ent-16β,17-epoxy-kauran-19-oic acid | 80442-69-9

• 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: ent-16β,17-epoxy-kauran-19-oic acid
• 英文别名: (-)-16β,17-epoxykauran-19-oic acid；(2R,4'R,4a'S,6a'S,9'R,11a'R,11b'S)-4',11b'-dimethyldodecahydro-7'H-spiro[oxirane-2,8'-[6a,9]methanocyclohepta[a]naphthalene]-4'-carboxylic acid；16α,17-epoxy-ent-kauran-19-oic acid；ent-16α,17-epoxy-kauran-19-oic acid；(1'S,2R,4'S,5'R,9'S,10'R,13'R)-5',9'-dimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.01,10.04,9]hexadecane]-5'-carboxylic acid
• CAS: 80442-69-9
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: YDGXRSPFVBSYLM-INIPNLRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ent-16β,17-epoxy-kauran-19-oic acid 在 2-硝基丙烷 、 氟磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以75%的产率得到ent-17-oxo-16R-kauran-19-oic acid
  参考文献：
  名称：

  天然含氧对映贝壳杉烯酸衍生物的直接合成

  摘要：

  本文介绍了从 ent-kaur-16-en-19-oic 酸开始合成一些具有 ent-kauranic 结构的天然二萜，这是一种易于从 s 的干燥废物中获得的天然二萜。

  DOI：

  10.1080/00397911.2020.1821225
• 作为产物：
  描述：

  贝壳杉烯酸 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 7.0h， 生成 ent-16β,17-epoxy-kauran-19-oic acid
  参考文献：
  名称：

  The microbiological transformation of two ent-16β,17-epoxykaurane derivatives by Gibberella fujikuroi

  摘要：

  The biotransformation of ent-16 beta,17-epoxy-7 alpha-hydroxykaurane by Gibberella fujikuroi affords ent-7 alpha,11 alpha,16 beta,17-tetrahydroxykaurane and ent-7 alpha,9 alpha,16 beta,17-tetrahydroxykaurane. These results indicated that the presence of the 16 alpha,17-diol group, into which the 16 alpha,17-epoxy is transformed in the medium, inhibits oxidation at C-19 and favours hydroxylation at C-11(beta). Incubation of ent-16 beta,17-epoxykauran-19-oic acid, via the 16 alpha,17-diol, gave the 7-aldehyde of 16 alpha,17-dihydroxy-GA(12).

  DOI：

  10.1016/s0031-9422(00)90345-5

文献信息

• Inhibition of Na⁺,K⁺-ATPase Activity by (-)-<i>ent</i>-Kaur-16-en-19-oic Acid and its Derivatives
  作者：Ngamrojnavanich, Nattaya、Sirimongkon, Supaporn、Roengsumran, Sophon、Petsom, Amorn、Kamimura, Hishashi

  DOI：10.1055/s-2003-40636

  日期：2003.6

  The diterpene, (-)- ent-kaur-16-en-19-oic acid, from Croton oblongifolius was identified as an Na +,K +-ATPase inhibitor. This compound exhibits an IC 50 of 2.2 x 10( -5 )M against crude enzyme Na +,K +-ATPase from rat brain. The semi-synthetic derivatives, (-)-methyl kaur-16-en-19-oate, (-)-kaur-16-en-19-ol, (-)-16beta,17-epoxykauran-19-oic acid and (-)-17-hydroxykaur-15-en-19-oic acid were also tested

  来自Croton oblongifolius的二萜，（-）-ent-kaur-16-en-19-oic酸被鉴定为Na +，K + -ATPase抑制剂。该化合物对大鼠脑中的粗酶Na +，K + -ATPase的IC 50为2.2 x 10（-5）M。半合成衍生物（-）-甲基kaur-16-en-19-oate，（-）kaur-16-en-19-ol，（-）-16beta，17-epoxykauran-19-oic acid和还测试了（-）-17-hydroxykaur-15-en-19-oic acid，其IC 50为5.5 x 10（-4），5.0 x 10（-4），4.8 x 10（-4）和6.0 x 10（-4）M。
• New Non-Toxic Semi-Synthetic Derivatives from Natural Diterpenes Displaying Anti-Tuberculosis Activity
  作者：Priscilla Matos、Brian Mahoney、Yohan Chan、David Day、Mirela Cabral、Carlos Martins、Raquel Santos、Jairo Bastos、Philip Page、Vladimir Heleno

  DOI：10.3390/molecules201018264

  日期：——

  We report herein the synthesis of six diterpene derivatives, three of which are new, generated through known organic chemistry reactions that allowed structural modification of the existing natural products kaurenoic acid (1) and copalic acid (2). The new compounds were fully characterized using high resolution mass spectrometry, infrared spectroscopy, 1H- and 13C-NMR experiments. We also report the evaluation of the anti-tuberculosis potential for all compounds, which showed some promising results for Micobacterium tuberculosis inhibition. Moreover, the toxicity for each of the most active compounds was also assessed.

  我们在此报告了六种二萜衍生物的合成，其中三种是新的，通过已知的有机化学反应产生，允许对现有天然产物贝壳杉烯酸 (1) 和柯巴酸 (2) 进行结构修饰。使用高分辨率质谱、红外光谱、1H 和 13C-NMR 实验对新化合物进行了全面表征。我们还报告了所有化合物的抗结核潜力的评估，这显示出抑制结核分枝杆菌的一些有希望的结果。此外，还评估了每种最活跃化合物的毒性。
• The microbiological transformation of two ent-16β,17-epoxykaurane derivatives by Gibberella fujikuroi
  作者：Braulio M. Fraga、Pedro González、Ricardo Guillermo、James R. Hanson、Melchor G. Hernández、Jacqueline A. Takahashi

  DOI：10.1016/s0031-9422(00)90345-5

  日期：1994.11

  The biotransformation of ent-16 beta,17-epoxy-7 alpha-hydroxykaurane by Gibberella fujikuroi affords ent-7 alpha,11 alpha,16 beta,17-tetrahydroxykaurane and ent-7 alpha,9 alpha,16 beta,17-tetrahydroxykaurane. These results indicated that the presence of the 16 alpha,17-diol group, into which the 16 alpha,17-epoxy is transformed in the medium, inhibits oxidation at C-19 and favours hydroxylation at C-11(beta). Incubation of ent-16 beta,17-epoxykauran-19-oic acid, via the 16 alpha,17-diol, gave the 7-aldehyde of 16 alpha,17-dihydroxy-GA(12).
• A straightforward synthesis of natural oxygenated <i>ent</i>-kaurenoic acid derivatives
  作者：Olga Morarescu、Marina Grinco、Veaceslav Kulciţki、Alic Barba、Olga Garbuz、Valentin Gudumac、Aurelian Gulea、Nicon Ungur

  DOI：10.1080/00397911.2020.1821225

  日期：2021.1.2

  The paper presents the synthesis of some natural diterpenoids of ent-kauranic structure, starting from ent-kaur-16-en-19-oic acid, a natural diterpenoid readily available from the dried wastes of s...

  本文介绍了从 ent-kaur-16-en-19-oic 酸开始合成一些具有 ent-kauranic 结构的天然二萜，这是一种易于从 s 的干燥废物中获得的天然二萜。