(-)-(2R,3S)-trans-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-ol | 332386-71-7

• 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: (-)-(2R,3S)-trans-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-ol
• 英文别名: 2,3-trans-5,7,3',4',5'-pentakis(benzyloxy)flavan-3-ol；(2S*,3R*)-trans-5,7-Bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-ol；(+)-[2R,3S]-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-ol；trans-5,7-bis-benzyloxy-2-[3,4,5-tris(benzyloxy)phenyl]-chroman-3-ol；(2R,3S)-5,7-bis(phenylmethoxy)-2-[3,4,5-tris(phenylmethoxy)phenyl]-3,4-dihydro-2H-chromen-3-ol
• CAS: 332386-71-7
• 化学式: C₅₀H₄₄O₇
• 分子量: 756.895
• InChiKey: GKTZINGANAELDT-AFRCBTSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (-)-(2R,3S)-trans-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-ol 在 palladium dihydroxide 4-二甲氨基吡啶 、 氢气 、 L-Selectride 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 (-)-表没食子儿茶素没食子酸酯
  参考文献：
  名称：

  Enantioselective Synthesis of Epigallocatechin-3-gallate (EGCG), the Active Polyphenol Component from Green Tea

  摘要：

  [GRAPHICS]Enantioselective synthesis of epigallocatechin-3-gallate (EGCG, 3b), the active polyphenol component from green tea, has been achieved by using a stereospecific cyclization of the Sharpless asymmetric dihydroxylation product 7c as the key step.

  DOI：

  10.1021/ol000394z
• 作为产物：
  描述：

  3,4,5-三(苄氧基)苯甲醇 在 咪唑 、 AD-mix-α 、 重铬酸吡啶 、 甲基磺酰胺 、 硫酸 、 四丁基氟化铵 、 水 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 原甲酸三乙酯 作用下， 以 四氢呋喃 、 二硫化碳 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 15.0h， 生成 (-)-(2R,3S)-trans-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-ol
  参考文献：
  名称：

  Enantioselective Synthesis of Epigallocatechin-3-gallate (EGCG), the Active Polyphenol Component from Green Tea

  摘要：

  [GRAPHICS]Enantioselective synthesis of epigallocatechin-3-gallate (EGCG, 3b), the active polyphenol component from green tea, has been achieved by using a stereospecific cyclization of the Sharpless asymmetric dihydroxylation product 7c as the key step.

  DOI：

  10.1021/ol000394z

文献信息

• Enantioselective Synthesis of Flavan-3-ols Using a Mitsunobu Cyclization
  作者：Karsten Krohn、Ishtiaq Ahmed、Markus John

  DOI：10.1055/s-0028-1083361

  日期：——

  The synthesis of four flavan-3-ols with different substitution patterns and electron densities has been achieved in high stereo- and regioselectivity by a one-step Mitsunobu reaction from the corresponding diols, which were prepared by enantioselective Sharpless dihydroxylation of suitable olefins. The six-membered flavan-3-ols were the only cyclization products and the theoretically possible formation of five-membered rings during the Mitsunobu cyclization was not observed. The flavanols are important starting materials for the synthesis of dimers such as the procyanidins or other coupling products such as the flavan part of the potent DNA polymerase β inhibitor myristinin A. The enantioselectivities of both the Sharpless dihydroxylation and the Mitsunobu cyclization steps were monitored by chiral HPLC.

  通过从相应的二醇进行一步Mitsunobu反应，以高立体选择性和区位选择性成功合成了四种具有不同取代模式和电子密度的黄酮-3-醇，这些二醇是通过对合适的烯烃进行手性选择性的Sharpless二羟基化制备的。在Mitsunobu环化过程中，六元环的黄酮-3-醇是唯一的环化产物，理论上可能形成的五元环并未被观察到。这些黄酮醇是合成二聚体（如原花青素）或其他偶联产物（如强效DNA聚合酶β抑制剂myristinin A中的黄酮部分）的重要起始材料。Sharpless二羟基化和Mitsunobu环化步骤的对映选择性通过手性高效液相色谱法进行了监测。
• Stereoselective Synthesis of Benzylated Prodelphinidins and Their Diastereomers with Use of the Mitsunobu Reaction in the Preparation of Their Gallocatechin Precursors
  作者：Karsten Krohn、Ishtiaq Ahmed、Markus John、Matthias C. Letzel、Dietmar Kuck

  DOI：10.1002/ejoc.201000053

  日期：2010.5

  coupled with the commercially unavailable pentabenzylated (-)-gallocatechin 10, prepared in a one-step Mitsunobu-type cyclization of the triol 8 The highly stereoselective synthesis of benzylated prodelphinidins - catechin-(4 alpha -> 8)-gallocatechin (13), gallocatechin-(4 alpha -> 8)-gallocatechin (14), and gallocatechin-(4 alpha -> 8)-catechin (15) - is reported for the first time. The ESI(+)-CID mass

  四苄基化儿茶素 9 是通过将市售的纯 (+)-儿茶素 (3) 苄基化并与市售的五苄基化 (-)-没食子儿茶素 10 偶联制备的，通过三醇 8 的一步 Mitsunobu 型环化制备。苄基化前飞燕草素的高度立体选择性合成 - 儿茶素-(4 α -> 8)-没食子儿茶素 (13)、没食子儿茶素-(4 α -> 8)-没食子儿茶素 (14) 和没食子儿茶素-(4 α -> 8)-儿茶素 ( 15) - 首次报道。发现偶联产物的 ESI(+)-CID 质谱具有区域选择性逆狄尔斯-阿尔德 (RDA) 反应和来自 Na+ 加合离子的 C7H7 自由基对 (182 u) 的异常连续损失
• (-)-Epigallocatechin gallate derivatives for inhibiting proteasome
  申请人：Chan Tak-Hang

  公开号：US20060041010A1

  公开（公告）日：2006-02-23

  (−)-EGCG, the most abundant catechin, was found to be chemopreventive and anticancer agent. However, (−)-EGCG has at least one limitation: it gives poor bioavailability. This invention provides compounds of generally formula 10, wherein R 1 is selected from the group of —H and C 1 to C 6 acyl group; R 2 , R 3 , and R 4 are each independently selected from the group of —H, —OH, and C 1 to C 6 acyloxyl group; and at least one of R 2 , R 3 , or R 4 is —H. The derivatives of (−)-EGCG that is at least as potent as (−)-EGCG. The carboxylate protected forms of (−)-EGCG and its derivatives are found to be more stable than the unprotected forms, which can be used as proteasome inhibitors to reduce tumor cell growth.

  (-)-EGCG，即（-）-表没食子酸咖啡因，是一种常见的儿茶素，被发现具有化学预防和抗癌作用。然而，(-)-EGCG 至少存在一个限制：其生物利用度低。本发明提供了一般式10的化合物，其中R1从—H和C1到C6酰基组中选择；R2、R3和R4分别独立地从—H、—OH和C1到C6酰氧基组中选择；并且R2、R3或R4中至少有一个是—H。这些（-）-EGCG的衍生物至少与(-)-EGCG一样有效。发现（-）-EGCG及其衍生物的羧酸酯保护形式比未保护形式更稳定，可用作蛋白酶体抑制剂，以减少肿瘤细胞生长。
• Polyphenol proteasome inhibitors, synthesis, and methods of use
  申请人：——

  公开号：US20040186167A1

  公开（公告）日：2004-09-23

  The present invention relates to synthetic green tea derived polyphenolic compounds, their modes of syntheses, and their use in inhibiting proteasomal activity and in treating cancers. The present invention is also directed to pharmaceutical compositions useful in methods of inhibiting proteasomes and of treating cancers.

  本发明涉及合成的绿茶多酚化合物，它们的合成方式以及它们在抑制蛋白酶体活性和治疗癌症方面的应用。本发明还涉及用于抑制蛋白酶体和治疗癌症的药物组合物。
• Inhibitory Activity of Synthesized Acetylated Procyanidin B1 Analogs against HeLa S3 Cells Proliferation
  作者：Syuhei Okamoto、Sayaka Ishihara、Taisuke Okamoto、Syoma Doi、Kota Harui、Yusuke Higashino、Takashi Kawasaki、Noriyuki Nakajima、Akiko Saito

  DOI：10.3390/molecules19021775

  日期：——

  Proanthocyanidins, also known as condensed tannins and/or oligomeric flavonoids, occur in many edible plants and have various interesting biological activities. Previously, we reported a synthetic method for the preparation of various procyanidins in pure form and described their biological activities. Here, we describe the synthesis of procyanidin B1 acetylated analogs and discuss their inhibition activities against HeLa S3 cell proliferation. Surprisingly, the lower-unit acetylated procyanidin B1 strongly inhibited the proliferation of HeLa S3 cells. This molecule showed much stronger inhibitory activity than did epigallocatechin-3-O-gallate (EGCG), green tea polyphenol, and dimeric compounds that included EGCG as a unit. This result suggests that the phenolic hydroxyl groups of the upper-units in flavan-3-ols are important for their inhibitory activity against cancer cell proliferation and that a hydrophobic lower unit dimer enhances this activity.

  原花青素又称缩合单宁和/或低聚黄酮，存在于许多可食用植物中，具有各种有趣的生物活性。此前，我们报道了一种制备各种原花青素纯品的合成方法，并描述了它们的生物活性。在此，我们介绍了原花青素 B1 乙酰化类似物的合成方法，并讨论了它们对 HeLa S3 细胞增殖的抑制活性。令人惊讶的是，低单位乙酰化原花青素 B1 能强烈抑制 HeLa S3 细胞的增殖。与表没食子儿茶素-3-O-没食子酸酯（EGCG）、绿茶多酚以及以 EGCG 为单位的二聚化合物相比，该分子表现出更强的抑制活性。这一结果表明，黄烷-3-醇中上单位的酚羟基对其抑制癌细胞增殖的活性非常重要，而疏水性的下单位二聚体能增强这种活性。