[1R-(1α,2α,3β)]-3-(6-氨基-9H-嘌呤-9-基)-5-(羟甲基)-4-环戊烯-1,2-二醇 | 156407-85-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 中文名称: [1R-(1α,2α,3β)]-3-(6-氨基-9H-嘌呤-9-基)-5-(羟甲基)-4-环戊烯-1,2-二醇
• 英文名称: (+)-neplanocin A
• 英文别名: (1R,2S,5S)-5-(6-aminopurin-9-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol
• CAS: 156407-85-1
• 化学式: C₁₁H₁₃N₅O₃
• 分子量: 263.256
• InChiKey: XUGWUUDOWNZAGW-CNUIFLNQSA-N

物化性质

• 沸点：
  632.6±65.0 °C(Predicted)
• 密度：
  1.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (+/-)-2,2-dimethyl-3αβ,6αβ-dihydro-4H-cyclopenta-1,3-dioxol-4-one 在 吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 氨 、 双氧水 、 三苯基膦 、 三氟乙酸 、 lithium diisopropyl amide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 环己烷 为溶剂， 反应 43.5h， 生成 [1R-(1α,2α,3β)]-3-(6-氨基-9H-嘌呤-9-基)-5-(羟甲基)-4-环戊烯-1,2-二醇
  参考文献：
  名称：

  Enantiomeric Synthesis of d- and l-Cyclopentenyl Nucleosides and Their Antiviral Activity Against HIV and West Nile Virus

  摘要：

  Enantiomeric synthesis Of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus are described. The key intermediate (-)- and (+)-cyclopentenyl alcohols (7 and 15) were prepared from D-gamma -ribonolactone and D-ribose, respectively. Coupling of 7 with appropriately blocked purine and pyrimidine bases via the Mitsunobu reaction followed by deprotection afforded the target L-(+)-cyclopentenyl nucleosides (24-28, 31, 33, and 36). D-(-)Cyclopentenyl nucleosides (1, 40, 43, and 52-56) were also prepared by a similar procedure for L-isomers from 15. The synthesized compounds were evaluated for their antiviral activity against two RNA viruses: HIV and West Nile virus. Among the synthesized D-(-)-nucleosides, adenine (1, neplanocin A), cytosine (55, CPE-C), and 5-fluorocytosine (56) analogues exhibited moderate to potent anti-HIV activity (EC50 0.1, 0.06, and 5.34 muM, respectively) with significant cytotoxicity in PBM, Vero, and CEM cells. Also, cytosine (55) and 5-fluorocytosine (56) analogues exhibited the most potent anti-West Nile virus activity (EC50 0.2-3.0 and 15-20 muM, respectively). Among L-(+)-nucleosides, only the cytosine (27) analogue exhibited weak anti-HIV activity (EC50 58.9 muM).

  DOI：

  10.1021/jm010256v

文献信息

• Total synthesis of carbocyclic nucleoside (+)-neplanocin A
  作者：Young Hoon Jung、Seung In Kim、Yeon Ju Hong、Sook Jin Park、Kyung Tae Kang、So Yeon Kim、In Su Kim

  DOI：10.1016/j.tet.2014.12.093

  日期：2015.2

  Asymmetric total synthesis of (+)-neplanocin A was concisely achieved from readily available d-galactose via the regioselective and diastereoselective amination of carbocyclic polybenzyl ether using chlorosulfonyl isocyanate and intramolecular olefin metathesis using second-generation Grubbs catalyst.

  使用氯磺酰基异氰酸酯通过碳环聚苄基醚的区域选择性和非对映选择性胺化以及使用第二代Grubbs催化剂进行的分子内烯烃复分解，从易于获得的d-半乳糖简明地实现了（+）-neplanocin A的不对称全合成。
• Synthesis of (+)-Neplanocin A from a Chromium−Carbene Complex-Derived Optically Active Butenolide
  作者：L. S. Hegedus、L. Geisler

  DOI：10.1021/jo000154x

  日期：2000.6.1
• Enantiomeric Synthesis of <scp>d</scp>- and <scp>l</scp>-Cyclopentenyl Nucleosides and Their Antiviral Activity Against HIV and West Nile Virus
  作者：Gyu Y. Song、Vincent Paul、Hyunah Choo、John Morrey、Robert W. Sidwell、Raymond F. Schinazi、Chung K. Chu

  DOI：10.1021/jm010256v

  日期：2001.11.1

  Enantiomeric synthesis Of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus are described. The key intermediate (-)- and (+)-cyclopentenyl alcohols (7 and 15) were prepared from D-gamma -ribonolactone and D-ribose, respectively. Coupling of 7 with appropriately blocked purine and pyrimidine bases via the Mitsunobu reaction followed by deprotection afforded the target L-(+)-cyclopentenyl nucleosides (24-28, 31, 33, and 36). D-(-)Cyclopentenyl nucleosides (1, 40, 43, and 52-56) were also prepared by a similar procedure for L-isomers from 15. The synthesized compounds were evaluated for their antiviral activity against two RNA viruses: HIV and West Nile virus. Among the synthesized D-(-)-nucleosides, adenine (1, neplanocin A), cytosine (55, CPE-C), and 5-fluorocytosine (56) analogues exhibited moderate to potent anti-HIV activity (EC50 0.1, 0.06, and 5.34 muM, respectively) with significant cytotoxicity in PBM, Vero, and CEM cells. Also, cytosine (55) and 5-fluorocytosine (56) analogues exhibited the most potent anti-West Nile virus activity (EC50 0.2-3.0 and 15-20 muM, respectively). Among L-(+)-nucleosides, only the cytosine (27) analogue exhibited weak anti-HIV activity (EC50 58.9 muM).