methyl 3β-hydroxyl-18β-olean-9(11),12-dien-30-oate | 62422-54-2

• 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: methyl 3β-hydroxyl-18β-olean-9(11),12-dien-30-oate
• 英文别名: 3β-hydroxy-18βH-oleanan-9(11),12(13)-dien-30-oic acid methyl ester；methyl (2S,4aS,6aR,6bS,8aR,10S,12aS,14bR)-10-hydroxy-2,4a,6a,6b, 9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14b-octadecahydropicene-2-carboxylate；3β-hydroxy-18βH-olean-9(10),11(12)-dien-30-oic acid methyl ester；(3β,18β,20β)-3-hydroxyoleana-9(11),12-dien-29-oic acidmethyl ester；3β-hydroxy-oleanadien-(9(11).12)-oic acid-(30)-methyl ester；3β-Hydroxy-oleanadien-(9(11).12)-saeure-(30)-methylester；methyl 3β-hydroxy-oleana-9(11),12-dien-30-oate；methyl (2S,4aS,6aR,6bS,8aR,10S,12aS,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,14b-dodecahydropicene-2-carboxylate
• CAS: 62422-54-2
• 化学式: C₃₁H₄₈O₃
• 分子量: 468.72
• InChiKey: DVXNGDZRHCYIIC-QSGSVZNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3β-hydroxyl-18β-olean-9(11),12-dien-30-oate 在 吡啶 、 碘 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 二甲基亚砜 为溶剂， 反应 29.0h， 生成 methyl 2-cyano-3-oxo-18β-olean-1,9(11),12-trien-30-oate
  参考文献：
  名称：

  Synthesis of methyl 2-cyano-3,12-dioxo-18β-olean-1,9(11)-dien-30-oate analogues to determine the active groups for inhibiting cell growth and inducing apoptosis in leukemia cells

  摘要：

  合成了14种具有不同C环结构的2-氰基-3,12-二氧-18β-油烯-1,9(11)-二烯-30-酸甲酯(CDODO-Me-12，10d)类似物，以确定抑制人白血病HL-60细胞增殖和诱导凋亡的活性基团。C环中需要一个不饱和基团来维持抑制细胞增殖和诱导凋亡的能力。C环中具有9(11),12-二烯的化合物10e显示出了与10d相当的诱导凋亡能力，这与其降低了c-FLIP而非Mcl-1和XIAP的水平有关。与化合物10d相比，化合物10e的耗竭谷胱甘肽能力降低。化合物10e是一种通过不同于化合物10d的作用机制发挥活性的新型活性化合物。

  DOI：

  10.1039/c4ob00703d
• 作为产物：
  描述：

  (3beta,20beta)-3-羟基-11-氧代-齐墩果-12-烯-29-酸甲酯 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以71%的产率得到methyl 3β-hydroxyl-18β-olean-9(11),12-dien-30-oate
  参考文献：
  名称：

  一个酮组重要吗？C-11位修饰的甘草次酸衍生物的构效关系

  摘要：

  几种三萜酸对肿瘤细胞显示出显着的细胞毒性。甘草次酸——甘草根的主要成分——对肿瘤细胞具有凋亡作用。先前的研究指出，甘草次酸衍生物中 C-11 位存在酮基是其凋亡活性的主要原因。合成了几对衍生物，仅在 C-11 位不同。这些化合物在 sulforhodamine B 比色法中进行了测试，用于对 12 种肿瘤细胞系和小鼠胚胎成纤维细胞 (NIH3T3) 进行细胞毒性筛选。我们的结果表明，C-11 酮基的存在与化合物的凋亡活性之间没有直接关系。

  DOI：

  10.1002/ardp.201000327

文献信息

• Oxidation of Licorice-Root Triterpene-Acid Derivatives by m-Chloroperbenzoic Acid
  作者：L. R. Mikhailova、A. S. Budaev、L. V. Spirikhin、L. A. Baltina

  DOI：10.1007/s10600-019-02619-5

  日期：2019.1

  12(13)-dien-30-oic, and 3β-O-acetoxy-18βH-olean-12-en-30-oic acids were oxidized by meta-chloroperbenzoic acid (m-CPBA) to produce methyl esters of 3β-O-acetoxy-12α,13α-epoxy-18β-oleanan-30-oic and 3β-O-acetoxy-18β-oleanan-12-on-30-oic acids in addition to 3β-hydroxy-12-oxo-18βH-olean-9(11)-en-30-oic and 3β-O-acetoxy-18β-oleanan-12-on-30-oic acids in 70–75% yields. The structures of the synthesized compounds

  3β-O-乙酰氧基-18βH-olean-12-en-30-oic、3β-羟基-9(11​​)、12(13)-dien-30-oic和3β-O-乙酰氧基-18βH-的甲酯olean-12-en-30-oic 酸被间氯过苯甲酸 (m-CPBA) 氧化生成 3β-O-acetoxy-12α,13α-epoxy-18β-oleanan-30-oic 和 3β-O 的甲酯-acetoxy-18β-oleanan-12-on-30-oic 酸以及 3β-hydroxy-12-oxo-18βH-olean-9(11​​)-en-30-oic 和 3β-O-acetoxy-18β-oleanan -12-on-30-油酸的产率为 70-75%。合成化合物的结构经PMR和13C NMR谱确证。
• Synthesis of new derivatives of 3β-hydroxy18βH-olean-9,12-dien-30-oic acid
  作者：L. R. Mikhailova、M. V. Khudobko、L. A. Baltina、L. V. Spirikhin、R. M. Kondratenko、L. A. Baltina

  DOI：10.1007/s10600-009-9336-8

  日期：2009.5

  Ring A was transformed and new A-homo-4-aza- and 3-cyano-3,4-seco-olean-4-ene derivatives of 3β-hydroxy18βH-olean-9,12-dien-30-oic acid were synthesized.

  环A被转化，合成了新的A-同源-4-氮和3-氰-3,4-秒-鞘烯-4-烯衍生物，具体为3β-羟基18βH-鞘烯-9,12-二烯-30-酸。
• Deconstruction of 18β-glycyrrhetinic acid into gram scale multifunctional chiral synthons
  作者：Ramesh Gorre、Chandra Shekhar、Nandikolla Krishna Chaitanya、Srivari Chandrasekhar

  DOI：10.1016/j.tetlet.2023.154715

  日期：2023.9

  The transformation of 18β-glycyrrhetinic acid into two significant chiral synthons has been successfully showcased employing gentle reaction conditions. The effectiveness of one of these chiral synthons has been exhibited by utilizing it as a key building block for the synthesis of tetracyclic meroterpenoid natural products (+)-hongoquercins A and B.

  18β-甘草次酸转化为两个重要的手性合成子已在温和的反应条件下成功展示。这些手性合成子之一的有效性已通过将其用作合成四环类萜天然产物 (+)-红槲皮素 A 和 B 的关键构件而得到展示。
• Synthesis of glycyrrhetinic acid derivatives for the treatment of metabolic diseases
  作者：Igor Beseda、Laszlo Czollner、Priti S. Shah、Rupesh Khunt、Rawindra Gaware、Paul Kosma、Christian Stanetty、Maria Carmen del Ruiz-Ruiz、Hassan Amer、Kurt Mereiter、Thierry Da Cunha、Alex Odermatt、Dirk Claßen-Houben、Ulrich Jordis

  DOI：10.1016/j.bmc.2009.10.036

  日期：2010.1

  The effect of glycyrrhetinic acid (GA) and GA-derivatives towards 11 beta-hydroxysteroid dehydrogenase (11 beta-HSD) was investigated. Novel compounds with modi. cations at positions C-3, C-11 and C-29 of the GA skeleton were prepared. Single crystal X-ray diffraction data of selected substances are reported and discussed. (C) 2009 Elsevier Ltd. All rights reserved.
• Conjugates of 18β-glycyrrhetinic acid derivatives with 3-(1H-benzo[d]imidazol-2-yl)propanoic acid as Pin1 inhibitors displaying anti-prostate cancer ability
  作者：Kun Li、Tianyi Ma、Jingjing Cai、Min Huang、Hongye Guo、Di Zhou、Shenglin Luan、Jinyu Yang、Dan Liu、Yongkui Jing、Linxiang Zhao

  DOI：10.1016/j.bmc.2017.08.002

  日期：2017.10

  Twenty-six conjugates of 18 beta-glycyrrhetinic acid derivatives with 3-(1H-benzo[d]imidazol-2-yl)propanoic acid were designed and synthesized as Pin1 inhibitors. Most of these semi-synthetic compounds showed improved Pin1 inhibitory activity and anti-proliferative effects against prostate cancer cells as compared to 3-(1H-benzo[d] imidazol-2-yl) propanoic acid and GA. Compounds 10a and 12i were the most potent to inhibit growth of prostate cancer PC-3 with GI(50) values of 7.80 mu M and 3.52 mu M, respectively. The enzyme inhibition ratio of nine compounds at 10 mu M was over 90%. Structure-activity relationships indicated that both appropriate structure at ring C of GA and suitable length of linker between GA skeleton and benzimidazole moiety had significant impact on improving activity. Western blot assay revealed that 10a decreased the level of cell cycle regulating protein cyclin D1. Thus, these compounds might represent a novel anti-proliferative agent working through Pin1 inhibition. (C) 2017 Published by Elsevier Ltd.