3-Flavanol, trans-(+)- | 184713-81-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3-Flavanol, trans-(+)-
• 英文别名: (2S,3R)-2-phenyl-3,4-dihydro-2H-chromen-3-ol
• CAS: 184713-81-3
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: OEIJRRGCTVHYTH-HIFRSBDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Flavanol, trans-(+)- 在 4-二甲氨基吡啶 、 10 wt% Pd(OH)2 on carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 17.5h， 生成 (-)-(2S,3R)-trans-phenylflavan-3-yl-O-gallate
  参考文献：
  名称：

  Improved synthesis of structural analogues of (−)-epicatechin gallate for modulation of staphylococcal β-lactam resistance

  摘要：

  The high-yielding synthesis of enantiomerically pure epicatechin gallate analogues where the A and/or B-ring hydroxylation is reduced or altered has been achieved by optimising routes to the catechin stereochemistry. The B-ring analogues were synthesised by using an electrophilic ring closure onto an enantiomerically enriched epoxide as a key step. The A and B-ring hydroxyl-deleted analogues were synthesised through a Mitsunobu cyclisation. For the B-ring analogues, the anti- (catechin) stereochemistry was converted to the syn- (epicatechin) stereochemistry by a known oxidation/reduction protocol. Absolute stereochemistry was derived from either a Sharpless epoxidation or asymmetric dihydroxylation. (C) 2014 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.052
• 作为产物：
  描述：

  2-phenylchromene 在 硼烷四氢呋喃络合物 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 3-Flavanol, trans-(+)-
  参考文献：
  名称：

  Towards the discovery of drug-like epigallocatechin gallate analogs as Hsp90 inhibitors

  摘要：

  (-)-表没食子儿茶素没食子酸酯(EGCG)是绿茶的主要黄酮类化合物,已被广泛研究用于多种生物活性,包括抗感染、抗炎、抗癌和神经营养。现有的EGCG结构活性数据主要局限于对简单醚和羟基缺失的探索。由于多个酚羟基和代谢不稳定的酯,EGCG的药物样性质较差。 本研究通过探索一系列半合成和合成的衍生物,显著扩展了结构活性的理解。这些衍生物具有酯替换和各种取代的芳香族和脂环族基团,包含更多的药物样取代基。获得这些分子的Hsp90抑制结构活性关系。 结果表明，酰胺和磺酰胺连接物是适合的酯替换。羟基化的芳香环和EGCG中的顺式立体化学并非Hsp90抑制所必需。系列中的选定类似物在Hsp90活性的荧光素酶重折叠测定中比EGCG更有效。© 2014 Elsevier Ltd. 保留所有权利。

  DOI：

  10.1016/j.bmcl.2014.03.088

文献信息

• VO(acac)2/TBHP Catalyzed Epoxidation of 2-(2-Alkenyl)phenols. Highly Regio- and Diastereoselective Oxidative Cyclization to 2,3-Dihydro-benzofuranols and 3-Chromanols
  作者：Alessandra Lattanzi、Arrigo Scettri

  DOI：10.1055/s-2002-31894

  日期：——

  The VO(acac) 2 /TBHP (1.5 mol%/1.3 equiv) system has been successfully used for the epoxidation of variously double bond substituted 2-(2-alkenyl)phenols under mild conditions. Moreover, a one-pot conversion to 2,3-dihydrobenzofuranols and 3-chromanols is achieved with high or complete regio- and diastereoselectivity in the presence of catalytic amounts of TFA (20 mol%). This metal-catalyzed methodology

  VO(acac) 2 /TBHP (1.5 mol%/1.3 equiv) 系统已成功用于各种双键取代的 2-(2-烯基) 苯酚在温和条件下的环氧化反应。此外，在催化量的 TFA (20 mol%) 存在下，以高或完全的区域选择性和非对映选择性实现了向 2,3-二氢苯并呋喃醇和 3-苯并二氢呋喃的一锅法转化。这种金属催化的方法被证明比以前用于环氧化和 2-(2-烯基) 苯酚氧化环化的 m-CPBA 更实用和更优越。
• Analogs of green tea polyphenols as chemotherapeutic and chemopreventive agents
  申请人：——

  公开号：US20040192723A1

  公开（公告）日：2004-09-30

  Novel compounds useful as chemotherapeutic and chemopreventive agents are provided. The compounds are analogs of polyphenol catechins that occur in green tea, such as epigallocatichin-3-gallate (EGCG), and have the structure of formula (I) 1 wherein R 1 through R 11 are defined herein. Preferred R 4 moieties are selected from O, S, NH and CH 2 , and in exemplary compounds, R 4 is O and R 5 is a tri-substituted aroyloxy substituent, such as a 3,4,5-substituted benzoyloxy group. Pharmaceutical compositions are provided as well, as are methods of chemotherapy and chemoprevention.

  提供了作为化疗和化学预防剂有用的新化合物。这些化合物是绿茶中存在的多酚儿茶素的类似物，例如表没食子儿茶素-3-没食子酸酯（EGCG），并具有公式（I）1的结构，其中R1到R11在此定义。优选的R4基团从O、S、NH和CH2中选择，在示例化合物中，R4为O，R5为三取代芳氧基取代基，例如3,4,5-取代苯甲酰氧基基团。还提供了制药组合物，以及化疗和化学预防的方法。
• Flavene and thioflavene derivatives, processes for their manufacture, pharmaceutical preparations that contain such compounds, and the use of the latter
  申请人：Zyma SA

  公开号：EP0139615A2

  公开（公告）日：1985-05-02

  Compounds of the formula I wherein rings A and B are each unsubstituted or substituted; Y is oxygen, sulfur, sulfinyl or sulfonyl; one of the symbols Z, and Z2 is halogen and the other formyl; and pharmaceutically acceptable salts of such compounds that contain a salt-forming group are useful for the treatment of diseases of the respiratory tract and of liver diseases. They are prepared by methods known per se.

  式 I 的化合物 其中，环 A 和环 B 各自是未取代的或取代的；Y 是氧、硫、亚砜基或磺酰基；符号 Z 和 Z2 中的一个是卤素，另一个是甲酰基；以及含有成盐基团的此类化合物的药学上可接受的盐，可用于治疗呼吸道疾病和肝脏疾病。它们是通过本身已知的方法制备的。
• Anti-staphylococcal activity and β-lactam resistance attenuating capacity of structural analogues of (−)-epicatechin gallate
  作者：James C. Anderson、Robert A. McCarthy、Sarah Paulin、Peter W. Taylor

  DOI：10.1016/j.bmcl.2011.09.116

  日期：2011.12

  We examined the impact of gradual removal of hydroxyl groups from the A- and B-rings of (-)-epicatechin gallate on antibacterial activity and oxacillin resistance attenuation of an epidemic strain of methicillin resistant Staphylococcus aureus. Removal of both hydroxyls from the B-ring effected a large reduction in oxacillin MIC (from 512 to 0.25 mg/mL at a concentration of 12.5 mg/L); further hydroxyl deletion of the A-ring reduced the oxacillin effect but increased intrinsic anti-staphylococcal activity (C) 2011 Elsevier Ltd. All rights reserved.
• MANIPULATION OF FLAVONOID BIOSYNTHETIC PATHWAY
  申请人：Agriculture Victoria Services Pty Ltd

  公开号：EP2488010A1

  公开（公告）日：2012-08-22