(3β,18α)-methyl 3-hydroxy-11-oxoolean-12-30-oate | 5092-01-3

• 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: (3β,18α)-methyl 3-hydroxy-11-oxoolean-12-30-oate
• 英文别名: 18α-glycyrrhetinic acid methyl ester；18α-glycyrrhetic acid methyl ester；methyl 18α-glycyrrhetinate；methyl glycyrrhetinate；3β-hydroxy-11-oxo-(18α)-olean-12-en-30-oic acid methyl ester；3β-hydroxy-11-oxo-18α-olean-12-en-30-oic acid methyl ester；18-Glycyrrhetic Acid Methyl Ester；methyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate
• CAS: 5092-01-3
• 化学式: C₃₁H₄₈O₄
• 分子量: 484.72
• InChiKey: RMIVRCBSQPCSCQ-BSMXFTQLSA-N

物化性质

• 熔点：
  264～266℃
• 沸点：
  559.0±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、DMSO（微溶、加热）、甲醇（微溶、加热)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3β,18α)-methyl 3-hydroxy-11-oxoolean-12-30-oate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.67h， 生成 3-Desoxy-2.3-didehydro-18α-glycyrrhetinsaeuremethylester
  参考文献：
  名称：

  Glycyrrhetinic acid derivatives as potent inhibitors of Na+, K+-ATPase. Synthesis and structure-activity relationships

  摘要：

  A series of ring A-modified GA derivatives (26 compounds) has been systematically synthesized and the structure-activity relationship investigated for inhibition of canine kidney Na+, K+-ATPase in vitro. The most potent inhibitory activity was found with a group of the 3-deoxygenated derivatives including 5, 6, 9, 10 and 11. The high inhibition may be closely related to the hydrophobic character of the A-ring of these compounds. This finding suggests that the ATP-binding site at the active center of the enzyme is located in a hydrophobic environment.

  DOI：

  10.1016/0223-5234(92)90147-s
• 作为产物：
  描述：

  18α-甘草次酸 在 重氮甲烷 、 甲醇 、 乙醚 作用下， 生成 (3β,18α)-methyl 3-hydroxy-11-oxoolean-12-30-oate
  参考文献：
  名称：

  Powdered neem seed and cake for management of the banana weevil,cosmopolites sordidus, and parasitic nematodes

  摘要：

  Field trials were conducted in Kenya with 'Nakyetengu', an East African highland banana cultivar (AAA-EA), highly susceptible to banana pests. Regardless of soil fertility levels, incorporation around the plant base of powdered neem (Azadirachta indica A. Juss.) seed or cake at 60-100 g/mat at 4-month intervals, gave better control of the banana weevil, Cosmopolites sordidus (Germar), and of parasitic nematodes, than that achieved with soil application of Furadan 5G (carbofuran) at 60-100 g/mat at 6-month intervals. Compared with untreated control, fruit yield in most of the neem treatments was significantly higher, particularly during the second cycle of crop production. Neem application conferred a net economic gain, whereas Furadan application proved uneconomical. Application of powdered neem seed or cake at higher rates (200-400 g/mat) at 6-month intervals caused phytotoxicity, resulting in drying up of banana plants before fruiting, or in 'chokethroat', i.e., inflorescence emergence failure.

  DOI：

  10.1007/bf02981827

文献信息

• First Occurrence of a Furano-glycyrrhetinoate and Its Cytotoxicity
  作者：Lucie Heller、Sven Sommerwerk、Felix Tzschöckell、Jana Wiemann、Stefan Schwarz、Bianka Siewert、Ahmed Al-Harrasi、René Csuk

  DOI：10.1002/ardp.201500318

  日期：2015.12

  (18β)‐glycyrrhetinic acid (1), and the cytotoxicity of some derivatives was investigated by photometric SRB assays employing several human tumor cell lines. In summary, (18β)‐1 is slightly more cytotoxic than its (18α) epimer 4, but its cytotoxicity is negligible. Higher cytotoxicity was observed for the esters 2 and 5 and for the 3‐O‐acetylated esters 3 and 6. Cytotoxicity was improved dramatically when the

  (18α)-甘草次酸 (4) 由 (18β)-甘草次酸 (1) 制备，并通过使用几种人类肿瘤细胞系的光度 SRB 测定研究了一些衍生物的细胞毒性。总之，(18β)-1 的细胞毒性略高于其 (18α) 差向异构体 4，但其细胞毒性可以忽略不计。对酯 2 和 5 以及 3-O-乙酰化酯 3 和 6 观察到更高的细胞毒性。当 C-3 位的羟基被氨基部分取代时，细胞毒性显着提高。SeO2 氧化提供了一种新型呋喃甘草次酸 15。有趣的是，它的硒类似物 16 对所测试的肿瘤细胞系的细胞毒性大约低 5 到 6 倍，并且在用硒替代氧气时失去了肿瘤/非肿瘤选择性取代基。
• METHOD FOR MODIFYING T CELL POPULATION
  申请人：Osaka University

  公开号：EP3539974A1

  公开（公告）日：2019-09-18

  Provided are: a compound represented by formula (I); a retinoid metabolic pathway inhibitor comprising the same; an agent for increasing the ratio of memory T cells; a prophylactic and/or therapeutic agent for cancer or an infectious disease; a cancer immunotherapeutic adjuvant; an immunopotentiator; and a method for preparing a T cell population wherein the ratio of memory T cells is increased, said method comprising using the compound of formula (I).

  提供了：由式（I）代表的化合物；包含该化合物的视黄醇代谢途径抑制剂；提高记忆 T 细胞比例的制剂；癌症或传染性疾病的预防和/或治疗剂；癌症免疫治疗辅助剂；免疫增强剂；以及制备记忆 T 细胞比例提高的 T 细胞群的方法，所述方法包括使用式（I）化合物。
• Method for modifying T cell population
  申请人：International Institute of Cancer Immunology, Inc.

  公开号：US10947503B2

  公开（公告）日：2021-03-16

  Provided is a method for increasing the proportion of memory T cells in a T cell population, said method comprising a step of adding a modulator for the retinoid metabolic pathway and/or a modulator for the retinoic acid signaling system to the T cell population.

  本发明提供了一种提高 T 细胞群中记忆 T 细胞比例的方法，所述方法包括向 T 细胞群中添加维甲酸代谢途径调节剂和/或维甲酸信号系统调节剂的步骤。
• ——
  作者：R. M. Kondratenko、S. R. Mustafina、L. A. Baltina、N. G. Vasil'eva、A. F. Ismagilova、E. V. Vasil'eva、Kh. M. Nasyrov、F. Z. Galin、G. A. Tolstikov

  DOI：10.1023/a:1011905103576

  日期：——
• 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.