2,2'-Dihydroxy-5'-brom-chalkon | 1776-03-0

• 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
• 英文名称: 2,2'-Dihydroxy-5'-brom-chalkon
• 英文别名: 5’-bromo-2’,2-dihydroxychalcone；5'-Brom-2',2-dihydroxychalkon
• CAS: 1776-03-0
• 化学式: C₁₅H₁₁BrO₃
• 分子量: 319.155
• InChiKey: UZEXZCVWQGHWCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,2'-Dihydroxy-5'-brom-chalkon 在 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以15%的产率得到benzofuran-2-yl(5-bromo-2-hydroxyphenyl)methanone
  参考文献：
  名称：

  碘介导的 C2'-OH-和 C2-OH-查耳酮环化合成黄酮的案例研究：再研究机制

  摘要：

  通过碘介导的环化从查耳酮合成黄酮需要在其 C 2 '-位至少有一个羟基。相反，C 2 -OH-查耳酮在相同条件下的环氧化环化是不寻常的，仅报道过一次。我们评估了上述方法并发现了不同的结果。详细讨论了这些机制。

  DOI：

  10.1002/jccs.202000482
• 作为产物：
  描述：

  4-溴苯基乙酸酯 在 sodium hydroxide 、 三氯化铝 作用下， 以 乙醇 为溶剂， 生成 2,2'-Dihydroxy-5'-brom-chalkon
  参考文献：
  名称：

  Brom-hydroxychalkone

  摘要：

  DOI：

  10.1007/bf00909453

文献信息

• Synthesis, antimicrobial activity and molecular docking of novel tetracyclic scaffolds incorporating a flavonoid framework with medium sized oxygen heterocycles
  作者：Ashok Dongamanti、Vikas Kumar Aamate、Mohan Gandhi Devulapally、Srinivas Gundu、Meena Kumari Kotni、Vijjulatha Manga、Sridhar Balasubramanian、Prasad Ernala

  DOI：10.1016/j.bmcl.2014.12.066

  日期：2015.2

  approach for the synthesis of novel tetracyclic scaffolds incorporating a flavonoid framework with medium sized heterocyclic rings (eight-, nine-, ten- and eleven-membered rings) containing two oxygen atoms from flavonols through alkylation using different dibromoalkanes was described. The synthesized compounds were established based on the spectral data and X-ray crystal structure for 6c. The synthesized

  描述了一种方便的方法，用于合成新型四环支架，该支架结合了类黄酮骨架和具有中等大小的杂环（八元，九元，十元和十一元环），其中杂环含有来自黄酮醇的烷基，使用不同的二溴代烷烃进行烷基化反应。根据光谱数据和6c的X射线晶体结构建立了合成的化合物。评价合成的化合物的体外抗菌活性。对活性最高的两种化合物6f和6i进行了对接研究。
• 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.
• Jadhav, K. P.; Ingle, D. B., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 2, p. 180 - 182
  作者：Jadhav, K. P.、Ingle, D. B.

  DOI：——

  日期：——
• Brom-hydroxychalkone
  作者：S. H. Dandegaonker、G. R. Revankar

  DOI：10.1007/bf00909453

  日期：——
• A case study of the iodine‐mediated cyclization of <scp> C ₂ </scp> ′‐ <scp>OH</scp> ‐ and <scp> C ₂ ‐OH </scp> ‐chalcones toward the synthesis of flavones: Reinvestigation of the mechanisms
  作者：Hsin Yen Tsai、Yu‐Tzu Huang、Cing‐Ling Kuo、Chia‐Jou Kuo、Anren Hu、Jih‐Jung Chen、Tzenge‐Lien Shih

  DOI：10.1002/jccs.202000482

  日期：2021.7

  Synthesis of flavones from chalcones via the iodine-mediated cyclization required at least one hydroxy group at their C2′-positions. On the contrary, the ring oxidative cyclization from C2-OH-chalcones under the same condition was unusual and reported only once. We evaluated the aforementioned method and found different results. The mechanisms in detail were discussed.

  通过碘介导的环化从查耳酮合成黄酮需要在其 C 2 '-位至少有一个羟基。相反，C 2 -OH-查耳酮在相同条件下的环氧化环化是不寻常的，仅报道过一次。我们评估了上述方法并发现了不同的结果。详细讨论了这些机制。