methyl 16-formyllambertianate | 176692-84-5

• 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: methyl 16-formyllambertianate
• 英文别名: methyl (1S,4aR,5S,8aR)-5-[2-(2-formylfuran-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate
• CAS: 176692-84-5
• 化学式: C₂₂H₃₀O₄
• 分子量: 358.478
• InChiKey: SGHGOYDALDCQEW-GWWHBBDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 16-formyllambertianate 在 sodium tetrahydroborate 作用下， 以 甲醇 、 苯 为溶剂， 反应 18.5h， 生成 methyl 16-[N-(indol-3'-yl-2'-ethyl)aminomethyl]-15,16-epoxy-8(17),13(16),14-labdtrien-18-oate
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1013329127494
• 作为产物：
  描述：

  lambertianic acid methyl ester 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 48.0h， 以61.5%的产率得到methyl 16-formyllambertianate
  参考文献：
  名称：

  Vilsmeier?Haack reaction of methyl lambertianate and non-sensitized photocyclization of the resulting product

  摘要：

  Vilsmeier-Haack formylation of methyl lambertianate results in its 16-formyl derivative as the predominant product, which readily enters the intramolecular reaction of photochemical [2+2]-cycloaddition in the absence of a sensitizer.

  DOI：

  10.1007/bf00713615

文献信息

• Synthetic transformation of higher terpenoids 31. Synthesis of 1,2,3-triazolyl-containing furan labdanoids and studies of their cytotoxic activity
  作者：Yu. V. Kharitonov、E. E. Shul’ts、M. M. Shakirov、M. A. Pokrovskii、A. G. Pokrovskii、G. A. Tolstikov

  DOI：10.1007/s11172-013-0297-5

  日期：2013.9

  Abstract16-(1-R-1,2,3-Triazol-4-ylethyl)-, 16-(1-R-1,2,3-triazol-4-ylmethoxymethyl)-, and 16-2-(1-R-1,2,3-triazol-4-yl)-1-[(1-R-1,2,3-triazol-4-ylmethoxy)ethyl]}-substituted derivatives of methyl lambertianate were synthesized by 1,3-cycloaddition of labdanoid alkynes with azides. The compounds obtained possess considerable cytotoxicity toward the human tumor cell lines CEM-13, MT-4, and U-937. The

  摘要 16-(1-R-1,2,3-Triazol-4-ylethyl)-, 16-(1-R-1,2,3-triazol-4-ylmethoxymethyl)-, 和 16-2-(1 -R-1,2,3-三唑-4-基)-1-[(1-R-1,2,3-三唑-4-基甲氧基)乙基]}-取代的朗伯坦酸甲酯衍生物由1,劳丹醇炔烃与叠氮化物的 3-环加成反应。获得的化合物对人肿瘤细胞系 CEM-13、MT-4 和 U-937 具有相当大的细胞毒性。发现最活跃的化合物 16-(2-2-[(1-benzyl-1H-1,2,3-triazol-4-yl)acetyl]furan-3-yl}ethyl)lambertianate 可抑制在 7–12 μmol L−1 的浓度下，肿瘤细胞的活力增加了 50% (CCID50)。
• Synthetic transformations of higher terpenoids: XIX. Synthesis of 1,7-epoxyisoindolones and 7,9a-epoxythiazolo[2,3-a]isoindolones from terpenoids
  作者：Yu. V. Kharitonov、E. E. Shults、M. M. Shakirov、G. A. Tolstikov

  DOI：10.1134/s1070428009050017

  日期：2009.5

  of the obtained methyl 16-thiazolidinyllambertianate with the above mentioned acid chlorides or with maleic anhydride, and the intramolecular cyclization of the arising furfurylamine we obtained terpenoid derivayives of 7,9a-epoxyhexahydrothiazolo[2,3-a]isoindol-5-one.

  用L-亮氨酸或L-蛋氨酸酯对16-甲酰基lambertianate甲酯进行的还原胺化反应产生了Labdanoid糠胺，其与马来酸酐在甲基丙烯酸或巴豆酸的氯化物上的酰化反应可生成相应的不饱和酰胺，这些酰胺易于进入分子内反应[4 + 2 ]-环加成，给出10-oxa-3-氮杂三环[5.2.1.0 1,5 ] dec-8-en-4-one的相应衍生物。反应序列的结果是：用胱胺胺化16-甲酰基lambertianate甲酯，将上述16-噻唑烷基lambertianate甲酯与上述酰氯或马来酸酐酰化，将生成的糠胺分子内环化，得到萜类化合物7,9a-环氧六氢噻唑[2,3-a] isoindol-5-one的衍生物。
• 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：——
• Synthetic transformations of higher terpenoids: XV. Transformations of azlactone derived from 16-formyllambertianic acid methyl ester
  作者：Yu. V. Kharitonov、E. E. Shul’ts、M. M. Shakirov、G. A. Tolstikov

  DOI：10.1134/s1070428007060073

  日期：2007.6

  Condensation of 16-formyllambertianic acid methyl ester with hippuric acid gave methyl 15,16-epoxy-16-[(4Z)-5-oxo-2-phenyl-4,5-dihydrooxazol-4-ylidenemethyl]labda-8(20),13(16),14-trien-19-oate which underwent ready transformation into 2-benzoylamino-3-(2-furyl)acrylic acid of the labdanoid series. Reactions of the diterpenoid azlactone with amines and alpha-amino acid esters led to the formation of the corresponding carbamoylvinylbenzamides and N-(2-benzoylaminoacryloyl) amino acid esters, and furylacrylic acid hydrazides were formed in reactions with hydrazines. Cyclization of the N'-phenylhydrazide by the action of 1 M aqueous sodium hydroxide gave the corresponding 1,2,4-triazin-6-one. By treatment of the azlactone with aqueous ammonia on heating, 4-substituted 2-phenyl-4,5-dihydroimidazol-5-one was obtained.
• Synthetic transformations of higher terpenoids. XXVI. 16-acetylaminomethyllabdanoids and their cytotoxicity
  作者：Yu. V. Kharitonov、E. E. Shul’ts、M. M. Shakirov、M. A. Pokrovsky、A. G. Pokrovsky、G. A. Tolstikov

  DOI：10.1134/s1068162011060082

  日期：2012.1

  Coupling of methyl 16-aminomethyllambertianate with N-Boc-protected omega-amino acids resulted in 16-(N-Boc-aminononan)- and 16-(N-Boc-aminoundecan)amidomethyllabdanoids. Interaction of methyl aminomethyllambertianate with bicyclo[2.2.1]hept-5-en-2,3-dicarboxylic acid anhydride led to the amide of bicyclo[2.2.1]heptan-1,2-dicarboxylic acid with a labdanoid substituent. Reaction of methyl 16-aminomethyllambertianate with chloroacetyl chloride resulted in methyl 16-(chloroacetylaminomethyl)lambertianate; coupling of the latter with methyl esters of amino acids gave the corresponding amides of methyl lambertianate. The compounds obtained were more cytotoxic toward CEM-13, MT-4, and U-937 tumor cell lines as compared with lambertianic acid; the dose inhibiting tumor cell viability by 50% (CCID50) of the more active compounds was 3.9-9.9 mu M.