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4'-amino-5,6,7-trihydroxyflavone

中文名称
——
中文别名
——
英文名称
4'-amino-5,6,7-trihydroxyflavone
英文别名
2-(4-Aminophenyl)-5,6,7-trihydroxychromen-4-one
4'-amino-5,6,7-trihydroxyflavone化学式
CAS
——
化学式
C15H11NO5
mdl
——
分子量
285.256
InChiKey
VHVHQZWFQHXSKY-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    1.1
  • 重原子数:
    21
  • 可旋转键数:
    1
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.0
  • 拓扑面积:
    113
  • 氢给体数:
    4
  • 氢受体数:
    6

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    描述:
    对硝基肉桂酸氯化亚砜三氟化硼乙醚氢溴酸溶剂黄146 、 tin(ll) chloride 作用下, 以 乙醇二甲基亚砜甲苯 为溶剂, 生成 4'-amino-5,6,7-trihydroxyflavone
    参考文献:
    名称:
    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
    摘要:
    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.
    DOI:
    10.1016/j.bmcl.2011.10.067
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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。
  • 一种黄芩素衍生物及其制备方法与应用
    申请人:中国人民解放军第二军医大学
    公开号:CN111057035B
    公开(公告)日:2021-10-26
    本发明公开了一种黄芩素衍生物,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衍生物合成方法比较简便,减少污染,通过实验验证发现本发明制备的黄芩素衍生物可以与唑类抗真菌药物共同使用,可提高耐药菌对唑类药物的敏感性,实现逆转耐药,因此本发明为临床耐药真菌的治疗提供了一种新途径。
  • Importance of the B Ring and Its Substitution on the α-Glucosidase Inhibitory Activity of Baicalein, 5,6,7-Trihydroxyflavone
    作者:Hong GAO、Jun KAWABATA
    DOI:10.1271/bbb.68.1858
    日期:2004.1
    Hydroxychromones and B-ring-substituted 5,6,7-trihydroxyflavones were prepared to evaluate the contribution of the B ring of baicalein (5,6,7-trihydroxyflavone, 1) to its potent α-glucosidase inhibitory activity. Hydroxychromones, which lack 6-hydroxyl substitution, did not show any inhibitory activity, while 5,6,7-trihydroxy-2-methylchromone (5) showed high activity. Among the tested B-ring-substituted 5,6,7-trihydroxyflavones, the 4′-hydroxy-, 3′,4′-dihydroxy-, and 3′,4′,5′-trihydroxy-substituted derivatives were found to give more activity than that of 1. The methoxy-substituted derivatives, however, showed less activity than 1. The results suggest that the B ring of 1 was not essential, although advantageous to the activity; hydroxyl substitution on the B ring of 5,6,7-trihydroxyflavones was favorable to the activity, whereas methoxyl substitution was unfavorable; at least 4′-hydroxyl substitution of 5,6,7-trihydroxyflavones was required for enhanced activity, in which the number of hydroxyl groups did not take part.
    为了评估黄芩素(5,6,7-三羟基黄酮,1)的 B 环对其强效α-葡萄糖苷酶抑制活性的贡献,我们制备了羟基色酮和 B 环取代的 5,6,7- 三羟基黄酮。缺乏 6-羟基取代的羟基色酮没有显示出任何抑制活性,而 5,6,7-三羟基-2-甲基色酮(5)则显示出较高的活性。在测试的 B 环取代的 5,6,7-三羟基黄酮中,4′-羟基、3′,4′-二羟基和 3′,4′,5′-三羟基取代的衍生物的活性高于 1。结果表明,1 的 B 环虽然对活性有利,但并不是必需的;5,6,7-三羟基黄酮 B 环上的羟基取代对活性有利,而甲氧基取代则不利;5,6,7-三羟基黄酮至少需要 4′-羟基取代才能提高活性,羟基的数量与活性无关。
  • Exploration of Baicalein-Core Derivatives as Potent Antifungal Agents: SAR and Mechanism Insights
    作者:Heyang Zhou、Niao Yang、Wei Li、Xuemi Peng、Jiaxiao Dong、Yuanying Jiang、Lan Yan、Dazhi Zhang、Yongsheng Jin
    DOI:10.3390/molecules28176340
    日期:——
    Baicalensis, exhibited potently antifungal activity against drug-resistant Candida albicans, and strong inhibition on biofilm formation. Therefore, a series of baicalein-core derivatives were designed and synthesized to find more potent compounds and investigate structure–activity relationship (SAR) and mode of action (MoA). Results demonstrate that A4 and B5 exert a more potent antifungal effect (MIC80
    黄芩素 (BE) 是黄芩的主要成分,对耐药白色念珠菌具有有效的抗真菌活性,并能强烈抑制生物膜的形成。因此,设计并合成了一系列黄芩素核心衍生物,以寻找更有效的化合物并研究构效关系(SAR)和作用模式(MoA)。结果表明,与氟康唑 (FLC) 联合使用时,A4 和 B5 比 BE (MIC80 = 4 μg/mL) 发挥更有效的抗真菌作用 (MIC80 = 0.125 μg/mL),而 FLC 的 MIC80 从 128 μg/mL 下降。毫升至 1 微克/毫升。SAR分析表明,5-OH的存在对于协同抗真菌活性至关重要,而邻二羟基和邻三羟基是重要的药效基团,无论它们位于黄酮类化合物的A环还是B环上。农业部证明这些化合物通过抑制白色念珠菌菌丝形成而表现出有效的抗真菌作用。然而,体外进行的甾醇成分测定和酶测定表明这些化合物对甾醇生物合成和 Eno1 的影响极小。计算机测定的结果进一步证实了这些发现
  • CHROMONES AND CHROMONE DERIVATIVES AND USES THEREOF
    申请人:Jenken Bioscience, Inc.
    公开号:EP1556031A2
    公开(公告)日:2005-07-27
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