1-(3-Nitrophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one

• 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-(3-Nitrophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
• 化学式: C18H17NO6
• 分子量: 343.3
• InChiKey: JZHJJZUKZQDJGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3-Nitrophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one 在 盐酸羟胺 、 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 以78.8 %的产率得到5-(3-nitrophenyl)-3-(2,4,5-trimethoxyphenyl)-1,2-oxazole
  参考文献：
  名称：

  Synthesis of Unusually Substituted 2,4,5-Trimethoxy 3,5-Diaryl Isoxazoles from Natural Precursor: Antimicrobial and Anticancer Activities

  摘要：

  In this work, 2,4,5-trimethoxy substituted 3,5-diaryl isoxazoles were synthesized via their chalcone intermediates and evaluated for antimicrobial and anticancer activities. The natural precursor 2,4,5-trimethoxy benzaldehyde (asaronaldehyde) was obtained from oxidation of β-asarone (Acorus calamus oil) and then reacted with substituted acetophenones via Claisen-Schmidt condensation yielded 2,4,5-trimethoxy substituted chalcones. These chalcones on further treatment with hydroxylamine in presence of sodium acetate and acetic acid cyclizes to give the corresponding 3,5-diaryl isoxazoles yields ranging from 65-80%. Structures were confirmed by IR, GC-MS, 1H NMR and 13C NMR. Synthesized compounds were screened for their antimicrobial activity against bacteria and fungi. The para-substituted isoxazoles (5b, 5c and 5d) exhibited good activity against Gram-negative (Escherichia coli) and (Pseudomonas aeruginosa) and Gram-positive (Bacillus subtilis) and Bacillus licheniformis bacteria and fungi (Phytophthora capsici, Sclerotirum rolfsii, Aspergillus niger and Alternaria alternate). Further, these novel analogues were evaluated for their in vitro anticancer activity against three human tumor cell lines (MCF-7, SW-982 and HeLa) using MTT assay. The anticancer results revealed that phenyl ring at C-3 position bearing electron donor groups in the para-position and 2,4,5-trimethoxy substitutent of the phenyl ring at C-5 position isoxazole showed better inhibitory activity (5b, 5c and 5d). Among synthesized isoxazoles due to the hyper conjugative effect, 2,4,5-trimethoxy 3,5-diaryl isoxazole (5g) having 3-triflouromethyl substitution showed good antimicrobial and higher inhibitory IC50 values 8.56 ± 0.32, 12.16 ± 0.86 and 10.16 ± 0.68 μg/mL (p < 0.05) respectively, when compared to natural precursor β-asarone.

  DOI：

  10.14233/ajchem.2024.31015
• 作为产物：
  描述：

  顺式-2,4,5-三甲氧基-1-丙烯基苯 在 potassium permanganate 、 碳酸氢钠 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1-(3-Nitrophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis of Unusually Substituted 2,4,5-Trimethoxy 3,5-Diaryl Isoxazoles from Natural Precursor: Antimicrobial and Anticancer Activities

  摘要：

  In this work, 2,4,5-trimethoxy substituted 3,5-diaryl isoxazoles were synthesized via their chalcone intermediates and evaluated for antimicrobial and anticancer activities. The natural precursor 2,4,5-trimethoxy benzaldehyde (asaronaldehyde) was obtained from oxidation of β-asarone (Acorus calamus oil) and then reacted with substituted acetophenones via Claisen-Schmidt condensation yielded 2,4,5-trimethoxy substituted chalcones. These chalcones on further treatment with hydroxylamine in presence of sodium acetate and acetic acid cyclizes to give the corresponding 3,5-diaryl isoxazoles yields ranging from 65-80%. Structures were confirmed by IR, GC-MS, 1H NMR and 13C NMR. Synthesized compounds were screened for their antimicrobial activity against bacteria and fungi. The para-substituted isoxazoles (5b, 5c and 5d) exhibited good activity against Gram-negative (Escherichia coli) and (Pseudomonas aeruginosa) and Gram-positive (Bacillus subtilis) and Bacillus licheniformis bacteria and fungi (Phytophthora capsici, Sclerotirum rolfsii, Aspergillus niger and Alternaria alternate). Further, these novel analogues were evaluated for their in vitro anticancer activity against three human tumor cell lines (MCF-7, SW-982 and HeLa) using MTT assay. The anticancer results revealed that phenyl ring at C-3 position bearing electron donor groups in the para-position and 2,4,5-trimethoxy substitutent of the phenyl ring at C-5 position isoxazole showed better inhibitory activity (5b, 5c and 5d). Among synthesized isoxazoles due to the hyper conjugative effect, 2,4,5-trimethoxy 3,5-diaryl isoxazole (5g) having 3-triflouromethyl substitution showed good antimicrobial and higher inhibitory IC50 values 8.56 ± 0.32, 12.16 ± 0.86 and 10.16 ± 0.68 μg/mL (p < 0.05) respectively, when compared to natural precursor β-asarone.

  DOI：

  10.14233/ajchem.2024.31015

文献信息

• Synthesis of Unusually Substituted 2,4,5-Trimethoxy 3,5-Diaryl Isoxazoles from Natural Precursor: Antimicrobial and Anticancer Activities
  作者：M.V. Ravindra、S. Suvarna、C.S. Ananda Kumar

  DOI：10.14233/ajchem.2024.31015

  日期：——

  In this work, 2,4,5-trimethoxy substituted 3,5-diaryl isoxazoles were synthesized via their chalcone intermediates and evaluated for antimicrobial and anticancer activities. The natural precursor 2,4,5-trimethoxy benzaldehyde (asaronaldehyde) was obtained from oxidation of β-asarone (Acorus calamus oil) and then reacted with substituted acetophenones via Claisen-Schmidt condensation yielded 2,4,5-trimethoxy substituted chalcones. These chalcones on further treatment with hydroxylamine in presence of sodium acetate and acetic acid cyclizes to give the corresponding 3,5-diaryl isoxazoles yields ranging from 65-80%. Structures were confirmed by IR, GC-MS, 1H NMR and 13C NMR. Synthesized compounds were screened for their antimicrobial activity against bacteria and fungi. The para-substituted isoxazoles (5b, 5c and 5d) exhibited good activity against Gram-negative (Escherichia coli) and (Pseudomonas aeruginosa) and Gram-positive (Bacillus subtilis) and Bacillus licheniformis bacteria and fungi (Phytophthora capsici, Sclerotirum rolfsii, Aspergillus niger and Alternaria alternate). Further, these novel analogues were evaluated for their in vitro anticancer activity against three human tumor cell lines (MCF-7, SW-982 and HeLa) using MTT assay. The anticancer results revealed that phenyl ring at C-3 position bearing electron donor groups in the para-position and 2,4,5-trimethoxy substitutent of the phenyl ring at C-5 position isoxazole showed better inhibitory activity (5b, 5c and 5d). Among synthesized isoxazoles due to the hyper conjugative effect, 2,4,5-trimethoxy 3,5-diaryl isoxazole (5g) having 3-triflouromethyl substitution showed good antimicrobial and higher inhibitory IC50 values 8.56 ± 0.32, 12.16 ± 0.86 and 10.16 ± 0.68 μg/mL (p < 0.05) respectively, when compared to natural precursor β-asarone.