S-methyl 4-di-n-propylamino-4-methyl-2-pentynethioate | 376630-95-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: S-methyl 4-di-n-propylamino-4-methyl-2-pentynethioate
• 英文别名: S-methyl 4-(dipropylamino)-4-methylpent-2-ynethioate
• CAS: 376630-95-4
• 化学式: C₁₃H₂₃NOS
• 分子量: 241.398
• InChiKey: BEXPPNNZLJYPQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-methyl 4-di-n-propylamino-4-methyl-2-pentynethioate 、 碘甲烷 以 乙酸乙酯 为溶剂， 生成 Trimethyl-(2-methyl-5-methylsulfanyl-5-oxopent-3-yn-2-yl)azanium;iodide
  参考文献：
  名称：

  Aldehyde dehydrogenase inhibitors: α,β-Acetylenic N-substituted aminothiolesters are reversible growth inhibitors of normal epithelial but irreversible apoptogens for cancer epithelial cells from human prostate in culture

  摘要：

  The pharmacomodulation of the N atom of alpha,beta-acetylenic aminothiolesters or the replacement of the thiolester moiety by more electroplfflic groups did not permit any clear rationale to be established for improving the selective growth-inhibitory activity of this family of compounds over that of the previously synthesized alpha,beta-acetylenic aminothiolesters DIMATE and MATE [G. Quash, G. Fournet, J. Chantepie, J. Gore, C. Ardiet, D. Ardail, Y. Michal, U. Reichert, Biochem Phannacol 64 (2002) 1279-92]. Hence DIMATE and MATE were investigated more thoroughly for selectivity and growth-inhibitory activity using human prostate epithelial normal cells (HPENC) on the one hand and human prostate epithelial cancer cells (DU145) on the other. Unequivocal evidence was obtained showing that both compounds were reversible growth inhibitors of HPENC but irreversible growth inhibitors of DU145. Growth-inhibition of DU145 was due to the induction of early apoptosis as revealed by the flow cytometric analytical profile of inhibitor-treated cells, of the decrease in the redox potential and increase in superoxide anion content of their mitochondria. Of the two intracellular enzymes: aldehyde dehydrogenases 1 and 3 (ALDH1 and ALDH3) targeted by DIMATE and MATE, ALDH3 was inhibited to the same extent by both compounds whereas ALDH1 was less susceptible to inhibition by MATE. As the induction of ALDH3 by xenobiotics is hormone-dependent, MATE, the more selective of the two inhibitors, is a useful tool not only for examining the role of the ALDH3 isoform in hormone-sensitive and resistant prostate cancer cells in culture but also for investigating if it can inhibit the growth of xenografts of prostate cancer in immunodeficient mice. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.06.004
• 作为产物：
  描述：

  2-methyl-N,N-dipropyl-3-butyn-2-amine 以75%的产率得到S-methyl 4-di-n-propylamino-4-methyl-2-pentynethioate
  参考文献：
  名称：

  Aminothiolester compounds, pharmaceutical and cosmetic compositions containing same and uses thereof

  摘要：

  该发明涉及一种具有通式(I)的新型氨基硫醇酯化合物，以及制备它们的方法，以及它们在制备用于人类或兽医学（尤其是癌症和癌前病变、皮肤病、风湿病和眼科疾病）的药物组合物或化妆品组合物中的使用。该发明还涉及一种药物或化妆品组合物，其特征在于它包含通式(I)的化合物作为活性剂，与药学或化妆品上可接受的载体相结合。

  公开号：

  US20030181443A1

文献信息

• Aldehyde dehydrogenase inhibitors: α,β-Acetylenic N-substituted aminothiolesters are reversible growth inhibitors of normal epithelial but irreversible apoptogens for cancer epithelial cells from human prostate in culture
  作者：Gerard Quash、Guy Fournet、Charlotte Courvoisier、Rosa M. Martinez、Jacqueline Chantepie、Marie Julie Paret、Julie Pharaboz、Marie Odile Joly-Pharaboz、Jacques Goré、Jean André

  DOI：10.1016/j.ejmech.2007.06.004

  日期：2008.5

  The pharmacomodulation of the N atom of alpha,beta-acetylenic aminothiolesters or the replacement of the thiolester moiety by more electroplfflic groups did not permit any clear rationale to be established for improving the selective growth-inhibitory activity of this family of compounds over that of the previously synthesized alpha,beta-acetylenic aminothiolesters DIMATE and MATE [G. Quash, G. Fournet, J. Chantepie, J. Gore, C. Ardiet, D. Ardail, Y. Michal, U. Reichert, Biochem Phannacol 64 (2002) 1279-92]. Hence DIMATE and MATE were investigated more thoroughly for selectivity and growth-inhibitory activity using human prostate epithelial normal cells (HPENC) on the one hand and human prostate epithelial cancer cells (DU145) on the other. Unequivocal evidence was obtained showing that both compounds were reversible growth inhibitors of HPENC but irreversible growth inhibitors of DU145. Growth-inhibition of DU145 was due to the induction of early apoptosis as revealed by the flow cytometric analytical profile of inhibitor-treated cells, of the decrease in the redox potential and increase in superoxide anion content of their mitochondria. Of the two intracellular enzymes: aldehyde dehydrogenases 1 and 3 (ALDH1 and ALDH3) targeted by DIMATE and MATE, ALDH3 was inhibited to the same extent by both compounds whereas ALDH1 was less susceptible to inhibition by MATE. As the induction of ALDH3 by xenobiotics is hormone-dependent, MATE, the more selective of the two inhibitors, is a useful tool not only for examining the role of the ALDH3 isoform in hormone-sensitive and resistant prostate cancer cells in culture but also for investigating if it can inhibit the growth of xenografts of prostate cancer in immunodeficient mice. (C) 2007 Elsevier Masson SAS. All rights reserved.
• Aminothiolester compounds, pharmaceutical and cosmetic compositions containing same and uses thereof
  申请人：——

  公开号：US20030181443A1

  公开（公告）日：2003-09-25

  The invention relates to novel aminothiol ester compounds having the general formula (I): 1 and to a method for preparing them and to their use in pharmaceutical compositions intended for use in human or veterinary medicine (cancers and precancers, dermatological, rheumatic and ophthalmological complaints in particular) or in cosmetic compositions. The invention also relates to a pharmaceutical or cosmetic composition, characterized in that it comprises, as active agent, a compound of general formula (I) in combination with a pharmaceutically or cosmetically acceptable support.

  该发明涉及一种具有通式(I)的新型氨基硫醇酯化合物，以及制备它们的方法，以及它们在制备用于人类或兽医学（尤其是癌症和癌前病变、皮肤病、风湿病和眼科疾病）的药物组合物或化妆品组合物中的使用。该发明还涉及一种药物或化妆品组合物，其特征在于它包含通式(I)的化合物作为活性剂，与药学或化妆品上可接受的载体相结合。