N-(3-chloropropyl)-3,4-dimethoxybenzamide | 346726-05-4

• 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: N-(3-chloropropyl)-3,4-dimethoxybenzamide
• CAS: 346726-05-4
• 化学式: C₁₂H₁₆ClNO₃
• mdl: MFCD01215797
• 分子量: 257.717
• InChiKey: LJVVOEULWZXMOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-chloropropyl)-3,4-dimethoxybenzamide 在 potassium carbonate 、 N,N'-羰基二咪唑 、 potassium iodide 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Design and synthesis of N-methylpyrimidone derivatives as HIV-1 integrase inhibitors

  摘要：

  A series of novel beta-diketo derivatives which combined the virtues of dihydroxypyrimidine carboxamide derived from the evolution of DKA and polyhydroxylated aromatics moieties, were designed and synthesized as potential HIV-1 integrase (IN) inhibitors and evaluated their inhibition to the strand transfer process of HIV-1 integrase and anti-HIV-1 activity. The result indicates that 3,4,5-trihydroxylated aromatic derivatives exhibit good inhibition to HIV-1 integrase, but dihydroxylated aromatic derivatives appear little inhibition to HIV-1 integrase. In addition, the preliminary structure-activity relationship (SAR) of these new derivatives was rationalized by docking studies. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.059
• 作为产物：
  描述：

  3,4-二甲氧基苯甲酰氯 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 N-(3-chloropropyl)-3,4-dimethoxybenzamide
  参考文献：
  名称：

  Design, synthesis and evaluation of novel heterodimers of donepezil and huperzine fragments as acetylcholinesterase inhibitors

  摘要：

  Four series of novel heterodimers comprised of donepezil and huperzine A (HupA) fragments were designed, synthesized, and evaluated in search of potent acetylcholinesterase (AChE) inhibitors as potential therapeutic treatment for Alzheimer's disease. Heterodimers comprised of dimethoxyindanone (from donepezil), hupyridone (from HupA), and connected with a multimethylene linker, were identified as potent and selective inhibitors of AChE. Diastereomeric heterodimers (RS,S)-17b (with a tetramethylene linker) exhibited the highest potency of inhibition towards AChE with an IC50 value of 9 nM and no detectable inhibitory effect on butyrylcholinesterase at 1 mM. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.044

文献信息

• Synthesis of polyhydroxylated aromatics having amidation of piperazine nitrogen as HIV-1 integrase inhibitor
  作者：Leifu Yang、Xuemei Xu、Yali Huang、Bin Zhang、Chengchu Zeng、Hongqiu He、Cunxin Wang、Liming Hu

  DOI：10.1016/j.bmcl.2010.07.087

  日期：2010.9

  (E)-N-[3-(4-Cinnamoylpiperazin-1-yl)propyl]-3,4-dihydroxybenzamide and (E)-N-[3-(4-cinnamoylpiperazin-1-yl)propyl]-3,4,5-trihydroxybenzamide were designed and synthesized as potential HIV-1 integrase inhibitors and evaluated their inhibition to the strand transfer process of HIV-1 integrase. The result indicates that 3,4,5-trihydroxylated aromatic derivatives exhibit good inhibition to HIV-1 integrase, however, corresponding 3,4-dihydroxylated aromatic derivatives appear little inhibition of HIV-1 integrase. (c) 2010 Elsevier Ltd. All rights reserved.

  (E)-N-[3-(4-丙烯氨基环-1-基)丙基]-3,4-二羟基苯甲酸和(E)-N-[3-(4-丙烯氨基环-1-基)丙基]-3,4,5-三羟基苯甲酸被设计并合成，作为潜在的HIV-1整合酶抑制剂，并评估了它们对HIV-1整合酶脱链转移过程的抑制效果。结果表明，三羟基取代的芳香化合物表现出良好的抑制效果，而相应的二羟基取代的芳香化合物对HIV-1整合酶的抑制作用较弱。(c) 2010 伊夫s尔_lim。
• Design, synthesis and evaluation of novel heterodimers of donepezil and huperzine fragments as acetylcholinesterase inhibitors
  作者：Yueqing Hu、Jun Zhang、Oormila Chandrashankra、Fanny C.F. Ip、Nancy Y. Ip

  DOI：10.1016/j.bmc.2012.11.044

  日期：2013.2

  Four series of novel heterodimers comprised of donepezil and huperzine A (HupA) fragments were designed, synthesized, and evaluated in search of potent acetylcholinesterase (AChE) inhibitors as potential therapeutic treatment for Alzheimer's disease. Heterodimers comprised of dimethoxyindanone (from donepezil), hupyridone (from HupA), and connected with a multimethylene linker, were identified as potent and selective inhibitors of AChE. Diastereomeric heterodimers (RS,S)-17b (with a tetramethylene linker) exhibited the highest potency of inhibition towards AChE with an IC50 value of 9 nM and no detectable inhibitory effect on butyrylcholinesterase at 1 mM. (C) 2012 Elsevier Ltd. All rights reserved.
• Design and synthesis of N-methylpyrimidone derivatives as HIV-1 integrase inhibitors
  作者：Yujie Wang、Jie Rong、Bin Zhang、Liming Hu、Xiaoli Wang、Chengchu Zeng

  DOI：10.1016/j.bmc.2014.12.059

  日期：2015.2

  A series of novel beta-diketo derivatives which combined the virtues of dihydroxypyrimidine carboxamide derived from the evolution of DKA and polyhydroxylated aromatics moieties, were designed and synthesized as potential HIV-1 integrase (IN) inhibitors and evaluated their inhibition to the strand transfer process of HIV-1 integrase and anti-HIV-1 activity. The result indicates that 3,4,5-trihydroxylated aromatic derivatives exhibit good inhibition to HIV-1 integrase, but dihydroxylated aromatic derivatives appear little inhibition to HIV-1 integrase. In addition, the preliminary structure-activity relationship (SAR) of these new derivatives was rationalized by docking studies. (c) 2014 Elsevier Ltd. All rights reserved.