2-(2,4-dimethoxyphenyl)-3-methyl-4-oxo-4-(4-(2-propenyloxy)phenyl)-butanenitrile | 213459-57-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,4-dimethoxyphenyl)-3-methyl-4-oxo-4-(4-(2-propenyloxy)phenyl)-butanenitrile
• 英文别名: 2-(2,4-dimethoxyphenyl)-3-methyl-4-oxo-4-(4-prop-2-enoxyphenyl)butanenitrile
• CAS: 213459-57-5
• 化学式: C₂₂H₂₃NO₄
• 分子量: 365.429
• InChiKey: QWEWDNHKRVWUBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2,4-dimethoxyphenyl)-3-methyl-4-oxo-4-(4-(2-propenyloxy)phenyl)-butanenitrile 在 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 0.03h， 以91%的产率得到(E)-1-(4-Allyloxy-phenyl)-3-(2,4-dimethoxy-phenyl)-2-methyl-propenone
  参考文献：
  名称：

  Modifications of the α,β-Double bond in chalcones only Marginally affect the antiprotozoal activities

  摘要：

  Methods for selective alkylation of chalcones in the alpha- or beta-position and for selective reduction of the alpha,beta-double bond have been developed. The antiparasitic potencies of the alpha,beta-double bond modified chalcones only differ marginally from the potencies of the parent chalcones indicating that the propenone residue only functions as a spacer between the two benzene rings, which are the true pharmacophore. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00051-0
• 作为产物：
  描述：

  (E)-1-(4-(allyloxy)phenyl)-3-(2,4-dimethoxyphenyl)prop-2-en-1-one 在 sodium hydride 、 氯化铵 、 cesium fluoride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 7.33h， 生成 2-(2,4-dimethoxyphenyl)-3-methyl-4-oxo-4-(4-(2-propenyloxy)phenyl)-butanenitrile
  参考文献：
  名称：

  Modifications of the α,β-Double bond in chalcones only Marginally affect the antiprotozoal activities

  摘要：

  Methods for selective alkylation of chalcones in the alpha- or beta-position and for selective reduction of the alpha,beta-double bond have been developed. The antiparasitic potencies of the alpha,beta-double bond modified chalcones only differ marginally from the potencies of the parent chalcones indicating that the propenone residue only functions as a spacer between the two benzene rings, which are the true pharmacophore. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00051-0

文献信息

• Biologically active 1,3-bis-aromatic-prop-2-en-1-ones, 1,3-bis-aromatic-propan-1-ones, and 1,3-bis-aromatic-prop-2-yn-1-ones
  申请人：Statens Serum Institute

  公开号：US20030065039A1

  公开（公告）日：2003-04-03

  The invention relates to the use of 1,3-bis-aromatic-prop-2-en-1-ones (chalcones), 1,3-bis-aromatic-propan-1-ones (dihydrochalcones), and 1,3-bis-aromatic-prop-2-yn-1-ones for the preparation of pharmaceutical compositions for the treatment or prophylaxis of a number of serious diseases including i) conditions relating to harmful effects of inflammatory cytokines, ii) conditions involving infection by Helicobacter species, iii) conditions involving infection by viruses, iv) neoplastic disorders, and v) conditions caused by microorganisms or parasites. The invention also relates to novel chalcones and dihydrochalcones (especially alkoxy substituted variants) having advantageous substitution patterns with respect to their effect as drug substances, and to methods of preparing them, as well as to pharmaceutical compositions comprising the novel chalcones. Moreover, the present invention relates to a method for the isolation of Leishmania fumarate reductase, QSAR methodologies for selecting potent compounds for the above-mentioned purposes.

  该发明涉及使用1,3-双芳基-丙-2-烯-1-酮（香豆素）、1,3-双芳基-丙酮-1-酮（二氢香豆素）和1,3-双芳基-丙-2-炔-1-酮制备用于治疗或预防多种严重疾病的药物组合物，包括i）与炎症细胞因子有害作用相关的疾病，ii）涉及幽门螺旋杆菌感染的疾病，iii）涉及病毒感染的疾病，iv）肿瘤性疾病，v）由微生物或寄生虫引起的疾病。该发明还涉及新型香豆素和二氢香豆素（特别是烷氧基取代变体），其具有有利的取代模式，对其作为药物物质的效果，以及制备它们的方法，以及包含新型香豆素的药物组合物。此外，本发明涉及一种用于分离利什曼氏弓形虫富马酸还原酶的方法，以及用于选择上述目的的有效化合物的QSAR方法。