mercaptoethylglycine disulfide | 29948-36-5

• 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: mercaptoethylglycine disulfide
• 英文别名: N,N'-(3,4-dithia-hexanediyl)-bis-glycine；N,N'-(3,4-Dithia-hexandiyl)-bis-glycin；Bis-(2-carboxymethylamino-aethyl)-disulfid；Ethylamine, 2,2'-dithiobis(N-carboxymethyl-, dihydrochloride；2-[2-[2-(carboxymethylamino)ethyldisulfanyl]ethylamino]acetic acid
• CAS: 29948-36-5
• 化学式: C₈H₁₆N₂O₄S₂
• 分子量: 268.358
• InChiKey: VGTZMOJZOBYPFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  mercaptoethylglycine ethyl ester 在 盐酸 、 碘 作用下， 生成 mercaptoethylglycine disulfide
  参考文献：
  名称：

  Structural requirements for the sequestration of metabolically generated acetaldehyde

  摘要：

  Of a series of polyfunctional compounds containing amino, hydroxyl, or mercapto groups in conjunction with the carboxyl group, only the 1,2- or 1,3-disubstituted aminothiols, namely, D-(-)-penicillamine (1), L-cysteine (2), L-cysteinyl-L-valine (3), mercaptoethylglycine (4), and DL-homocysteine (12), showed any propensity to sequester acetaldehyde (AcH) when tested in vitro in a buffered system at pH 7.5. In vivo, however, only D-(-)-penicillamine (1) was effective in lowering ethanol-derived blood AcH in rats that had been treated with disulfiram and ethanol. These results suggest that, in addition to the functionality in the molecule, pharmacokinetic and metabolic factors must also be considered when designing AcH-sequestering agents for use in vivo.

  DOI：

  10.1021/jm00176a007

文献信息

• Cysteamin-N-essigsäure, ein neuer Strahlenschutzstoff
  作者：E. Felder、F. Bonati、S. Bianchi

  DOI：10.1007/bf02157090

  日期：1959.1
• Bulawin, Zhurnal Organicheskoi Khimii, 1971, vol. 7, p. 2086,2089,2091;engl.Ausg.S.2168,2172
  作者：Bulawin

  DOI：——

  日期：——
• Structural requirements for the sequestration of metabolically generated acetaldehyde
  作者：Herbert T. Nagasawa、James A. Elberling、Eugene G. DeMaster

  DOI：10.1021/jm00176a007

  日期：1980.2

  Of a series of polyfunctional compounds containing amino, hydroxyl, or mercapto groups in conjunction with the carboxyl group, only the 1,2- or 1,3-disubstituted aminothiols, namely, D-(-)-penicillamine (1), L-cysteine (2), L-cysteinyl-L-valine (3), mercaptoethylglycine (4), and DL-homocysteine (12), showed any propensity to sequester acetaldehyde (AcH) when tested in vitro in a buffered system at pH 7.5. In vivo, however, only D-(-)-penicillamine (1) was effective in lowering ethanol-derived blood AcH in rats that had been treated with disulfiram and ethanol. These results suggest that, in addition to the functionality in the molecule, pharmacokinetic and metabolic factors must also be considered when designing AcH-sequestering agents for use in vivo.