8-mercaptoimidazo<4,5-g>quinazoline | 53449-19-7

• 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: 8-mercaptoimidazo<4,5-g>quinazoline
• 英文别名: 8-mercaptoimidazo[4,5-g]quinazoline；1(3),7-dihydro-imidazo[4,5-g]quinazoline-8-thione；8-Merkaptimidazo<4,5-g>chinazolin；1,5-Dihydroimidazo[4,5-g]quinazoline-8-thione
• CAS: 53449-19-7
• 化学式: C₉H₆N₄S
• 分子量: 202.239
• InChiKey: GWVFHJBBHQTWAM-UHFFFAOYSA-N

物化性质

• 沸点：
  562.6±42.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 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：
  85.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-mercaptoimidazo<4,5-g>quinazoline 在 氢氧化钾 、 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 8-methylthio-3-(2'-deoxy-3',5'-di-O-toluoyl-β-D-ribofuranosyl)imidazo[4,5-g]quinazoline
  参考文献：
  名称：

  Toward a New Genetic System with Expanded Dimensions:  Size-Expanded Analogues of Deoxyadenosine and Thymidine

  摘要：

  We describe the design, preparation, and properties of two key building blocks of a size-expanded genetic system. Nucleoside analogues of the natural nucleosides dA and dT are reported in which the fusion of a benzo ring increases their size by ca. 2.4 Angstrom. The expanded dA analogue (dxA), having a tricyclic base, was first reported by Leonard nearly three decades ago. We describe a shortened and more efficient approach to this compound. The expanded dT analogue (dxT), a methylquinazolinedione C-glycoside, was previously unknown; we describe its preparation in eight steps from 5-methylanthranilic acid. The key glycoside bond formation employed Pd-mediated coupling of an aryl iodide precursor with a dihydrofuran derivative of deoxyribose. Both nucleosides are shown to be efficient fluorophores, emitting light in the blue-violet range. The base-protected phosphoramidite derivatives were prepared, and short oligonucleotides containing them were characterized. The two size-expanded nuclecisides are key components of a new four-base genetic system designed to form helical paired structures having a diameter greater than that of natural DNA. Elements of the design of this expanded genetic molecule, termed xDNA, are discussed, including the possibility of up to eight base pairs of information storage capability.

  DOI：

  10.1021/ja038384r
• 作为产物：
  描述：

  5,6-二甲基苯并咪唑 在 吡啶 、 potassium permanganate 、 tetraphosphorus decasulfide 、 叠氮基三甲基硅烷 作用下， 以 叔丁醇 为溶剂， 反应 46.5h， 生成 8-mercaptoimidazo<4,5-g>quinazoline
  参考文献：
  名称：

  Toward a New Genetic System with Expanded Dimensions:  Size-Expanded Analogues of Deoxyadenosine and Thymidine

  摘要：

  We describe the design, preparation, and properties of two key building blocks of a size-expanded genetic system. Nucleoside analogues of the natural nucleosides dA and dT are reported in which the fusion of a benzo ring increases their size by ca. 2.4 Angstrom. The expanded dA analogue (dxA), having a tricyclic base, was first reported by Leonard nearly three decades ago. We describe a shortened and more efficient approach to this compound. The expanded dT analogue (dxT), a methylquinazolinedione C-glycoside, was previously unknown; we describe its preparation in eight steps from 5-methylanthranilic acid. The key glycoside bond formation employed Pd-mediated coupling of an aryl iodide precursor with a dihydrofuran derivative of deoxyribose. Both nucleosides are shown to be efficient fluorophores, emitting light in the blue-violet range. The base-protected phosphoramidite derivatives were prepared, and short oligonucleotides containing them were characterized. The two size-expanded nuclecisides are key components of a new four-base genetic system designed to form helical paired structures having a diameter greater than that of natural DNA. Elements of the design of this expanded genetic molecule, termed xDNA, are discussed, including the possibility of up to eight base pairs of information storage capability.

  DOI：

  10.1021/ja038384r

文献信息

• Quinazoline derivatives and therapeutic use thereof
  申请人：Lee B. Young

  公开号：US20050187231A1

  公开（公告）日：2005-08-25

  Quinazoline derivatives represented by the general formula pharmacologically acceptable salts thereof, and compositions containing such compounds are described. Methods for using the compounds for treatment of hyperproliferative disorders are also described.

  描述了由一般式表示的喹唑啉衍生物及其药理学可接受的盐，以及含有这些化合物的组合物。还描述了使用这些化合物治疗过度增生性疾病的方法。
• Quinazoline Derivatives and Therapeutic Use Thereof
  申请人：Lee Young B.

  公开号：US20090030021A1

  公开（公告）日：2009-01-29

  Quinazoline derivatives represented by the general formula pharmacologically acceptable salts thereof, and compositions containing such compounds are described. Methods for using the compounds for treatment of hyperproliferative disorders are also disclosed.

  本发明涉及一般式所代表的喹唑啉衍生物，其药物学上可接受的盐以及含有这些化合物的组合物。还公开了使用这些化合物治疗过度增殖性疾病的方法。
• The Components of xRNA: Synthesis and Fluorescence of a Full Genetic Set of Size-Expanded Ribonucleosides
  作者：Armando R. Hernández、Eric T. Kool

  DOI：10.1021/ol102915f

  日期：2011.2.18

  The synthesis and properties of a full set of four benzo-expanded ribonucleosides (xRNA), analogous to A, G, C, and U RNA monomers, are described. The nucleosides are efficient fluorophores with emission maxima of 369-411 nm. The compounds are expected to be useful as RNA pathway probes and as components of an unnatural ribopolymer.
• 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
  作者：Nelson J. Leonard、Andrej Petric、Andrzej Rykowski

  DOI：10.1021/jo00251a045

  日期：1988.8
• US7388014B2
  申请人：——

  公开号：US7388014B2

  公开（公告）日：2008-06-17