(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-carbonyl chloride | 1416254-40-4

• 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: (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-carbonyl chloride
• CAS: 1416254-40-4
• 化学式: C₃₀H₄₄ClNO₂
• 分子量: 486.138
• InChiKey: OHQMUKGZOLQTTL-INPVNEGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 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：
  57.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氨基-1-丁醇 、 (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-carbonyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以42%的产率得到N-[1-cyano-2,3-seco-2-norlup-20(29)-en-3-al-28-oyl]-(2R,S)-aminobutan-1-ol
  参考文献：
  名称：

  以2-氨基丁烷-1-醇为有效杀菌剂的三萜共轭物的合成和抗病毒活性评估

  摘要：

  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。

  DOI：

  10.1007/s00044-019-02401-w
• 作为产物：
  描述：

  路路通酸 在 sodium tetrahydroborate 、 氯化亚砜 、 potassium tert-butylate 、 亚硝酸异戊酯 作用下， 以 甲醇 、 二氯甲烷 、 叔丁醇 为溶剂， 生成 (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-carbonyl chloride
  参考文献：
  名称：

  羽扇豆和α-癸烷烯丙酰胺的合成

  摘要：

  由桦木酸制备在环 A 中具有 α-酮肟和 α-羟基肟基团的 Lupane C-28 单烯丙酰胺。以 A-secolupane C-3(28) 单和二烯丙酰胺的形成为例，证明了通过草酰氯或草酰氯裂解桦木脑和桦木酸 α-肟，可以一步合成 2,3-次三萜酰胺。亚硫酰氯，随后由烯丙胺原位形成的 2,3-次氯三萜酸进行酰胺化。与之前描述的从桦木酸制备 A-secotriteperene 酰胺的五步方法相比，所提出的方法使 2,3-secolupane C-3,C-28 二酰胺的产率提高了五倍。

  DOI：

  10.1007/s10600-013-0582-4

文献信息

• Synthesis and antiviral activity of C-3(C-28)-substituted 2,3-seco-triterpenoids
  作者：I. A. Tolmacheva、E. V. Igosheva、O. V. Savinova、E. I. Boreko、V. V. Grishko

  DOI：10.1007/s10600-014-0821-3

  日期：2014.1

  Amide conjugates with four structural types of β-amino alcohols were synthesized from 2,3-seco-18αH-oleananoic and 2,3-seco-lupane C-3(C-28) mono- and dicarboxylic acids. Esters were prepared by reaction of C-3-hydroxy derivatives of A-seco-triterpenoids with dicarboxylic acid anhydrides. The antiviral activity of the synthesized compounds was studied against herpes simplex virus type I. The most active amide was 5a (5.7 μM, MTC/EC50 32.2).

  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)。
• 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.
• 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 a-secolupane allylamides
  作者：G. F. Krainova、I. A. Tolmacheva、M. N. Gorbunova、V. V. Grishko

  DOI：10.1007/s10600-013-0582-4

  日期：2013.5

  C-3(28) mono- and diallylamides was used as an example to demonstrate that a one-step synthesis of 2,3-secotriterpene amides was possible by fragmentation of betulin and betulonic acid α-oximes by oxalylchloride or thionylchloride with subsequent amidation of the 2,3-secotriterpenoic acids formed in situ by allylamine. The proposed method enabled the yield of 2,3-secolupane C-3,C-28 diamides to be increased

  由桦木酸制备在环 A 中具有 α-酮肟和 α-羟基肟基团的 Lupane C-28 单烯丙酰胺。以 A-secolupane C-3(28) 单和二烯丙酰胺的形成为例，证明了通过草酰氯或草酰氯裂解桦木脑和桦木酸 α-肟，可以一步合成 2,3-次三萜酰胺。亚硫酰氯，随后由烯丙胺原位形成的 2,3-次氯三萜酸进行酰胺化。与之前描述的从桦木酸制备 A-secotriteperene 酰胺的五步方法相比，所提出的方法使 2,3-secolupane C-3,C-28 二酰胺的产率提高了五倍。