6′-hydroxy-2′,3′,4′-trimethoxychalcone | 70185-52-3

• 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: 6′-hydroxy-2′,3′,4′-trimethoxychalcone
• 英文别名: 2'-hydroxy-4',5',6'-tetramethoxychalcone；2'-hydroxy-4',5',6'-trimethoxychalcone；6-hydroxy-2',3',4'-trimethoxychalcone；2,3,4-trimethoxy-6-hydroxychalcone；2-Hydroxy-4,5,6-trimethoxy-chalkon；2-Hydroxy-4.5.6-trimethoxy-chalkon；1-(6-Hydroxy-2,3,4-trimethoxyphenyl)-3-phenylprop-2-en-1-one
• CAS: 70185-52-3；74064-14-5
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: PSHNFUINYKNYTK-UHFFFAOYSA-N

物化性质

• 熔点：
  98-100 °C
• 沸点：
  529.9±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6′-hydroxy-2′,3′,4′-trimethoxychalcone 在 氢溴酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 溶剂黄146 为溶剂， 反应 18.0h， 生成 汉黄芩素
  参考文献：
  名称：

  一种新的多米诺骨牌氧化-将2,3-二氢沃戈宁重排为negletein

  摘要：

  我们报道了碘的快速催化氧化作用，将2,3-二氢牛精蛋白氧化为神经节蛋白，该蛋白包括Wessely-Moser重排（WMR），与通常的O-去甲基化无关，而是氧到氧的甲基转移。相反，在1，4-二恶烷中的DDQ将2，3-二氢沃戈宁氧化成沃戈宁而没有重排。

  DOI：

  10.1016/j.tetlet.2016.02.093
• 作为产物：
  描述：

  3,4,5-三甲氧基苯酚 在 碳酸氢钠 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 6′-hydroxy-2′,3′,4′-trimethoxychalcone
  参考文献：
  名称：

  一种新的多米诺骨牌氧化-将2,3-二氢沃戈宁重排为negletein

  摘要：

  我们报道了碘的快速催化氧化作用，将2,3-二氢牛精蛋白氧化为神经节蛋白，该蛋白包括Wessely-Moser重排（WMR），与通常的O-去甲基化无关，而是氧到氧的甲基转移。相反，在1，4-二恶烷中的DDQ将2，3-二氢沃戈宁氧化成沃戈宁而没有重排。

  DOI：

  10.1016/j.tetlet.2016.02.093

文献信息

• Synthesis and Anti-influenza Activities of Novel Baicalein Analogs
  作者：Shu-Ting Chung、Pei-Yu Chien、Wen-Hsin Huang、Chen-Wen Yao、An-Rong Lee

  DOI：10.1248/cpb.c13-00897

  日期：——

  A series of novel flavones derivatives were synthesized based on modification of the active ingredients of a traditional Chinese medicine Scutellaria baicalensis GEORGI and screened for anti-influenza activity. The synthetic baicalein (flavone) analogs, especially with the B-rings substituted with bromine atoms, were much more potent than oseltamivir or ribavirin against H1N1 Tamiflu-resistant (H1N1 TR) virus and usually with more favorable selectivity. The most promising were 5b, 5c, 6b and 6c, all displaying an 50% effective concentration (EC50) at around 4.0–4.5 µM, and a selective index (SI=50% cytotoxic concentration (CC50)/EC50)>70. For seasonal H3N2-infected influenza virus, both 5a and 5b with SI >17.3 indicated superior to ribavirin. The flavonoids having both not-naturally-occurring bromo-substituted B-rings and appropriate hydroxyls positioning on the A-rings might be critical in determining the activity and selectivity against H1N1-Tamiflu-resistant infected influenza viruses.

  一系列新型黄酮衍生物是基于对传统中药黄芩（Scutellaria baicalensis GEORGI）活性成分的修饰合成的，并进行了抗流感活性筛选。合成的大黄素（黄酮）类似物，特别是B环上带有溴原子取代的类似物，对H1N1达菲耐药（H1N1 TR）病毒的活性远超奥司他韦或利巴韦林，并且通常具有更优越的选择性。最有希望的化合物是5b、5c、6b和6c，它们的50%有效浓度（EC50）都在4.0–4.5 µM左右，选择指数（SI=50%细胞毒性浓度（CC50）/EC50）>70。对于季节性H3N2流感病毒感染，5a和5b的SI均大于17.3，优于利巴韦林。这些具有非天然溴取代B环和A环上适当羟基位置的黄酮类化合物可能在决定抗H1N1达菲耐药流感病毒的活性和选择性方面起关键作用。
• Total synthesis of baicalein
  作者：Duo-Zhi Chen、Jian Yang、Bo Yang、Yuan-Shuang Wu、Ting Wu

  DOI：10.1080/10286020903508416

  日期：2010.2.1

  In this paper, a simple and novel synthesis of baicalein is described. This transformation features the novel synthesis of helilandin B and a different way to demethylate. The overall yield of 59% is acceptable.

  在本文中，描述了一种简单而新颖的黄ical素合成方法。这种转化具有Helinlandin B的新颖合成和不同的脱甲基方式。59％的总产率是可以接受的。
• 4′-Bromo-5,6,7-trimethoxyflavone represses lipopolysaccharide-induced iNOS and COX-2 expressions by suppressing the NF-κB signaling pathway in RAW 264.7 macrophages
  作者：Dong Han Kim、Chang Hyeon Yun、Min Hwan Kim、Ch. Naveen Kumar、Bo Hee Yun、Ji-Sun Shin、Hyo Jin An、Young Hun Lee、Yong Don Yun、Hong-Kun Rim、Min-Sang Yoo、Kyung-Tae Lee、Yong Sup Lee

  DOI：10.1016/j.bmcl.2011.10.067

  日期：2012.1

  The regulations of the NO and PGE(2) productions are research topics of interest in the field of anti-inflammatory drug development. In the present study, 5,6,7-trimethoxy- and 5,6,7-trihydroxyflavones 3a-3g were synthesized from cinnamic acid derivatives. In particular, 4'-bromo-5,6,7-trimethoxyflavone ( 3b) most potently inhibited the productions of NO and PGE(2) in LPS-treated RAW 264.7 cells ( IC(50) = 14.22 +/- 1.25 and 10.98 +/- 6.25 mu M, respectively), and these inhibitory effects were more potent than those of oroxylin A or baicalein. Consistent with these findings, 3b concentration-dependently reduced the LPS-induced expressions of iNOS and COX-2 at the protein and mRNA levels. In addition, the release of TNF-alpha, IL-6, and IL-1 beta and the mRNA expressions of these cytokines were reduced by 3b in a concentration-dependent manner. Furthermore, 3b attenuated the LPS-induced transcriptional activities of NF-kappa B and this was accompanied by parallel reductions in the degradation and phosphorylation of I kappa B-alpha, and consequently by a decrease in the nuclear translocation of the p65 subunit of NF-kappa B. Taken together, these results suggest that suppressions of the expressions of iNOS, COX-2, TNF-alpha, IL-6, and IL-1 beta via NF-kappa B inactivation are responsible for the anti-inflammatory effects of 3b. (C) 2011 Elsevier Ltd. All rights reserved.
• Parmar, Virinder S.; Gupta, Sandhya; Sinha, Rita, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 2, p. 244 - 256
  作者：Parmar, Virinder S.、Gupta, Sandhya、Sinha, Rita、Sharma, Sunil K.

  DOI：——

  日期：——
• Oroxylin A analogs exhibited strong inhibitory activities against iNOS-mediated nitric oxide (NO) production
  作者：Tuan-Ahn. N. Pham、Haiyan Che、Phuong-Thuy T. Phan、Jae-Won Lee、Sung-Soo Kim、Haeil Park

  DOI：10.1016/j.bmcl.2012.01.135

  日期：2012.4

  A number of oroxylin A analogs were prepared and evaluated for their inhibitory activities against iNOS-mediated nitric oxide (NO) production from LPS-stimulated BV2 cells. The analogs were synthesized from purchased 2'-hydroxy-4,5,6-trimethoxyacetophenone and aldehydes in 3 steps. Among the tested compounds, several analogs (3b, 3c, 3d, 3f) exhibited strong inhibitory activities. Especially, the analog with 4-nitrophenyl group (3b) showed stronger inhibitory activity (IC50 = 4.73 mu M) than that of wogonin (IC50 = 7.80 mu M). (C) 2012 Published by Elsevier Ltd.