(E)-1-(2-prop-2-ynoxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one | 1217264-18-0

• 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)-1-(2-prop-2-ynoxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one
• CAS: 1217264-18-0
• 化学式: C₂₁H₂₀O₅
• 分子量: 352.387
• InChiKey: NFDPXXREMVBFHF-ZRDIBKRKSA-N

物化性质

• 沸点：
  526.5±50.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-prop-2-ynoxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one 、 3-azidopropylsilatrane 在 溴化三(三苯基磷)铜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以89%的产率得到
  参考文献：
  名称：

  Design, synthesis and biological evaluation of chalconyl blended triazole allied organosilatranes as giardicidal and trichomonacidal agents

  摘要：

  A series of chalconyl blended triazole allied silatranes (7a-g/8a-g/9a-g) were synthesized in good yields using a simple, economical and biocompatible synthetic route. The blend of three different pharmacologically active moieties into a single scaffold resulted into synergistic effect in their bioactivity. Various substitutions were tried to study the structure activity relationship (SAR) of the synthesized compounds on the basis of biological results. All the newly synthesized compounds were well characterized by IR, H-1 and C-13 NMR, low resolution mass spectroscopy and elemental analysis. The structures of 7a and 7c were authenticated by single crystal X-ray crystallography. These compounds were screened by using Molinspiration software for their physicochemical properties and all the compounds showed good oral bioavailability. The antiparasitic activity of the newly synthesized compounds was evaluated against unicellular parasites (Giardia lamblia and Trichomonas vaginalis) in comparison to standard drug (metronidazole) by 3-(4,5-dimethylthiazol-yl)-diphenyl tetrazolium bromide (MTT) assay. All the compounds displayed significant activity against G. lamblia and T. vaginalis with IC50 values ranging from 19.58-131.2 mu M to 18.24-101.26 mu M respectively. The entire library of compounds was found to be more active than metronidazole except 9a, 9f and 9g. Notably, 9e and 7e were found to be most significant against G. lamblia and T vaginalis respectively. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.029
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 (E)-1-(2-prop-2-ynoxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of chalconyl blended triazole allied organosilatranes as giardicidal and trichomonacidal agents

  摘要：

  A series of chalconyl blended triazole allied silatranes (7a-g/8a-g/9a-g) were synthesized in good yields using a simple, economical and biocompatible synthetic route. The blend of three different pharmacologically active moieties into a single scaffold resulted into synergistic effect in their bioactivity. Various substitutions were tried to study the structure activity relationship (SAR) of the synthesized compounds on the basis of biological results. All the newly synthesized compounds were well characterized by IR, H-1 and C-13 NMR, low resolution mass spectroscopy and elemental analysis. The structures of 7a and 7c were authenticated by single crystal X-ray crystallography. These compounds were screened by using Molinspiration software for their physicochemical properties and all the compounds showed good oral bioavailability. The antiparasitic activity of the newly synthesized compounds was evaluated against unicellular parasites (Giardia lamblia and Trichomonas vaginalis) in comparison to standard drug (metronidazole) by 3-(4,5-dimethylthiazol-yl)-diphenyl tetrazolium bromide (MTT) assay. All the compounds displayed significant activity against G. lamblia and T. vaginalis with IC50 values ranging from 19.58-131.2 mu M to 18.24-101.26 mu M respectively. The entire library of compounds was found to be more active than metronidazole except 9a, 9f and 9g. Notably, 9e and 7e were found to be most significant against G. lamblia and T vaginalis respectively. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.029

文献信息

• Synthetic investigations and photo-physical properties of 1,2,3-triazole encapped chalconyl substituted organotriethoxysilanes
  作者：Gurjaspreet Singh、Aanchal Arora、Satinderpal Singh Mangat、Jandeep Singh、Sunita Rani、Navneet Kaur

  DOI：10.1016/j.jorganchem.2014.11.022

  日期：2015.2

  Organotriethoxysilanes (OTES) play an impressive role in the designing of organic-inorganic hybrid materials. The highly efficient copper catalysed 'Click Silylation' is followed for the functionalization of 3-azidopropyltriethoxysilane (AzPTES) with a series of acetylinic chalcones. Chalcones being ubiquitous subunits present in various natural products possess a wide variety of biological activities and are thus considered for the synthesis of new hybrid templates. Twenty one new chalcone holding triazole encapped OTES were synthesized in quantitative yields. All the synthesized compounds were well characterized by IR, H-1 and C-13 NMR spectroscopic techniques. The photo-physical properties of all the OTES were compared and the effect of different substitutions was explicated. These OTES can be put to amazing applications in the field of medicine and material chemistry. (C) 2014 Elsevier B.V. All rights reserved.
• Comparison of the antiplasmodial and falcipain-2 inhibitory activity of β-amino alcohol thiolactone-chalcone and isatin-chalcone hybrids
  作者：Renate H. Hans、Jiri Gut、Philip J. Rosenthal、Kelly Chibale

  DOI：10.1016/j.bmcl.2010.02.017

  日期：2010.4

  The synthesis and biological evaluation of two novel series of natural-product-like hybrids based on the chalcone, thiolactone and isatin scaffolds is herein described. Results for a 36-member beta-amino alcohol triazole library showed that the thiolactone-chalcones, with IC(50)s ranging from 0.68 to 6.08 mu M, were more active against W2 strain Plasmodium falciparum than the isatin-chalcones with IC(50)s of 14.9 mu M or less. Also of interest is falcipain-2 inhibitory activity displayed by the latter, whereas the thiolactone-chalcones lacked enzyme inhibitory activity. (C) 2010 Elsevier Ltd. All rights reserved.
• Design, synthesis and biological evaluation of chalconyl blended triazole allied organosilatranes as giardicidal and trichomonacidal agents
  作者：Gurjaspreet Singh、Aanchal Arora、Satinderpal Singh Mangat、Sunita Rani、Hargobinder Kaur、Kapil Goyal、Rakesh Sehgal、Indresh Kumar Maurya、Rupinder Tewari、Duane Choquesillo-Lazarte、Subash Sahoo、Navneet Kaur

  DOI：10.1016/j.ejmech.2015.11.029

  日期：2016.1

  A series of chalconyl blended triazole allied silatranes (7a-g/8a-g/9a-g) were synthesized in good yields using a simple, economical and biocompatible synthetic route. The blend of three different pharmacologically active moieties into a single scaffold resulted into synergistic effect in their bioactivity. Various substitutions were tried to study the structure activity relationship (SAR) of the synthesized compounds on the basis of biological results. All the newly synthesized compounds were well characterized by IR, H-1 and C-13 NMR, low resolution mass spectroscopy and elemental analysis. The structures of 7a and 7c were authenticated by single crystal X-ray crystallography. These compounds were screened by using Molinspiration software for their physicochemical properties and all the compounds showed good oral bioavailability. The antiparasitic activity of the newly synthesized compounds was evaluated against unicellular parasites (Giardia lamblia and Trichomonas vaginalis) in comparison to standard drug (metronidazole) by 3-(4,5-dimethylthiazol-yl)-diphenyl tetrazolium bromide (MTT) assay. All the compounds displayed significant activity against G. lamblia and T. vaginalis with IC50 values ranging from 19.58-131.2 mu M to 18.24-101.26 mu M respectively. The entire library of compounds was found to be more active than metronidazole except 9a, 9f and 9g. Notably, 9e and 7e were found to be most significant against G. lamblia and T vaginalis respectively. (C) 2015 Elsevier Masson SAS. All rights reserved.