(-)-licarin A | 83377-50-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: (-)-licarin A
• 英文别名: (+)-Licarin A；(−)-licarin A；(-)-licarin-A；licarin A；(E)-Dehydrodi-isoeugenol；2-methoxy-4-[(2S,3S)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydro-1-benzofuran-2-yl]phenol
• CAS: 83377-50-8
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: ITDOFWOJEDZPCF-FNINDUDTSA-N

物化性质

• 沸点：
  452.0±45.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-licarin A 在 sodium hydroxide 、 2-(吡咯烷-1-基)吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 乙醇 、 苯 为溶剂， 反应 9.0h， 生成 粗毛淫羊藿苷
  参考文献：
  名称：

  Optical resolution of (±)-dehydrodiisoeugenol: Structure revision of acuminatin

  摘要：

  DOI：

  10.1016/s0031-9422(00)82431-0
• 作为产物：
  描述：

  反式-3-(4-羟基-3-甲氧基苯基)-2-丙烯-1-醇 在 吡啶 、 双氧水 、 三乙基硼氢化锂 、 三乙胺 、 horseradish peroxidase 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 (-)-licarin A
  参考文献：
  名称：

  Stereoselective Synthesis of 8,9-Licarinediols

  摘要：

  The total synthesis of 8,9-licarinediols was selectively carried out from licarin A, previously obtained by oxidative coupling of (E)-isoeugenol. The corresponding enantiomerically pure (+)- and(-)-licarin A ester derivatives were subjected to Sharpless oxidation to yield the asymmetric C-8, C-9 dihydroxylation products, whose absolute configurations were established by means of the CD and NMR spectroscopic analyses of their Mosher ester derivatives. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00873-5

文献信息

• (±)-trans-2-phenyl-2,3-dihydrobenzofurans as leishmanicidal agents: Synthesis, in vitro evaluation and SAR analysis
  作者：Freddy A. Bernal、Marcel Gerhards、Marcel Kaiser、Bernhard Wünsch、Thomas J. Schmidt

  DOI：10.1016/j.ejmech.2020.112493

  日期：2020.11

  (SI > 4.6). Nonetheless, structural optimization as further requirement was inferred from the high clearance of the most potent compound (8m) observed during determination in vitro of its metabolic stability. On the other hand, chiral separation of 8m and subsequent biological evaluation of its enantiomers demonstrated no effect of chirality on activity and cytotoxicity. Holistic analysis of in silico

  利什曼病是由利什曼原虫属的寄生虫引起的一种被忽视的热带病，在世界范围内造成了严重的疾病负担，对数百万人的生命构成了威胁，因此是主要的公共卫生问题。需要更有效且无毒的新疗法，特别是对于内脏利什曼病（一种最严重的疾病）。在二氢苯并呋喃以前具有抗霉菌活性的背景下，我们在此介绍一组70种反式-2-苯基-2,3-二氢苯并呋喃的合成及其对利什曼原虫donovani的体外活性的评估，并讨论结构-活动关系。化合物8m-o和8r表现出最高的效价（IC 50  <2μmol/ L）和抗真菌活性相对于对哺乳动物细胞的细胞毒性的有趣的选择性（SI> 4.6）。尽管如此，从体外代谢测定中观察到的最有效化合物（8m）的高清除率可以推断出结构优化是进一步的要求。另一方面，手性分离8m并随后对其对映异构体进行生物学评估表明，手性对活性和细胞毒性没有影响。通过简单的评分函数估算药物相似性对计算机模拟ADME的性质和配体效率
• Photosensitized Oxidation of Isoeugenol in Protic and Aprotic Solvents.
  作者：Yueh-Hsiung KUO、Lien-Huei CHEN、Li-Ming WANG

  DOI：10.1248/cpb.39.2196

  日期：——

  Sensitized photooxygenation of isoeugenol gave seven products in methanol, seven products in ethanol, six products in acetone, and five products in acetonitrile. One of the products is a 7, 7'-linked lignan of a type which has not yet been observed in nature. The structures of these products were elucidated and the mechanisms of their formation are discussed.

  敏化光氧化香豆素在甲醇中产生了七种产物，在乙醇中产生了七种产物，在丙酮中产生了六种产物，在乙腈中产生了五种产物。其中一个产物是7, 7'-连接的木质素，这种类型在自然界中尚未被观察到。这些产物的结构得到了阐明，并讨论了它们形成的机制。
• USE OF DIHYDRODEHYDRODIISOEUGENOL AND PREPARATIONS COMPRISING DIHYDRODEHYDRODIISOEUGENOL
  申请人：Meyer Imke

  公开号：US20130101650A1

  公开（公告）日：2013-04-25

  This invention relates to cosmetic and pharmaceutical preparations comprising (i) a diastereomer or a mixture of two or more diastereomers of the compound of formula (I) or (ii) a salt of a diastereomer or of a mixture of two or more diastereomers of the compound of formula (I) or (iii) a mixture of two or more salts of a diastereomer or of a mixture of two or more diastereomers of the compound of formula (I), a diastereomer, salt or a mixture as defined above as a drug for topical application and/or for the treatment of lipoatrophy; the non-therapeutic use of a diastereomer, salt or a mixture as defined above for the prevention, treatment or reduction of skin aging, especially skin wrinkles; the use of a diastereomer, salt or a mixture as defined above for the production of an orally administered non-pharmaceutical preparation.

  本发明涉及包含(i)化合物的对映异构体或两个或两个以上对映异构体的混合物或(ii)化合物的对映异构体或两个或两个以上对映异构体的混合物的盐或(iii)化合物的对映异构体或两个或两个以上对映异构体的混合物的两个或两个以上盐的混合物的化妆品和药用制剂，上述对映异构体、盐或混合物被定义为用于局部应用的药物和/或治疗脂肪萎缩；上述对映异构体、盐或混合物的非治疗用途被定义为用于预防、治疗或减少皮肤老化，特别是皱纹；上述对映异构体、盐或混合物被定义为用于制造口服非药用制剂。
• CAFFEIC ACID DERIVATIVES FOR ANTI-ANGIOGENESIS
  申请人：Taipei Medical University

  公开号：US20160355493A1

  公开（公告）日：2016-12-08

  The present invention develops a series of methyl caffeate derivatives having biological activity in anti-angiogenesis. The present invention suggests that the compounds of the invention possess inhibiting angiogenesis through regulation of VEGF/VEGFR-2 and its downstream signaling cascades in the vascular endothelial cells (VECs).

  本发明开发了一系列具有抗血管生成生物活性的甲基咖啡酸衍生物。本发明表明，本发明的化合物通过调节血管内皮细胞（VECs）中的VEGF/VEGFR-2及其下游信号级联来抑制血管生成。
• Anodic oxidation of some propenylphenols: Synthesis of physiologically active neolignans.
  作者：ATSUKO NISHIYAMA、HIDEO ETO、YUKIMASA TERADA、MASANOBU IGUCHI、SHOSUKE YAMAMURA

  DOI：10.1248/cpb.31.2834

  日期：——

  Some propenylphenols have been subjected to anodic oxidation to afford a number of oxidation products including arylpropanoid-, asatone-, austrobailignan-, carpanone- and licarin-type neolignans. The formation process of these compounds involves both radical and cationic reactions controlled by the applied potentials, solvent media and substituents on the aromatic rings.

  一些丙烯基苯酚在阳极氧化过程中会产生一系列氧化产物，包括芳基丙酮、asatone、austrobailignan、carpanone 和 licarin 型新木质素。这些化合物的形成过程涉及自由基反应和阳离子反应，受应用电位、溶剂介质和芳香环上取代基的控制。