lambertianic acid methyl ester

• 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: lambertianic acid methyl ester
• 英文别名: methyl lambertianate；1-naphthalenecarboxylic acid, 5-[2-(3-furanyl)ethyl]decahydro-1,4a-dimethyl-6-methylene-, methyl ester, (1S,4aR,5S,8aR)-；methyl (1S,4aR,5S,8aR)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: DCZZBGIVZGGJDO-ZSXPUABSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  lambertianic acid methyl ester 在 potassium permanganate 、 四丁基溴化铵 、 magnesium sulfate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 水 、 苯 为溶剂， 反应 9.0h， 生成 methyl 3a-formyl-2-(3-furyl)-6,9a-dimethylperhydronaphtho[2,1-b]furan-6-carboxylate
  参考文献：
  名称：

  Synthetic Transformations of Higher Terpenoids: IX. Nitrogen-Containing Heterocyclic Compounds on the Basis of Lambertianic Acid

  摘要：

  朗伯酸甲酯和 15,16-环氧-17-羟基labda-13(16)14-二烯-18-酸甲酯的氧化得到 17-正-8-氧代-, 8,12-环氧-17-羟基-,和8-甲酰基-17-去甲二烯酸酯，其经过还原胺化，以及随后的分子内氨甲基化17-正-8(R)-甲基氨基-和17-甲基氨基劳达二烯酸酯与甲醛反应得到新的多环化合物、呋喃佐辛和呋喃嗪衍生物。

  DOI：

  10.1007/s11178-005-0200-4
• 作为产物：
  描述：

  红松内酯 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 以10 mg的产率得到lambertianic acid methyl ester
  参考文献：
  名称：

  In Vitro Platelet-Activating Factor Receptor Binding Inhibitory Activity of Pinusolide Derivatives: A Structure−Activity Study

  摘要：

  Pinusolide, a labdane-type diterpene lactone isolated from Biota orientalis, was found to be a potent platelet-activating factor (PAF) receptor binding antagonist. To investigate the structure-activity relationship and find derivatives with improved pharmacological profiles, 17 pinusolide derivatives were prepared and tested for their ability to inhibit the PAF receptor binding. The results demonstrated that the carboxymethyl ester group at C-19, the integrity of the alpha,beta-unsaturated butenolide ring, and the exocyclic olefinic function of pinusolide are all necessary for its maximum PAF receptor binding inhibitory activity. Among the derivatives, the 17-nor-8-oxo derivative 8 was found to be as potent as pinusolide. The results also suggested that several derivatives warrant further pharmaceutical and pharmacological studies due to their improved water solubility (8 and 11) and apparent lack of susceptibility to Michael-type nucleophilic addition (13 and 18).

  DOI：

  10.1021/jm970569j

文献信息

• Synthetic Transformations of Higher Terpenoids: X. Intramolecular Cyclization of N-Allyl- and N-Propargyl-16-dialkylammoniomethyl-12-furfuryl-13,14,15,16-tetranorlabdanoid Bromides
  作者：Yu.V. Kharitonov、E.E. Shults、M.M. Shakirov、G.A. Tolstikov

  DOI：10.1007/s11178-005-0307-7

  日期：2005.8

  Quaternary ammonium salts obtained by quaternization of lambertian acid 16-dialkylaminomethyl derivatives effected by allyl halides or propargyl bromide undergo intramolecular [4+2]-cycloaddition resulting in diterpenoids of labdane type containing a heterocyclic fragment of 10-oxa-3-azatricyclo[5.2.1.01,5]decene or 10-oxa-3-azatricyclo[5.2.1.01,5]deca-6,8-diene.

  通过烯丙基卤化物或炔丙基溴作用下使扁柏酸16-二烷基氨基甲基衍生物季铵化的四级铵盐，经历分子内[4+2]环加成反应，生成含有10-氧杂-3-氮杂三环[5.2.1.01,5]癸烯或10-氧杂-3-氮杂三环[5.2.1.01,5]癸-6,8-二烯杂环片段的半日花烷型二萜化合物。
• Synthetic Transformations of Higher Terpenoids. XXXV.* Synthesis and Cytotoxicity of Macroheterocyclic Compounds Based on Lambertianic Acid
  作者：Yu. V. Kharitonov、M. M. Shakirov、M. A. Pokrovskii、A. G. Pokrovskii、E. E. Shul’ts

  DOI：10.1007/s10600-017-1915-5

  日期：2017.1

  (17R)-17,18-Dipropargyloxylabda-13,15-diene was synthesized and underwent Cu-catalyzed cycloaddition with 1,10-diazodecane or 1,2-bis(2-azidoethoxy)ethane to produce macroheterocycles of the furanolabdanoid decalin fragment. The macroheterocyclic labdanoids showed significant cytotoxicity in MEL-8, MT-4, and U-937 human tumor cell models.

  (17R)-17,18-Dipropargyloxylabda-13,15-diene 被合成，并与 1,10-diazodecane 或 1,2-bis(2-azidoethoxy)ethane 发生 Cu 催化的环加成反应，生成了呋喃类巴豆烷癸醛片段的大杂环。这些大杂环类唇形酮在 MEL-8、MT-4 和 U-937 人类肿瘤细胞模型中显示出显著的细胞毒性。
• Synthesis and spectroscopic studies of chiral macrocyclic furanolabdanoids connected on the 16,17-positions by 1,2,3-triazole rings with methylene or oxamethylene units
  作者：Yurii V. Kharitonov、Makhmut M. Shakirov、Elvira E. Shults

  DOI：10.1007/s10847-016-0596-1

  日期：2016.4

  Derivatives of natural diterpenoid methyl lambertianate containing propargyloxy substituents in 16,17-positions were obtained. CuAAC reaction of methyl 17-propargyloxy-16-[(prop-2-yn-1-yloxy)methyl]labdadienoate with various diazides in the presence of Cu(II)/sodium ascorbate in methylene chloride/water reaction medium gave chiral macrocyclic compounds connected on the 16 and 17-positions by 1,2,3-triazole

  获得了在 16,17 位含有炔丙氧基取代基的天然二萜类甲基朗伯酯衍生物。17-炔丙基氧基-16-[(prop-2-yn-1-yloxy)methyl]labdadienoate 与各种二叠氮化物在 Cu(II)/抗坏血酸钠的存在下在二氯甲烷/水反应介质中的 CuAAC 反应得到手性大环化合物在16和17位通过1,2,3-三唑环与亚甲基、乙氧基乙基或乙基乙氧基乙基单元连接。获得的大环结构通过 1,2,3-三唑环对 Hg2+ 离子显示出高选择性和亲和力。
• Chernov; Shul'ts; Shakirov, Russian Journal of Organic Chemistry, 2000, vol. 36, # 10, p. 1455 - 1464
  作者：Chernov、Shul'ts、Shakirov、Tolstikov

  DOI：——

  日期：——
• New Nitrogen-Containing Labdanoids from Lambertianic Acid
  作者：Yu. V. Kharitonov、E. E. Shults、M. M. Shakirov、G. A. Tolstikov

  DOI：10.1023/b:doch.0000021273.00956.30

  日期：2004.3

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