7-amino-3H-1,2,3-triazolo<4,5-b>pyridine | 34550-46-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并吡啶类
• 英文名称: 7-amino-3H-1,2,3-triazolo<4,5-b>pyridine
• 英文别名: 7-amino-3H-<1,2,3>triazolo<4,5-b>pyridine；7-Amino-3H-v-triazolo<4,5-b>pyridin；7-Amino-vic-triazolo<4.5-b>pyridin；7-Amino-3H-o-triazolo<4,5-c>pyridin；1H-[1,2,3]triazolo[4,5-b]pyridin-7-ylamine；2h-[1,2,3]Triazolo[4,5-b]pyridin-7-amine；2H-triazolo[4,5-b]pyridin-7-amine
• CAS: 34550-46-4
• 化学式: C₅H₅N₅
• mdl: MFCD18384439
• 分子量: 135.128
• InChiKey: KDLCYJQDDUBLCW-UHFFFAOYSA-N

物化性质

• 沸点：
  177.7±50.0 °C(Predicted)
• 密度：
  1.89±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-amino-3H-1,2,3-triazolo<4,5-b>pyridine 在 四丁基氟化铵 、 二氯乙基铝 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 7-amino-4-<2,3-dideoxy-β-D-glycero-pentofuranosyl>-4H-1,2,3-triazolo<4,5-b>pyridine
  参考文献：
  名称：

  8-Aza-1-deazapurine Nucleosides as Antiviral Agents

  摘要：

  2',3'-Dideoxy-8-aza-1-deazaadenosine (21) and its alpha-anomer (20) were synthesized via glycosylation of 7-chloro-3H-1,2,3-triazolo[4,5-b]pyridine with 2,3-dideoxy-5-0-[(1,1)-dimethylethyl)diphenylsilyl]-D-glycero-pentofuranosyl chloride. The reaction gave a mixture of alpha- and beta-anomers of N-3-, N-2- and N-1-glycosylated regioisomers (12-15). The alpha- and beta-anomers of the N-4-glycosylated isomer 26 and 27 were also synthesized through the glycosylation of 8-aza-1-deazaadenine with 1-acetoxy-2,3-dideoxy-5-0-[(1,1-dimethylethyl)dimethylsilyl]-D-glycero-pen. These dideoxynucleosides and a series of previously synthesized 8-aza-1-deazapurine nucleosides were tested for activity against several DNA and RNA viruses, HIV-1 included. The alpha- and beta-anomers of 7-chloro-3-(2-deoxy-D-erythro-pentofuranosyl)-3H-1,2,3-triazolo[4,5-b]pyridine (3a and 4) showed activities against Sb-1 and Coxs viruses. The alpha- and beta-anomers of 2',3'-dideoxy-8-aza-1-deazaadenosine (20 and 21) were found active as inhibitors of adenosine deaminase.

  DOI：

  10.1080/15257779408009477

文献信息

• Synthesis and Evaluation of the Anti-HIV Activity of Aza and Deaza Analogs of IsoddA and Their Phosphates as Prodrugs
  作者：Palmarisa Franchetti、Loredana Cappellacci、Mario Grifantini、Lea Messini、Ghassan Abu Sheikha、Anna Giulia Loi、Enzo Tramontano、Antonella De Montis、Maria Grazia Spiga、Paolo La Colla

  DOI：10.1021/jm00047a011

  日期：1994.10

  2-trichloroethyl) phosphate] triesters and 5'-phenyl phosphoramidate derivatives which, acting as membrane soluble prodrugs, could release the free phosphate form inside the cell. The 5'-(phenylmethoxy)alaninyl phosphate derived from 8-aza-isoddA was found active against HIV-1 and HIV-2 with a potency similar to that of isoddA, while the anti-HIV potency of 5'-(phenylmethoxy)alaninyl phosphate of isoddA proved

  抗HIV剂2'，3'-dideoxy-3'-oxoadenosine（isoddA）的某些aza和deaza类似物（8-aza-，8-aza-1-deaza，8-aza-3-deaza-，1 -deaza-和3-deaza-isoddA）已合成，并且在体外对HIV没有活性。通过合成一系列5'-[磷酸双（2,2,2-三氯乙基）]三酯和5'-苯基来检验这些异核苷无活性可能是由于它们对细胞核苷激酶亲和力较弱的假设。可用作膜可溶前药的氨基磷酸酯衍生物可以释放细胞内的游离磷酸盐形式。发现源自8-氮杂-isoddA的5'-（苯基甲氧基）丙氨酰磷酸对HIV-1和HIV-2有活性，其功效与isoddA相似，而抗HIV的功效为5' 证明isoddA的-（苯基甲氧基）丙氨酸磷酸酯显着高于isoddA的磷酸，特别是针对HIV-2，与AZT相似。进一步的证据表明，通过合成其5'-三磷酸衍生物可以得到8-aza-i
• 8-Aza-1-deazapurine Nucleosides as Antiviral Agents
  作者：P. Franchetti、L. Messini、L. Cappellacci、G. Abu Sheikha、M. Grifantini、P. Guarracino、A. De Montis、A. G. Loi、M. E. Marongiu、P. La Colla

  DOI：10.1080/15257779408009477

  日期：1994.9

  2',3'-Dideoxy-8-aza-1-deazaadenosine (21) and its alpha-anomer (20) were synthesized via glycosylation of 7-chloro-3H-1,2,3-triazolo[4,5-b]pyridine with 2,3-dideoxy-5-0-[(1,1)-dimethylethyl)diphenylsilyl]-D-glycero-pentofuranosyl chloride. The reaction gave a mixture of alpha- and beta-anomers of N-3-, N-2- and N-1-glycosylated regioisomers (12-15). The alpha- and beta-anomers of the N-4-glycosylated isomer 26 and 27 were also synthesized through the glycosylation of 8-aza-1-deazaadenine with 1-acetoxy-2,3-dideoxy-5-0-[(1,1-dimethylethyl)dimethylsilyl]-D-glycero-pen. These dideoxynucleosides and a series of previously synthesized 8-aza-1-deazapurine nucleosides were tested for activity against several DNA and RNA viruses, HIV-1 included. The alpha- and beta-anomers of 7-chloro-3-(2-deoxy-D-erythro-pentofuranosyl)-3H-1,2,3-triazolo[4,5-b]pyridine (3a and 4) showed activities against Sb-1 and Coxs viruses. The alpha- and beta-anomers of 2',3'-dideoxy-8-aza-1-deazaadenosine (20 and 21) were found active as inhibitors of adenosine deaminase.