3,23-O-isopropylidene hederagenin | 60684-64-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,23-O-isopropylidene hederagenin
• 英文别名: 3β,23-O-isopropylidene-3β,23-dihydroxyolean-12-en-28-oic acid；(1R,2R,5S,10R,11R,14R,15S,18S,23S)-2,7,7,10,14,15,21,21-octamethyl-6,8-dioxahexacyclo[12.12.0.02,11.05,10.015,24.018,23]hexacos-24-ene-18-carboxylic acid
• CAS: 60684-64-2
• 化学式: C₃₃H₅₂O₄
• 分子量: 512.773
• InChiKey: GZTXRAOZNVKIDQ-ZOGWWOATSA-N

物化性质

• 沸点：
  579.9±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  37
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,23-O-isopropylidene hederagenin 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium hydride 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-5-O-acetyl-3,4-di-O-benzyl-L-arabinose(open)-[(1R)->3,23]-28-benzyl hederagenate
  参考文献：
  名称：

  Synthesis of Anemoclemoside B, the First Natural Product with an Open-Chain Cyclic Acetal Glycosidic Linkage

  摘要：

  [GRAPHICS]Anemoclemoside B (1), the first natural product containing a brand-new glycosidic linkage, the open-chain cyclic acetal linkage, was synthesized.

  DOI：

  10.1021/ol050324y
• 作为产物：
  描述：

  常春藤皂苷元 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以100%的产率得到3,23-O-isopropylidene hederagenin
  参考文献：
  名称：

  Synthesis of Anemoclemoside B, the First Natural Product with an Open-Chain Cyclic Acetal Glycosidic Linkage

  摘要：

  [GRAPHICS]Anemoclemoside B (1), the first natural product containing a brand-new glycosidic linkage, the open-chain cyclic acetal linkage, was synthesized.

  DOI：

  10.1021/ol050324y

文献信息

• Concise synthesis of a new triterpenoid saponin from the roots of Gypsophila oldhamiana and its derivatives as α-glucosidase inhibitors
  作者：Qingchao Liu、Tiantian Guo、Fahui Li、Dong Li

  DOI：10.1039/c6nj01602b

  日期：——

  The first synthesis of the triterpenoid saponin 1 and its derivatives 2–3 was efficiently achieved in an efficient and practical strategy with an odourless 2-methyl-5-tert-butylphenyl (Mbp) thioglycoside and a N-phenyltrifluoroacetimidate donor as a key step, and their inhibitory activities against α-glucosidase and α-amylase were evaluated in vitro. The preliminary structure–activity relationship

  以无味的2-甲基-5-叔丁基苯基（Mbp）硫代糖苷和N-苯基三氟乙酰亚氨酸酯供体为关键步骤，有效而有效地实现了三萜皂苷1及其衍生物2-3的首次合成，和它们对α葡糖苷酶和α淀粉酶抑制活性进行评价体外。初步的结构-活性关系研究表明，C4-CHO和C4-CH 2 OH对α-葡萄糖苷酶抑制活性不是必需的。在这三种化合物中，化合物3表现出对α-葡萄糖苷酶的显着抑制活性，IC 50为值为9.17μM。根据Dixon图上的截距确定为9.35μM的K i，抗α-葡萄糖苷酶的更强皂苷3可能是非竞争性抑制模式。同时，计算化合物1-3的亲脂性，作为药理效力的预测。根据预测的log  P值，亲脂性可能与评估的生物学潜能相关。
• Modified Hederagenin Derivatives Demonstrate Ex Vivo Anthelmintic Activity against Fasciola hepatica
  作者：Anand Chakroborty、Deiniol R. Pritchard、Marc E. Bouillon、Anna Cervi、Rolf Kraehenbuehl、Charlotte Wild、Caroline Fenn、Peter Holdsworth、Colin Capner、Gilda Padalino、Josephine E. Forde-Thomas、Joseph Payne、Brendan G. Smith、Maggie Fisher、Martina Lahmann、Mark S. Baird、Karl F. Hoffmann

  DOI：10.3390/pharmaceutics15071869

  日期：——

  Infection with Fasciola hepatica (liver fluke) causes fasciolosis (or fascioliasis) and poses a considerable economic as well as welfare burden to both the agricultural and animal health sectors. Here, we explore the ex vivo anthelmintic potential of synthetic derivatives of hederagenin, isolated in bulk from Hedera helix. Thirty-six compounds were initially screened against F. hepatica newly excysted juveniles (NEJs) of the Italian strain. Eleven of these compounds were active against NEJs and were selected for further study, using adult F. hepatica derived from a local abattoir (provenance unknown). From these eleven compounds, six demonstrated activity and were further assessed against immature liver flukes of the Italian strain. Subsequently, the most active compounds (n = 5) were further evaluated in ex vivo dose response experiments against adult Italian strain liver flukes. Overall, MC042 was identified as the most active molecule and the EC50 obtained from immature and adult liver fluke assays (at 24 h post co-culture) are estimated as 1.07 μM and 13.02 μM, respectively. When compared to the in vitro cytotoxicity of MDBK bovine cell line, MC042 demonstrated the highest anthelmintic selectivity (44.37 for immature and 3.64 for adult flukes). These data indicate that modified hederagenins display properties suitable for further investigations as candidate flukicides.

  肝吸虫（Fasciola hepatica）感染会引起肝吸虫病（或称肝吸虫病），给农业和动物卫生部门带来巨大的经济和福利负担。在此，我们探讨了从黑齿楠中分离出的大量黑齿楠素合成衍生物的体内外驱虫潜力。我们初步筛选了 36 种化合物，以对抗意大利菌株的肝吸虫新脱囊幼虫（NEJs）。其中 11 种化合物对 NEJs 具有活性，并被选作进一步研究的对象，使用的是来自当地屠宰场（来源不明）的成虫肝吸虫。在这 11 种化合物中，有 6 种显示出活性，并针对意大利菌株的未成熟肝吸虫进行了进一步评估。随后，在针对成年意大利株肝吸虫的体内外剂量反应实验中进一步评估了活性最强的化合物（n = 5）。总体而言，MC042 被确定为最有活性的分子，从未成熟和成年肝吸虫实验（共培养后 24 小时）中获得的 EC50 分别为 1.07 μM 和 13.02 μM。与 MDBK 牛细胞系的体外细胞毒性相比，MC042 的抗蠕虫选择性最高（对未成熟吸虫的选择性为 44.37，对成虫的选择性为 3.64）。这些数据表明，改性赤霉烯酮具有适合作为候选杀卵剂进行进一步研究的特性。
• Synthesis of Anemoclemoside B, the First Natural Product with an Open-Chain Cyclic Acetal Glycosidic Linkage
  作者：Jiansong Sun、Xiuwen Han、Biao Yu

  DOI：10.1021/ol050324y

  日期：2005.5.1

  [GRAPHICS]Anemoclemoside B (1), the first natural product containing a brand-new glycosidic linkage, the open-chain cyclic acetal linkage, was synthesized.