5,6-dihydroxy-7,3',4'-trimethoxyflavone | 25782-23-4

• 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: 5,6-dihydroxy-7,3',4'-trimethoxyflavone
• 英文别名: 2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxychromen-4-one
• CAS: 25782-23-4
• 化学式: C₁₈H₁₆O₇
• 分子量: 344.321
• InChiKey: QIEMGQKOGFTYLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5,6-dihydroxy-7,3',4'-trimethoxyflavone 、 乙酸酐 以31%的产率得到
  参考文献：
  名称：

  HORIE TOKUHARU, NIXON KAGAKU KAJSI, NIRRON KAGAKU KAISNI, J. CHEM. SOS. JAR., CHEM. AND I+

  摘要：

  DOI：
• 作为产物：
  描述：

  6-benzyloxy-5,7,3',4'-tetramethoxyflavone 在 三氯化铝 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以50 mg的产率得到5,6-dihydroxy-7,3',4'-trimethoxyflavone
  参考文献：
  名称：

  Malhotra, S.; Sharma, V. K.; Gupta, S. R., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, p. 705 - 706

  摘要：

  DOI：

文献信息

• Compositions of flavonoids and flavonoid-containing extracts and the treatment of diseases
  申请人：Gong Qiang Bang

  公开号：US20050049206A1

  公开（公告）日：2005-03-03

  In this invention, we describe a group of flavonoids and flavonoid-containing extracts that have pharmaceutical properties which are useful in the medicinal therapy of fibrotic diseases for the treatment or reparation and prevention of fibrotic lesional tissues. Representative flavonoids and flavonoid-containing extracts have the active compositions of the below formula. Those compositions can be extracted and purified from the botanicals, including Scutellaria baicalensis Georgi, Scutellaria scordifolia Fisch,Oroxylum indicum(L.) Vent, Plantago major L. The compositions of the invention are novel as an anti-fibrotic drugs, as agents for treating fibrosis.

  在这项发明中，我们描述了一组黄酮类化合物和含黄酮类化合物的提取物，具有药物特性，可用于治疗纤维化疾病的药物疗法，用于治疗、修复和预防纤维化病变组织。代表性的黄酮类化合物和含黄酮类化合物的提取物具有以下公式的活性成分。这些成分可以从植物中提取和纯化，包括黄芩、紫花地丁、橙黄木、车前草等。本发明的成分作为抗纤维化药物和治疗纤维化的药剂是新颖的。
• Antitumor Activity of Flavones Isolated from<i>Artemisia argyi</i>
  作者：Jeong-Min Seo、Hyun-Mi Kang、Kwang-Hee Son、Jong Han Kim、Chang Woo Lee、Hwan Mook Kim、Soo-Ik Chang、Byoung-Mog Kwon

  DOI：10.1055/s-2003-38486

  日期：2003.3

  The flavones 5,6-dihydroxy-7,3′,4′-trimethoxyflavone (1), 5,6,4′-trihydroxy-7,3′-dimethoxyflavone (2), 5-hydroxy-3′,4′,6,7-tetramethoxyflavone, 5,7,3′-trihydroxy-6,4′,5′-trimethoxyflavone, ladanein, and hispidulin were isolated from the methanolic extracts of the aerial parts of Artemisia argyi and structures of the compounds were elucidated on the basis of their spectral data. These flavones inhibited farnesyl protein transferase with IC50 values of 25 - 200 μg/mL. Compound 2 inhibited proliferation of a couple of tumor cell lines and also inhibited neovascularization in a chick chorioallantoic membrane assay. Without loss of body weight of nude mice, compounds 1 and 2 inhibited growth of a colon tumor (SW620) by 44.6 % and 14.6 %, respectively.

  从艾蒿地上部分的甲醇提取物中分离出黄酮类化合物5,6-二羟基-7,3′,4′-三甲氧基黄酮（1）、5,6,4′-三羟基-7,3′-二甲氧基黄酮（2）、5-羟基-3′,4′,6,7-四甲氧基黄酮、5,7,3′-三羟基-6,4′,5′-三甲氧基黄酮、ladanein和hispidulin，并根据其光谱数据阐明了这些化合物的结构。这些黄酮类化合物抑制法呢基转移酶，IC50值为25-200微克/毫升。化合物2抑制了几个肿瘤细胞系的增殖，并在鸡绒毛尿囊膜实验中抑制了新生血管的形成。在不影响裸鼠体重的情况下，化合物1和2分别抑制结肠肿瘤（SW620）的生长44.6%和14.6%。
• Studies of the selective O-alkylation and dealkylation of flavonoids. 13. An improved method for synthesizing 5,6,7-trihydroxyflavones from 6-hydroxy-5,7-dimethoxyflavones
  作者：Tokunaru Horie、Hideaki Tominaga、Yasuhiko Kawamura、Toshihide Yamada

  DOI：10.1021/jo00038a023

  日期：1992.6

  The demethylation of five 6-hydroxy-5,7-dimethoxyflavones 1 and their acetates with 30% w/v anhydrous aluminum chloride in acetonitrile was studied, and the following results were found. In the demethylation of 6-hydroxy-4',5,7-trimethoxyflavone (1a), 5,6-dihydroxy-4',7-dimethoxyflavone (2a) and 5,6,7-trihydroxy-4'-methoxyflavone (3a) were produced. Although the ratio of the two products varied according to the amount of aluminum chloride used, it became constant after 12-24 h because the cleavage of the 7-methoxy group in 2a was suppressed by iminoesterification of the 6-hydroxy group. In contrast, the demethylation of the 5- and 7-methoxy groups of acetate 4a proceeded smoothly by the process shown in Scheme II. The amount of 3a increased with increasing reaction time to give 3a as the main product after 36-48 h. The same phenomena were observed in the demethylation of the other 6-hydroxyflavones 1b-1e and their acetates 4b-4e. The demethylation of the acetates is widely applicable as a general method for synthesizing 5,6,7-trihydroxyflavones because the protection of hydroxy groups also suppresses the further cleavage of the methoxy group adjacent to the acetoxy group on the B ring of compounds such as 4d and 4e.
• MALHOTRA, S.;SHARMA, V. K.;GUPTA, S. R.;PARMAR, V. S., INDIAN J. CHEM., 26,(1987) N 7, 705-706
  作者：MALHOTRA, S.、SHARMA, V. K.、GUPTA, S. R.、PARMAR, V. S.

  DOI：——

  日期：——
• USE OF FLAVONES FOR TREATING PSYCHIATRIC DISORDERS WITH SENSORIMOTOR GATING DEFICITS
  申请人：CHIOU Lih-Chu

  公开号：US20120029066A1

  公开（公告）日：2012-02-02

  Novel Use of flavones having 2-phenylchromen-4-one skeleton is disclosed herein. The flavones are useful as lead compounds for manufacturing a medicament or a pharmaceutical composition for treating a patient diagnosed with a psychiatric disorder with sensorimotor gating deficits.