3’-氨基-2’,3’-二脱氧尿苷 | 84472-86-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 3’-氨基-2’,3’-二脱氧尿苷
• 中文别名: 3'-氨基-2',3'-二脱氧尿苷；3'-氨基-2',3'-双脱氧尿苷
• 英文名称: 3'-amino-2',3'-dideoxyuridine
• 英文别名: 1-[(2R,4S,5S)-4-amino-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 84472-86-6
• 化学式: C₉H₁₃N₃O₄
• 分子量: 227.22
• InChiKey: NDGYFDPAEFUDKS-SHYZEUOFSA-N

物化性质

• 熔点：
  174-176℃
• 密度：
  1.425

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3’-氨基-2’,3’-二脱氧尿苷 在 溶剂黄146 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 3'-(3-(2-氯乙基)-3-亚硝基脲基)-2',3'-二脱氧尿苷
  参考文献：
  名称：

  2′-脱氧尿苷和2′-脱氧-5-氟尿苷的3′-（氯乙基）亚硝基脲类似物的抗肿瘤活性。

  摘要：

  2'-脱氧尿苷和2'-脱氧-5-氟尿苷，3'-[3-（2-氯乙基）-3-亚硝基脲基] -2'，3'-二脱氧尿苷（3'-CdUNU）的（氯乙基）亚硝基脲类似物，7）和3'-[3-（2-氯乙基）-3-亚硝基脲基] -2,3'-二脱氧-5-氟尿苷（3'-CFdUNU，8），通过处理相应的3' -氨基核苷与氯乙基异氰酸酯，然后亚硝化所得的脲。核苷亚硝基脲7和8在荷瘤小鼠中对L1210白血病表现出显着的抗癌活性。在40 mg / kg的最佳剂量水平下，7和8分别产生90％和60％的“治愈”（大于60天存活者）。讨论了构效关系。

  DOI：

  10.1021/jm00155a044
• 作为产物：
  描述：

  Navuridine 在 ammonium hydroxide 、 Polystyryl diphenylphosphine resin 作用下， 生成 3’-氨基-2’,3’-二脱氧尿苷
  参考文献：
  名称：

  A Facile Procedure for the Reduction of Azido Nucleosides to Amines Using Polymer Bound Triphenylphosphine

  摘要：

  在温和条件下，通过聚苯乙烯二苯膦树脂将叠氮核苷还原为胺的方法被详细描述。该方法仅需通过过滤和蒸发过程即可实现产物分离。

  DOI：

  10.1055/s-1994-25575

文献信息

• 3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities
  作者：Thomas A. Krenitsky、G. Andrew Freeman、Sammy R. Shaver、Lowrie M. Beacham、Stuart Hurlbert、Naomi K. Cohn、Lynn P. Elwell、John W. T. Selway

  DOI：10.1021/jm00360a019

  日期：1983.6

  the catalyst. 3'-Amino-2',3'-dideoxycytidine (7) was synthesized by amination of the 3'-azido precursor of 3'-amino-2',3'-dideoxyuridine. The biological activity of 3'-amino-2',3'-dideoxy-5-fluorouridine (6) was notable among this group of aminonucleosides. It had an ED50 of 10 microM against adenovirus and was not appreciably cytotoxic to mammalian cells in culture. It also had activity against some

  胸腺嘧啶，尿嘧啶和5-碘尿嘧啶的3'-氨基-2'，3'-二脱氧核糖核苷（1-3）是通过相应的2'-脱氧核糖核苷通过threo-3'-chloro和erythro-3'-合成的叠氮基衍生物。以3'-氨基-2'，3'-二脱氧胸苷为氨基戊糖基供体，以胸苷磷酸化酶（EC 2.4.2.4）为酶促合成了5-溴尿嘧啶，5-氯尿嘧啶和5-氟尿嘧啶（4-6）的相应氨基核苷催化剂。通过氨基化3′-氨基-2′，3′-二脱氧尿苷的3′-叠氮基前体合成3′-氨基-2′，3′-二脱氧胞苷（7）。在这组氨基核苷中，3'-氨基-2'，3'-二脱氧-5-氟尿苷的生物活性显着（6）。它对腺病毒的ED50为10 microM，对培养的哺乳动物细胞没有明显的细胞毒性。它也对某些革兰氏阳性细菌有活性，但对多种革兰氏阴性细菌没有活性。其他氨基核苷（1-5和7）缺乏或表现出弱的抗病毒和抗菌活性。该组中唯一对培养的哺乳动物细胞有明显毒性
• Synthesis of 3′-(4-Nitroimidazol-1-yl)-2′,3′-dideoxynucleosides of Pyrimidine Analogues and their Biological Evaluation against HIV
  作者：Mohammed S. Motawia、Erik B. Pedersen、Jerzy Suwinski、Carsten M. Nielsen

  DOI：10.1002/ardp.19903231203

  日期：——

  1,5‐di‐O‐acetyl‐2,3‐dideoxy‐3‐phthalimido‐β‐D‐erythro‐pentofuranose (1) with silylated pyrimidinediones 2a–c using the Lewis acid trimethylsilyl triflate as catalyst afforded nucleosides 3a–c and 4a,c which were deprotected with 33% methylamine/ethanol to give the corresponding 3‐aminonucleosides 5a–c and 6. These were reacted with 1,4‐dinitroimidazoles 7a,b to give the 3‐imidazolyldideoxynucleosides

  1,5-di-O-acetyl-2,3-dideoxy-3-phthalimido-β-D-erythro-pentofuranose (1) 与甲硅烷基化嘧啶二酮 2a – c 使用路易斯酸三甲基甲硅烷基三氟甲磺酸酯作为催化剂反应得到核苷 3a– c 和 4a、c 用 33% 甲胺/乙醇脱保护得到相应的 3-氨基核苷 5a-c 和 6。这些与 1,4-二硝基咪唑 7a、b 反应得到 3-咪唑基二脱氧核苷 8a、b 和 9a -F。在亚毒性浓度下，这些化合物对 HIV-1 无效。
• Synthesis and biological activity of various 3'-azido and 3'-amino analogs of 5-substituted pyrimidine deoxyribonucleosides
  作者：Tai Shun Lin、You Song Gao、William R. Mancini

  DOI：10.1021/jm00366a006

  日期：1983.12

  Various new 5-substituted 3'-azido- and 3'-amino derivatives of 2'-deoxyuridine and 2'-deoxycytidine have been synthesized and biologically evaluated. Among these compounds, 3'-amino-2',3'-dideoxy-5-fluorouridine (3), 3'-amino-2',3'-dideoxycytidine (7a), and 3'-amino-2',3'-dideoxy-5-fluorocytidine (7c) were found to be the most active against murine L1210 and sarcoma 180 neoplastic cells in vitro, with an ED50 of 15 and 1 microM, 0.7 and 4 microM, and 10 and 1 microM, respectively. The 3'-azido derivatives, 2 and 6c, were less active in comparison with their 3'-amino counterparts. In addition, the 5-fluoro-3'-amino nucleosides, 3 and 7c, were tested against L1210 leukemia bearing CDF1 mice. Our preliminary findings indicate that compound 7c (6 X 200 mg/kg) was as active as the positive control, 5-fluorouracil (6 X 20 mg/kg), yielding a T/C X 100 of 146 and 129, respectively. However, 3 was found to be inactive in this experiment.
• Synthesis and antineoplastic activity of 3'-azido and 3'-amino analogs of pyrimidine deoxyribonucleoside
  作者：Tai Shun Lin、William R. Mancini

  DOI：10.1021/jm00358a016

  日期：1983.4

  Several new 3'-azido and 3'-amino nucleosides (8, 9, 12, and 13) have been synthesized and their biological activities evaluated. Among them, 3'-amino-2',3'-dideoxycytidine (13) was found to exhibit potent cytotoxic activity against both L1210 and S-180 cells in vitro with an ID50 of 0.7 and 4.0 microM, respectively. Furthermore, 13 has also shown antitumor activity against L1210 tumor bearing mice with a T/C X 100 value of 283.
• Chemical-Enzymatic Synthesis of 3′-Amino-2′, 3′-dideoxy-β-D-ribofuranosides of Natural Heterocyclic Bases and Their 5′-Monophosphates
  作者：Galina V. Zaitseva、Evgenii I. Kvasyuk、Elena V. Vaaks、Vladimir N. Barai、Sergei B. Bokut、Anatolii I. Zinchenko、Igor A. Mikhailopulo

  DOI：10.1080/15257779408013281

  日期：1994.3

  Treatment of O-2,3'-anhydro-5'-O-trityl derivatives of thymidine (1) and 2'-deoxyuridine (2) with lithium azide in dimethylformamide at 150 degrees C resulted in the formation of the corresponding isomeric 3'-azido-2',3'-dideoxy-5'-O-trityl-beta-D-ribofuranosyl N1- (the major products) and N-3-nucleosides (3/4 and 5/6). 3'-Amino-2',3'-dideoxy-beta-D-ribofuranosides of thymidine [Thd(3'NH2)], uridine [dUrd(3'NH2)], and cytidine [dCyd(3'NH2)] were synthesized from the corresponding 3'-azido derivatives. The Thd(3'NH2) and dUrd(3'NH2) were used as donors of carbohydrate moiety in the reaction of enzymatic transglycosylation of adenine and guanine to afford dAdo(3'NH2) and dGuo(3'NH2). The substrate activity of dN(3'NH2) vs. nucleoside phosphotransferase of the whole cells of Erwinia herbicola was studied.