2-isobutyrylamino-7-β-D-ribofuranosyl-5H-pyrrolo[3,2-d]pyrimidin-4-one | 149099-48-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-isobutyrylamino-7-β-D-ribofuranosyl-5H-pyrrolo[3,2-d]pyrimidin-4-one
• 英文别名: 2-isobutyrylamino-9-deazaguanosine；N²-isobuturyl-9-deazaguanosine；N-[7-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-oxo-3,5-dihydropyrrolo[3,2-d]pyrimidin-2-yl]-2-methylpropanamide
• CAS: 149099-48-9
• 化学式: C₁₅H₂₀N₄O₆
• 分子量: 352.347
• InChiKey: SZJDEOYAXURURF-PUYANOKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.0
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  160.56
• 氢给体数：
  6.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-isobutyrylamino-7-β-D-ribofuranosyl-5H-pyrrolo[3,2-d]pyrimidin-4-one 在 咪唑 、 sodium hydroxide 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-isobutyrylamino-7-[5-tert-butyldiphenylsilyl-2,3-bis-O-(methylthio)thiocarbonyl-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：

  2-amino-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo<3,2-d>pyrimidin-4(3H)-one 在 sodium methylate 、 六甲基二硅氮烷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 2-isobutyrylamino-7-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

文献信息

• A total synthesis of 2′-deoxy-9-deazaguanosine (9-deaza-dG) and its incorporation into triple helix forming oligodeoxyribonucleotides with antiparallel motif
  作者：T.Sudhakar Rao、Arthur F. Lewis、Ross H. Durland、Ganapathi R. Revankar

  DOI：10.1016/s0040-4039(00)61681-7

  日期：1993.10

  A simple synthesis of 2-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)pyrrolo-[3,2-d]pyrimidin-4(3H)-one (9-deaza-dG) has been achieved and it has been incorporated into triplex forming oligonucleotides using the solid-support, phosphoramidite chemistry. 9-Deaza-dG is effective in preventing the formation of G-tetrads in G-rich oligonucleotides.

  已经简单地合成了2-氨基-7-（2-脱氧-β-D-赤型-戊呋喃糖基）吡咯并-[3,2 - d ]嘧啶-4（3 H）-一个（9-脱氮-dG）。通过固相载体，亚磷酰胺化学，已将其掺入形成三链体的寡核苷酸中。9-Deaza-dG可有效防止富含G的寡核苷酸中G-tetrads的形成。