3beta-[(6-脱氧-beta-D-古洛吡喃糖基)氧基]-5,12beta,14-三羟基-19-氧代-5beta-心甾-20(22)-烯内酯 | 23605-05-2

• 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
• 中文名称: 3beta-[(6-脱氧-beta-D-古洛吡喃糖基)氧基]-5,12beta,14-三羟基-19-氧代-5beta-心甾-20(22)-烯内酯
• 英文名称: α-antiarin
• 英文别名: 3β-(6-deoxy-β-D-gulopyranosyloxy)-5,12β,14-trihydroxy-19-oxo-5β,14β-card-20(22)-enolide；3β-(6-Desoxy-β-D-gulopyranosyloxy)-5,12β,14-trihydroxy-19-oxo-5β,14β-card-20(22)-enolid；alpha-Antiarin；(3S,5S,8R,9S,10S,12R,13S,14S,17R)-5,12,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• CAS: 23605-05-2
• 化学式: C₂₉H₄₂O₁₁
• 分子量: 566.646
• InChiKey: MFIXZHBJWSBQJA-OZQKXHGLSA-N

物化性质

• 熔点：
  239°C
• 比旋光度：
  D17 -3.9° (c = 0.905 in methanol)
• 沸点：
  551.36°C (rough estimate)
• 密度：
  1.1849 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  40
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  183
• 氢给体数：
  6
• 氢受体数：
  11

制备方法与用途

类别：有毒物品

• 毒性分级：剧毒
• 急性毒性：
  • 静脉给猫 LD50: 0.09 毫克/公斤
  • 静脉给兔子 LDL0: 1 毫克/公斤

可燃性危险特性：

• 可燃；燃烧时产生刺激烟雾

储运特性：

• 库房需通风、低温干燥
• 与食品原料分开存放

灭火剂：

• 干粉、泡沫、沙土、二氧化碳、雾状水

反应信息

• 作为反应物：
  描述：

  3beta-[(6-脱氧-beta-D-古洛吡喃糖基)氧基]-5,12beta,14-三羟基-19-氧代-5beta-心甾-20(22)-烯内酯 在 盐酸 作用下， 生成 3β,12β-dihydroxy-19-oxo-carda-5,14,20(22)-trienolide
  参考文献：
  名称：

  Tschesche; Haupt, Chemische Berichte, 1936, vol. 69, p. 1377

  摘要：

  DOI：

文献信息

• Design and synthesis of biotinylated cardiac glycosides for probing Nur77 protein inducting pathway
  作者：Dan-mei Tian、Jia Qiao、Yu-zhou Bao、Jie Liu、Xiao-kun Zhang、Xue-long Sun、You-wei Zhang、Xin-sheng Yao、Jin-shan Tang

  DOI：10.1016/j.bmcl.2019.01.015

  日期：2019.3

  mitochondria, leading to apoptosis of cancer cells. In order to probe the Nur77 protein inducting pathway, we designed and synthesized a series of novel biotinylated cardiac glycosides from β-Antiarin and α-Antiarin, two typical cardiac glycosides from the plant of Antiaris toxicaria. The induction of Nur77 protein expression of these biotinylated cardiac glycosides and their inhibitory effects on NIH-H460

  孤儿核受体Nur77（也称为TR3或神经生长因子诱导的克隆B NGFI-B）在调节靶基因表达中起核转录因子的作用，并且在分化，增殖，凋亡，和许多不同细胞类型的存活率 最近的研究表明，Nur77还涉及许多重要的生理和病理过程，包括癌症，炎症和免疫力，心血管疾病和骨骼疾病。我们以前的研究表明强心苷可以诱导Nur77蛋白的表达及其从细胞核到细胞质的转运，然后靶向线粒体，从而导致癌细胞凋亡。为了探测Nur77蛋白的诱导途径，我们设计并合成了一系列新型的生物素化的强心苷，它们分别来自β-安提香和α-安提香，这是两种来自安提阿里斯毒株的典型强心苷。评价了这些生物素化强心苷Nur77蛋白表达的诱导及其对NIH-H460癌细胞增殖的抑制作用。结果表明，一些生物素化的强心苷可以显着诱导Nur77蛋白的表达，与它们的母体化合物β-Antiarin和α-Antiarin相当。而且，评估了它们的抗生蛋白链菌素结合
• Ueber den Milchsaft von Antiaris toxicaria
  作者：H. Kiliani

  DOI：10.1002/ardp.18962340603

  日期：——
• Compounds exhibiting efflux inhibitor activity and composition and uses thereof
  申请人：Wempe Fitzpatrick Michael

  公开号：US20070254859A1

  公开（公告）日：2007-11-01

  At least one compound chosen from compounds of Formula I: a pharmaceutically acceptable salt or ester thereof, a solvate thereof, a chelate thereof, a non-covalent complex thereof, a prodrug thereof, and mixtures of any of the foregoing, wherein: n is a number from 1 to 900, wherein the individual units may be the same or different; W is chosen from alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl; each of R 2 , R 3 , R 4 and R 5 is independently chosen from —H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl; Z′ is chosen from —O—, —N—, —NO—, —NR 4 —, —S—, —SO— and —SO 2 —, wherein R 4 is defined as above; each of X, X′, Y and Z is independently chosen from —CR 4 R 5 —, —NH—, —NR 4 —, —NO—, —O—, —NOR 4 —, —S—, —SO—, —SO 2 —, wherein R 4 and R 5 are defined as above; R 1 is chosen from a tocopherol, a steroid and a flavonoid; and R 6 is chosen from any R 1 , alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl.
• [EN] COMPOUNDS EXHIBITING EFFLUX INHIBITOR ACTIVITY AND COMPOSITIONS AND USES THEREOF<br/>[FR] COMPOSES PRESENTANT UNE ACTIVITE INHIBITRICE DE L'ECOULEMENT, COMPOSITIONS ET UTILISATIONS DE CEUX-CI
  申请人：EASTMAN CHEM CO

  公开号：WO2007115181A9

  公开（公告）日：2008-04-03

  [EN] At least one compound chosen from compounds of Formula 1: a pharmaceutically acceptable salt or ester thereof, a solvate thereof, a chelate thereof, a non-covalent complex thereof, a prodrug thereof, and mixtures of any of the foregoing, wherein: n is a number from 1 to 900, wherein the individual units may be the same or different; W is chosen from alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl; each Of R₂, R₃, R₄ and R₅ is independently chosen from -H, alkyl, substituted aikyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl; Z' is chosen from -O-, -N-, -NO-, - NR₄-, -S-, -SO- and -SO₂-, wherein R₄ is defined as above; each of X, X', Y and Z is independently chosen from -CR₄R₅-, -NH-, -NR₄-, -NO-. -O-, -NOR₄-, -S-, -SO-, -SO₂-, wherein R₄ and R₅ are defined as above; R₁ is chosen from a tocopherol, a steroid and a flavonoid; and R₆, is chosen from any R₁, alkyl. substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl.
  [FR] La présente invention concerne au moins un composé choisi parmi les composés de formule 1 : un sel ou un ester pharmaceutiquement acceptable de celui-ci, un solvate de celui-ci, un chélate de celui-ci, un complexe non covalent de celui-ci, un promédicament de celui-ci et des mélanges de ces derniers, n étant un nombre de 1 à 900, les unités individuelles pouvant être identiques ou différentes, W étant choisi parmi l'alkyle, l'alkyle substitué, le cycloalkyle, le cycloalkyle substitué, l'aryle, l'aryle substitué, l'aralkyle et l'aralkyle substitué, R₂, R₃, R₄ et R₅ étant chacun indépendamment choisi parmi -H, alkyle, alkyle substitué, cycloalkyle, cycloalkyle substitué, aryle, aryle substitué, aralkyle et aralkyle substitué, Z' étant choisi parmi -O-, -N-, -NO-, - NR₄-, -S-, -SO- et -SO₂-, R₄ étant tel que défini ci-dessus, X, X', Y et Z étant chacun indépendamment choisi parmi -CR₄R₅-, -NH-, -NR₄-, -NO-, -O-, -NOR₄-, -S-, -SO-, -SO₂-, R₄ et R₅ étant tels que définis ci-dessus, R₁ étant choisi parmi un tocophérol, un stéroïde et un anthoxanthine, et R₆ étant choisi parmi R₁, alkyle, alkyle substitué, cycloalkyle, cycloalkyle substitué, aryle, aryle substitué, aralkyle et aralkyle substitué.