1-(2,4-dimethoxy-phenyl)-3-(3-methoxy-4-prop-2-ynyloxy-phenyl)-propenone | 1261145-42-9

• 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: 1-(2,4-dimethoxy-phenyl)-3-(3-methoxy-4-prop-2-ynyloxy-phenyl)-propenone
• 英文别名: 1-(2,4-dimethoxyphenyl)-3-(3-methoxy-4-prop-2-ynoxyphenyl)prop-2-en-1-one
• CAS: 1261145-42-9
• 化学式: C₂₁H₂₀O₅
• 分子量: 352.387
• InChiKey: GSEXYCOBDQEKGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(2,4-dimethoxy-phenyl)-3-(3-methoxy-4-prop-2-ynyloxy-phenyl)-propenone 、 齐多夫定 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以47%的产率得到(2R,4S,5S)-1-[4-(4-(4-[3-(2,4-dimethoxy-phenyl)-3-oxo-propenyl]-2-methoxy-phenoxymethyl)-[1,2,3]triazol-1-yl)-5-hydroxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Design, synthesis and in vitro antimalarial evaluation of triazole-linked chalcone and dienone hybrid compounds

  摘要：

  A targeted series of chalcone and dienone hybrid compounds containing aminoquinoline and nucleoside templates was synthesized and evaluated for in vitro antimalarial activity. The Cu(I)-catalyzed cycloaddition of azides and terminal alkynes was applied as the hybridization strategy. Several chalcone-chloroquinoline hybrid compounds were found to be notably active, with compound 8b the most active, exhibiting submicromolar IC50 values against the D10, Dd2 and W2 strains of Plasmodium falciparum. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.009
• 作为产物：
  描述：

  2,4-二甲氧基苯乙酮 、 3-甲氧基-4-丙-2-炔基氧基-苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.25h， 以90%的产率得到1-(2,4-dimethoxy-phenyl)-3-(3-methoxy-4-prop-2-ynyloxy-phenyl)-propenone
  参考文献：
  名称：

  炔属查耳酮的合成，抗疟和抗结核活性

  摘要：

  评估了一系列炔属查耳酮的抗疟和抗结核活性。该系列的抗疟数据表明，恶性疟原虫W2菌株的生长抑制可通过在炔基上邻位引入甲氧基来实现。与结核分枝杆菌H 37 Rv的复制培养相比，大多数化合物对非复制的活性更高，这对现有的抗结核病药物而言是不同寻常的模式。

  DOI：

  10.1016/j.bmcl.2009.12.062

文献信息

• 1,2,3-Triazole tethered β-lactam-Chalcone bifunctional hybrids: Synthesis and anticancer evaluation
  作者：Pardeep Singh、Raghu Raj、Vipan Kumar、Mohinder P. Mahajan、P.M.S. Bedi、Tandeep Kaur、A.K. Saxena

  DOI：10.1016/j.ejmech.2011.10.033

  日期：2012.1

  The manuscript describes the synthesis of novel 1,2,3-triazole tethered β-lactam-chalcone bifunctional hybrids via click chemistry approach utilizing azide-alkyne cycloaddition reactions and their evaluation as anticancer agents against four human cancer cell lines. The presence of a cyclohexyl substituent at N-1 of β-lactam ring and methoxy substituents, preferably ortho on ring A and para on ring

  原稿描述了新的1,2,3-三唑系留的合成β内酰胺的查耳酮的双官能杂合体通过利用叠氮化物-炔烃环加成反应和它们作为针对四种人类肿瘤细胞株的抗癌药物评价点击化学的方法。环己取代基中的N-1的存在下β内酰胺环和甲氧基取代基，优选邻位上环A和对位上的环B上的查耳酮显着提高合成支架的抗癌型材的最有效的表现出的试验化合物的分别针对A-549（肺），PC-3（前列腺），THP-1（白血病）和Caco-2（结肠）细胞系的IC 50值分别为<1、67.1，<1和6.37μM。
• Synthesis, antimalarial and antitubercular activity of acetylenic chalcones
  作者：Renate H. Hans、Eric M. Guantai、Carmen Lategan、Peter J. Smith、Baojie Wan、Scott G. Franzblau、Jiri Gut、Philip J. Rosenthal、Kelly Chibale

  DOI：10.1016/j.bmcl.2009.12.062

  日期：2010.2

  A series of acetylenic chalcones were evaluated for antimalarial and antitubercular activity. The antimalarial data for this series suggests that growth inhibition of the W2 strain of Plasmodium falciparum can be imparted by the introduction of a methoxy group ortho to the acetylenic group. Most compounds were more active against non-replicating than replicating cultures of Mycobacterium tuberculosis

  评估了一系列炔属查耳酮的抗疟和抗结核活性。该系列的抗疟数据表明，恶性疟原虫W2菌株的生长抑制可通过在炔基上邻位引入甲氧基来实现。与结核分枝杆菌H 37 Rv的复制培养相比，大多数化合物对非复制的活性更高，这对现有的抗结核病药物而言是不同寻常的模式。
• Design, synthesis and in vitro antimalarial evaluation of triazole-linked chalcone and dienone hybrid compounds
  作者：Eric M. Guantai、Kanyile Ncokazi、Timothy J. Egan、Jiri Gut、Philip J. Rosenthal、Peter J. Smith、Kelly Chibale

  DOI：10.1016/j.bmc.2010.10.009

  日期：2010.12

  A targeted series of chalcone and dienone hybrid compounds containing aminoquinoline and nucleoside templates was synthesized and evaluated for in vitro antimalarial activity. The Cu(I)-catalyzed cycloaddition of azides and terminal alkynes was applied as the hybridization strategy. Several chalcone-chloroquinoline hybrid compounds were found to be notably active, with compound 8b the most active, exhibiting submicromolar IC50 values against the D10, Dd2 and W2 strains of Plasmodium falciparum. (C) 2010 Elsevier Ltd. All rights reserved.