3-(3,4-dimethoxyphenyl)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-propanone | 743442-96-8

• 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: 3-(3,4-dimethoxyphenyl)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-propanone
• 英文别名: 3-(3,4-dimethoxyphenyl)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)propan-1-one；3-(3,4-Dimethoxyphenyl)-1-(5-hydroxy-2,2-dimethyl-chromen-6-yl)propan-1-one；3-(3,4-dimethoxyphenyl)-1-(5-hydroxy-2,2-dimethylchromen-6-yl)propan-1-one
• CAS: 743442-96-8
• 化学式: C₂₂H₂₄O₅
• 分子量: 368.43
• InChiKey: IJHLKMBROXTELK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  3-(3,4-dimethoxyphenyl)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-propanone 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以24%的产率得到巴豆毒素
  参考文献：
  名称：

  Isolation and synthesis of chalcones with different degrees of saturation

  摘要：

  Crotaoprostrin, a chalcone not yet known as a plant constituent, was isolated from the aerial parts of the Indian medicinal plant Crotalaria prostrata. The structures of the chalcone polyarvin and the partially hydrogenated naturally occurring derivatives crotaramin, crotaramosmin, and crotin were confirmed by chemical synthesis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(02)00475-2
• 作为产物：
  描述：

  3,4-二甲氧基苯丙酸 在 copper(l) iodide 、 三氟化硼乙醚 、 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基苯胺 、 乙腈 为溶剂， 反应 37.5h， 生成 3-(3,4-dimethoxyphenyl)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-propanone
  参考文献：
  名称：

  设计，合成和生物学评估截短的Deguelin衍生物作为Hsp90抑制剂

  摘要：

  在本研究中，已经设计并合成了一系列新颖的B和C环截短的deguelin衍生物，作为热激蛋白90（Hsp90）抑制剂。合成的化合物对一组人类癌细胞系表现出微摩尔的抗增殖能力。以系统的方式研究了它们的构效关系（SAR）。鉴定出化合物21c具有高的Hsp90结合能力（60nM），并通过遍在蛋白蛋白酶体系统引起客户蛋白降解。进一步的生物学研究表明，化合物21c诱导了人乳腺癌MCF-7细胞的剂量依赖性S和G2期细胞周期停滞。流式细胞仪和蛋白质印迹分析证实了化合物21c导致MCF-7细胞凋亡。另外，化合物21c对MCF-7细胞的迁移和侵袭表现出很强的抑制作用。综上所述，这些结果表明21c可能是Hsp90抑制剂进一步开发的有前途的先导化合物。

  DOI：

  10.1016/j.ejmech.2019.02.014

文献信息

• Synthesis and Insight into the Structure–Activity Relationships of Chalcones as Antimalarial Agents
  作者：Narender Tadigoppula、Venkateswarlu Korthikunta、Shweta Gupta、Papireddy Kancharla、Tanvir Khaliq、Awakash Soni、Rajeev Kumar Srivastava、Kumkum Srivastava、Sunil Kumar Puri、Kanumuri Siva Rama Raju、Wahajuddin、Puran Singh Sijwali、Vikash Kumar、Imran Siddiqi Mohammad

  DOI：10.1021/jm300588j

  日期：2013.1.10

  licorice, is the most promising antimalarial compound reported so far. In continuation of our drug discovery program, we isolated two similar chalcones, medicagenin (II) and munchiwarin (III), from Crotalaria medicagenia, which exhibited antimalarial activity against Plasmodium falciparum. A library of 88 chalcones were synthesized and evaluated for their in vitro antimalarial activity. Among these, 67,

  从中国甘草的根中分离得到的Licochalcone A（I）是迄今为止报道的最有前途的抗疟化合物。在继续我们的药物发现计划时，我们从猪屎豆属中分离了两个类似的查耳酮，medicageninin（II）和munchiwarin（III），它们对恶性疟原虫具有抗疟活性。合成了88个查耳酮的文库，并对其体外抗疟活性进行了评估。在这些中，67，68，74，77，和78显示出在体外对抗疟疾活性良好恶性疟原虫具有低细胞毒性的3D7和K1菌株。这些查耳酮还显示出寄生虫约瑟氏疟原虫（N-67株）感染的瑞士小鼠的寄生虫病减少和存活时间增加。药代动力学研究表明，不良的ADME特性导致口服生物利用度低。分子对接研究揭示了这些抑制剂在falcipain-2（FP-2）酶的活性位点的结合方向。化合物67，68，和78显示出对主要血红蛋白降解半胱氨酸适度抑制活性蛋白酶FP-2。
• 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
• A convenient and biogenetic type synthesis of few naturally occurring chromeno dihydrochalcones and their in vitro antileishmanial activity
  作者：Tadigoppula Narender、Shweta、Suman Gupta

  DOI：10.1016/j.bmcl.2004.05.071

  日期：2004.8

  2',2'-Dimethyl chromeno dihydrochalcones are very rare in nature as plant secondary metabolites. Recently we have reported three such compounds from the plant Crotalaria ramosissima. Chromeno dihydrochalcones contain a 2',2'-dimethyl benzopyran system, which are frequently encountered in many natural products and exhibit a variety of biological activities. We here report the strategy to conveniently synthesize naturally occurring chromeno dihydrochalcones by biogenetic type pyridine or Amberlyst-15 catalyzed chromenylation of dihydrochalcones and in vitro antileishmanial activity of chromeno dihydrochalcones and their intermediates. (C) 2004 Elsevier Ltd. All rights reserved.
• US9745280B2
  申请人：——

  公开号：US9745280B2

  公开（公告）日：2017-08-29
• Isolation and synthesis of chalcones with different degrees of saturation
  作者：Karsten Krohn、Klaus Steingröver、M Srinivasa Rao

  DOI：10.1016/s0031-9422(02)00475-2

  日期：2002.12

  Crotaoprostrin, a chalcone not yet known as a plant constituent, was isolated from the aerial parts of the Indian medicinal plant Crotalaria prostrata. The structures of the chalcone polyarvin and the partially hydrogenated naturally occurring derivatives crotaramin, crotaramosmin, and crotin were confirmed by chemical synthesis. (C) 2002 Elsevier Science Ltd. All rights reserved.