5'-chloro-2'-hydroxy-2-methoxychalcone | 28328-72-5

• 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: 5'-chloro-2'-hydroxy-2-methoxychalcone
• 英文别名: 1-(5-Chloro-2-hydroxyphenyl)-3-(2-methoxyphenyl)prop-2-en-1-one
• CAS: 28328-72-5
• 化学式: C₁₆H₁₃ClO₃
• 分子量: 288.73
• InChiKey: RNKUTENPRDOAMH-UHFFFAOYSA-N

物化性质

• 沸点：
  469.0±45.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  异烟肼 、 5'-chloro-2'-hydroxy-2-methoxychalcone 以 乙醇 为溶剂， 生成 (3-(5-chloro-2-hydroxyphenyl)-5-(2-methoxyphenyl)-4,5-dihydropyrazol-1-yl)(pyridin-4-yl)methanone
  参考文献：
  名称：

  Pyrazoline and Hydrazone Derivatives as Potent Membrane Stabilizer and Antioxidant Compounds

  摘要：

  研究了 26 种吡唑啉和腙衍生物的膜稳定和抗氧化活性。这些化合物的抗氧化活性是通过体外 2,2-氮基-双（3-乙基-苯并噻唑啉-6-磺酸）（ABTS）和 2,2-二苯基-1-苦基肼（DPPH）自由基清除试验进行检测的。丁基羟基甲苯（BHT）用作 DPPH-自由基清除剂标准，三氧化锡用作 ABTS-+ 自由基清除剂标准。一些化合物（D13、D16 和 D22）显示出良好的抗氧化活性。所有化合物的膜稳定活性均优于参考物质乙酰水杨酸。

  DOI：

  10.1007/s11094-022-02624-z
• 作为产物：
  描述：

  水杨醛 在 potassium hydroxide 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 8.5h， 生成 5'-chloro-2'-hydroxy-2-methoxychalcone
  参考文献：
  名称：

  5′-Chloro-2,2′-dihydroxychalcone and related flavanoids as treatments for prostate cancer

  摘要：

  Several flavonoids and their biosynthetic precursor chalcones were designed and synthesized to improve the biological effects of the lead compound 2'-hydroxyflavonone against androgen receptor (AR)-dependent transcriptional stimulation. Newly synthesized chalcones 19 and 26 suppressed AR dependent transcription as well as DHT-dependent growth stimulation at a low micromolar level. These compounds were also effective against ligand-independent constitutively active mutant AR derived from castration-resistant PCa (CRPC). Compounds 19 and 26 showed broad spectrum anti-proliferative activity at 5-10 mu M against multiple tumor cell lines including androgen-independent and taxane-resistant prostate cancer as well as a multidrug-resistant subline. Mode of action studies suggested that 19 induced sub-G1 accumulation in PC-3 cells by disrupting the microtubule network without affecting cell cycle progression. Furthermore, the in vivo effectiveness of chalcone 19 was confirmed in a xenograft model antitumor assay. Thus, chalcone 19 has the potential to be a bifunctional lead for treatment of AR-dependent PCa at lower doses as well as AR-independent PCa, including CRPC, at higher doses. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.08.069

文献信息

• Tin(IV) complexes with 2-methoxy-2′-hydroxy chalkones
  作者：N.S. Biradar、B.R. Patil、V.H. Kulkarni

  DOI：10.1016/s0020-1693(00)94112-4

  日期：1976.1
• 5′-Chloro-2,2′-dihydroxychalcone and related flavanoids as treatments for prostate cancer
  作者：Yohei Saito、Atsushi Mizokami、Hiroyuki Tsurimoto、Kouji Izumi、Masuo Goto、Kyoko Nakagawa-Goto

  DOI：10.1016/j.ejmech.2018.08.069

  日期：2018.9

  Several flavonoids and their biosynthetic precursor chalcones were designed and synthesized to improve the biological effects of the lead compound 2'-hydroxyflavonone against androgen receptor (AR)-dependent transcriptional stimulation. Newly synthesized chalcones 19 and 26 suppressed AR dependent transcription as well as DHT-dependent growth stimulation at a low micromolar level. These compounds were also effective against ligand-independent constitutively active mutant AR derived from castration-resistant PCa (CRPC). Compounds 19 and 26 showed broad spectrum anti-proliferative activity at 5-10 mu M against multiple tumor cell lines including androgen-independent and taxane-resistant prostate cancer as well as a multidrug-resistant subline. Mode of action studies suggested that 19 induced sub-G1 accumulation in PC-3 cells by disrupting the microtubule network without affecting cell cycle progression. Furthermore, the in vivo effectiveness of chalcone 19 was confirmed in a xenograft model antitumor assay. Thus, chalcone 19 has the potential to be a bifunctional lead for treatment of AR-dependent PCa at lower doses as well as AR-independent PCa, including CRPC, at higher doses. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Pyrazoline and Hydrazone Derivatives as Potent Membrane Stabilizer and Antioxidant Compounds
  作者：Begum Evranos Aksoz、Sezen Yilmaz Sarialtın、Tulay Coban

  DOI：10.1007/s11094-022-02624-z

  日期：2022.5

  Membrane-stabilizing and antioxidant activities of twenty six pyrazoline and hydrazone derivatives were investigated. Antioxidant activity of these compounds was examined by using in vitro 2,2-azino-bis(3-ethyl-benzothiazoline-6-sulphonic acid) (ABTS) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging assays. Butylated hydroxytoluene (BHT) was used as DPPH• free radical scavenger standard, and trolox was used as ABTS•+ free radical scavenger standard. Some compounds (D13, D16 and D22) showed good antioxidant activity. All compounds were found to exhibit better membrane stabilizing activity than the reference acetylsalicylic acid.

  研究了 26 种吡唑啉和腙衍生物的膜稳定和抗氧化活性。这些化合物的抗氧化活性是通过体外 2,2-氮基-双（3-乙基-苯并噻唑啉-6-磺酸）（ABTS）和 2,2-二苯基-1-苦基肼（DPPH）自由基清除试验进行检测的。丁基羟基甲苯（BHT）用作 DPPH-自由基清除剂标准，三氧化锡用作 ABTS-+ 自由基清除剂标准。一些化合物（D13、D16 和 D22）显示出良好的抗氧化活性。所有化合物的膜稳定活性均优于参考物质乙酰水杨酸。