9-[(1'R,2'S,3'R)-2',3'-O-isopropylidenedioxy-4'-cyclopenten-1'-yl]-9-H-adenine | 263721-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-[(1'R,2'S,3'R)-2',3'-O-isopropylidenedioxy-4'-cyclopenten-1'-yl]-9-H-adenine
• 英文别名: 9-[(3aS,4R,6aR)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]purin-6-amine
• CAS: 263721-48-8
• 化学式: C₁₃H₁₅N₅O₂
• 分子量: 273.294
• InChiKey: LSKGFYBDLUHSLV-MRTMQBJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  88.08
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  9-[(1'R,2'S,3'R)-2',3'-O-isopropylidenedioxy-4'-cyclopenten-1'-yl]-9-H-adenine 在 三氟乙酸 作用下， 反应 0.25h， 以100%的产率得到(-)-9β-(2'α,3'α-dihydroxypent-4'-enyl)adenine
  参考文献：
  名称：

  Facile synthesis of 9-[(1′R,2′S)-2′-hydroxy-3′-oxocyclopentan-1′-yl]-9-H-adenine possessing inhibitory activity against human recombinant S-adenosyl-l-homocysteine hydrolase

  摘要：

  Treatment of 4'-O-methanesulfonyl-2',3'-O-isopropylideneoraisteromycin with KOBut gave the corresponding 3',4'-dehydro derivative, and subsequent deprotection resulted in the formation of 9-[(1'R,2'S)-2'-hydroxy-3'-oxocyclopentan-1'-yl]-9-H-adenine possessing inhibitory activity against human recombinant S-adenosyl-L homocysteine hydrolase (EC 3.3.1.1). In sharp contrast to KOBut, when lithium azide was adopted as a base, 9-[(1'R,2'S,3'R)-2',3'-O-isopropylidened ioxy-4'-cyclopenten-1'-yl]-H-adenine was selectively obtained, and subsequent deprotection afforded DHCeA, which is a well-known potential antiviral agent. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01978-x
• 作为产物：
  描述：

  (3AS,4S,6AR)-2,2-二甲基-3A,6A-二氢-4H-环戊[D][1,3]二噁酚-4-醇 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二甲酸二异丙酯 、 水 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 124.0h， 生成 9-[(1'R,2'S,3'R)-2',3'-O-isopropylidenedioxy-4'-cyclopenten-1'-yl]-9-H-adenine
  参考文献：
  名称：

  Carbocyclic Isoadenosine Analogues of Neplanocin A

  摘要：

  Isoadenosine (IsoA), a structural isomer of adenosine, was shown to possess interesting biological activity but was inherently unstable. In an effort to overcome this, we have designed a series of carbocyclic IsoA analogues, combining the unique connectivity of IsoA with the structural features of some biologically significant Neplanocin A analogues. Their design, synthesis, and structural elucidation is reported.

  DOI：

  10.1021/ol035696q

文献信息

• Synthesis of fluorinated cyclopentenyladenine as potent inhibitor of S -adenosylhomocysteine hydrolase
  作者：Hea Ok Kim、Su Jeong Yoo、Hee Sung Ahn、Won Jun Choi、Hyung Ryong Moon、Kang Man Lee、Moon Woo Chun、Lak Shin Jeong

  DOI：10.1016/j.bmcl.2004.02.039

  日期：2004.5

  Fluoro-DHCeA (4) was efficiently synthesized from D-cyclopentenone derivative 5 using electrophilic fluorination as a key step. Fluoro-DHCeA (4) was found to be as potent as DHCeA (3), but exhibited irreversible inhibition of enzyme unlike DHCeA (3) showing reversible inhibition. From this Study, 4'-hydroxymethyl groups of neplanocin A and fluoro-neplanocin A played an important role in binding to the active site of the enzyme. (C) 2004 Elsevier Ltd. All rights reserved.