金鸡菊查耳酮 | 484-76-4

• 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
• 中文名称: 金鸡菊查耳酮
• 中文别名: 奥卡宁
• 英文名称: okanin
• 英文别名: (E)-3-(3,4-dihydroxyphenyl)-1-(2,3,4-trihydroxyphenyl)prop-2-en-1-one；3,4,2',3',4'-pentahydroxy-trans-chalcone；3,4,2',3',4'-pentahydroxy-trans-chalcone；3,4,2',3',4'-Pentahydroxy-trans-chalkon；2'.3'.4'.3.4-Pentahydroxy-chalkon
• CAS: 484-76-4
• 化学式: C₁₅H₁₂O₆
• 分子量: 288.257
• InChiKey: GSBNFGRTUCCBTK-DAFODLJHSA-N

物化性质

• 熔点：
  235-242 °C
• 沸点：
  638.0±55.0 °C(Predicted)
• 密度：
  1.584±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮（少许）、DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  118
• 氢给体数：
  5
• 氢受体数：
  6

制备方法与用途

生物活性

Okanin 是 Coreopsis tinctoria 的有效成分，能够通过抑制 TLR4/NF-κB 信号通路减弱 LPS 诱导的小胶质细胞活化。

靶点

| TLR4 | | | | p65 | | |

体外研究

Okanin 显著抑制了 LPS 刺激的 BV-2 细胞中 TLR4 的表达。同时，Okanin 抑制 NF-κB p65 子单位从细胞质向细胞核的转运，并显著抑制了 LPS 刺激的 BV-2 细胞中 iNOS 的表达以及 IL-6 和 TNF-α 的产生和 mRNA 表达。

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
  2',3',4'-三羟基苯乙酮	2',3',4'-trihydroxyacetophenone	528-21-2	C8H8O4	168.149
  ——	1-(2-hydroxy-3,4-bis(methoxymethoxy)phenyl)ethan-1-one	1610522-92-3	C12H16O6	256.255

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	3,4,2',3',4'-pentaacetoxy-trans-chalcone	102891-69-0	C25H22O11	498.443

反应信息

• 作为反应物：
  描述：

  金鸡菊查耳酮 、 乙酸酐 在 吡啶 作用下， 生成 3,4,3',4'-tetraacetoxy-2'-hydroxy-trans-chalcone
  参考文献：
  名称：

  Anthochlor Pigments of Coreopsis tinctoria

  摘要：

  DOI：

  10.1021/ja01558a057
• 作为产物：
  描述：

  2',3',4'-三羟基苯乙酮 在 盐酸 、 水 、 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 1.75h， 生成 金鸡菊查耳酮
  参考文献：
  名称：

  Potential application value of hydroxychalcones based on isoliquiritigenin in agricultural plant diseases

  摘要：

  为了提高领先化合物异黄酮的杀真菌活性，设计并制备了33种羟基查尔酮。

  DOI：

  10.1039/d2nj03261a

文献信息

• [EN] STREPTOCOCCUS MUTANS GLUCOSYL TRANSFERASE INHIBITORS FOR DENTAL CARIES THERAPY<br/>[FR] INHIBITEURS DE GLUCOSYLE TRANSFÉRASE DE STREPTOCOCCUS MUTANS POUR LA THÉRAPIE DES CARIES DENTAIRES
  申请人：UAB RESEARCH FOUNDATION

  公开号：WO2019195430A1

  公开（公告）日：2019-10-10

  The present invention is related to the inhibition of the formation of Streptococci biofilms through the inhibition of glucosyl transferase (Gtf). Compounds, compositions and methods for inhibiting Streptococcus biofilm formation, as well as for preventing, inhibiting and/or treating the formation of dental caries, and methods of identifying compounds that prevent, inhibit and/or treat the formation of dental caries are provided.

  本发明涉及通过抑制葡萄糖基转移酶(Gtf)来抑制链球菌生物膜形成的方法。提供了用于抑制链球菌生物膜形成的化合物、组合物和方法，以及用于预防、抑制和/或治疗龋齿形成的方法，以及用于识别能够预防、抑制和/或治疗龋齿形成的化合物的方法。
• Potential application value of hydroxychalcones based on isoliquiritigenin in agricultural plant diseases
  作者：Hu Li、Zheng-Rong Wu、Qing-Ru Chu、Hong-Jie Liang、Ying-Qian Liu、Tian-Lin Wu、Yue Ma

  DOI：10.1039/d2nj03261a

  日期：——

  To improve the fungicidal activity of the lead compound isoliquiritigenin, 33 hydroxychalcones were designed and prepared.

  为了提高领先化合物异黄酮的杀真菌活性，设计并制备了33种羟基查尔酮。
• Methods and compositions to prevent addiction
  申请人：FLORIDA STATE UNIVERSITY RESEARCH FOUNDATION, INC.

  公开号：US11045465B2

  公开（公告）日：2021-06-29

  Disclosed herein is a method of reducing or preventing the development of aversion to a CNS stimulant in a subject comprising, administering a therapeutic amount of the neurological stimulant and administering an antagonist of the kappa opioid receptor, to thereby reduce or prevent the development of aversion to the CNS stimulant in the subject. Also disclosed is a method of reducing or preventing the development of addiction to a CNS stimulant in a subject, comprising, administering the CNS stimulant and administering a mu opioid receptor antagonist to thereby reduce or prevent the development of addiction to the CNS stimulant in the subject. Also disclosed are pharmaceutical compositions comprising a central nervous system stimulant and an opioid receptor antagonist. Examples of central nervous system stimulants (such as methylphenidate) and opioid receptor antagonists (such as naltrexone) are provided.

  本文公开了一种减少或防止受试者对中枢神经系统兴奋剂产生厌恶感的方法，包括施用治疗量的神经兴奋剂和施用卡巴阿片受体拮抗剂，从而减少或防止受试者对中枢神经系统兴奋剂产生厌恶感。还公开了一种减少或防止受试者对中枢神经刺激物成瘾的方法，包括施用中枢神经刺激物和施用μ阿片受体拮抗剂，从而减少或防止受试者对中枢神经刺激物成瘾。还公开了包含中枢神经系统兴奋剂和阿片受体拮抗剂的药物组合物。提供了中枢神经系统兴奋剂（如哌醋甲酯）和阿片受体拮抗剂（如纳曲酮）的实例。
• Hydroxylated chalcones with dual properties: Xanthine oxidase inhibitors and radical scavengers
  作者：Emily Hofmann、Jonathan Webster、Thuy Do、Reid Kline、Lindsey Snider、Quintin Hauser、Grace Higginbottom、Austin Campbell、Lili Ma、Stefan Paula

  DOI：10.1016/j.bmc.2015.12.024

  日期：2016.2

  In this study, we evaluated the abilities of a series of chalcones to inhibit the activity of the enzyme xanthine oxidase (XO) and to scavenge radicals. 20 mono-and polyhydroxylated chalcone derivatives were synthesized by Claisen-Schmidt condensation reactions and then tested for inhibitory potency against XO, a known generator of reactive oxygen species (ROS). In parallel, the ability of the synthesized chalcones to scavenge a stable radical was determined. Structure-activity relationship analysis in conjunction with molecular docking indicated that the most active XO inhibitors carried a minimum of three hydroxyl groups. Moreover, the most effective radical scavengers had two neighboring hydroxyl groups on at least one of the two phenyl rings. Since it has been proposed previously that XO inhibition and radical scavenging could be useful properties for reduction of ROS-levels in tissue, we determined the chalcones' effects to rescue neurons subjected to ROS-induced stress created by the addition of beta-amyloid peptide. Best protection was provided by chalcones that combined good inhibitory potency with high radical scavenging ability in a single molecule, an observation that points to a potential therapeutic value of this compound class. (c) 2015 Elsevier Ltd. All rights reserved.
• The Preparation of the Polyhydroxychalcones
  作者：Ervin F. Kurth

  DOI：10.1021/ja01873a023

  日期：1939.4