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Δ12-Oleanen-3β,11β,30-triol | 13947-06-3

中文名称
——
中文别名
——
英文名称
Δ12-Oleanen-3β,11β,30-triol
英文别名
18β-olean-12-ene-3β,11β,30-triol;(3S,4aR,6aR,6bS,8aS,11S,12aR,14S,14aR,14bS)-11-(hydroxymethyl)-4,4,6a,6b,8a,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,14-diol
Δ<sup>12</sup>-Oleanen-3β,11β,30-triol化学式
CAS
13947-06-3
化学式
C30H50O3
mdl
——
分子量
458.725
InChiKey
LOBOMSGBFMNHBJ-FAAJIGJPSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    557.9±50.0 °C(Predicted)
  • 密度:
    1.10±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    6.5
  • 重原子数:
    33
  • 可旋转键数:
    1
  • 环数:
    5.0
  • sp3杂化的碳原子比例:
    0.93
  • 拓扑面积:
    60.7
  • 氢给体数:
    3
  • 氢受体数:
    3

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

点击查看最新优质反应信息

文献信息

  • Chemical modification of glycyrrhetinic acid in relation to the biological activities.
    作者:SHOJI SHIBATA、KUNIO TAKAHASHI、SHINGO YANO、MASATOSHI HARADA、HIROSHI SAITO、YASUSHI TAMURA、AKIRA KUMAGAI、KAZUHIRO HIRABAYASHI、MIDORI YAMAMOTO、NOBUYUKI NAGATA
    DOI:10.1248/cpb.35.1910
    日期:——
    18β-Olean-12-ene-3β, 30-diol (deoxoglycyrrhetol) (4a) was prepared with a view to eliminating pseudoaldosteronism, a side-effect of glycyrrhetinic acid (1b), which is the sapogenin of Licorice saponin, glycyrrhizin (1a), while maintaining or enhancing the therapeutic activities. On reduction of the 11-keto and 30-carboxyl groups of 1b with NaAlH2- (OCH2CH2OCH3) 2, olean-12-ene-3β, 11β, 30-triol (9) and olean-12-ene-3β, 11α, 30-triol (10) were obtained. On catalytic hydrogenation of 9 and 10 with Pd-C as a catalyst, 4a was formed in an overall yield of 80%. On treatment with conc. HCl, 9 yielded 18β-olean-9 (11), 12-diene-3β, 30-diol (11a), while 10 yielded olean-11, 13 (18) -diene-3β, 30-diol (12a). Mono-and di-β-carboxy-propionyl and mono-and di-ο-pbthaloyl esters of 4a, lla and 12a were prepared to increase the hydrophilic character. The competitive inhibition of 5β, Δ4-reductase of corticosteroids in the liver which is caused by lb to induce pseudoaldosteronism was not observed in the case of 4a. Compounds 4a, 11a and 12a and their β-carboxypropionyl and ο-phthaloyl esters were studied pharmacologically, and showed antiulcerogenic, antiallergic and antiinflammatory activities.
    18β-烯-12-烯-3β, 30-醇(去氧甘草醇)(4a)的制备旨在消除甘草酸(1b)的副作用假性醛固酮症,这是甘草皂苷甘草苷(1a)的薯蓣皂苷,同时保持或增强其治疗活性。通过用NaAlH2-(OCH2CH2OCH3)2还原1b的11-酮和30-羧基,获得了烯-12-烯-3β, 11β, 30-三醇(9)和烯-12-烯-3β, 11α, 30-三醇(10)。用Pd-C作为催化剂对9和10进行催化氢化反应,最终产率为80%得到了4a。用浓盐酸处理9时,生成了18β-烯-9(11)-12-烯-3β, 30-醇(11a),而10则生成了烯-11, 13(18)-烯-3β, 30-醇(12a)。制备了4a、11a和12a的单-和双-β-羧基-丙酰基及单-和双-邻-苯二甲酰基酯,以增强其亲性。与1b引起的假性醛固酮症不同,在4a的情况下未观察到在肝脏中对皮质类固醇的5β, Δ4-还原酶的竞争抑制。化合物4a、11a和12a及其β-羧基丙酰基和邻-苯二甲酰基酯在药理学上进行了研究,显示出抗溃疡生成、抗过敏和抗炎活性。
  • Synthesis and in Vitro Antioxidant Activity of Glycyrrhetinic Acid Derivatives Tested with the Cytochrome P450/NADPH System
    作者:Mourboul Ablise、Brigitte Leininger-Muller、Choi Dal Wong、Gérard Siest、Vincent Loppinet、Sophie Visvikis
    DOI:10.1248/cpb.52.1436
    日期:——
    Five glycyrrhetinic acid (Ib) derivatives have been synthesized to try to improve the antioxidant activity. Their in vitro antioxidant activities were studied using a cytochrome P450/NADPH reductase system from rat liver microsomes. The generation of microsomal free radicals was followed by oxidation of the DCFH-DA probe, while evaluating the capacity to inhibit reactive oxygen species (ROS) formation. Two hydroxylated derivatives, 18β-olean-12-ene-3β,11α,30-triol (II) and 18β-olean-12-ene-3β,11β,30-triol (IV), exhibited strong antioxidant activities. At a concentration of 1.0 mg/ml, these derivatives inhibited ROS formation by 50% and 51%, respectively. Moreover, two homo- and heterocyclic diene derivatives, 18β-olean-11,13(18)-diene-3β,30-diol (III) and 18β-olean-9(11),12-diene-3β,30-diol (V), were also effective in ROS-scavenging activity (inhibition of 41% and 44% of ROS activity, respectively). In the same conditions, the lead compound (Ib) and the reference vitamin E inhibited ROS activity by 31% and 32%, respectively. Our results suggest that the chemical reduction of the 11-keto and 30-carboxyl groups into hydroxyl function (example, II, IV) can increase the antioxidant activity of Ib significantly. In view of these results, our study represents a further approach to the development of potential therapeutic agents from Ib derivatives for use in pathologic events in which, free radical damage could be involved.
    为了提高抗氧化活性,我们合成了五种甘草次酸(Ib)衍生物。我们利用大鼠肝脏微粒体的细胞色素 P450/NADPH 还原酶系统研究了它们的体外抗氧化活性。微粒体自由基的生成是通过 DCFH-DA 探针的氧化进行的,同时还评估了抑制活性氧(ROS)形成的能力。18β-olean-12-ene-3β,11α,30 三醇(II)和 18β-olean-12-ene-3β,11β,30 三醇(IV)这两种羟基化衍生物表现出很强的抗氧化活性。在 1.0 毫克/毫升的浓度下,这些衍生物对 ROS 形成的抑制率分别为 50%和 51%。此外,18β-烯-11,13(18)-二烯-3β,30-二醇(III)和 18β-烯-9(11),12-二烯-3β,30-二醇(V)这两种同环和杂环二烯衍生物也具有有效的 ROS 清除活性(分别抑制了 41% 和 44% 的 ROS 活性)。在相同条件下,先导化合物(Ib)和参考维生素 E 对 ROS 活性的抑制率分别为 31% 和 32%。我们的研究结果表明,将 11-酮基和 30-羧基化学还原成羟基功能(例如,II、IV)可以显著提高 Ib 的抗氧化活性。鉴于这些结果,我们的研究为开发 Ib 衍生物的潜在治疗药物提供了进一步的思路,这些药物可用于可能涉及自由基损伤的病理事件。
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