1-(2-氯-苯基)-3-(2-羟基-5-甲基-苯基)-丙烷-1,3-二酮 | 106551-40-0

• 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
• 中文名称: 1-(2-氯-苯基)-3-(2-羟基-5-甲基-苯基)-丙烷-1,3-二酮
• 英文名称: 1-(2-hydroxy-5-methylphenyl)-3-(2-chlorophenyl)propane-1,3-dione
• 英文别名: 1-(2-chlorophenyl)-3-(2-hydroxy-5-methylphenyl)propane-1,3-dione
• CAS: 106551-40-0
• 化学式: C₁₆H₁₃ClO₃
• 分子量: 288.73
• InChiKey: DBNXUUKMCWJITD-UHFFFAOYSA-N

物化性质

• 熔点：
  168 °C(Solv: ethanol (64-17-5))
• 沸点：
  442.3±40.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-氯-苯基)-3-(2-羟基-5-甲基-苯基)-丙烷-1,3-二酮 在 N-溴代丁二酰亚胺(NBS) 、 sodium acetate 、 溶剂黄146 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 N-((2-(2-chlorophenyl)-4-oxo-4H-chromen-6-yl)methyl)-N,N-diethylethanaminium
  参考文献：
  名称：

  黄酮类化合物作为有效抗癌药的替代作用研究：结构-活性关系研究

  摘要：

  设计并合成了三个系列的类黄酮类似物，这些类黄酮类似物在C-6，C-7和C-8处被不同的氨甲基取代，作为有效的抗癌药进行结构-活性关系研究。评价了制备的类似物对肝癌细胞HepG2和SMMC-7721生长的体外抑制活性。结构-活性关系表明，不仅具有氨基甲基的化合物比没有相同系列基团的化合物更具活性，而且在C-8位被氨基甲基取代的化合物比在C-6和C-6位的化合物更具活性。 C-7。

  DOI：

  10.1007/s00044-011-9701-6
• 作为产物：
  描述：

  乙酸对甲酚酯 在 aluminum (III) chloride 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 14.0h， 生成 1-(2-氯-苯基)-3-(2-羟基-5-甲基-苯基)-丙烷-1,3-二酮
  参考文献：
  名称：

  黄酮类化合物作为有效抗癌药的替代作用研究：结构-活性关系研究

  摘要：

  设计并合成了三个系列的类黄酮类似物，这些类黄酮类似物在C-6，C-7和C-8处被不同的氨甲基取代，作为有效的抗癌药进行结构-活性关系研究。评价了制备的类似物对肝癌细胞HepG2和SMMC-7721生长的体外抑制活性。结构-活性关系表明，不仅具有氨基甲基的化合物比没有相同系列基团的化合物更具活性，而且在C-8位被氨基甲基取代的化合物比在C-6和C-6位的化合物更具活性。 C-7。

  DOI：

  10.1007/s00044-011-9701-6

文献信息

• New Synthesis of 3-Bromoflavones via Bromination of 1-(2-Hydroxyphenyl)-3-arylpropane-1,3-dione by CuBr₂, and Conversion into 3-Aminoflavones
  作者：Hideyoshi Miyake、Shouko Nishino、Akinori Nishimura、Mitsuru Sasaki

  DOI：10.1246/cl.2007.522

  日期：2007.4.5

  A new synthesis of 3-bromoflavones from 1-(2-hydroxyphenyl)-3-arylpropane-1,3-dione using CuBr2 is described. The usefulness of 3-bromoflavone as a precursor of 3-aminoflavone is also described.

  描述了一种使用CuBr2从1-(2-羟基苯基)-3-芳基丙烯-1,3-二酮合成3-溴黄酮的新方法。此外，3-溴黄酮作为3-氨基黄酮前体的有用性也进行了描述。
• A New Protocol for Total Synthesis of Natural Product Frutinone A and Its Derivatives
  作者：Kang Lei、Dong-Wei Sun、Yuan-Yuan Tao、Xiao-Hua Xu

  DOI：10.1071/ch15267

  日期：——

  A new protocol for total synthesis of natural product frutinone A was accomplished in three steps by using inexpensive 2′-hydroxyacetophenone as starting material. The key intermediate 3-(2-chlorobenzoyl)-4-hydroxycoumarin was synthesized in one pot through Baker–Venkataraman rearrangement of 2-acetylphenyl 2-chlorobenzoate followed by introduction of methyl chloroformate under basic conditions. Then

  通过使用廉价的2'-羟基苯乙酮作为起始原料，分三步完成了天然产物果胶酮A的全合成新方案。关键中间体3-（2-氯苯甲酰基）-4-羟基香豆素是通过2-氯苯基2-乙酰基苯基的Baker-Venkataraman重排反应，然后在碱性条件下引入氯甲酸甲酯在一个罐中合成的。然后，碱促进的3-（2-氯苯甲酰基）-4-羟基香豆素的分子内亲核取代反应以优异的产率提供了果丁酮A。合成路线具有高收率，无过渡金属和温和的反应条件，以及对功能性的高度耐受性，因此可以在果胶酮A核周围轻松取代。
• Banerji; Kumar; Saha, Journal of the Indian Chemical Society, 1985, vol. 62, # 7, p. 531 - 533
  作者：Banerji、Kumar、Saha、Mazumdar

  DOI：——

  日期：——
• Involvement of selective GABA-A receptor subtypes in amelioration of cisplatin-induced neuropathic pain by 2’-chloro-6-methyl flavone (2’-Cl-6MF)
  作者：Nasiara Karim、Imran Khan、Abeer Abdelhalim、Sobia Ahsan Halim、Ajmal Khan、Nouman Altaf、Waqar Ahmad、Rukhsana Ghaffar、Ahmed Al-Harrasi

  DOI：10.1007/s00210-020-02021-x

  日期：2021.5

  Cisplatin-induced peripheral neuropathic pain is a common adverse effect of chemotherapy. The present study evaluated the effects of 2'-chloro-6-methylflavone (2'-Cl-6MF) at recombinant alpha 1 beta 2 gamma 2L, alpha 2 beta 1-3 gamma 2L, and alpha 3 beta 1-3 gamma 2L GABA-A receptor subtypes expressed in Xenopus oocytes and subsequently evaluated its effectiveness in cisplatin-induced neuropathic pain. The results showed that 2'-Cl-6MF potentiated GABA-elicited currents at alpha 2 beta 2/3 gamma 2L and alpha 3 beta 2/3 gamma 2L GABA-A receptor subtypes. The potentiation was blocked by the co-application of flumazenil (a benzodiazepine (BDZs) site antagonist). In behavioral studies, mechanical allodynia was induced by intraplantar injection of cisplatin (40 mu g/paw) in Sprague Dawley rats, and behavioral assessments were made 24 h after injection. 2'-Cl-6MF (1, 10, 30, and 100 mg/kg, i.p.), was administered 1 h before behavioral evaluation. Administration of 2'-Cl-6MF (30 and 100 mg/kg, i.p) significantly enhanced the paw withdrawal threshold and decreased mechanical allodynia. The standard drugs, gabapentin (GBP) at the dose of 70 mg/kg, and HZ 166 (16 mg/kg), i.p. also significantly enhanced the paw withdrawal threshold in mechanical allodynia. Pretreatment with pentylenetetrazole (PTZ) (15 mg/kg, i.p.) and flumazenil reversed the antinociceptive effect of 2'-Cl-6MF in mechanical allodynia indicating GABAergic mechanisms. Moreover, the binding mechanism of 2'-Cl-6MF was rationalized by in silico modeling tools. The 3D-coordinates of alpha 2 beta 2 gamma 2L and alpha 2 beta 3 gamma 2L were generated after homology modeling of the alpha 2 subtype and 2'-Cl-6MF was at predicted binding sites of the developed models. The alpha 2 model was compared with the alpha 1 and alpha 3 subunits via structural and sequence alignment. Molecular docking depicted that the compound binds efficiently at the neuromodulator binding site of the receptors. The findings of this study revealed that 2'-Cl-6MF ameliorated the manifestations of cisplatin-induced neuropathic pain in rats. Furthermore, we also conclude that GABAergic mechanisms may contribute to the antinociceptive effect of 2'-Cl-6MF. The molecular docking studies also confirm the involvement of the BDZs site of GABA-A receptors. It was observed that Ile230 of alpha 2 stabilize the chlorophenyl ring of 2'-Cl-6MF through hydrophobic interactions, which is replaced by Val203 in alpha 1 subunit. However, the smaller side chain of Val203 does not provide hydrophobic interaction to the compound due to high conformational flexibility of alpha 1 subunit.
• BANERJI, K. D.;KUMAR, K.;SAHA, G. C.;MAZUMDAR, A. K. D., J. INDIAN CHEM. SOC., 1985, 62, N 7, 531-533
  作者：BANERJI, K. D.、KUMAR, K.、SAHA, G. C.、MAZUMDAR, A. K. D.

  DOI：——

  日期：——