N-(1,4-dihydro-1-methylnicotinoyl)-DL-tryptophan butyl ester | 128577-02-6

• 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: N-(1,4-dihydro-1-methylnicotinoyl)-DL-tryptophan butyl ester
• 英文别名: butyl 3-(1H-indol-3-yl)-2-[(1-methyl-4H-pyridine-3-carbonyl)amino]propanoate
• CAS: 128577-02-6
• 化学式: C₂₂H₂₇N₃O₃
• 分子量: 381.475
• InChiKey: LGCMPSVKKHSWRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-<<(R,S)-1-carboxy-2-indol-3-ylethyl>carbamoyl>-1-methylpyridinium iodide butyl ester 在 sodium dithionite 、 碳酸氢钠 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 5.0h， 以70.7%的产率得到N-(1,4-dihydro-1-methylnicotinoyl)-DL-tryptophan butyl ester
  参考文献：
  名称：

  Improved delivery through biological membranes. 50. Antihypertensive activity of redox derivatives of tryptophan

  摘要：

  The essential amino acid, tryptophan, has been shown to lower blood pressure in rats when administered orally or intravenously. In order to potentially enhance this action, a brain-targeting chemical delivery system (CDS) approach was applied to this compound. The CDS is based on a dihydropyridine----pyridinium ion redox system, chemically analogous to the naturally occurring NADH----NAD+ system. The dihydropyridine moiety containing carrier is chemically attached to the amino group by an amide-type bonding while the carboxylic acid functionality is esterified to various alcohols. Physicochemical studies of the new derivatives were performed. The determined chromatographic Rm values indicate an increased lipophilicity for the CDSs compared to the parent compound. Oxidation stability studies performed on selected compounds using a ferricyanide-mediated method showed that the CDSs are oxidized to the respective quaternary salt forms. Activity studies performed in deoxycorticosterone acetate induced hypertensive rats, demonstrated that the delivery system for tryptophan reduced blood pressure more efficiently for a longer time than did the parent compound.

  DOI：

  10.1021/jm00170a028

文献信息

• POP, EMIL;ANDERSON, WESLEY;PROKAJ-TATRAI, KATALIN;BREWSTER, MARCUS E.;FRE+, J. MED. CHEM., 33,(1990) N, C. 2216-2221
  作者：POP, EMIL、ANDERSON, WESLEY、PROKAJ-TATRAI, KATALIN、BREWSTER, MARCUS E.、FRE+

  DOI：——

  日期：——