(E)-3-(3,4-dimethoxyphenyl)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)prop-2-en-1-one | 179003-85-1

• 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: (E)-3-(3,4-dimethoxyphenyl)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)prop-2-en-1-one
• 英文别名: 3,4-Dimethoxylonchocarpin；(E)-3-(3,4-dimethoxyphenyl)-1-(5-hydroxy-2,2-dimethylchromen-6-yl)prop-2-en-1-one
• CAS: 179003-85-1
• 化学式: C₂₂H₂₂O₅
• 分子量: 366.414
• InChiKey: NPDBZFZFFJSOFA-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  (E)-3-(3,4-dimethoxyphenyl)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)prop-2-en-1-one 在 盐酸 、 thallium(III) nitrate trihydrate 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 生成 3-(3,4-dimethoxyphenyl)-8,8-dimethyl-4-oxo-4H,8H-benzo[1,2-b:3,4-b']dipyran
  参考文献：
  名称：

  Synthesis and biological evaluation of pyranoisoflavone derivatives as anti-inflammatory agents

  摘要：

  In this paper, barbigerone (1a) and its twenty-seven related structural analogues were synthesized via complementary synthetic routes and their anti-inflammatory effects on the expression of TNF-α in LPS-stimulated splenocytes were evaluated. Among these compounds, 1a, 1d, 1f and 1g were found to remarkably inhibit TNF-α production. Furthermore, 1g showed the most potent and dose-dependent manner inhibitory effect on TNF-α release, with better IC50 value (3.58 μM) than barbigerone (8.46 μM). Oral administration of 1g at 20 mg/kg/day for two weeks obviously demonstrated protective effect in adjuvant-induced arthritis models as evaluated by clinical score of paws, and histological examination of joint tissues from rats. Mechanism studies on mRNA and protein level suggested that 1g inhibited the TNF-α production via depressing TNF-α converting enzyme (TACE) mRNA expression. In conclusion, these data show 1g with potential therapeutic effects as an anti-inflammatory agent.

  DOI：

  10.1016/j.fitote.2014.06.002
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 氢氧化钾 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 苯 为溶剂， 反应 49.0h， 生成 (E)-3-(3,4-dimethoxyphenyl)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)prop-2-en-1-one
  参考文献：
  名称：

  3',4'-亚甲二氧基-2",2"-二甲基吡喃-[5",6":7,8]-黄酮和(±)-Ponganone III的简便合成，两种吡喃类黄酮

  摘要：

  摘要 两种天然吡喃黄酮类化合物 3',4'-亚甲二氧基-2",2"-二甲基吡喃-[5",6":7,8]-黄酮 (1) 和 (±)-ponganone III (2) 的简便合成)，已通过 DDQ 诱导的氧化环化通过关键中间体色烯 6 实现。

  DOI：

  10.1080/00397919908085964

文献信息

• Natural Product-like Combinatorial Libraries Based on Privileged Structures. 1. General Principles and Solid-Phase Synthesis of Benzopyrans
  作者：K. C. Nicolaou、J. A. Pfefferkorn、A. J. Roecker、G.-Q. Cao、S. Barluenga、H. J. Mitchell

  DOI：10.1021/ja002033k

  日期：2000.10.1

  report a novel strategy for the design and construction of natural and natural product-like libraries based on the principle of privileged structures, a term originally introduced to describe structural motifs capable of interacting with a variety of unrelated molecular targets. The identification of such privileged structures in natural products is discussed, and subsequently the 2,2-dimethylbenzopyran

  在此，我们报告了一种基于特权结构原理设计和构建天然和天然产物类库的新策略，该术语最初用于描述能够与各种不相关的分子靶标相互作用的结构基序。讨论了天然产物中此类特权结构的鉴定，随后选择 2,2-二甲基苯并吡喃部分作为通过该策略构建类天然产物库的初始模板。最初，采用独特的环加载策略开发了苯并吡喃基序的新型固相合成，该策略依赖于使用新的聚苯乙烯基溴化硒树脂。一旦确定了这些苯并吡喃的加载、加工和裂解，
• Rational design, synthesis, and pharmacological properties of pyranochalcone derivatives as potent anti-inflammatory agents
  作者：Fei Peng、Guangcheng Wang、Xiuxia Li、Dong Cao、Zhuang Yang、Liang Ma、Haoyu Ye、Xiaolin Liang、Yan Ran、Jinying Chen、Jingxiang Qiu、Caifeng Xie、Chongyang Deng、Mingli Xiang、Aihua Peng、Yuquan Wei、Lijuan Chen

  DOI：10.1016/j.ejmech.2012.05.005

  日期：2012.8

  24 derivatives (5a–x) derived from natural pyranochalcones (I and II) were designed and evaluated for their inhibitory potency on the production of nitric oxide (NO) in LPS-stimulated RAW264.7 cells. Among them, four compounds (5b, 5d, 5f, and 5h) exhibited more potent inhibitory effects on iNOS activity and iNOS-mediated NO production than a positive control indomethacin. Furthermore, 5b could significantly

  设计并评估了24种衍生自天然吡喃并二氢呋喃酮（I和II）的衍生物（5a – x）对LPS刺激的RAW264.7细胞中一氧化氮（NO）产生的抑制作用。其中，与阳性对照消炎痛相比，四种化合物（5b，5d，5f和5h）对iNOS活性和iNOS介导的NO产生更有效的抑制作用。而且5b与吲哚美辛相比，剂量为10 mg / kg / day的大鼠可显着抑制角叉菜胶诱发的后足水肿的进展，并通过关节炎评分和关节H＆E染色验证了剂量依赖性地改善了佐剂诱发的关节炎（AIA）的发展。此外，对接研究证实5b是与鼠iNOS活性位点结合的iNOS抑制剂。
• Facile Syntheses of 3′,4′-Methylenedioxy- 2″,2″-dimethylpyrano-[5″,6″:7,8]-flavoneand (±)-Ponganone III, Two Pyranoflavanoids
  作者：Wenfei Tan、Wei-Dong Z. Li、Chusheng Huang、Yulin Li、Yacheng Xing

  DOI：10.1080/00397919908085964

  日期：1999.10

  Abstract Facile syntheses of two naturally occurring pyranoflavanoids, 3′,4′-methylenedioxy-2″,2″-dimethylpyrano-[5″,6″:7,8]-flavone (1) and (±)-ponganone III (2), have been achieved through the key intermediate chromene 6 by a DDQ-induced oxidative cyclization.

  摘要 两种天然吡喃黄酮类化合物 3',4'-亚甲二氧基-2",2"-二甲基吡喃-[5",6":7,8]-黄酮 (1) 和 (±)-ponganone III (2) 的简便合成)，已通过 DDQ 诱导的氧化环化通过关键中间体色烯 6 实现。
• NOVEL COMPOUND OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT
  申请人：SNU R&DB Foundation

  公开号：EP2871187B1

  公开（公告）日：2017-09-20
• Identification of small molecule inhibitors of the STAT3 signaling pathway: Insights into their structural features and mode of action
  作者：Kyeojin Kim、Su-Jung Kim、Young Taek Han、Sung-Jun Hong、Hongchan An、Dong-Jo Chang、Taewoo Kim、Bumhee Lim、Jeeyeon Lee、Young-Joon Surh、Young-Ger Suh

  DOI：10.1016/j.bmcl.2015.07.063

  日期：2015.11

  A series of novel STAT3 inhibitors consisting of Michael acceptor has been identified through assays of the focused in-house library. In addition, their mode of action and structural feature responsible for the STAT3 inhibition were investigated. In particular, analog 6 revealed promising STAT3 inhibitory activity in HeLa cell lines. The analog also exhibited selective inhibition of STAT3 phosphorylation without affecting STAT1 phosphorylation and cytostatic effect in human breast epithelial cells (MCF10A-ras), which supports cancer cell-specific inhibitory properties. (C) 2015 Elsevier Ltd. All rights reserved.