2-cyano-2,3-seco-lup-20(29)-en-3-al-28-oic acid methyl ester | 1114876-84-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 2-cyano-2,3-seco-lup-20(29)-en-3-al-28-oic acid methyl ester
• 英文别名: 28-methoxy-28-oxo-2-cyano-1-nor-2,3-secolup-20(29)-en-3-al；28-methoxy-28-oxo-1-cyano-2,3-secolup-20(29)-en-3-al
• CAS: 1114876-84-4
• 化学式: C₃₁H₄₇NO₃
• 分子量: 481.719
• InChiKey: CWTFHSOVHJZBFR-SRACOBAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.14
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  67.16
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-cyano-2,3-seco-lup-20(29)-en-3-al-28-oic acid methyl ester 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 1.5h， 以30%的产率得到methyl 1-cyano-2-norlup-1(3),20(29)-diene-28-oate
  参考文献：
  名称：

  Functionalization, cyclization and antiviral activity of A-secotriterpenoids

  摘要：

  Triterpene derivatives with an α,β-alkenenitrile moiety in the five-membered ring A have been synthesized by nitrile anion cyclizations of 1-cyano-2,3-secotriterpenoids. Oxime-containing precursors, 2,3-secointermediates and five-membered ring A products of cyclizations were screened for in vitro antiviral activity against enveloped viruses - influenza A virus and human immunodeficiency virus type I (HIV-1). Lupane ketoxime and the 2,3-secolupane C-3 aldoxime which possess antiviral activities against both influenza A virus (EC50 12.9-18.2 μM) and HIV-1 (EC50 0.06 μM) were the most promising compounds.

  DOI：

  10.1016/j.ejmech.2013.12.058
• 作为产物：
  描述：

  2-hydroxyimino-3-oxolup-20(29)-en-28-oic acid methyl ester 在 吡啶 、 sodium tetrahydroborate 、 对甲苯磺酰氯 作用下， 以 甲醇 为溶剂， 生成 2-cyano-2,3-seco-lup-20(29)-en-3-al-28-oic acid methyl ester
  参考文献：
  名称：

  The immunotropic activity of lupane and oleanane 2,3-seco-triterpenoids

  摘要：

  The immunotropic effect of the 2,3-seco derivatives of allobetulon, betulonic acid, and the methyl ester of betulonic acid were studied. It was found that the highest activity is shown by compounds with an oleanane fragment. The presence of a free C28-carboxyl group enhances the activity of lupane 2,3-seco derivatives. A significant contribution to the development of the immune response is introduced by a functional group at the C3 atom in the A ring-the C3-carboxy derivatives intensify the processes of antibody production and alter the number and ratio of leukocyte forms. It is shown that 2,3-seco-1-cyano-19 beta,28-epoxy-18 alpha-olean-3-oic acid stimulates humoral immunity with a positive influence on hematopoiesis.

  DOI：

  10.1134/s1068162010020147

文献信息

• Synthesis of lupane and 19β,28-epoxy-18α-oleanane 2,3-seco-derivatives based on betulin
  作者：I. A. Tolmacheva、A. V. Nazarov、O. A. Maiorova、V. V. Grishko

  DOI：10.1007/s10600-008-9135-7

  日期：2008.9

  The α-hydroxyoximes of methyl betulonate and allobetulone were synthesized. Beckmann fragmentation of them produced the lupane and 19β,28-epoxy-18α-oleanane 2,3-seco-derivatives.

  合成了甲基白桦酸酯和异白桦酮的α-羟基肟。对它们进行贝克曼裂解反应，产生了萊潞烯和19β,28-环氧-18α-橄榄烯2,3-酮衍生物。
• Syntheses, Transformations, and Cytotoxicities of 2,3-Secolupane Acetylhydrazones
  作者：I. A. Tolmacheva、D. V. Eroshenko、V. V. Grishko

  DOI：10.1007/s10600-018-2450-8

  日期：2018.7

  New 2,3-secolupane derivatives with methylketone, acetylhydrazone, and 1,3,4-oxadiazoline fragments were prepared via chemical modification of ring A and the isopropylene group of 1-cyano-2,3-secotriterpenoids. Cytotoxicity studies of the synthesized compounds using four tumor cell lines (HEp-2 human epithelial type 2 carcinoma, MS melanoma, RD TE32 rhabdomyosarcoma, and A549 lung carcinoma) showed

  新的 2,3-secolupane 衍生物与甲基酮、乙酰腙和 1,3,4-恶二唑啉片段是通过环 A 和 1-氰基-2,3-secotriterpenoids 的异丙烯基团的化学修饰制备的。使用四种肿瘤细胞系（HEp-2 人类上皮 2 型癌、MS 黑色素瘤、RD TE32 横纹肌肉瘤和 A549 肺癌）对合成化合物的细胞毒性研究表明，3,30-二醛 3 (IC50 3.98 μM) 和 30-乙酰腙10 (IC50 8.95 μM) 对 MS 黑色素瘤细胞的细胞毒性最强。中间体 3 对 RD TE32 横纹肌肉瘤细胞也有活性（IC50 6.70 μM）。
• Synthesis of acylhydrazones from lupane and 19β,28-epoxy-18α-oleanane 2,3-seco-aldehydonitriles
  作者：I. A. Tolmacheva、N. V. Galaiko、V. V. Grishko

  DOI：10.1007/s10600-010-9520-x

  日期：2010.3

  2,3-seco-Triterpene acylhydrazones, which are interesting as new biologically active compounds, were prepared by reaction of lupane and 19β,28-epoxy-18α-oleanane 2,3-seco-aldehydonitriles with acylated hydrazines.

  通过将羽扇豆和 19β,28-环氧-18α-齐墩果烷 2,3-seco-aldehydonitriles 与酰化肼反应，制备了 2,3-seco-三萜酰肼，这是一种具有生物活性的新化合物。
• Synthesis of A-Pentacyclic Triterpene α,β-Alkenenitriles
  作者：A. V. Pereslavtseva、I. A. Tolmacheva、P. A. Slepukhin、O. S. El’tsov、I. I. Kucherov、V. F. Eremin、V. V. Grishko

  DOI：10.1007/s10600-014-0822-2

  日期：2014.1

  A-seco-triterpenoids with a methylketone group were synthesized from epimeric 3-hydroxy-3-methyl-1-cyano-2,3-seco-triterpenoids of the lupane and 19β,28-epoxy-18αH-oleanane types, which were formed by a Grignard reaction. The resulting methylketones underwent under base-catalysis conditions an intramolecular cyclization to form A-pentacyclic β-substituted alkenenitriles. The synthesized compounds included 3-methyl-1-cyano-19β,28-epoxy-2,3-seco-2-nor-18αH-olean-3-one and methyl 3-methyl-1-cyano-2-norlup-1(3),20(29)-dien-28-oate, which inhibited in vitro reproduction of human immunodeficiency virus type 1.

  通过格氏反应，合成了具有甲基酮基的 A-共三萜类化合物，其原料为 3-羟基-3-甲基-1-氰基-2,3-共三萜类化合物（鲁帕烷和 19β,28-环氧-18αH-油烷类型）。在碱催化条件下，生成的甲基酮发生分子内环化反应，形成 A-五环 β 取代烯腈。合成的化合物包括 3-甲基-1-氰基-19β,28-环氧-2,3-seco-2-nor-18αH-olean-3-酮和 3-甲基-1-氰基-2-norlup-1(3),20(29)-dien-28-oate 甲酯，它们能抑制人类免疫缺陷病毒 1 型的体外繁殖。
• Antiviral activity of 2,3-secotriterpenic hydrazones of the lupane and 19β,28-epoxy-18α-oleanane types
  作者：N. V. Galayko、I. A. Tolmacheva、V. V. Grishko、L. V. Volkova、E. N. Perevozchikova、S. A. Pestereva

  DOI：10.1134/s1068162010040114

  日期：2010.7

  Novel hydrazones of the lupane and 19 beta,28-epoxy-18 alpha-oleanane types have been synthesized via the interaction of 2,3-secotriterpenic aldehydonitriles with substituted hydrazines. As a result of the investigation of the antiviral activity of 2,3-secotriterpenic hydrazones against the Indiana strain of the vesicular stomatitis virus on two models of mammalian cell line infection, the acetylhydrazone of 1-cyano-2,3-seco-19 beta,28-epoxy-18 alpha-olean-3-al has been found to have a high prophylactic activity of 0.00016 mu g/ml to the vesicular stomatitis virus and to inhibit virus reproduction in primarily infected cells in a 0.21-mu g/ml concentration.