(2E)-3-[3-methoxy-4-(prop-2-en-1-yloxy)phenyl]-1-phenylprop-2-en-1-one | 1609628-35-4

• 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: (2E)-3-[3-methoxy-4-(prop-2-en-1-yloxy)phenyl]-1-phenylprop-2-en-1-one
• 英文别名: (E)-3-(4-(allyloxy)-3-methoxyphenyl)-1-phenylprop-2-en-1-one；(E)-3-(4-allyloxy-3-methoxy-phenyl)-1-phenyl-prop-2-en-1-one；(E)-3-(3-methoxy-4-prop-2-enoxyphenyl)-1-phenylprop-2-en-1-one
• CAS: 1609628-35-4
• 化学式: C₁₉H₁₈O₃
• 分子量: 294.35
• InChiKey: NBKQUVCPGJUGSS-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E)-3-[3-methoxy-4-(prop-2-en-1-yloxy)phenyl]-1-phenylprop-2-en-1-one 以 氘代甲醇 为溶剂， 反应 2.0h， 生成 (Z)-3-(4-(allyloxy)-3-methoxyphenyl)-1-phenylprop-2-en-1-one
  参考文献：
  名称：

  阿魏酸衍生物的光异构化的深入研究

  摘要：

  阿魏酸衍生的酯，酰胺和酮的光异构化进行了全面的研究。仅在脂族叔酰胺的情况下，才实现了几乎完全的E→Z转化。

  DOI：

  10.1002/ejoc.202100064
• 作为产物：
  描述：

  (E)-3-methoxy-4-allyloxycinnamoyl chloride 在 咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (2E)-3-[3-methoxy-4-(prop-2-en-1-yloxy)phenyl]-1-phenylprop-2-en-1-one
  参考文献：
  名称：

  阿魏酸衍生物的光异构化的深入研究

  摘要：

  阿魏酸衍生的酯，酰胺和酮的光异构化进行了全面的研究。仅在脂族叔酰胺的情况下，才实现了几乎完全的E→Z转化。

  DOI：

  10.1002/ejoc.202100064

文献信息

• Design, economical synthesis and antiplasmodial evaluation of vanillin derived allylated chalcones and their marked synergism with artemisinin against chloroquine resistant strains of Plasmodium falciparum
  作者：Nandini Sharma、Dinesh Mohanakrishnan、Upendra Kumar Sharma、Rajesh Kumar、Richa、Arun Kumar Sinha、Dinkar Sahal

  DOI：10.1016/j.ejmech.2014.03.079

  日期：2014.5

  The in vitro blood stage antiplasmodial activity of a series of allylated chalcones based on the licochalcone A as lead molecule was investigated against chloroquine (CQ) sensitive Pf3D7 and CQ resistant PfINDO strains of Plasmodium falciparum using SYBR Green I assay. Of the forty two chalcones tested, eight showed IC50 < 5 mu M. Structure-activity relationship (SAR) studies revealed 9 1-(4-Chlorophenyl)-3-[3-methoxy-4-(prop-2-en-1-yloxy)phenyl]-prop-2-en-1-one} as the most potent (IC50: 2.5 mu M) against Pf3D7 with resistance indices of 1.2 and 6.6 against PfDd2 and PfINDO strains, respectively. Later on, the synergistic effects 9 with standard antimalarials fartemisinin (ART) and chloroquine (CQ)} were studied in order to provide the basis for the selection of the best partner drug. In vitro combinations of 9 with ART showed strong synergy against PfINDO (Sigma FIC50: 0.31-0.72) but additive to slight antagonistic effects (Sigma FIC50: 1.97-2.64) against Pf3D7. Sigma FIC50 0.31 of ART+9 combination corresponded to a 320 fold and 3 fold reduction in IC50 of 9 and ART, respectively. Similar combinations of 9 with CQ showed synergy to additivity to mild antagonism against the two strains Sigma FIC50: 0.668-2269 (PfINDO); 1.45-2.83 (Pf3D7)}. Drug exposure followed by drug withdrawal indicated that 9 taken alone at IC100 killed rings, trophozoites and schizonts of P. falciparum. The combination of ART and 9 (1X Sigma FIC100) selectively inhibited the growth of rings while the 2X Sigma FIC100 combination of the same caused killing of rings without affecting trophozoites and schizonts. In contrast, the 1x combination of CQ and 9 (Sigma FIC100: 0.5) killed rings and trophozoites. DNA fragmentation and loss of mitochondrial membrane potential (Delta Psi m) in the 9 treated P. falciparum culture indicated apoptotic death in malaria parasites. Prediction of ADME properties revealed that most of the molecules did not violate Lipinski's parameters and have low TPSA value suggesting good absorption. The results suggest the promising drug-like properties of 9 against CQ resistant Pf and propensity for synergy with classical antimalarial drugs together with easy and economical synthesis. (C) 2014 Elsevier Masson SAS. All rights reserved.
• A Thorough Study on the Photoisomerization of Ferulic Acid Derivatives
  作者：Lisa Moni、Luca Banfi、Andrea Basso、Alessia Mori、Federica Risso、Renata Riva、Chiara Lambruschini

  DOI：10.1002/ejoc.202100064

  日期：2021.3.19

  A comprehensive study of photoisomerzation of ferulic acid derived esters, amides, and ketones was carried out. Only in the case of aliphatic tertiary amides, a nearly complete E→Z conversion was achieved.

  阿魏酸衍生的酯，酰胺和酮的光异构化进行了全面的研究。仅在脂族叔酰胺的情况下，才实现了几乎完全的E→Z转化。