3’-氨基-2’,3’-二脱氧胞苷 | 84472-90-2

• 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’-二脱氧胞苷
• 中文别名: 3'-氨基-2',3'-双脱氧胞苷；3'-氨基-2',3'-二脱氧胞苷
• 英文名称: 3'-amino-2',3'-dideoxycytidine
• 英文别名: 3,-amino-2',3'-dideoxycytidine；3'-amino-2',3'-dideoxcytidine；4-amino-1-[(2R,4S,5S)-4-amino-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• CAS: 84472-90-2
• 化学式: C₉H₁₄N₄O₃
• 分子量: 226.235
• InChiKey: LDQAHTVPOZCQNH-SHYZEUOFSA-N

物化性质

• 熔点：
  >210°C (dec.)
• 沸点：
  450.2±55.0 °C(Predicted)
• 密度：
  1.73±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 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：
  114
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 储存条件：
  -20°C，干燥，惰性气体

反应信息

• 作为反应物：
  描述：

  3’-氨基-2’,3’-二脱氧胞苷 在 三乙胺 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.0h， 生成 N4-benzoyl-3'-aminotrityl-2',3'-dideoxycytidine
  参考文献：
  名称：

  A new approach to oligonucleotide N3′→P5′ phosphoramidate building blocks

  摘要：

  A new synthetic approach to 5'-phosphoramidites of 3'-aminonucleosides was developed. The methodology relics upon the use of 3'-amino-2',3'-dideoxynucleosides as the key starting materials. The final products were obtained in high yields via 2-3-step processes using selective introduction of orthogonal protective groups to the 3'-aminonucleoside sugar and base moieties. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.100
• 作为产物：
  描述：

  Navuridine 在 palladium on activated charcoal 吡啶 、 氯化亚砜 、 氨 、 氢气 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 4.0~25.0 ℃ 、344.73 kPa 条件下， 反应 176.0h， 生成 3’-氨基-2’,3’-二脱氧胞苷
  参考文献：
  名称：

  Synthesis and antineoplastic activity of 3'-azido and 3'-amino analogs of pyrimidine deoxyribonucleoside

  摘要：

  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.

  DOI：

  10.1021/jm00358a016

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 protected 3'-amino nucleoside monomers
  申请人：Gryaznov M. Sergei

  公开号：US20060009636A1

  公开（公告）日：2006-01-12

  Orthogonally protected 3′-amino nucleoside monomers and efficient methods for their synthesis are described. The methods employ selective protection of the 3′-amino group in the presence of the unprotected nucleoside base.

  正交保护的3′-氨基核苷单体及其高效合成方法被描述。这些方法在未保护的核苷碱基存在下，采用对3′-氨基基团的选择性保护。
• A Facile Procedure for the Reduction of Azido Nucleosides to Amines Using Polymer Bound Triphenylphosphine
  作者：Torsten Holletz、Dieter Cech

  DOI：10.1055/s-1994-25575

  日期：——

  A very convenient reduction of azido nucleosides to amines under mild conditions using polystyryl diphenylphosphine resin is described. The method requiers only a filtration and evaporation process for product isolation.

  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。
• Synthesis and Antileukemic Activity of Chymotrypsin-Activated Derivatives of 3'-Amino-2',3'-dideoxycytidine. (Synthetic Nucleosides and Nucleotides.XXXIII).
  作者：Takeo KAWAGUCHI、Hiroshi SAKAIRI、Shigeru KIMURA、Toyofumi YAMAGUCHI、Mineo SANEYOSHI

  DOI：10.1248/cpb.43.501

  日期：——

  3'-Amino-2',3'-dideoxycytidine (8) was directly synthesized from 2'-deoxycytidine. 2',3'-Dideoxy-3'-(N-acyl-L-phenylalanylamino)cytidines (acyl = butoxycarbonyl (9a), acetyl (9b), benzoyl (9c), and n-hexanoyl (9d)) were synthesized as chymotrypsin-activated prodrugs of 8. This N-protection was required for activation by chymotrypsin to 8. In vitro, compound 8 showed high cytotoxic activity against

  由2′-脱氧胞苷直接合成3′-氨基-2′，3′-二脱氧胞苷（8）。2'，3'-Dideoxy-3'-（N-acyl-L-phenylalanylamino）cytidines（酰基=丁氧羰基（9a），乙酰基（9b），苯甲酰基（9c）和正己酰基（9d））合成为胰凝乳蛋白酶活化的8的前药。胰凝乳蛋白酶活化至8所需的这种N保护作用。在体外，化合物8对P388细胞显示出高细胞毒性，但前药9a-d无效。然而，在体内，这些前药在携带P388细胞的小鼠中显示出比8更高的活性。
• Intermediates in the preparation of 3'-amino-2',3'-dideoxycytidine and
  申请人：Research Corporation

  公开号：US05099010A1

  公开（公告）日：1992-03-24

  This disclosure describes the preparation of 3'-amino-2', 3'-dideoxyctidine and the pharmacologically acceptable salts thereof which are useful in inhibiting the growth of transplanted tumors in mammals.

  本公开说明了制备3'-氨基-2'，3'-二脱氧胞苷及其药理学上可接受的盐，其在抑制哺乳动物移植肿瘤生长方面具有用途。