(3β,18β,20β)-3-(acetoxy)-20-isocyanato-30-norolean-12-en-11-one | 30244-17-8

• 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,18β,20β)-3-(acetoxy)-20-isocyanato-30-norolean-12-en-11-one
• 英文别名: (3β,18β,20β)-3-(acetyloxy)-20-isocyanato-30-norolean-12-en-11-one；[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-isocyanato-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl] acetate
• CAS: 30244-17-8
• 化学式: C₃₂H₄₇NO₄
• 分子量: 509.729
• InChiKey: LFQNVIDLTICHQM-JETOYTNCSA-N

物化性质

• 熔点：
  295-297 °C
• 沸点：
  566.5±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  37
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  72.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3β,18β,20β)-3-(acetoxy)-20-isocyanato-30-norolean-12-en-11-one 在 氨 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 (3β,18β,20β)-N-[-3-(acetoxy)-11-oxo-30-norolean-12-en-20-yl]urea
  参考文献：
  名称：

  新型甘草甜素脲类抗炎药治疗急性肾损伤的设计与合成

  摘要：

  为了开发用于预防和治疗急性肾损伤的新型抗炎药，使用 RAW264.7 细胞设计、合成和评估了一系列新型甘草酸尿素的抗炎活性。具有酸性或中性氨基酸的化合物5r-5u（分别为 2.04、2.50、3.25 和 2.48 μM）显示出有效的抗炎活性（ 对于 NO 抑制，IC 50 = 2-3 μM），其中，化合物5r还抑制肿瘤坏死因子-α (TNF-α) 和白细胞介素-6 (IL-6) 呈剂量依赖性。在顺铂诱导的 AKI 小鼠模型中，化合物5r显着降低促炎因子水平，改善肾脏组织病理损伤，维持正常代谢能力。

  DOI：

  10.1016/j.bioorg.2021.104755
• 作为产物：
  描述：

  在 sodium azide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.25h， 生成 (3β,18β,20β)-3-(acetoxy)-20-isocyanato-30-norolean-12-en-11-one
  参考文献：
  名称：

  Ibrahim, Yehia Abdu; Hanna, Atef G.; Elgamal, M. Hani A., Pakistan Journal of Scientific and Industrial Research, 1995, vol. 38, # 3-4, p. 101 - 107

  摘要：

  DOI：

文献信息

• [EN] NOVEL TRITERPENE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS TRITERPÉNIQUES
  申请人：ONEPHARM RES & DEV GMBH

  公开号：WO2012020019A1

  公开（公告）日：2012-02-16

  The present invention encompasses compounds of general formula (I) wherein R11a to R30 and X are defined as in claim 1, which are suitable for the treatment of and/or prevention of chronic inflammatory diseases, autoimmune diseases, skin diseases, bone diseases, metabolic diseases, infectious diseases and cancer.

  本发明涵盖了一般式（I）中R11a到R30和X的化合物，其中如权利要求书中所定义的，适用于治疗和/或预防慢性炎症性疾病、自身免疫疾病、皮肤疾病、骨疾病、代谢性疾病、传染病和癌症。
• Synthesis of new glycyrrhetinic acid derived ring A azepanone, 29-urea and 29-hydroxamic acid derivatives as selective 11β-hydroxysteroid dehydrogenase 2 inhibitors
  作者：Rawindra Gaware、Rupesh Khunt、Laszlo Czollner、Christian Stanetty、Thierry Da Cunha、Denise V. Kratschmar、Alex Odermatt、Paul Kosma、Ulrich Jordis、Dirk Claßen-Houben

  DOI：10.1016/j.bmc.2011.02.005

  日期：2011.3

  Glycyrrhetinic acid, the metabolite of the natural product glycyrrhizin, is a well known nonselective inhibitor of 11 beta-hydroxysteroid dehydrogenase (11 beta-HSD) type 1 and type 2. Whereas inhibition of 11 beta-HSD1 is currently under consideration for treatment of metabolic diseases, such as obesity and diabetes, 11 beta-HSD2 inhibitors may find therapeutic applications in chronic inflammatory diseases and certain forms of cancer. Recently, we published a series of hydroxamic acid derivatives of glycyrrhetinic acid showing high selectivity for 11 beta-HSD2. The most potent and selective compound is active against human 11 beta-HSD2 in the low nanomolar range with a 350-fold selectivity over human 11 beta-HSD1. Starting from the lead compounds glycyrrhetinic acid and the hydroxamic acid derivatives, novel triterpene type derivatives were synthesized and analyzed for their biological activity against overexpressed human 11 beta-HSD1 and 11 beta-HSD2 in cell lysates. Here we describe novel 29-urea- and 29-hydroxamic acid derivatives of glycyrrhetinic acid as well as derivatives with the Beckman rearrangement of the 3-oxime to a seven-membered ring, and the rearrangement of the C-ring from 11-keto-12-ene to 12-keto-9(11)-ene. The combination of modifications on different positions led to compounds comprising further improved selective inhibition of 11 beta-HSD2 in the lower nanomolar range with up to 3600-fold selectivity. (C) 2011 Elsevier Ltd. All rights reserved.
• [EN] GLYCYRRHETINIC ACID AMINE ANALOGUES FOR USE IN THE TREATMENT OF INFLAMMATION, INFECTIOUS DISEASES, CANCER, AUTOIMMUNE DISEASES, SKIN DISEASES, BONE DISEASES AND METABOLIC DISEASES<br/>[FR] ANALOGUES AMINE D'ACIDE GLYCYRRHÉTINIQUE DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT DE L'INFLAMMATION, DES MALADIES INFECTIEUSES, DU CANCER, DES MALADIES AUTO-IMMUNES, DES MALADIES DE LA PEAU, DES MALADIES DES OS ET DES MALADIES MÉTABOLIQUES
  申请人：ONEPHARM RES & DEV GMBH

  公开号：WO2012020021A9

  公开（公告）日：2012-05-10