1-(4-bromophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one | 941607-52-9

• 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-(4-bromophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: 2,4,5-TMBC
• CAS: 941607-52-9
• 化学式: C₁₈H₁₇BrO₄
• 分子量: 377.235
• InChiKey: BTBDJBDSXAPLSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 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：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)-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72.3 %的产率得到5-(4-bromophenyl)-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-(4-bromophenyl)-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

• Reinvestigation of structure–activity relationship of methoxylated chalcones as antimalarials: Synthesis and evaluation of 2,4,5-trimethoxy substituted patterns as lead candidates derived from abundantly available natural β-asarone
  作者：Rakesh Kumar、Dinesh Mohanakrishnan、Abhishek Sharma、Naveen Kumar Kaushik、Kalpana Kalia、Arun Kumar Sinha、Dinkar Sahal

  DOI：10.1016/j.ejmech.2010.08.049

  日期：2010.11

  causes a decrease. In particular, 2,4,5-trimethoxy substitution pattern at ring A provided potent analogues which were easily derived from abundantly available natural β-asarone rich Acorus calamus oil. Cytotoxic evaluation indicated that the most active compounds 27 (IC50: 1.8 μM) and 26 (IC50: 2 μM) were also relatively non-toxic. Furthermore, compound 12 showed excellent resistance index of 1.1 against

  我们已经使用基于荧光的SYBR Green分析方法检测了一系列甲氧基化查耳酮（A –CH CH–CO– B）对恶性疟原虫（3D7株）的抗疟结构与活性的关系。我们的研究表明，环A上的释放电子的甲氧基和环B上的吸电子基团提高了抗疟药的效力，而这些基团的位置互换导致其降低。特别地，在环2,4,5-三甲氧基取代模式甲提供一种很容易从可大量获得的天然衍生的强效的类似物β细辛醚丰富菖蒲油。细胞毒性评估表明，活性最高的化合物27（IC 50：1.8μM）和26（IC 50：2μM）也是相对无毒的。此外，化合物12对P的耐氯喹Dd2菌株显示出优异的抗性指数1.1 。恶性肿瘤。
• An investigation on the key features of a D–π–A type novel chalcone derivative for opto-electronic applications
  作者：Mohd. Shkir、Shabbir Muhammad、Salem AlFaify、Ahmad Irfan、Parutagouda Shankaragouda Patil、Manju Arora、Hamed Algarni、Zhang Jingping

  DOI：10.1039/c5ra13494c

  日期：——

  The calculated UV-visible optical spectra at different levels of theory.

  在不同理论水平下计算得到的UV-可见光谱。
• 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.