3-[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-3-[[(2S,3R,6R)-3-hydroxy-2-methyl-3,6-dihydro-2H-pyran-6-yl]oxy]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one | 33156-32-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3-[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-3-[[(2S,3R,6R)-3-hydroxy-2-methyl-3,6-dihydro-2H-pyran-6-yl]oxy]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• CAS: 33156-32-0
• 化学式: C₂₉H₄₂O₆
• 分子量: 486.649
• InChiKey: CHRXFDFTUNRGAB-XZUAUHNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-3-[[(2S,3R,6R)-3-hydroxy-2-methyl-3,6-dihydro-2H-pyran-6-yl]oxy]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one 在 N-甲基吗啉 、 2-硝基苯磺酰肼 、 三乙胺 作用下， 反应 24.0h， 以90%的产率得到兰诺地近
  参考文献：
  名称：

  α-d-/α-l-鼠李糖基和氨乙酰洋地黄毒苷低聚物作为抗肿瘤剂的合成和评价

  摘要：

  通过钯催化的糖基化，然后是双-/三-二羟基化或双-/三-二亚胺还原，已经建立了鼠李糖基-和氨乙酰-洋地黄毒苷类似物的高度区域和立体选择性不对称合成。α- l-鼠李糖和 α- l-鼠李糖单糖类似物对非小细胞人肺癌细胞 (NCI-H460) 显示出更强的凋亡诱导活性和细胞毒性，比其d-非对映异构体以糖链长度依赖性方式。

  DOI：

  10.1021/ml100290d
• 作为产物：
  描述：

  洋地黄毒苷 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 sodium tetrahydroborate 、 cerium(III) chloride 、 硫酸 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 3-[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-3-[[(2S,3R,6R)-3-hydroxy-2-methyl-3,6-dihydro-2H-pyran-6-yl]oxy]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
  参考文献：
  名称：

  [EN] GLYCOSYLATED CARDIOTONIC STEROIDS
  [FR] STÉROÏDES CARDIOTONIQUES GLYCOSYLÉS

  摘要：

  提供了一种心力衰竭类固醇A环的糖基化化合物，其中类固醇连接到（a）包含C-4氨基团的单糖的环氧位置，或（b）寡糖的环氧位置。

  公开号：

  WO2014194068A1

文献信息

• Stereochemical Survey of Digitoxin Monosaccharides
  作者：Hua-Yu Leo Wang、Wenjun Xin、Maoquan Zhou、Todd A. Stueckle、Yon Rojanasakul、George A. O'Doherty

  DOI：10.1021/ml100219d

  日期：2011.1.13

  A stereochemically diverse array of monosaccharide analogues of the trisaccharide-based cardiac glycoside natural product digitoxin has been synthesized using a de novo asymmetric approach. The analogues were tested for cytotoxicity against nonsmall cell human lung cancer cells (NCI-H460). The results were compared with digitoxin and its aglycone digitoxigenin. Three novel digitoxin monosaccharide analogues with beta-D-digitoxose, alpha-L-rhamnose, and alpha-L-amicetose sugar moieties showed excellent selectivity and activity. Further investigation revealed that digitoxin alpha-L-rhamnose and alpha-L-amicetose analogues displayed similar anti-proliferation effects but with at least 5-fold greater potency in apoptosis induction than digitoxin against NCI-H460. This study demonstrates the ability to improve the digitoxin anticancer activity by modification of the stereochemistry and substitution of the carbohydrate moiety of this known cardiac drug.
• C5′-Alkyl Substitution Effects on Digitoxigenin α-<scp>l</scp>-Glycoside Cancer Cytotoxicity
  作者：Hua-Yu Leo Wang、Bulan Wu、Qi Zhang、Sang-Woo Kang、Yon Rojanasakul、George A. O’Doherty

  DOI：10.1021/ml100291n

  日期：2011.4.14

  A highly regio- and stereoselective asymmetric synthesis of various CS'-alkyl side chains of rhamnosyl- and amicetosyl-digitoxigenin analogues has been established via palladium-catalyzed glycosylation with postglycosylated dihydroxylation or diimide reduction. The C5'-methyl group in both alpha-L-rhamnose and cc-L-amicetose digitoxin analogues displayed a steric directed apoptosis induction and tumor growth inhibition against nonsmall cell human lung cancer cells (NCI-H460). The antitumor activity is significantly reduced when the steric hindrance is increased at the C5'-stereocenter.
• Synthesis and Evaluation of the α-<scp>d</scp>-/α-<scp>l</scp>-Rhamnosyl and Amicetosyl Digitoxigenin Oligomers as Antitumor Agents
  作者：Hua-Yu Leo Wang、Yon Rojanasakul、George A. O’Doherty

  DOI：10.1021/ml100290d

  日期：2011.4.14

  A highly regio- and stereoselective asymmetric synthesis of rhamnosyl- and amicetosyl-digitoxigenin analogues has been established via palladium-catalyzed glycosylation followed by bis-/tris-dihydroxylation or bis-/tris-diimide reduction. The α-l-rhamnose and α-l-amicetose digitoxin monosaccharide analogues displayed stronger apoptosis inducing activity and cytotoxicity against nonsmall cell human

  通过钯催化的糖基化，然后是双-/三-二羟基化或双-/三-二亚胺还原，已经建立了鼠李糖基-和氨乙酰-洋地黄毒苷类似物的高度区域和立体选择性不对称合成。α- l-鼠李糖和 α- l-鼠李糖单糖类似物对非小细胞人肺癌细胞 (NCI-H460) 显示出更强的凋亡诱导活性和细胞毒性，比其d-非对映异构体以糖链长度依赖性方式。
• [EN] GLYCOSYLATED CARDIOTONIC STEROIDS<br/>[FR] STÉROÏDES CARDIOTONIQUES GLYCOSYLÉS
  申请人：UNIV NORTHEASTERN

  公开号：WO2014194068A1

  公开（公告）日：2014-12-04

  Compounds which are glycosylates of an A-ring of a cardiotonic steroid, wherein the steroid is attached to the anomeric position of (a) a monosaccharide comprising a C-4 amino group, or (b) an oligosaccharide are provided.

  提供了一种心力衰竭类固醇A环的糖基化化合物，其中类固醇连接到（a）包含C-4氨基团的单糖的环氧位置，或（b）寡糖的环氧位置。