6,2′-dimethoxyflavone | 156464-92-5

• 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: 6,2′-dimethoxyflavone
• 英文别名: 2',6-dimethoxyflavone；6-methoxy-2-(2-methoxy-phenyl)-chromen-4-one；6-Methoxy-2-(2-methoxy-phenyl)-chromen-4-on；6,2'-Dimethoxyflavone；6-methoxy-2-(2-methoxyphenyl)chromen-4-one
• CAS: 156464-92-5
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: PJJFYUAXYSKODT-UHFFFAOYSA-N

物化性质

• 熔点：
  146 °C
• 沸点：
  461.5±45.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)
• 碰撞截面：
  161.4 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,2′-dimethoxyflavone 在 三氯化铝 、 硝基苯 作用下， 生成 2,6-二羟基黄酮
  参考文献：
  名称：

  Gallagher et al., Journal of the Chemical Society, 1953, p. 3770,3777

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-羟基-5'-甲氧基苯乙酮 在 碘 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 生成 6,2′-dimethoxyflavone
  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

• [EN] N-CONTAINING CHROMEN-4-ONE DERIVATIVES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION<br/>[FR] DÉRIVÉS DE CHROMEN-4-ONE CONTENANT N POUR LE TRAITEMENT ET LA PROPHYLAXIE D'UNE INFECTION PAR LE VIRUS DE L'HÉPATITE B
  申请人：HOFFMANN LA ROCHE

  公开号：WO2020120528A1

  公开（公告）日：2020-06-18

  The present invention provides the compounds having the general formula: (I) wherein R1 to R8, and X are as described herein, compositions including the compounds and methods of using the compounds.

  本发明提供具有一般式：(I)的化合物，其中R1至R8和X如本文所述，包括这些化合物的组合物和使用这些化合物的方法。
• USE OF FLAVONE AND FLAVANONE DERIVATIVES IN PREPARATION OF SEDATIVE AND HYPNOTIC DRUGS
  申请人：Jin Yongri

  公开号：US20150196529A1

  公开（公告）日：2015-07-16

  Disclosed is a use of flavones derivatives and flavanone derivatives in preparation of sedative and hypnotic drugs.

  本发明揭示了在制备镇静催眠药物中使用黄酮衍生物和黄酮酮衍生物的用途。
• Sulfoxide-mediated approach to flavones through one-pot Knoevenagel condensation/oxa-Michael addition/sulfoxide elimination process of β-(o-hydroxyaryl)-ketosulfone with arylaldehydes
  作者：Mei-Lin Tang、Jin-Feng Ning、Yu-Hui Li、Heyanhao Zhang、Mi Liu、Ye-Jun Dong、Jun Chang

  DOI：10.1016/j.tetlet.2022.154336

  日期：2023.2

  gram-scale synthesis of flavones is described by a one-pot straightforward sulfoxide-mediated Knoevenagel condensation/intermolecular oxa-Michael annulation/sulfoxide elimination process of β-(o-hydroxyaryl)-ketosulfones (dual nucleophile) and arylaldehydes (dual electrophile). The expeditious synthetic route sets up flavones, including the bond formation of one CO and one double CC bonds via a formal (5 + 1)

  在本文中，通过一锅法直接亚砜介导的 Knoevenagel 缩合/分子间 oxa-Michael 环化/β-(o-羟基芳基）-酮砜（双亲核试剂）和芳基醛（双亲电试剂）。快速合成路线建立了黄酮，包括通过形式 (5 + 1) 环加成形成一个 C O 键和一个双 C C 键。此外，其中，化合物70 亿可能是进一步开发药物以造福抗衰老领域的绝佳起点。
• Tire with rubber containing flavone
  申请人：THE GOODYEAR TIRE & RUBBER COMPANY

  公开号：EP1391327A1

  公开（公告）日：2004-02-25

  The invention relates to a rubber composition and a pneumatic tire having a component comprising a rubber containing the reaction product of a flavone and a methylene donor.

  本发明涉及一种橡胶组合物和充气轮胎，其成分包括含有黄酮和亚甲基供体反应产物的橡胶。
• Rubber composition and tire with rubber containing flavone
  申请人：The Goodyear Tire & Rubber Company

  公开号：EP2730431A1

  公开（公告）日：2014-05-14

  A rubber composition comprising a diene based elastomer and an adhesion promoter derived from a flavone, a methylene donor and a methylene acceptor is disclosed. The rubber composition is essentially free of cobalt. Also, a pneumatic tire comprising such a rubber composition is disclosed.

  本发明公开了一种橡胶组合物，该组合物包含一种二烯基弹性体和一种由黄酮、亚甲基供体和亚甲基受体衍生的附着力促进剂。该橡胶组合物基本上不含钴。此外，还公开了一种包含这种橡胶组合物的充气轮胎。