3'-azido-2',3'-dideoxy-5'-O-tritylcytidine | 142820-94-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3'-azido-2',3'-dideoxy-5'-O-tritylcytidine
• 英文别名: 3'-Azido-5'-trityl-2',3'-dideoxycytidine；4-amino-1-[(2R,4S,5S)-4-azido-5-(trityloxymethyl)oxolan-2-yl]pyrimidin-2-one
• CAS: 142820-94-8
• 化学式: C₂₈H₂₆N₆O₃
• 分子量: 494.553
• InChiKey: SFJKLAWPYFYDJA-BFLUCZKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  91.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3'-azido-2',3'-dideoxy-5'-O-tritylcytidine 在 吡啶 、 ammonium hydroxide 、 溶剂黄146 、 三苯基膦 作用下， 反应 5.0h， 生成 3’-氨基-2’,3’-二脱氧胞苷
  参考文献：
  名称：

  Chemical-Enzymatic Synthesis of 3′-Amino-2′, 3′-dideoxy-β-D-ribofuranosides of Natural Heterocyclic Bases and Their 5′-Monophosphates

  摘要：

  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.

  DOI：

  10.1080/15257779408013281
• 作为产物：
  描述：

  1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-1-β-D-xylofuranosyl)cytosine 在 叠氮化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以96%的产率得到3'-azido-2',3'-dideoxy-5'-O-tritylcytidine
  参考文献：
  名称：

  胰凝乳蛋白酶激活的3'-氨基-2'，3'-二脱氧胞苷的衍生物的合成和抗白血病活性。（合成核苷和核苷酸.XXXIII。

  摘要：

  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。

  DOI：

  10.1248/cpb.43.501

文献信息

• 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.
• 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。