cholesteryl 2-cyanoethyl N,N-diisopropylphosphoramidite | 143723-63-1

• 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: cholesteryl 2-cyanoethyl N,N-diisopropylphosphoramidite
• 英文别名: 3-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
• CAS: 143723-63-1
• 化学式: C₃₆H₆₃N₂O₂P
• 分子量: 586.882
• InChiKey: GEWXBLDKGPFRKC-BJIOHNQXSA-N

物化性质

• 沸点：
  594.2±39.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cholesteryl 2-cyanoethyl N,N-diisopropylphosphoramidite 在 四氮唑 、 碘 作用下， 以 乙腈 为溶剂， 反应 0.67h， 生成 3'-azido-3'-deoxythymidine-5'-<(cholest-5-en-3β-yl) (β-cyanoethyl)> phosphate
  参考文献：
  名称：

  Synthesis and Anti-HIV Activity of Alkyl Steroidal 3′-Azido-3′-deoxythymidin-5′-yl Phosphotriesters as Prodrugs of AZT

  摘要：

  Alkyl steroidal AZT 5'-monophosphate triesters are designed as lipophilic prodrugs of AZT to improve its therapeutic efficiency. We have synthesized four phosphotriesters of AZT, in one-pot, using phosphoramidite-phosphite triester methodology. This method afforded the desired prodrugs in high yields under mild conditions. The in vitro evaluation of anti-HIV activity of these prodrugs is also reported.

  DOI：

  10.1080/15257779408010667
• 作为产物：
  描述：

  胆固醇 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以95%的产率得到cholesteryl 2-cyanoethyl N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  NUCLEIC ACID DERIVATIVE HAVING IMMUNOSTIMULATORY ACTIVITY

  摘要：

  本发明的目的是提供包含如下所述CpG寡核苷酸的双链寡核苷酸，作为一种具有免疫刺激活性的核酸衍生物。 一种包含双链寡核苷酸的佐剂，其中 第一链是由8到50个核苷酸组成的CpG寡核苷酸， 第二链是由8到60个核苷酸组成的寡核苷酸，并且包括 能够与第一链杂交的序列，以及通过连接器与第二链结合的脂质。

  公开号：

  US20180264105A1

文献信息

• Biologically Active Oligodeoxyribonucleotides - II¹: Structure Activity Relationships of Anti-HIV-1 Pentadecadeoxyribonucleotides Bearing 5′-End-Modifications
  作者：Hitoshi Hotoda、Kenji Momota、Hidehiko Furukawa、Takemichi Nakamura、Masakatsu Kaneko、Satcshi Kimura、Kawu Shimada

  DOI：10.1080/15257779408012159

  日期：1994.7

  5'-End-modified pentadecadeoxyribonucleotides (15mers) with a sequence complementary to the tat 2nd splicing acceptor region of human immunodeficiency virus type 1 (HIV-1) were prepared and evaluated for anti-HIV-1 activity. The structures of modified 15mers were confirmed by negative ion LSI mass spectroscopy, and the anti-HIV-1 activities were evaluated in vitro by MTT assay using MT-4 cells. While the unmodified 15mer had no activity in our assay system, the 15mers bearing modifications with trityl-type substituents at the 5'-end showed potent anti-HIV-1 activities.