9-(2-chloro-2,3-dideoxy-β-D-threo-pentofuranosyl)adenine | 115913-80-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 9-(2-chloro-2,3-dideoxy-β-D-threo-pentofuranosyl)adenine
• 英文别名: 9H-Purin-6-amine, 9-(2-chloro-2,3-dideoxy-beta-D-threo-pentofuranosyl)-；[(2S,4S,5R)-5-(6-aminopurin-9-yl)-4-chlorooxolan-2-yl]methanol
• CAS: 115913-80-9
• 化学式: C₁₀H₁₂ClN₅O₂
• 分子量: 269.691
• InChiKey: RHPYWNXOKZLKEM-JFWOZONXSA-N

物化性质

• 沸点：
  591.5±60.0 °C(Predicted)
• 密度：
  1.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  9-(2-O-mesyl-3-deoxy-β-D-erythro-pentofuranosyl)adenine 在 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以37%的产率得到9-(2-chloro-2,3-dideoxy-β-D-threo-pentofuranosyl)adenine
  参考文献：
  名称：

  Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides

  摘要：

  A series of base-modified pyrimidine 3'-azido-2',3'-dideoxynucleosides and 3'-substituted purine and pyrimidine 2',3'-dideoxynucleosides have been synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV) replication in MT-4 cells. The following pyrimidine derivatives emerged as the most potent and/or selective inhibitors of HIV-induced cytopathogenicity (in order of decreasing selectivity: 3'-azido-3'-deoxythymidine (AZT), 3'-azido-2',3'-dideoxyuridine (AzddUrd), 3'-azido-2',3'-dideoxy-5-methylcytidine (AzddMeCyd), 3'-fluoro-ddUrd (FddUrd), 3'-fluoro-ddThd (FddThd), the N4-hydroxylated derivative of AzddMeCyd and the N4-methylated derivative of AzddMeCyd. Among the purine 2',3'-dideoxynucleosides, 3'-azido-2',3'-dideoxyguanosine (AzddGuo), 3'-fluoro-ddGuo (FddGuo), and 3'-fluoro-2,6-diaminopurine 2',3'-dideoxynucleoside (FddDAPR) were the most selective inhibitors of HIV replication.

  DOI：

  10.1021/jm00118a033

文献信息

• HERDEWIJN, PIET;BALZARINI, JAN;BADA, MASANORI;PAUWELS, RUDI;VAN, AERSCHOT+, J. MED. CHEM., 31,(1988) N 10, C. 2040-2048
  作者：HERDEWIJN, PIET、BALZARINI, JAN、BADA, MASANORI、PAUWELS, RUDI、VAN, AERSCHOT+

  DOI：——

  日期：——
• NUCLEOSIDE DERIVATIVES
  申请人：NYCOMED IMAGING AS

  公开号：EP0523110A1

  公开（公告）日：1993-01-20
• [EN] NUCLEOSIDE DERIVATIVES
  申请人：——

  公开号：WO1991015498A2

  公开（公告）日：1991-10-17

  [EN] Nucleoside compounds of formula (I): Y<1>O-G-X wherein Y<1> is a hydrogen atom or an acyl or acyloxymethyl group; G is the residue of the glycone moiety of the nucleoside; and X is a purine or pyrimidine base or an ester, amide or acyloxyalkyl derivative thereof. The compounds have antiviral activity.
  [FR] Composés nucléosidiques répondant à la formule (I): Y1O-G-X dans laquelle Y1 est un atome d'hydrogène ou un groupe acyle ou acyloxyméthyle; G est le résidu de la moitié glycone du nucléoside; et X est une base de purine ou de pyrimidine ou un dérivé ester, amide ou acyloxyalkyle de cette base. Les composés présentent une activité antivirale.
• Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides
  作者：Piet Herdewijn、Jan Balzarini、Masanori Baba、Rudi Pauwels、Arthur Van Aerschot、Gerard Janssen、Erik De Clercq

  DOI：10.1021/jm00118a033

  日期：1988.10

  A series of base-modified pyrimidine 3'-azido-2',3'-dideoxynucleosides and 3'-substituted purine and pyrimidine 2',3'-dideoxynucleosides have been synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV) replication in MT-4 cells. The following pyrimidine derivatives emerged as the most potent and/or selective inhibitors of HIV-induced cytopathogenicity (in order of decreasing selectivity: 3'-azido-3'-deoxythymidine (AZT), 3'-azido-2',3'-dideoxyuridine (AzddUrd), 3'-azido-2',3'-dideoxy-5-methylcytidine (AzddMeCyd), 3'-fluoro-ddUrd (FddUrd), 3'-fluoro-ddThd (FddThd), the N4-hydroxylated derivative of AzddMeCyd and the N4-methylated derivative of AzddMeCyd. Among the purine 2',3'-dideoxynucleosides, 3'-azido-2',3'-dideoxyguanosine (AzddGuo), 3'-fluoro-ddGuo (FddGuo), and 3'-fluoro-2,6-diaminopurine 2',3'-dideoxynucleoside (FddDAPR) were the most selective inhibitors of HIV replication.