1-(6-hydroxy-2,3,4-trimethoxyphenyl)-3-(4-nitro-phenyl)-2-propen-1-one | 685143-77-5

• 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: 1-(6-hydroxy-2,3,4-trimethoxyphenyl)-3-(4-nitro-phenyl)-2-propen-1-one
• 英文别名: 2'-Hydroxy-4',5',6'-trimethoxy-4-nitrochalcone；1-(6-hydroxy-2,3,4-trimethoxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-one
• CAS: 685143-77-5
• 化学式: C₁₈H₁₇NO₇
• 分子量: 359.335
• InChiKey: NVRLJSDYZJVGSQ-UHFFFAOYSA-N

物化性质

• 沸点：
  581.7±50.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 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：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(6-hydroxy-2,3,4-trimethoxyphenyl)-3-(4-nitro-phenyl)-2-propen-1-one 在 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 生成 5,6,7-trimethoxy-2-(4-nitrophenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis and Anti-influenza Activities of Novel Baicalein Analogs

  摘要：

  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。

  DOI：

  10.1248/cpb.c13-00897
• 作为产物：
  描述：

  对硝基肉桂酸 在 草酰氯 、 三氟化硼乙醚 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 生成 1-(6-hydroxy-2,3,4-trimethoxyphenyl)-3-(4-nitro-phenyl)-2-propen-1-one
  参考文献：
  名称：

  Synthesis and Anti-influenza Activities of Novel Baicalein Analogs

  摘要：

  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。

  DOI：

  10.1248/cpb.c13-00897

文献信息

• 一种黄芩素或其衍生物、制备方法与应用
  申请人：中国人民解放军第二军医大学

  公开号：CN110950828B

  公开（公告）日：2021-08-17

  本发明公开了一种黄芩素或其衍生物，结构如下所示：其中，R1为氢、烷基、取代或未取代芳基；R2为氢、卤素、烷基、烷氧基、取代或未取代氨基、取代或未取代芳基；R3为氧、硫；R4为取代或未取代芳基。本发明制备的黄芩素或其衍生物合成方法比较简便，适合批量生产，催化剂可回收，减少污染，本发明制备的黄芩素或其衍生物具有抗基孔肯雅病毒活性，可以作为抗基孔肯雅病毒药物使用。
• Chromones and chromone derivatives and uses thereof
  申请人：Yen Mao-Hsiung

  公开号：US20060142211A1

  公开（公告）日：2006-06-29

  The present invention relates to chromones, novel chromone derivatives, and pharmaceutical formulations containing the same and methods of use thereof. Uses of the present invention include, but are not limited to, use for the prevention and treatment of septic shock, organ injury and other disorders. The compounds described herein can be salt forms and also water-soluble compounds.

  本发明涉及香豆素，新型香豆素衍生物，以及含有它们的制药配方和使用方法。本发明的用途包括但不限于预防和治疗败血性休克、器官损伤和其他疾病。所述化合物可以是盐形式和水溶性化合物。
• 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.
• 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.