QYL-546 | 210355-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: QYL-546
• 英文别名: syn-2,6-diamino-N⁹-(2-hydroxymethylcyclopropylidenemethyl)purine；[(2Z)-2-[(2,6-diaminopurin-9-yl)methylidene]cyclopropyl]methanol
• CAS: 210355-04-7
• 化学式: C₁₀H₁₂N₆O
• 分子量: 232.245
• InChiKey: OSPGBSRVIFWAPG-DJWKRKHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  QYL-546 在 吡啶 、 亚硝酸特丁酯 、 氢氟酸 作用下， 以 甲苯 为溶剂， 以14.5%的产率得到{2-[1-(6-Amino-2-fluoro-purin-9-yl)-meth-(Z)-ylidene]-cyclopropyl}-methanol
  参考文献：
  名称：

  Synthesis, antiviral, and antitumor activity of 2-substituted purine methylenecyclopropane analogues of nucleosides

  摘要：

  The Z- and E-2-fluoro- and 2-chloropurine methylenecyclopropanes 9a,b and 10a,b as well as enantiomeric Z-isoguanine methylenecyclopropanes 11a,b and their phenyl phosphoralaninate pronucleotides 11c,d were synthesized and their antiviral activity against several viruses was evaluated. Fluoro analogues 9a and 10a were active against human cytomegalovirus but they were cytotoxic at approximately the same concentrations. Chloro derivatives 9b and 10b were non-cytotoxic and effective against Epstein-Barr virus in Daudi cells. Isoguanine analogues 11a-d lacked antiviral activity but pronucleotides 11c,d were substrates for porcine liver esterase. From the group of 9a,b and 10a,b, the fluoro analogues 9a and 10a exhibited antitumor activity but only the Z-isomer 9a had a selective effect. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.052
• 作为产物：
  描述：

  syn-2-amino-6-chloro-N⁹-(2-carbethoxycyclopropylidenemethyl)purine 在 氨 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以81.4%的产率得到QYL-546
  参考文献：
  名称：

  2-hydroxymethylcyclopropylidenemethylpurines and -pyrimidines as antiviral agents

  摘要：

  具有抗病毒活性的化合物具有以下配方：其中B是嘌呤或嘧啶杂环环，最好从包括6-氨基嘌呤（腺嘌呤）、2,6-二氨基嘌呤、2-氨基-6-偶氮基嘌呤、2-氨基-6-环丙胺基嘌呤、6-羟基嘌呤（次黄嘌呤）、2-氨基-6-卤代嘌呤、2-氨基-6-烷氧基嘌呤、2-氨基-6-羟基嘌呤（鸟嘌呤）、3-去氮嘌呤、7-去氮嘌呤、8-氮杂嘌呤、胞嘧啶、5-卤代胞嘧啶、5-烷基取代胞嘧啶、胸腺嘧啶、尿嘧啶和6-氮杂嘧啶中选择；X为O；R1和R2是烷基或芳基基团。本发明的化合物还包括上述化合物的R-和S-对映体。R1X和/或R2X也可以是带有X为NH的氨基酸残基。

  公开号：

  US06352991B1

文献信息

• [EN] 2-HYDROXY METHYLCYCLOPRO PYLIDENEMETHYL PURINES AND -PYRIMIDINES AS ANTIVIRAL AGENTS<br/>[FR] 2-HYDROXY METHYLCYCLOPRO PYLIDENEMETHYL PURINES ET PYRIMIDINES COMME AGENTS ANTIVIRAUX
  申请人：UNIV MICHIGAN

  公开号：WO2000053603A1

  公开（公告）日：2000-09-14

  Compounds which are active against viruses have Formulas (1, 2, 3 and 4) wherein B is a purine or pyrimidine heterocyclic ring and is preferably selected from the group consisting of 6-aminopurine (adenine), 2,6-diaminopurine, 2-amino-6-azidopurine, 2-amino-6-cyclopropylaminopurine, 6-hydroxypurine (hypoxanthine), 2-amino-6-halo substituted purines, 2-amino-6-alkoxy substituted purines, 2-amino-6-hydroxypurine (guanine), 3-deazapurines, 7-deaza-purines, 8-azapurines, cytosine, 5-halo substituted cytosines, 5-alkyl substituted cytosines, thymine, uracil and 6-azapyrimidines; X is O; and, R1 and R2 are alkyl or aryl groups. The compounds of the present invention also include the R- and S-enantiomers of the above compounds. The R1X and/or R2X can also be amino acid residues with X as NH.

  具有抗病毒活性的化合物具有公式（1、2、3和4），其中B是嘌呤或嘧啶杂环，最好从以下组中选择：6-氨基嘌呤（腺嘌呤）、2,6-二氨基嘌呤、2-氨基-6-叠氮基嘌呤、2-氨基-6-环丙氨基嘌呤、6-羟基嘌呤（次黄嘌呤）、2-氨基-6-卤代嘌呤、2-氨基-6-烷氧基嘌呤、2-氨基-6-羟基嘌呤（鸟嘌呤）、3-去气嘌呤、7-去氮嘌呤、8-氮杂嘌呤、胞嘧啶、5-卤代胞嘧啶、5-烷基取代胞嘧啶、胸腺嘧啶、尿嘧啶和6-氮杂嘧啶；X为O；R1和R2为烷基或芳基基团。本发明的化合物还包括上述化合物的R-和S-对映体。R1X和/或R2X也可以是带有X为NH的氨基酸残基。
• 2-Hydroxymethylcyclopropylidenemethylpurines and - pyrimidines as antiviral agents
  申请人：Zemlicka Jiri

  公开号：US20060122203A1

  公开（公告）日：2006-06-08

  Compounds which are active against viruses have the following Formulas: wherein B is a purine or pyrimidine heterocyclic ring and is preferably selected from the group consisting of 6-aminopurine (adenine), 2,6-diaminopurine, 2-amino-6-azidopurine, 2-amino-6-cyclopropylaminopurine, 6-hydroxypurine (hypoxanthine), 2-amino-6-halo substituted purines, 2-amino-6-alkoxy substituted purines, 2-amino-6-hydroxypurine (guanine), 3-deazapurines, 7-deaza-purines, 8-azapurines, cytosine, 5-halo substituted cytosines, 5-alkyl substituted cytosines, thymine, uracil and 6-azapyrimidines; X is O; and, R 1 and R 2 are alkyl or aryl groups. The compounds of the present invention also include the R- and S-enantiomers of the above compounds. The R 1 X and/or R 2 X can also be amino acid residues with X as NH.

  具有抗病毒活性的化合物具有以下公式：其中B是嘌呤或嘧啶杂环，并且优选从6-氨基嘌呤（腺嘌呤），2,6-二氨基嘌呤，2-氨基-6-叠氮基嘌呤，2-氨基-6-环丙基氨基嘌呤，6-羟基嘌呤（次黄嘌呤），2-氨基-6-卤代嘌呤，2-氨基-6-烷氧基嘌呤，2-氨基-6-羟基嘌呤（鸟嘌呤），3-脱氮嘌呤，7-脱氮嘌呤，8-氮杂嘌呤，胞嘧啶，5-卤代胞嘧啶，5-烷基胞嘧啶，胸腺嘧啶，尿嘧啶和6-氮杂嘧啶中选择；X为O；R1和R2为烷基或芳基基团。本发明的化合物还包括上述化合物的R-和S-对映体。R1X和/或R2X也可以是氨基酸残基，其中X为NH。
• 2-hydroxymethylcyclopropylidene methylpurines and -pyrimidines as antiviral agents
  申请人：Zemlicka Jiri

  公开号：US20050009842A1

  公开（公告）日：2005-01-13

  Compounds which are active against viruses have the following Formulas: wherein B is a purine or pyrimidine heterocyclic ring and is preferably selected from the group consisting of 6-aminopurine (adenine), 2,6-diaminopurine, 2-amino-6-azidopurine, 2-amino-6-cyclopropylaminopurine, 6-hydroxypurine (hypoxanthine), 2-amino-6-halo substituted purines, 2-amino-6-alkoxy substituted purines, 2-amino-6-hydroxypurine (guanine), 3-deazapurines, 7-deaza-purines, 8-azapurines, cytosine, 5-halo substituted cytosines, 5-alkyl substituted cytosines, thymine, uracil and 6-azapyrimidines; X is 0; and, R 1 and R 2 are alkyl or aryl groups. The compounds of the present invention also include the R- and S-enantiomers of the above compounds. The R,X and/or R 2 X can also be amino acid residues with X as NH.

  具有抗病毒活性的化合物具有以下公式：其中B是一种嘌呤或嘧啶杂环环，最好从以下组中选择：6-氨基嘌呤（腺嘌呤）、2,6-二氨基嘌呤、2-氨基-6-叠氮嘌呤、2-氨基-6-环丙基氨基嘌呤、6-羟基嘌呤（次黄嘌呤）、2-氨基-6-卤代嘌呤、2-氨基-6-烷氧基取代嘌呤、2-氨基-6-羟基嘌呤（鸟嘌呤）、3-脱氮嘌呤、7-脱氮嘌呤、8-氮杂嘌呤、胞嘧啶、5-卤代胞嘧啶、5-烷基取代胞嘧啶、胸腺嘧啶、尿嘧啶和6-氮杂嘧啶；X为0；R1和R2是烷基或芳基基团。本发明的化合物还包括上述化合物的R-和S-对映异构体。R、X和/或R2X也可以是氨基酸残基，其中X为NH。
• 2-HYDROXY METHYLCYCLOPRO PYLIDENEMETHYL PURINES AS ANTIVIRAL AGENTS
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：EP1165560B1

  公开（公告）日：2004-11-17
• 2-HYDROXY METHYLCYCLOPRO PYLIDENEMETHYL PURINES AND -PYRIMIDINES AS ANTIVIRAL AGENTS
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：EP1165560A1

  公开（公告）日：2002-01-02