1-cyano-2,3-seco-2-norlup-20(29)-en-3-al-28-oic acid | 1205673-84-2

• 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: 1-cyano-2,3-seco-2-norlup-20(29)-en-3-al-28-oic acid
• 英文别名: 2,3-seco-1-cyanolup-20(29)-en-3-al-28-oic acid；(3R,4R,5R,8R,9R,10R,13S,14R,15R)-4-(cyanomethyl)-4,9,10-trimethyl-3-(2-methyl-1-oxopropan-2-yl)-15-prop-1-en-2-yl-2,3,5,6,7,8,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-13-carboxylic acid
• CAS: 1205673-84-2
• 化学式: C₃₀H₄₅NO₃
• 分子量: 467.692
• InChiKey: MHLBXLHEIGKUET-INPVNEGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-cyano-2,3-seco-2-norlup-20(29)-en-3-al-28-oic acid 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-cyano-2,3-seco-2-norlup-20(29)-en-3-al-28-oic acid 2-(indol-3-yl)ethylamide
  参考文献：
  名称：

  Synthesis and biological activity of mono- and diamides of 2,3-secotriterpene acids

  摘要：

  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.

  DOI：

  10.1134/s1068162013020143
• 作为产物：
  描述：

  路路通酸 在 吡啶 、 sodium tetrahydroborate 、 4-methyl-1-nitrosooxy-pentane 、 potassium tert-butylate 、 对甲苯磺酰氯 作用下， 以 甲醇 、 叔丁醇 为溶剂， 生成 1-cyano-2,3-seco-2-norlup-20(29)-en-3-al-28-oic acid
  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 and antiviralactivity of 2,3-seco-derivatives of betulonic acid
  作者：I. A. Tolmacheva、V. V. Grishko、E. I. Boreko、O. V. Savinova、N. I. Pavlova

  DOI：10.1007/s10600-009-9436-5

  日期：2009.9

  A lupane 2,3-seco-aldehydoacid that was oxidized further to the 2,3-seco-diacid was synthesized by Beckmann fragmentation of the α-hydroxyoxime of betulonic acid. It was found that both 2,3-seco-derivatives were capable of suppresing reproduction of Herpes type 1 and flu A viruses (EC50 from 1.9 to 21.3 μM).

  通过贝克曼重排反应，将桦木酮酸的α-羟基肟分解合成了A lupane 2,3-裂醛酸，并进一步氧化为2,3-裂二酸。研究发现，这两种2,3-裂衍生物均能抑制I型单纯疱疹病毒和甲型流感病毒的复制（EC50值从1.9到21.3微摩尔）。
• Functionalization, cyclization and antiviral activity of A-secotriterpenoids
  作者：Victoria V. Grishko、Natalia V. Galaiko、Irina A. Tolmacheva、Igor I. Kucherov、Vladimir F. Eremin、Eugene I. Boreko、Olga V. Savinova、Pavel A. Slepukhin

  DOI：10.1016/j.ejmech.2013.12.058

  日期：2014.8

  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.
• The immunotropic activity of lupane and oleanane 2,3-seco-triterpenoids
  作者：L. V. Anikina、I. A. Tolmacheva、Yu. B. Vikharev、V. V. Grishko

  DOI：10.1134/s1068162010020147

  日期：2010.3

  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.
• 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.