9-[(1'R,4'S)-4'-hydroxy-2'-cyclopenten-1'-yl]-9-H-N⁶-benzoyladenine | 150018-17-0

• 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,4'S)-4'-hydroxy-2'-cyclopenten-1'-yl]-9-H-N⁶-benzoyladenine
• 英文别名: (1R,4S)-N⁶-Benzoyl-9-(4-hydroxy-2-cyclopenten-1-yl)-9H-adenine；N-(9-((1R,4S)-4-hydroxycyclopent-2-en-1-yl)-9H-purin-6-yl)benzamide；N-[9-[(1R,4S)-4-hydroxycyclopent-2-en-1-yl]purin-6-yl]benzamide
• CAS: 150018-17-0
• 化学式: C₁₇H₁₅N₅O₂
• 分子量: 321.338
• InChiKey: JSYCEHPLTOQMCV-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  92.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-[(1'R,4'S)-4'-hydroxy-2'-cyclopenten-1'-yl]-9-H-N⁶-benzoyladenine 在 甲醇 、 四氧化锇 、 N-甲基吲哚酮 、 氨 、 水 、 原甲酸三乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 (-)-β-(4'β-hydroxy-2'α,3'α-O-isopropylidenedioxycyclopent-1'-yl)-9-H-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：

  (1S,4R)-顺式-4-乙酰氧基-2-环戊烯-1-醇 、 N6-苯甲酰基腺嘌呤 在 四(三苯基膦)钯 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 以59%的产率得到9-[(1'R,4'S)-4'-hydroxy-2'-cyclopenten-1'-yl]-9-H-N⁶-benzoyladenine
  参考文献：
  名称：

  Synthesis of (+)-5'-nor-2'-deoxyaristeromycin and (-)-5'-nor-3'-deoxyaristeromycin

  摘要：

  DOI：

  10.1021/jo00075a052

文献信息

• Cyclopentane-Based Modulators of STING (Stimulator of Interferon Genes)
  申请人：PFIZER INC.

  公开号：US20190284216A1

  公开（公告）日：2019-09-19

  Compounds of the general formula (I): or a pharmaceutically acceptable salt thereof, processes for the preparation of these compounds, compositions containing these compounds, and the uses of these compounds.

  通式（I）的化合物，或其药用盐，这些化合物的制备方法，含有这些化合物的组合物，以及这些化合物的用途。
• Cyclopentane-based modulators of STING (stimulator of interferon genes)
  申请人：PFIZER INC.

  公开号：US10968242B2

  公开（公告）日：2021-04-06

  Compounds of the general formula (I): or a pharmaceutically acceptable salt thereof, processes for the preparation of these compounds, compositions containing these compounds, and the uses of these compounds.

  通式 (I) 的化合物： 或其药学上可接受的盐、制备这些化合物的工艺、含有这些化合物的组合物以及这些化合物的用途。
• Synthesis of base-modified noraristeromycin derivatives and their inhibitory activity against human and Plasmodium falciparum recombinant S-adenosyl-l-homocysteine hydrolase
  作者：Yukio Kitade、Atushi Kozaki、Toshihiro Miwa、Masayuki Nakanishi

  DOI：10.1016/s0040-4020(01)01247-9

  日期：2002.2

  Noraristeromycin derivatives possessing 2- or 8-position modified adenine or 8-aza-7-deazaadenine were synthesized, and their inhibitory activity against human and Plasmodium falciparum (P. falciparum) recombinant SAH hydrolases was investigated. Among these noraristeromycin derivatives, 2-aminonoraristeromycin selectively showed inhibitory activity against P. falciparum recombinant SAH hydrolase. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 5‘-Amino-5‘-deoxy-5‘-noraristeromycin
  作者：Vishnumurthy R. Hegde、Katherine L. Seley、Stewart W. Schneller、Thomas J. J. Elder

  DOI：10.1021/jo972078c

  日期：1998.10.1
• CYCLOPENTANE-BASED MODULATORS OF STING (STIMULATOR OF INTERFERON GENES)
  申请人：Pfizer Inc.

  公开号：EP3765474A1

  公开（公告）日：2021-01-20