lin-benzoguanine | 60064-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: lin-benzoguanine
• 英文别名: 6-Amino-3,7-Dihydro-Imidazo[4,5-G]quinazolin-8-One；6-amino-1,7-dihydroimidazo[4,5-g]quinazolin-8-one
• CAS: 60064-29-1
• 化学式: C₉H₇N₅O
• 分子量: 201.187
• InChiKey: VQSMWFVKBKMHTO-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C(Solv: N,N-dimethylformamide (68-12-2); water (7732-18-5))
• 沸点：
  632.5±47.0 °C(Predicted)
• 密度：
  1.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  lin-benzoguanine 在 氨 、 lithium 作用下， 以 叔丁醇 为溶剂， 反应 0.5h， 以71%的产率得到4,9-dihydro-lin-benzoguanine
  参考文献：
  名称：

  Defined dimensional alterations in enzyme substrates. Birch reduction of lin-benzopurines. A contribution to information concerning the binding sites of adenosine deaminase and xanthine oxidase

  摘要：

  DOI：

  10.1021/jo00251a045
• 作为产物：
  描述：

  5,6-二甲基苯并咪唑 在 potassium permanganate 、 氰胺 、 叠氮基三甲基硅烷 、 potassium tert-butylate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 9.0h， 生成 lin-benzoguanine
  参考文献：
  名称：

  Convenient synthesis of linear benzopurines through a common intermediate

  摘要：

  DOI：

  10.1021/jo00389a055

文献信息

• Synthesis, Biological Evaluation, and Crystallographic Studies of Extended Guanine-Based (lin-Benzoguanine) Inhibitors for tRNA-Guanine Transglycosylase (TGT)
  作者：Emmanuel A. Meyer、Nicola Donati、Marine Guillot、W. Bernd Schweizer、François Diederich、Bernhard Stengl、Ruth Brenk、Klaus Reuter、Gerhard Klebe

  DOI：10.1002/hlca.200690062

  日期：2006.4

  This paper describes the rational design, synthesis, and biological evaluation of a new generation of inhibitors of the bacterial enzyme tRNA-guanine transglycosylase (TGT), which has been identified as a new target in the fight against bacillary dysentery (Shigellosis). The enzyme catalyzes the exchange of guanine in the anticodon wobble position of tRNA by the modified base preQ1, a guanine derivative

  本文描述了新一代细菌酶tRNA-鸟嘌呤转糖基酶（TGT）抑制剂的合理设计，合成和生物学评估，该抑制剂已被确定为对抗细菌性痢疾（志贺氏菌病）的新目标。根据涉及共价TGT-tRNA中间体的乒乓机制，该酶通过修饰的碱基preQ 1（鸟嘌呤衍生物）催化tRNA的反密码子摆动位置中的鸟嘌呤交换（图2）。基于计算机建模（图3），林-benzoguanine（6-氨基咪唑并[4,5-克]喹唑啉-8-（7 ħ） -酮（2））被选作延伸的中心支架，与该蛋白质形成多达七个平面内分子间H键，同时夹在Tyr106和Met260之间。多功能的合成方案被用于合成开发2，和用苯基，苄基和2-苯乙基侧链（衍生物即，16，17A，和12A，12B，13，17，RESP）伸进林立的亲脂性口袋由Val282，Val45和Leu68设计（方案1-3）。考虑到新配体的溶解度有限，并且由于最近对TGT催化机理的详细了解（图2），对酶
• Size-Expanded Analogues of dG and dC:  Synthesis and Pairing Properties in DNA
  作者：Haibo Liu、Jianmin Gao、Eric T. Kool

  DOI：10.1021/jo048357z

  日期：2005.1.1

  We describe the completion of the set of four benzo-fused expanded DNA (xDNA) nucleoside analogues. We previously reported the development of benzo-fused analogues of dA and dT and their inclusion in an exceptionally stable new four-base genetic system. termed xDNA. in which the base pairs were expanded in size. Here we describe the preparation and properties of the-second half of this nucleotide set: namely, the previously unknown dxC and dxG nucleosides. The dxC analogue was prepared from the previously reported dxT nucleoside in three steps and 57%, yield. The large-sized deoxyguanosine analogue was prepared from an intermediate in the synthesis of dxA, yielding dxG in 14 steps overall (2.4%). Suitably protected versions of the deoxynucleosides were prepared for oligonucleotide synthesis following standard procedures, and they were readily incorporated into DNA by automated synthesizer. "Dangling-end" measurements revealed that the benzo-fused homologues stack considerably more strongly on neighbor DNA sequences h do their natural counterparts. Base pairing experiments with xC or xG bases showed that they pair selectively with their Watson-Crick partners, but with mild destabilization. due apparently to their larger size. Overall, the data suggest that the fluorescent xG and xG bases may he useful probes of steric effects in the study of biological nucleotide recognition mechanisms. In addition. the completion of the xDNA nucleoside set makes it possible in the future to construct full four-base xDNA strands that can target any sequence of natural DNA and RNA.
• Modifications on the heterocyclic base of acyclovir: syntheses and antiviral properties
  作者：Lilia M. Beauchamp、Bart L. Dolmatch、Howard J. Schaeffer、Peter Collins、D. J. Bauer、Paul M. Keller、James A. Fyfe

  DOI：10.1021/jm00146a002

  日期：1985.8

  A group of compounds was prepared in which variations of the ring portion of the acyclovir (ACV) structure were made. These modifications included monocyclic (isocytosine, triazole, imidazole), bicyclic (8-azapurine, pyrrolo[2,3-d]pyrimidine, pyrazolo[3,4-d]pyrimidine) and tricyclic (linear benzoguanine) congeners. The derivatives were evaluated against herpes simplex virus type 1 (HSV-1) by the plaque-inhibition and plaque-reduction methods with only the 8-azapurine analogue 28 showing some activity. In a test measuring the ability of these compounds to inhibit the HSV-1 thymidine kinase, 28 and the tricyclic derivative 38 exhibited competition with ACV for binding to the enzyme. The inability of the group to exert significant antiherpetic action is attributed to their lack of phosphorylation to the requisite triphosphate stage.
• LEONARD N. J.; KAZMIERCZAK F.; RYKOWSKI A., J. ORG. CHEM., 52,(1987) N 13, 2933-2935
  作者：LEONARD N. J.、 KAZMIERCZAK F.、 RYKOWSKI A.

  DOI：——

  日期：——
• LEONARD, NELSON J.;PETRIC, ANDREJ;RYKOWSKI, ANDRZEJ, J. ORG. CHEM., 53,(1988) N 16, C. 3873-3875
  作者：LEONARD, NELSON J.、PETRIC, ANDREJ、RYKOWSKI, ANDRZEJ

  DOI：——

  日期：——