(1S,2Xi)-1-(2-氨基-4-氧代-4,7-二氢-1H-吡咯并[3,2-d]嘧啶-7-基)-1,4-脱水-D-苏-戊糖醇 | 102731-45-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1S,2Xi)-1-(2-氨基-4-氧代-4,7-二氢-1H-吡咯并[3,2-d]嘧啶-7-基)-1,4-脱水-D-苏-戊糖醇
• 英文名称: 9-deazaguanosine
• 英文别名: 2-Amino-7-((2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-pyrrolo[3,2-d]pyrimidin-4(5H)-one；2-amino-7-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one
• CAS: 102731-45-3
• 化学式: C₁₁H₁₄N₄O₅
• 分子量: 282.256
• InChiKey: RBYIXGAYDLAKCC-GXTPVXIHSA-N

物化性质

• 熔点：
  259-264°C
• 密度：
  2.15±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于二甲基亚砜、甲醇、水

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  153
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2Xi)-1-(2-氨基-4-氧代-4,7-二氢-1H-吡咯并[3,2-d]嘧啶-7-基)-1,4-脱水-D-苏-戊糖醇 在 咪唑 、 六甲基二硅氮烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-isobutyrylamino-7-(5-tert-butyldiphenylsilyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidin-4-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2',3'-Didehydro-2',3'-Dideoxy-9-Deazaguanosine, a Monophosphate Prodrug and Two Analogues, 2',3'-Dideoxy-9-Deazaguanosine and 2',3'-Didehydro-2',3'-Dideoxy-9-Deazainosine

  摘要：

  2',3'-Didehydro-2',3'-dideoxy-9-deazaguanosine (1), its monaphosphate prodrug (2), and two analogues, 2',3'-dideoxy-9-deazaguanosine (3) and 2',3'-didehydro-2',3'-dideoxy-9-deazainosine (4), have been synthesized from benzoylated 9-deazaguanosine (5). Basic hydrolysis of 5, selective protection of the 2-amino and 5'-hydroxy functions with isobulyryl and silyl groups, respectively, followed by reaction with thiocarbonyldiimidazole gave the cyclic thiocarbonate, which, upon reaction with triethyl phosphite, followed 4 deprotection, afforded 1. Treatment of 1 with phenyl methoxyalaninyl phosphochloridate and N-methylimidazole gave 2. Catalytic hydrogenation of 1 gave 3. Hydrodediazoniation of 1 with tert-butyl nitrite and tris(trimethylsilyl)silane gave 4. Compounds 1-4 were found to be inactive against the human immunodeficiency virus and exhibited minimal to no cytotoxic activity against the L1210 leukemia, CCRF-CEM lymphoblastic leukemia, and B16F10 melanoma in vitro.

  DOI：

  10.1081/ncn-200051898
• 作为产物：
  描述：

  1-乙酰基-三-苄氧基-罗伯糖 在 sodium methylate 、 四氯化锡 作用下， 以 甲醇 、 硝基甲烷 为溶剂， 反应 3.0h， 生成 (1S,2Xi)-1-(2-氨基-4-氧代-4,7-二氢-1H-吡咯并[3,2-d]嘧啶-7-基)-1,4-脱水-D-苏-戊糖醇
  参考文献：
  名称：

  Direct C-glycosylation of guanine analogs: the synthesis and antiviral activity of certain 7- and 9-deazaguanine C-nucleosides

  摘要：

  C-Glycosylation of two guanine analogues, 9-deaza- and 7-deazaguanine, has been achieved under Friedel-Crafts conditions, providing a direct synthetic route to 9-deazaguanosine (4; 2-amino-7-beta-D-ribofuranosyl-5H-pyrrolo[3,2-d]pyrimidin-4(3H)-one) and 8-beta-D-ribofuranosyl-7-deazaguanine (16), respectively. This electrophilic C-glycosylation was applied successfully to six guanine and substituted-guanine analogues resulting in yields of approximately 50%. This represents the first reported C-ribosylation of preformed nitrogen heterocycles isosteric with guanine. These C-nucleosides were evaluated for their ability to provide protection against a lethal Semliki Forest virus infection in mice, relative to 7-thia-8-oxoguanosine which was used as a positive control. Two of the C-nucleosides, 2-amino-6-chloro-5-methyl-7-beta-D-ribofuranosyl-5H-pyrrolo [3,2-d]pyrimidin-4(3H)-one (12) and the corresponding 6-bromo derivative (13), showed good prophylactic activity in this virus model system.

  DOI：

  10.1021/jm00172a011

文献信息

• METHODS FOR THE PREPARATION OF 9-DEAZAPURINE DERIVATIVES
  申请人：Chand Pooran

  公开号：US20100093991A1

  公开（公告）日：2010-04-15

  Methods for the preparation of the β isomer of a 9-deazapurine derivatives using benzyl protecting groups as the protecting groups for the 2 and 3 hydroxyl groups in ribose are provided.

  本文提供了一种使用苄基保护基作为核糖中2和3羟基的保护基来制备9-脱氮嘌呤衍生物β异构体的方法。
• Incorporation of 2′-Deoxy-9-deazaguanosine and 2′-Deoxy-7-deaza-6-thioguanosine into G-Rich Oligodeoxyribonucleotides
  作者：T. Sudhakar Rao、Arthur F. Lewis、Theresa Schmaltz Hill、Ganapathi R. Revankar

  DOI：10.1080/15257779508014648

  日期：1995.2

  The preparation of suitably protected monomeric phosphoramidite building blocks of 2'-deoxy-9-deazaguanosine (8) and 2'-deoxy-7-deaza-6-thioguanosine (12) and their incorporation into G-rich oligodeoxyribonucleotides are described.
• GIRGIS, NABIH S.;MICHAEL, MAGED A.;SMEE, DONALD F.;ALAGHAMANDAN, HASSAN A+, J. MED. CHEM., 33,(1990) N0, C. 2750-2755
  作者：GIRGIS, NABIH S.、MICHAEL, MAGED A.、SMEE, DONALD F.、ALAGHAMANDAN, HASSAN A+

  DOI：——

  日期：——
• PURINE BASE MODIFIED 2'-DEOXYRIBONUCLEOSIDES, USE IN TRIPLEX FORMING OLIGONUCLEOTIDES AND PROCESS FOR PREPARING THE SAME
  申请人：TRIPLEX PHARMACEUTICAL CORPORATION

  公开号：EP0543004A1

  公开（公告）日：1993-05-26
• US8344132B2
  申请人：——

  公开号：US8344132B2

  公开（公告）日：2013-01-01