crotaramosmin

• 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: crotaramosmin
• 英文别名: 1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-hydroxyphenyl)propan-1-one；4-hydroxydihydrolonchocarpin；1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-hydroxyphenyl)propanone；1-(5-Hydroxy-2,2-dimethyl-chromen-6-yl)-3-(4-hydroxyphenyl)propan-1-one；1-(5-hydroxy-2,2-dimethylchromen-6-yl)-3-(4-hydroxyphenyl)propan-1-one
• 化学式: C₂₀H₂₀O₄
• 分子量: 324.376
• InChiKey: BHFVJSQVKWDKGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异甘草素 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 生成 crotaramosmin
  参考文献：
  名称：

  A convenient and biogenetic type synthesis of few naturally occurring chromeno dihydrochalcones and their in vitro antileishmanial activity

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2004.05.071

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。
• Hemisynthesis and Spectroscopic Characterization of Three New Chalcone Derivatives from Dorstenia barteri
  作者：Bathelemy Ngameni、Ghislain Wabo Fotso、Pantaleon Ambassa、Justin Kamga、Arif Dastan、Bonaventure Tchaleu Ngadjui

  DOI：10.1007/s10600-017-1962-y

  日期：2017.3

  The hemisynthesis of three new chalcones, namely kenzanol, kelianol A, and kelianol B, from Dorstenia barteri (Moraceae) is described here for the first time. The synthetic pathways employed in this work involved the pyrolysis and catalytic hydrogenation of readily available and starting materials, 4-hydroxylonchocarpin and isobavachalcone, two major constituents of the herbaceous plant D. barteri

  此处首次描述了来自 Dorstenia barteri（桑科）的三种新查耳酮的半合成，即 kenzanol、kelianol A 和 kelianol B。这项工作中采用的合成途径涉及容易获得的起始材料 4-羟基磷酰胆碱和异巴伐查酮（草本植物 D. barteri 的两种主要成分）的热解和催化氢化。所有化合物的结构解析均通过质谱、红外、紫外、一维和二维核磁共振分析进行，并与以前的报告进行比较。
• 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.
• 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.