N-(1,1-dimethyl-2-propynyl)-N-methyl-benzenamine | 14465-43-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(1,1-dimethyl-2-propynyl)-N-methyl-benzenamine
• 英文别名: N-methyl-N-(2-methyl-3-butyn-2-yl)aniline；3--3-methyl-butin-(1)；N-(1.1-Dimethyl-2-propinyl)-N-methylanilin；N-methyl-N-(2-methylbut-3-yn-2-yl)aniline
• CAS: 14465-43-1
• 化学式: C₁₂H₁₅N
• 分子量: 173.258
• InChiKey: FPCTZKIZEWLBSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  羰基硫 、 N-(1,1-dimethyl-2-propynyl)-N-methyl-benzenamine 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 4-methyl-4-(N-methylanilino)pent-2-ynethioic S-acid
  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：

  3-氯-3-甲基-1-丁炔 、 N-甲基苯胺 在 铜 、 三乙胺 、 copper(l) chloride 作用下， 以 乙醚 为溶剂， 生成 N-(1,1-dimethyl-2-propynyl)-N-methyl-benzenamine
  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

文献信息

• Synthesis and Structure-Activity Relationships of Side-Chain-Substituted Analogs of the Allylamine Antimycotic Terbinafine Lacking the Central Amino Function
  作者：Peter Nussbaumer、Ingrid Leitner、Karin Mraz、Anton Stuetz

  DOI：10.1021/jm00010a029

  日期：1995.5

  Terbinafine is a therapeutically used inhibitor of fungal squalene epoxidase that has prompted extensive derivatization programs for structure-activity relationship studies. In the present study, derivatives of terbinafine were synthesized that lack the central tertiary amino group but have polar substitutents at the tert-butyl residue of the side chain. Evaluation of the antifungal potential revealed

  特比萘芬是一种治疗性使用的真菌角鲨烯环氧酶抑制剂，已为结构-活性关系研究提供了广泛的衍生程序。在本研究中，合成了特比萘芬的衍生物，这些衍生物缺乏中心的叔氨基，但在侧链的叔丁基残基上具有极性取代基。对抗真菌潜力的评估表明，这种新型结构类型的代表也可以表现出广泛的抗真菌活性，这表明烯丙胺类抗真菌药的中心氨基功能对于抑制真菌生长不是必需的。效力似乎与引入的官能团的极性相关，而广泛的抗真菌活性似乎仅限于具有碱性取代基的化合物。二甲氨基取代的“碳水化合物类似物”
• The Alkylation of Amines with t-Acetylenic Chlorides. Preparation of Sterically Hindered Amines¹
  作者：G. F. Hennion、Robert S. Hanzel

  DOI：10.1021/ja01503a040

  日期：1960.9
• Synthesis and inhibitory activity of 4-alkynyl and 4-alkenylquinazolines: Identification of new scaffolds for potent EGFR tyrosine kinase inhibitors
  作者：Yasunori Kitano、Tsuyoshi Suzuki、Eiji Kawahara、Takahisa Yamazaki

  DOI：10.1016/j.bmcl.2007.08.020

  日期：2007.11

  The present study identified several 4-alkynyl and 4-alkenylquinazolines that serve as novel and potent EGFR tyrosine kinase inhibitors. The IC50 values of these compounds are in the nanomolar range. In addition, the 4-(4-phenylbut-1-yl/en-yl)quinazolines provided scaffolds for potent enzyme inhibition. Chiral discrimination was observed to occur in one of the 4-alkynylquinazoline derivatives with the (R)-isomer being more than 150 times as potent as the (S)-isomer. (c) 2007 Elsevier Ltd. All rights reserved.
• Palladium-Catalyzed Carbonylation of Propargylamines. Selective Insertion of Carbon Monoxide into a Carbon−Nitrogen Bond
  作者：Yasushi Imada、Howard Alper

  DOI：10.1021/jo9613545

  日期：1996.1.1