(E)-3-(4-chlorophenyl)-1-(4-(furan-2-ylmethylamino)phenyl)prop-2-en-1-one | 1260214-48-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-(4-chlorophenyl)-1-(4-(furan-2-ylmethylamino)phenyl)prop-2-en-1-one
• 英文别名: 3-(4-Chlorophenyl)-1-{4-[(furan-2-ylmethyl)amino]phenyl}prop-2-en-1-one；(E)-3-(4-chlorophenyl)-1-[4-(furan-2-ylmethylamino)phenyl]prop-2-en-1-one
• CAS: 1260214-48-9
• 化学式: C₂₀H₁₆ClNO₂
• 分子量: 337.806
• InChiKey: HTQZXBVVZYOJIV-LFYBBSHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-chlorophenyl)-1-(4-(furan-2-ylmethylamino)phenyl)prop-2-en-1-one 、 三甲基碘化亚砜 在 四丁基溴化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 以85%的产率得到(2-(4-chlorophenyl)cyclopropyl)(4-(furan-2-ylmethylamino)phenyl)methanone
  参考文献：
  名称：

  Synthesis and bio-evaluation of alkylaminoaryl phenyl cyclopropyl methanones as antitubercular and antimalarial agents

  摘要：

  A series of 4-alkylaminoaryl phenyl cyclopropyl methanones (6a-6u and 8a-8c) were synthesized from 4-fluorochalcones (3a and 3b) by cyclopropanation of double bond followed by nucleophilic substitution of F with different amines. The compounds were screened for their antitubercular and antimalarial activities against Mycobacterium tuberculosis H37Rv and Plasmodium falciparum 3D7 strains in vitro respectively. Several compounds (6a, 6d-6h, 6p, 6q and 8a-8c) exhibited good in vitro antitubercular activities with MIC values 3.12-12.5 mu g/mL and preferentially inhibited the growth of P. falciparum in vitro (4a, 4c, 6a-6d, 6f, 6s, 8a and 8c) with IC50 as low as 0.080 and 0.035 mu g/mL and SI values 4975 and 6948, respectively. Molecular docking studies and in vitro evaluation against FAS-II enzymes using reporter gene assays were carried out to elucidate the mode of action of these molecules. Two compounds 4a and 6g showed significant inhibition at 25 mu M concentration of the compound. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.071
• 作为产物：
  描述：

  2-呋喃甲胺 、 3-(4-氯苯基)-1-(4-氟苯基)丙-2-烯-1-酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以40%的产率得到(E)-3-(4-chlorophenyl)-1-(4-(furan-2-ylmethylamino)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and bio-evaluation of alkylaminoaryl phenyl cyclopropyl methanones as antitubercular and antimalarial agents

  摘要：

  A series of 4-alkylaminoaryl phenyl cyclopropyl methanones (6a-6u and 8a-8c) were synthesized from 4-fluorochalcones (3a and 3b) by cyclopropanation of double bond followed by nucleophilic substitution of F with different amines. The compounds were screened for their antitubercular and antimalarial activities against Mycobacterium tuberculosis H37Rv and Plasmodium falciparum 3D7 strains in vitro respectively. Several compounds (6a, 6d-6h, 6p, 6q and 8a-8c) exhibited good in vitro antitubercular activities with MIC values 3.12-12.5 mu g/mL and preferentially inhibited the growth of P. falciparum in vitro (4a, 4c, 6a-6d, 6f, 6s, 8a and 8c) with IC50 as low as 0.080 and 0.035 mu g/mL and SI values 4975 and 6948, respectively. Molecular docking studies and in vitro evaluation against FAS-II enzymes using reporter gene assays were carried out to elucidate the mode of action of these molecules. Two compounds 4a and 6g showed significant inhibition at 25 mu M concentration of the compound. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.071

文献信息

• Synthesis and bio-evaluation of alkylaminoaryl phenyl cyclopropyl methanones as antitubercular and antimalarial agents
  作者：Arya Ajay、Vandana Singh、Shubhra Singh、Swaroop Pandey、Sarika Gunjan、Divya Dubey、Sudhir Kumar Sinha、Bhupendra N. Singh、Vinita Chaturvedi、Renu Tripathi、Ravishankar Ramchandran、Rama P. Tripathi

  DOI：10.1016/j.bmc.2010.09.071

  日期：2010.12

  A series of 4-alkylaminoaryl phenyl cyclopropyl methanones (6a-6u and 8a-8c) were synthesized from 4-fluorochalcones (3a and 3b) by cyclopropanation of double bond followed by nucleophilic substitution of F with different amines. The compounds were screened for their antitubercular and antimalarial activities against Mycobacterium tuberculosis H37Rv and Plasmodium falciparum 3D7 strains in vitro respectively. Several compounds (6a, 6d-6h, 6p, 6q and 8a-8c) exhibited good in vitro antitubercular activities with MIC values 3.12-12.5 mu g/mL and preferentially inhibited the growth of P. falciparum in vitro (4a, 4c, 6a-6d, 6f, 6s, 8a and 8c) with IC50 as low as 0.080 and 0.035 mu g/mL and SI values 4975 and 6948, respectively. Molecular docking studies and in vitro evaluation against FAS-II enzymes using reporter gene assays were carried out to elucidate the mode of action of these molecules. Two compounds 4a and 6g showed significant inhibition at 25 mu M concentration of the compound. (C) 2010 Elsevier Ltd. All rights reserved.