{4-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]phenyl}-3-(methoxyphenyl)prop-2-en-1-one | 1350753-42-2

• 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: {4-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]phenyl}-3-(methoxyphenyl)prop-2-en-1-one
• 英文别名: (E)-1-[4-[(E)-2-(4-hydroxy-3-methoxy-phenyl)vinyl]phenyl]-3-(4-methoxyphenyl)prop-2-en-1-one；(E)-1-[4-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]phenyl]-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 1350753-42-2
• 化学式: C₂₅H₂₂O₄
• 分子量: 386.447
• InChiKey: VKDPWLZJNHCFOC-BJIYECEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 哌啶 、 四(三苯基膦)钯 、 lithium chloride 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 {4-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]phenyl}-3-(methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Stilbene–Chalcone Hybrids: Design, Synthesis, and Evaluation as a New Class of Antimalarial Scaffolds That Trigger Cell Death through Stage Specific Apoptosis

  摘要：

  Novel stilbene-chalcone (S-C) hybrids were synthesized via a sequential Claisen-Schmidt-Knoevenagel-Heck approach and evaluated for antiplasmodial activity in in vitro red cell culture using SYBR Green I assay. The most potent hybrid (11) showed IC50 of 2.2, 1.4, and 6.4 mu M against 3D7 (chloroquine sensitive), Indo, and Dd2 (chloroquine resistant) strains of Plasmodium falciparum, respectively. Interestingly, the respective individual stilbene (IC50 > 100 mu M), chalcone (IC50 = 11.5 mu M), or an equimolar mixture of stilbene and chalcone (IC50 = 32.5 mu M) were less potent than 11. Studies done using specific stage enriched cultures and parasite in continuous culture indicate that 11 and 18 spare the schizont but block the progression of the parasite life cycle at the ring or the trophozoite stages. Further, 11 and 18 caused chromatin condensation, DNA fragmentation, and loss of mitochondrial membrane potential in Plasmodium falciparum, thereby suggesting their ability to cause apoptosis in malaria parasite.

  DOI：

  10.1021/jm201216y

文献信息

• ONE POT MULTICOMPONENT SYNTHESIS OF SOME NOVEL HYDROXY STILBENE DERIVATIVES WITH ALPHA, BETA-CARBONYL CONJUGATION UNDER MICROWAVE IRRADIATION
  申请人：Sharma Abhishek

  公开号：US20120165567A1

  公开（公告）日：2012-06-28

  The present invention provides a method for the preparation of some novel multiconjugated 2- or 4-hydroxy substituted stilbenes. The method provides one pot multicomponent approach wherein 3-4 step reaction sequences viz. condensation, decarboxylation and Heck coupling occur simultaneously which results in an enhanced yield of desired products and reduced reaction times

  本发明提供了一种制备一些新型多共轭2-或4-羟基取代的stilbenes的方法。该方法提供了一锅多组分方法，其中包括3-4步反应序列，即缩合、脱羧和Heck偶联同时发生，从而提高了所需产品的产量，减少了反应时间。
• US8716532B2
  申请人：——

  公开号：US8716532B2

  公开（公告）日：2014-05-06
• [EN] ONE POT MULTICOMPONENT SYNTHESIS OF SOME NOVEL HYDROXY STILBENE DERIVATIVES WITH ALPHA, BETA-CARBONYL CONJUGATION UNDER MICROWAVE IRRADIATION<br/>[FR] SYNTHÈSE MULTICOMPOSANTS EN UN SEUL RÉCIPIENT DE CERTAINS NOUVEAUX DÉRIVÉS HYDROXYSTILBÈNE AVEC CONJUGAISON ALPHA, BÊTA-CARBONYLE SOUS RAYONNEMENT MICROONDE
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2010113005A2

  公开（公告）日：2010-10-07

  The present invention provides a method for the preparation of some novel commercially important multiconjugated 2- or 4-hydroxy substituted stilbenes including lithospermic acid based stilbene analogues possessing an α, β-unsaturated carboxylic acid moiety i.e. (C6-C2-C6-C3 chain) with wide ranging applications as potent pharmcophores for diverse ailments including diabetes and cardiovascular disorders, besides finding usage in non-linear optical devices and optoelectronics etc. The method provides a unique one pot multicomponent approach wherein 3-4 step reaction sequences viz. condensation, decarboxylation and Heck coupling occur simultaneously either the need for decarboxylating/protection-deprotection agents or individual isolation of highly reactive intermediates which results in an enhanced yield of desired products and reduced reaction times. The present invention dispenses with the hitherto indispensable requirement for multistep approaches for a diverse range of hydroxy stilbene derivatives through a one pot muticomponent synthetic strategy.
• Stilbene–Chalcone Hybrids: Design, Synthesis, and Evaluation as a New Class of Antimalarial Scaffolds That Trigger Cell Death through Stage Specific Apoptosis
  作者：Naina Sharma、Dinesh Mohanakrishnan、Amit Shard、Abhishek Sharma、Saima、Arun K. Sinha、Dinkar Sahal

  DOI：10.1021/jm201216y

  日期：2012.1.12

  Novel stilbene-chalcone (S-C) hybrids were synthesized via a sequential Claisen-Schmidt-Knoevenagel-Heck approach and evaluated for antiplasmodial activity in in vitro red cell culture using SYBR Green I assay. The most potent hybrid (11) showed IC50 of 2.2, 1.4, and 6.4 mu M against 3D7 (chloroquine sensitive), Indo, and Dd2 (chloroquine resistant) strains of Plasmodium falciparum, respectively. Interestingly, the respective individual stilbene (IC50 > 100 mu M), chalcone (IC50 = 11.5 mu M), or an equimolar mixture of stilbene and chalcone (IC50 = 32.5 mu M) were less potent than 11. Studies done using specific stage enriched cultures and parasite in continuous culture indicate that 11 and 18 spare the schizont but block the progression of the parasite life cycle at the ring or the trophozoite stages. Further, 11 and 18 caused chromatin condensation, DNA fragmentation, and loss of mitochondrial membrane potential in Plasmodium falciparum, thereby suggesting their ability to cause apoptosis in malaria parasite.