6-chloro-2'-hydroxyflavanone | 108718-33-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 6-chloro-2'-hydroxyflavanone
• 英文别名: 6-chloro-2-(2-hydroxy-phenyl)-chroman-4-one；6-Chlor-2-(2-hydroxy-phenyl)-chroman-4-on；6-Chloro-2-(2-hydroxyphenyl)-2,3-dihydrochromen-4-one；6-chloro-2-(2-hydroxyphenyl)-2,3-dihydrochromen-4-one
• CAS: 108718-33-8
• 化学式: C₁₅H₁₁ClO₃
• 分子量: 274.704
• InChiKey: MAHBEANQJZMPIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  6-chloro-2'-hydroxyflavanone 在 selenium(IV) oxide 、 异戊醇 作用下， 生成 6-Chlor-2'-hydroxy-flavon
  参考文献：
  名称：

  Parikh; Shah, Journal of the Indian Chemical Society, 1959, vol. 36, p. 729

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-3-(5-chloro-2-hydroxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 在 盐酸 作用下， 生成 6-chloro-2'-hydroxyflavanone
  参考文献：
  名称：

  Parikh; Shah, Journal of the Indian Chemical Society, 1959, vol. 36, p. 729

  摘要：

  DOI：

文献信息

• 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.
• Kamboj, Ramesh C.; Berar, Surinder; Berar, Urmila, Journal of the Indian Chemical Society, 2011, vol. 88, # 6, p. 879 - 885
  作者：Kamboj, Ramesh C.、Berar, Surinder、Berar, Urmila、Gupta, Satish C.

  DOI：——

  日期：——
• Parikh; Shah, Journal of the Indian Chemical Society, 1959, vol. 36, p. 729
  作者：Parikh、Shah

  DOI：——

  日期：——