promise as a general class of carnitine acyltransferase inhibitors.

  DOI：

  10.1021/jo00038a035