2,4-dimethoxy-4'-methylchalcone | 22920-53-2

• 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: 2,4-dimethoxy-4'-methylchalcone
• 英文别名: 3-p-Tolyl-1-(2,4-dimethoxy-phenyl)-propen-(1)-on-(3)；p-Tolyl-β-(2,4-dimethoxy-phenyl)-vinyl-keton；3-(2,4-dimethoxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one
• CAS: 22920-53-2
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: YRNWOYJYVPHYFY-UHFFFAOYSA-N

物化性质

• 熔点：
  74 °C
• 沸点：
  458.4±45.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  2,4-dimethoxy-4'-methylchalcone 在 葡萄糖 、 sodium chloride 作用下， 以 水 、 丙酮 为溶剂， 反应 24.0h， 以96.4%的产率得到2,4-dimethoxy-4'-methyl-α,β-dihydrochalcone
  参考文献：
  名称：

  Microbial transformations of 4′-methylchalcones as an efficient method of obtaining novel alcohol and dihydrochalcone derivatives with antimicrobial activity

  摘要：

  使用细菌整细胞对4'-甲基茵黄酮进行生物转化，可以获得高收率的二氢黄酮和醇。对所有衍生物的抗菌活性进行了评估，针对选择的细菌和真菌菌株。

  DOI：

  10.1039/c8ra04669g
• 作为产物：
  描述：

  对甲基苯乙酮 、 2,4-二甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以96%的产率得到2,4-dimethoxy-4'-methylchalcone
  参考文献：
  名称：

  Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents

  摘要：

  Chalcones have been identified as interesting compounds with cytotoxicity, anti-inflammatory and antioxidant properties. In the present study, simple methoxychalcones were synthesized by Claisen-Schmidt condensation reaction and evaluated for above biological activities. The structures of the compounds were established by IR, (1)H NMR and mass spectral analysis. The data revealed that compound 3s (99-100% at 10 mu M concentration) completely inhibit the selected five human cancer cell lines as compared to standard flavopiridol and gemcitabine (70-90% at 700 nM and 500 nM concentrations, respectively), followed by 3a, 3n, 3o, 3p, 3q, 3r. Among the tested compounds 3l, 3m, 3r, and 3s exhibited promising anti-inflammatory activity against TNF-alpha and IL-6 with 90-100% inhibition at 10 mu M concentration. DPPH free radical scavenging activity was given by the compounds 3o, 3n, 3l, 3r, 3m, 3a, 3p, 3c and 3s at 1 mM concentration. Overall, 3s was obtained as lead compound with promising anticancer, anti-inflammatory and antioxidant activities. Bioavailability of compounds were checked by in vitro cytotoxicity study and confirmed to be nontoxic. The structure activity relationship (SAR) and in silico drug relevant properties (HBDs, HBAs, PSA, c Log P, ionization potential, molecular weight, E(HOMO) and E(LUMO)) further confirmed that the compounds were potential candidates for future drug discovery study. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.066

文献信息

• Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents
  作者：Babasaheb P. Bandgar、Shrikant S. Gawande、Ragini G. Bodade、Jalinder V. Totre、Chandrahas N. Khobragade

  DOI：10.1016/j.bmc.2009.11.066

  日期：2010.2

  Chalcones have been identified as interesting compounds with cytotoxicity, anti-inflammatory and antioxidant properties. In the present study, simple methoxychalcones were synthesized by Claisen-Schmidt condensation reaction and evaluated for above biological activities. The structures of the compounds were established by IR, (1)H NMR and mass spectral analysis. The data revealed that compound 3s (99-100% at 10 mu M concentration) completely inhibit the selected five human cancer cell lines as compared to standard flavopiridol and gemcitabine (70-90% at 700 nM and 500 nM concentrations, respectively), followed by 3a, 3n, 3o, 3p, 3q, 3r. Among the tested compounds 3l, 3m, 3r, and 3s exhibited promising anti-inflammatory activity against TNF-alpha and IL-6 with 90-100% inhibition at 10 mu M concentration. DPPH free radical scavenging activity was given by the compounds 3o, 3n, 3l, 3r, 3m, 3a, 3p, 3c and 3s at 1 mM concentration. Overall, 3s was obtained as lead compound with promising anticancer, anti-inflammatory and antioxidant activities. Bioavailability of compounds were checked by in vitro cytotoxicity study and confirmed to be nontoxic. The structure activity relationship (SAR) and in silico drug relevant properties (HBDs, HBAs, PSA, c Log P, ionization potential, molecular weight, E(HOMO) and E(LUMO)) further confirmed that the compounds were potential candidates for future drug discovery study. (C) 2009 Elsevier Ltd. All rights reserved.
• Microbial transformations of 4′-methylchalcones as an efficient method of obtaining novel alcohol and dihydrochalcone derivatives with antimicrobial activity
  作者：Joanna Kozłowska、Bartłomiej Potaniec、Barbara Żarowska、Mirosław Anioł

  DOI：10.1039/c8ra04669g

  日期：——

  Biotransformations of 4′-methylchalcones using whole cells of bacteria allowed to obtain dihydrochalcones and alcohol with high isolated yields. The antimicrobial activity of all derivatives was evaluated against selected bacteria and fungi strains.

  使用细菌整细胞对4'-甲基茵黄酮进行生物转化，可以获得高收率的二氢黄酮和醇。对所有衍生物的抗菌活性进行了评估，针对选择的细菌和真菌菌株。