(1S,2S,4aR,4bS,6aS,9R,10S,10aS,12aR)-1-(2-Cyano-ethyl)-2-isopropenyl-1,4a,4b,9,10-pentamethyl-1,3,4,4a,4b,5,6,7,8,9,10,10a,12,12a-tetradecahydro-2H-chrysene-6a-carboxylic acid | 192864-85-0

• 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: (1S,2S,4aR,4bS,6aS,9R,10S,10aS,12aR)-1-(2-Cyano-ethyl)-2-isopropenyl-1,4a,4b,9,10-pentamethyl-1,3,4,4a,4b,5,6,7,8,9,10,10a,12,12a-tetradecahydro-2H-chrysene-6a-carboxylic acid
• 英文别名: 2-Cyano-2,3-seco-4-yliden-olean-12-enoic acid；(1S,2S,4aR,4bS,6aS,9R,10S,10aS,12aR)-1-(2-cyanoethyl)-1,4a,4b,9,10-pentamethyl-2-prop-1-en-2-yl-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysene-6a-carboxylic acid
• CAS: 192864-85-0
• 化学式: C₃₀H₄₅NO₂
• 分子量: 451.693
• InChiKey: SXPZSMMJUUHTBE-MTCIRRIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S,4aR,4bS,6aS,9R,10S,10aS,12aR)-1-(2-Cyano-ethyl)-2-isopropenyl-1,4a,4b,9,10-pentamethyl-1,3,4,4a,4b,5,6,7,8,9,10,10a,12,12a-tetradecahydro-2H-chrysene-6a-carboxylic acid 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 以68%的产率得到5β-(1-methyl-2-ethyl)-10α-(3-aminopropyl)-des-A-urs-12-en-28-oic acid
  参考文献：
  名称：

  Novel A-ring cleaved analogs of oleanolic and ursolic acids which affect growth regulation in NRP.152 prostate cells

  摘要：

  Syntheses of eight novel A-ring cleaved oleanane and ursane analogs an described. These compounds were assessed for their ability to inhibit cell proliferation in NRP.152 prostate cells. Four A-ring cleaved derivatives showed significant activity; 5 beta-(1-methyl-2-ethyl)-10 alpha-(3-aminopropyl)-des-A-urs-12-en-28-oic acid was the most active compound, (IC50, 0.3 mu M). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00310-7
• 作为产物：
  描述：

  熊果酸 在 sodium azide 、 jones reagent 、 硫酸 作用下， 以 溶剂黄146 为溶剂， 生成 (1S,2S,4aR,4bS,6aS,9R,10S,10aS,12aR)-1-(2-Cyano-ethyl)-2-isopropenyl-1,4a,4b,9,10-pentamethyl-1,3,4,4a,4b,5,6,7,8,9,10,10a,12,12a-tetradecahydro-2H-chrysene-6a-carboxylic acid
  参考文献：
  名称：

  Novel A-ring cleaved analogs of oleanolic and ursolic acids which affect growth regulation in NRP.152 prostate cells

  摘要：

  Syntheses of eight novel A-ring cleaved oleanane and ursane analogs an described. These compounds were assessed for their ability to inhibit cell proliferation in NRP.152 prostate cells. Four A-ring cleaved derivatives showed significant activity; 5 beta-(1-methyl-2-ethyl)-10 alpha-(3-aminopropyl)-des-A-urs-12-en-28-oic acid was the most active compound, (IC50, 0.3 mu M). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00310-7

文献信息

• Synthesis and cholinesterase inhibiting potential of A-ring azepano- and 3-amino-3,4-seco-triterpenoids
  作者：Oxana Kazakova、Irina Smirnova、Tatyana Lopatina、Gul'nara Giniyatullina、Anastasiya Petrova、Elmira Khusnutdinova、René Csuk、Immo Serbian、Anne Loesche

  DOI：10.1016/j.bioorg.2020.104001

  日期：2020.8

  In this study, a series of A-ring azepano- and 3-amino-3,4-seco-derivatives were synthesized from betulin, oleanolic, ursolic and glycyrrhetinic acids aiming to develop new cholinesterase inhibitors. Azepanobetulin, azepanoerythrodiol and azepanouvaol were modified to give amide and tosyl derivatives, while azepano-anhydrobetulines and azepano-glycyrrhetols were obtained for the first time. Oleanane

  在这项研究中，从甜菜碱，齐墩果酸，熊果酸和甘草次酸中合成了一系列A环Aze环和3-氨基-3,4-seco衍生物，目的是开发新的胆碱酯酶抑制剂。修饰了叠氮青霉素，氮杂四氢呋喃二醇和氮杂泛醇，以产生酰胺和甲苯磺酰基衍生物，而首次获得了氮杂-脱水甜菜碱和氮杂-甘草醇。通过还原可从贝克曼2型重排获得的相应2-氰基衍生物，合成了齐墩果烷和乌苏烷3-氨基-3,4-seco-4（23）-三萜烯醇。在比色Ellman分析中筛选了这些化合物，以确定它们充当酶乙酰胆碱酯酶（AChE，来自鳗鱼）和丁酰胆碱酯酶（BChE，来自马血清）的抑制剂的能力。尽管这些化合物中的大多数仅是AChE的中度抑制剂，但其中一些化合物被证明是作为混合型抑制剂的BChE抑制剂。阿奇巴贝汀如图1所示，其C28-酰胺衍生物7和8，氮杂环庚烷-11-脱氧-甘草油醇12和氮杂环庚烷醇18保持抑制常数K i在0.21±0.06至0.68± 0.
• Evaluation of ursolic acid isolated from Ilex paraguariensis and derivatives on aromatase inhibition
  作者：Simone C.B. Gnoatto、Alexandra Dassonville-Klimpt、Sophie Da Nascimento、Philippe Galéra、Karim Boumediene、Grace Gosmann、Pascal Sonnet、Safa Moslemi

  DOI：10.1016/j.ejmech.2007.11.021

  日期：2008.9

  The inhibitory potency of ursolic acid extracted from Ilex paraguariensis, a plant used in South American population for a tea preparation known as mate, and its derivatives to inhibit aromatase activity was assessed and compared to a phytoestrogen apigenin and a steroidal aromatase inhibitor 4-hyroxyandrostenedione (4-OHA). Among all compounds tested only ursolic acid 1 showed an efficient and dose-dependent

  评估了从南美番石榴（Ilex paraguariensis）提取的熊果酸的抑菌能力，该植物在南美人中被称为茶伴侣，用于茶制品；其衍生物具有抑制芳香化酶活性的作用，并与植物雌激素芹菜素和甾体芳香化酶抑制剂4-hyyryandrostenedione（ 4-OHA）。在所有测试的化合物中，只有乌索酸1像芹菜素（IC50 = 10 microM）一样显示出有效且剂量依赖性的芳香酶抑制作用，IC50值为32 microM，而4-OHA的IC50值为0.8 microM。我们的结果表明，将金属茂部分并入熊果酸衍生物中会降低对芳香化酶的抑制作用。而且，
• The Beckmann Rearrangement Applied to Ursolic Acid with Antimalarial Activity in Medicinal Chemistry Studies
  作者：Luciana Dalla-Vechia、Alexandra Dassonville-Klimpt、Philippe Grellier、Pascal Sonnet、Grace Gosmann、Simone C.B. Gnoatto

  DOI：10.2174/157017812800221708

  日期：2012.2.1

  The A ring-expanded derivative of ursolic acid and the corresponding fragmentation product were obtained through the Beckmann rearrangement under optimized reaction conditions. A mechanistic approach was taken in order to explain both the specificity of the rearrangement and the fragmentation of the cycle. The intermediates and the final products of the route were evaluated for antimalarial activity.

  在优化的反应条件下，通过贝克曼重排获得了熊果酸的 A 环扩展衍生物和相应的破碎产物。为了解释重排和循环破碎的特异性，我们采用了一种机理方法。对该路线的中间产物和最终产物进行了抗疟活性评估。
• Acetylcholinesterase Inhibitory Activity of Modified Lupane, Oleanane, and Ursane A‐ <i>seco</i> ‐Triterpenoids
  作者：Anastasiya V. Petrova、Oxana B. Kazakova、Ivan S. Nazarov、René Csuk、Niels V. Heise

  DOI：10.1002/cbdv.202300185

  日期：——

  A series of new lupane, ursane, and oleanane type triterpenic A-seco-derivatives containing bromo-, azido-, alkyne-, 1H-tetrazol-5-yl-, 5-methyloxazol-2-yl-, N-(4-(4-methylpiperazin-1-yl)but-2-yn-1-yl), and a carbonyl group at C2, C24, C28, C30 positions has been synthesized. The bioactivity was evaluated by Ellman's method, and the results showed that most of the compounds displayed moderate acetylcholinesterase

  一系列新的羽扇烷、熊烷和齐墩果烷型三萜类A- seco-衍生物，含溴-、叠氮基-、炔-、1H-四唑-5-基-、5-甲基恶唑-2-基-、N- (4 -(4-甲基哌嗪-1-基)丁-2-炔-1-基)和C2、C24、C28、C30位的羰基已合成。采用Ellman法评价生物活性，结果表明大部分化合物在体外表现出中度的乙酰胆碱酯酶抑制活性。其中，具有溴基和叠氮基的 28-氧代别白桦林和桦木酸的 A- seco衍生物对 AChE 表现出最强的抑制活性。额外的实验表明甲基 2-cyano-3,4- seco -dibromo- 和 2-cyano-3,4-桦木酸的二叠氮基衍生物作为混合型抑制剂，Ki 值分别低至 K i =0.18 μM 和 K i =0.21 μM。