N¹-(3-methoxybenzyl)-N³,N³-dimethylpropane-1,3-diamine | 893613-31-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N¹-(3-methoxybenzyl)-N³,N³-dimethylpropane-1,3-diamine
• 英文别名: N'-(3-methoxybenzyl)-N,N-dimethylpropane-1,3-diamine；N-[(3-methoxyphenyl)methyl]-N',N'-dimethylpropane-1,3-diamine
• CAS: 893613-31-5
• 化学式: C₁₃H₂₂N₂O
• mdl: MFCD07407132
• 分子量: 222.33
• InChiKey: CHTUVBVTLXJMNP-UHFFFAOYSA-N

物化性质

• 沸点：
  317.0±27.0 °C(Predicted)
• 密度：
  0.973±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  24.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N¹-(3-methoxybenzyl)-N³,N³-dimethylpropane-1,3-diamine 、 C₁₈H₁₃N₃O₂ 在 三乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(3-(dimethylamino)propyl)-N-(3-methoxybenzyl)-1-methyl-6-(1H-pyrazol-4-yl)-1H-indole-3-carboxamide
  参考文献：
  名称：

  Discovery and optimization of indole and 7-azaindoles as Rho kinase (ROCK) inhibitors (Part-II)

  摘要：

  Therapeutic interventions with Rho kinase (ROCK) inhibitors may effectively treat several disorders such as hypertension, stroke, cancer, and glaucoma. Herein we disclose the optimization and biological evaluation of potent novel ROCK inhibitors based on substituted indole and 7-azaindole core scaffolds. Substitutions on the indole C3 position and on the indole NH and/or amide NH positions all yielded potent and selective ROCK inhibitors (25, 42, and 50). Improvement of aqueous solubility and tailoring of in vitro and in vivo DMPK properties could be achieved through these substitutions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.084
• 作为产物：
  描述：

  N,N-二甲基-1,3-二氨基丙烷 、 3-甲氧基苯甲醛 在 sodium sulfate 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 118.0h， 以66%的产率得到N¹-(3-methoxybenzyl)-N³,N³-dimethylpropane-1,3-diamine
  参考文献：
  名称：

  N1,N1-Dimethyl-N3-(3-(trifluoromethyl)phenethyl)propane-1,3-diamine, a new lead for the treatment of human African trypanosomiasis

  摘要：

  The natural product, convolutamine I (1), has anti-trypanosomal activity however it has a high molecular weight of 473 due to a presence of 3 bromine atoms. The synthesis of the natural product convolutamine I (1) together with its analogues are presented. A SAR study against Trypanosoma brucei brucei led to compounds with improved physico-chemical properties: lower molecular weight and lower log P while maintaining potency (with a slight 2-fold improvement). (C) 2014 The Authors. Published by Elsevier Masson SAS. All rights

  DOI：

  10.1016/j.ejmech.2013.12.050

文献信息

• N1,N1-Dimethyl-N3-(3-(trifluoromethyl)phenethyl)propane-1,3-diamine, a new lead for the treatment of human African trypanosomiasis
  作者：Ngoc B. Pham、Sophie Deydier、Mehdi Labaied、Séverine Monnerat、Kenneth Stuart、Ronald J. Quinn

  DOI：10.1016/j.ejmech.2013.12.050

  日期：2014.3

  The natural product, convolutamine I (1), has anti-trypanosomal activity however it has a high molecular weight of 473 due to a presence of 3 bromine atoms. The synthesis of the natural product convolutamine I (1) together with its analogues are presented. A SAR study against Trypanosoma brucei brucei led to compounds with improved physico-chemical properties: lower molecular weight and lower log P while maintaining potency (with a slight 2-fold improvement). (C) 2014 The Authors. Published by Elsevier Masson SAS. All rights
• Discovery and optimization of indole and 7-azaindoles as Rho kinase (ROCK) inhibitors (Part-II)
  作者：E. Hampton Sessions、Sarwat Chowdhury、Yan Yin、Jennifer R. Pocas、Wayne Grant、Thomas Schröter、Li Lin、Claudia Ruiz、Michael D. Cameron、Philip LoGrasso、Thomas D. Bannister、Yangbo Feng

  DOI：10.1016/j.bmcl.2011.09.084

  日期：2011.12

  Therapeutic interventions with Rho kinase (ROCK) inhibitors may effectively treat several disorders such as hypertension, stroke, cancer, and glaucoma. Herein we disclose the optimization and biological evaluation of potent novel ROCK inhibitors based on substituted indole and 7-azaindole core scaffolds. Substitutions on the indole C3 position and on the indole NH and/or amide NH positions all yielded potent and selective ROCK inhibitors (25, 42, and 50). Improvement of aqueous solubility and tailoring of in vitro and in vivo DMPK properties could be achieved through these substitutions. (C) 2011 Elsevier Ltd. All rights reserved.