methyl 28-methoxy-28-oxo-1-cyano-2,3-seco-2-norlup-20(29)-en-3-oate | 1114876-86-6

• 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: methyl 28-methoxy-28-oxo-1-cyano-2,3-seco-2-norlup-20(29)-en-3-oate
• 英文别名: 28-methoxycarbonyl-2-cyano-2,3-seco-lup-20(29)-en-3-oic acid
• CAS: 1114876-86-6
• 化学式: C₃₁H₄₇NO₄
• 分子量: 497.718
• InChiKey: NCWOQYBIEKFXFL-AJNNAGPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.02
• 重原子数：
  36.0
• 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：
  87.39
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 28-methoxy-28-oxo-1-cyano-2,3-seco-2-norlup-20(29)-en-3-oate 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 N-[28-methoxy-28-oxo-1-cyano-2,3-seco-2-norlup-20(29)-en-3-oyl]-2-aminopropane-1,3-diol
  参考文献：
  名称：

  Synthesis and antiviral activity of C-3(C-28)-substituted 2,3-seco-triterpenoids

  摘要：

  用四种结构类型的β-氨基醇与2,3-seco-18αH-普罗兰酸和2,3-seco-路烯C-3(C-28)单羧酸及二羧酸合成了酰胺共轭物。通过A-seco-三萜丙醇衍生物与二羧酸酸酐反应制备了酯类化合物。合成化合物的抗病毒活性在对抗一型单纯疱疹病毒时进行了研究。最活跃的酰胺是5a (5.7 μM, MTC/EC50 32.2)。

  DOI：

  10.1007/s10600-014-0821-3
• 作为产物：
  描述：

  2-hydroxyimino-3-oxolup-20(29)-en-28-oic acid methyl ester 在 吡啶 、 chromium(III) oxide 、 sodium tetrahydroborate 、 硫酸 、 对甲苯磺酰氯 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 methyl 28-methoxy-28-oxo-1-cyano-2,3-seco-2-norlup-20(29)-en-3-oate
  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 and evaluation of antiviral activities of triterpenic conjugates with 2-aminobutan-1-ol as potent microbicidal agents
  作者：Irina A. Tolmacheva、Ekaterina V. Igosheva、Olga V. Savinova、Eugene I. Boreko、Vladimir F. Eremin、Victoria V. Grishko

  DOI：10.1007/s00044-019-02401-w

  日期：2019.10

  triterpenic A ring on the level of antiviral activity of triterpenic C3, C28 amides with a residue of racemic, (S), or (R)-enantiomeric 2-aminobutan-1-ol against herpes simplex viruses type I (HSV-I) and type II (HSV-II), as well as against human immunodeficiency virus type I (HIV-1) was investigated. The 2,3-secolupane racemic amide 5a was selected as a potent microbicidal agent with the highest virus inhibitory

  三萜A环的合成修饰对三萜C3，C28酰胺具有外消旋，（S）或（R）-对映异构体2-氨基丁烷-1-醇残基的抗病毒活性水平对单纯疱疹病毒的影响研究了I型（HSV-I）和II型（HSV-II）以及针对人类I型免疫缺陷病毒（HIV-1）的病毒。选择2,3-seculupane消旋酰胺5a作为有效的杀微生物剂，具有最高的病毒抑制作用（针对HSV-I和HSV-II）和杀病毒（针对HSV-1和HIV-1），其抗病毒活性由（S）-对映体共轭5b提供。
• 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。
• Synthesis of 2,3-seco-triterpene hydrazonohydrazides of the lupane and 19β,28-epoxy-18α-oleanane types
  作者：N. V. Galaiko、I. A. Tolmacheva、L. V. Volkova、V. V. Grishko

  DOI：10.1007/s10600-012-0161-0

  日期：2012.3

  Hydrazonohydrazides were synthesized by acid-catalyzed condensation of 2,3-seco-triterpene 1-cyano-3hydrazides with aldehydes. The antiviral action of the hydrazonohydrazides was studied against vesicular stomatitis Indiana virus.

  在酸催化下，2,3-seco-triterpene 1-cyano-3-hydrazides与醛缩合合成了肼酰肼。研究了这些酰肼对印第安纳水泡性口炎病毒的抗病毒作用。
• Synthesis and biological activity of mono- and diamides of 2,3-secotriterpene acids
  作者：I. A. Tolmacheva、E. V. Igosheva、Yu. B. Vikharev、V. V. Grishko、O. V. Savinova、E. I. Boreko、V. F. Eremin

  DOI：10.1134/s1068162013020143

  日期：2013.3

  Amides of four types were synthesized derived from 2,3-seco-18 alpha H-oleanane and 2,3-secolupane mono- and dicarboxylic acids. The spectrum of diamide derivatives was expanded with C3-C3' and C28-C28' biscondensed amides with two A-secotriterpene backbones obtained by the interaction of monocarboxylic A-seco acids with lysine. Among the synthesized monoand diamide derivatives, potential inhibitors of herpes simplex virus type 1 replication were found, namely, some compounds with an ethyl beta-alaninate fragment (EC50 8.7 and 4.1 mu M). The ethyl beta-alaninate diamide was shown to combine antiherpetic and anti-HIV activity (EC50 5.1 mu M). For the active compounds, the ratios of maximum tolerable concentrations to EC50 ranged from 9.7 to 40.8. The synthesized amides did not show any marked cytotoxic effects against human rabdomiosarcoma RD TE32, A549 lung carcinoma, and melanoma MS cell lines.