(1R,4S)-1-(9-adenyl)-4-hydroxycyclopent-2-ene | 142695-05-4

• 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
• 英文名称: (1R,4S)-1-(9-adenyl)-4-hydroxycyclopent-2-ene
• 英文别名: (1R,4S)-9-(4-Hydroxy-2-cyclopenten-1-yl)-9H-adenine；(1R,4S)-9-(4-hydroxycyclopent-2-en-1-yl)adenine；(+)-<(1'R,4'S)-4'-hydroxy-2'-cyclopenten-1'-yl>-9-H-adenine；(1'R,4'S)-9-(4'-hydroxycyclopent-2'-enyl)adenine；(+/-)-9-(4-β-Hydroxycyclopent-2-ene-1-β-yl)adenine；(-)-9-(4'-hydroxy-2'-cyclopenten-1'-yl)adenine；(1S,4R)-4-(6-aminopurin-9-yl)cyclopent-2-en-1-ol
• CAS: 142695-05-4
• 化学式: C₁₀H₁₁N₅O
• 分子量: 217.23
• InChiKey: LBGHDVYWPMQKBS-NKWVEPMBSA-N

物化性质

• 沸点：
  520.9±60.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  89.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,4S)-1-(9-adenyl)-4-hydroxycyclopent-2-ene 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以49%的产率得到9-[(1'R,4'R)-4'-fluoro-2'-cyclopenten-1'-yl]-9H-adenine
  参考文献：
  名称：

  4′-Fluorinated carbocyclic nucleosides: Synthesis and inhibitory activity against S-adenosyl-l-homocysteine hydrolase

  摘要：

  4 '-Fluorinated analogue of 9-[(1 ' R,2 ' S,3 ' R)-2 ',3 '-dihydroxy-eyelopentan-1 '-yl]adenine (DHCaA) and their related analogues were systematically synthesized under the Mitsunobu and palladium(O) coupling conditions followed by fluorination with inversion of the configuration by using diethylammosulfur trifluoride, respectively. 4 '-P-Fluoro DHCaA and 2-amino-4 '-alpha-fluoro DHCaA demonstrated slight inhibitory activity against human and Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase, respectively.(c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.04.023
• 作为产物：
  描述：

  (1S,4R)-4-(6-chloro-9H-purin-9-yl)cyclopent-2-en-1-ol 在 氨 作用下， 以 甲醇 为溶剂， 生成 (1R,4S)-1-(9-adenyl)-4-hydroxycyclopent-2-ene
  参考文献：
  名称：

  从一种常见的对映体纯的起始原料合成四种可能的立体异构5'-碳环核苷

  摘要：

  从常见的对映体纯的烯丙基单乙酸酯1开始，已开发出四种立体异构体对映体纯的5'-去碳环核苷2b，ent - 2b，3b和ent - 3b的灵活合成方法。

  DOI：

  10.1016/s0040-4039(00)73022-x

文献信息

• Phosphonomethoxy carbocyclic nucleosides and nucleotides
  申请人：Institute of Organic Chemistry and Biochemistry of the Academy of

  公开号：US05744600A1

  公开（公告）日：1998-04-28

  A compound of the Formula I or Formula II ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen, hydroxy, chlorine, fluorine, bromine, or an organic substituent having 1 to 5 carbon atoms and selected from acyloxy having a hydrocarbon stem of 1 to 4 carbon atoms, alkoxy, alkylthio, amino, alkylamino and dialkylamino; R.sup.3 and R.sup.4 are independently hydrogen, or organic phosphonic ester substituents having 1 to 12 carbon atoms and selected from alkyl, alkenyl, aryl, and aralkyl; and B is a heterocyclic group selected from the group consisting of pyrimidine, purine, triazine, deazapurine, and triazole, attached through a ring nitrogen atom thereof optionally substituted with 1 to 3 substituents selected from the group consisting of hydroxy, mercapto, amino, hydrazino, fluoro, chloro, bromo, iodo, C.sub.1 to C.sub.3 alkyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C1-C3 alkoxy, and C1-C3 alkylthio; and the pharmaceutically acceptable acid addition, metal, and amine salts thereof. The compositions of the invention are useful for, among other things, antiviral agents.

  公式I或公式II的化合物##STR1##其中R.sup.1和R.sup.2分别是氢、羟基、氯、氟、溴或有1至5个碳原子的有机取代基，选自具有1至4个碳原子的烃基茎的酰氧基、烷氧基、烷基硫基、氨基、烷基氨基和二烷基氨基; R.sup.3和R.sup.4分别是氢，或有1至12个碳原子的有机膦酸酯取代基，选自烷基、烯基、芳基和芳基烷基; B是从嘧啶、嘌呤、三嗪、去氧嘌呤和三唑组成的异环族，通过其环氮原子连接，可选地取代有1至3个取代基，选自羟基、巯基、氨基、双氨基、氟、氯、溴、碘、C.sub.1至C.sub.3烷基、C2-C3烯基、C2-C3卤代烯基、C1-C3烷氧基和C1-C3烷基硫基;以及其药学上可接受的酸盐、金属盐和胺盐。本发明的组合物可用于抗病毒药物等用途。
• Uracil-Containing Heterodimers of a New Type: Synthesis and Study of Their Anti-Viral Properties
  作者：Anna A. Maslova、Elena S. Matyugina、Robert Snoeck、Graciela Andrei、Sergey N. Kochetkov、Anastasia L. Khandazhinskaya、Mikhail S. Novikov

  DOI：10.3390/molecules25153350

  日期：——

  Widespread latent herpes viral infections within a population can lead to the development of co-infections in HIV-infected patients. These infections are not particularly dangerous for healthy individuals and often occur with minimal symptoms, but for those who are immunocompromised, these infections can accelerate the acute phase of HIV infection and AIDS. Thus, the idea of designing compounds that could combine activity against HIV and co-infections would seem promising. In that regard, eleven compounds were synthesized that represent conjugates of non-nucleoside HIV reverse transcriptase inhibitors and nucleoside inhibitors of the herpes family viruses with the hope that these novel heterodimers will result in dual activity against HIV and concomitant herpes virus infections.

  广泛存在的潜在疱疹病毒感染可能导致HIV感染患者出现共感染。这些感染对健康个体通常不特别危险，并且通常以轻微症状发生，但对于免疫受损的人来说，这些感染可能加速HIV感染和艾滋病的急性阶段。因此，设计能够同时对抗HIV和共感染的化合物的想法似乎很有前途。在这方面，合成了十一种代表非核苷类HIV逆转录酶抑制剂和疱疹家族病毒核苷类抑制剂的共轭物，希望这些新颖的异源二聚体将对HIV和同时存在的疱疹病毒感染具有双重活性。
• Stereocontrolled synthesis of the four stereoisomeric diphosphorylphosphonates of carbocyclic 2′,3′-dideoxy-2′,3′-didehydro-5′-noradenosine
  作者：Natalia B. Dyatkina、Fritz Theil、Martin von Janta-Lipinski

  DOI：10.1016/0040-4020(94)00986-5

  日期：1995.1

  A flexible synthesis of the four stereoisomeric enantiomerically pure 5′-nor carbocyclic adenosine analogues 4b, ent-4b, 5b and ent-5b starting from the common enantio-merically pure allylic monoacetate 3 has been developed. Each of the nucleoside analogues was transformed into the corresponding 4′-phosphonates and subsequently into the diphosphoryl-phosphonates 4e, ent-4e, 5e, and ent-5e, respectively

  已经开发了从常见的对映体纯的烯丙基单乙酸酯3开始的四个立体异构对映体纯的5'-去碳环腺苷类似物4b，ent - 4b，5b和ent - 5b的灵活合成。将每个核苷类似物分别转化为相应的4'-膦酸酯，然后分别转化为二磷酸基膦酸酯4e，ent - 4e，5e和ent - 5e。
• Carbocyclic Nucleosides as Inhibitors of Human Tumor Necrosis Factor-α Production:  Effects of the Stereoisomers of (3-Hydroxycyclopentyl)adenines
  作者：David R. Borcherding、Norton P. Peet、H. Randall Munson、Hao Zhang、Paul F. Hoffman、Terry L. Bowlin、Carl K. Edwards

  DOI：10.1021/jm950906t

  日期：1996.1.1

  A series of four structurally related carbocyclic nucleosides (6a, 6b, 10a, and 10b) were synthesized and evaluated for their ability to inhibit tumor necrosis factor-alpha (TNF-alpha), interleukin-1 beta (IL-1 beta), and interleukin-6 (IL-6) production from human primary macrophages. These compounds had little effect on the production of IL-1 beta and IL-6. It was determined that compound 10a was

  合成了一系列四个结构相关的碳环核苷（6a，6b，10a和10b），并评估了它们抑制肿瘤坏死因子-α（TNF-α），白介素-1β（IL-1 beta）和从人类原代巨噬细胞中产生白介素6（IL-6）。这些化合物对IL-1β和IL-6的产生几乎没有影响。已确定化合物10a是最有效的TNF-α抑制剂（IC50 = 10 microM），与其对映异构体10b或其非对映异构体6a和6b相比，活性高2至5倍。此外，还测试了这些化合物保护小鼠免受脂多糖（LPS）和D-半乳糖胺（D-Gal）致命攻击的能力。
• Expeditious enantioselective synthesis of carbocyclic nucleosides with antileishmanial activity
  作者：Adilson D. Da Silva、Elaine S. Coimbra、Jean-Louis Fourrey、Antonio S. Machado、Malka Robert-Géro

  DOI：10.1016/s0040-4039(00)61691-x

  日期：1993.10

  A short synthesis of the neplanocin A analogue 1, lacking the hydroxymethylene at C-4 of the parent naturally occurring carbocyclic nucleoside, is described. Moreover, the non toxic noraristeromycin 3, an intermediate in the synthetic scheme, was shown to exhibit a promising anti-leishmanial activity.

  描述了neplanocin A类似物1的简短合成，该类似物在亲本天然存在的碳环核苷的C-4处缺少羟亚甲基。此外，合成方案中的中间体无毒诺拉霉素3被证明具有良好的抗利什曼活性。