lin-benzohypoxanthine | 53449-18-6

• 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-benzohypoxanthine
• 英文别名: 1,5-Dihydroimidazo[4,5-g]quinazolin-8-one；1,7-dihydroimidazo[4,5-g]quinazolin-8-one
• CAS: 53449-18-6
• 化学式: C₉H₆N₄O
• mdl: MFCD00835101
• 分子量: 186.173
• InChiKey: ZLJSWBSUEOZJDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 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：
  70.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  lin-benzohypoxanthine 生成 5,9-Dihydro-1H-imidazo[4,5-g]quinazolin-8(4H)-one
  参考文献：
  名称：

  LEONARD, NELSON J.;PETRIC, ANDREJ;RYKOWSKI, ANDRZEJ, J. ORG. CHEM., 53,(1988) N 16, C. 3873-3875

  摘要：

  DOI：
• 作为产物：
  描述：

  5,6-二甲基苯并咪唑 在 potassium permanganate 、 叠氮基三甲基硅烷 、 醋酸甲脒 作用下， 以 水 、 叔丁醇 为溶剂， 反应 9.0h， 生成 lin-benzohypoxanthine
  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

• 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。
• [EN] QUINAZOLINONE INHIBITORS OF cGMP PHOSPHODIESTERASE<br/>[FR] INHIBITEURS QUINAZOLINONE DE LA PHOSPHODIESTERASE cGMP
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：WO1999064004A1

  公开（公告）日：1999-12-16

  (EN) Novel quinazolinone compounds, methods of using such compounds in the treatment of cGMP-associated conditions such as erectile dysfunction, and pharmaceutical compositions containing such compounds.(FR) Nouveaux composés quinazolinone, procédés d'utilisation desdits composés dans le traitement d'états pathologiques associés à l'acide guanosine-3'5'-monosphosphate cyclique (cGMP), tels que les troubles de l'érection, et compositions pharmaceutiques contenant lesdits composés.

  （中文）一种新型的喹唑啉酮化合物，以及在治疗与cGMP相关的疾病，如勃起功能障碍方面使用这种化合物的方法和含有这种化合物的制药组合物。
• 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。
• Regioselective synthesis of imidazo[4,5-g]quinazoline quinone nucleosides and quinazoline amino nucleosides. Studies of their xanthine oxidase and purine nucleoside phosphorylase substrate activity
  作者：Robert O'Hara Dempcy、Edward B. Skibo

  DOI：10.1021/jo00002a052

  日期：1991.1

  The regioselective synthesis of 3-ribofuranosylimidazo[4,5-g]quinazoline-4,8-9(3H,7H)-trione (1) (benzoquinone-stretched-out inosine) and 8-(ribofuranosylamino)quinaozlin-4(3G)-one (2) was carried out in conjunction with the design of reductive alkylating nuclosides and new purine nucleoside mimics, respectively. The preparation of 1 was carried out by regioselective ribosylation of 4-nitroimidazo[4,5-g]quinazolin-8(3H,7H)-one (3) followed by nitro group reduction, Fremy oxidation, and deacetylation. Regiocontrol of ribosylation has steric origions: the 4-nitro group of 3 directs silylation to the N(1) position, which results in ribosylation exclusively at the N(3) position under Vorbruggen reaction conditions. Regiocontrol during the preparation of 2 was possible by generating a stabilized ribofuranosyl carbocation, which selectively reacts with the amine group of the base. Nucleoside 1 is a purine-like quinone by virtue of its oxidation by xanthine oxidase. The potential inosine mimic 2 does not undergo phosphorolysis by purine nucleoside phosphorylase (PNPase), but the base form (8-amino-quinazolin-4(3H)-one) does bind to the PNPase active site as tightly as hypoxanthine. Factors which contribute to this binding behavior are discussed.
• Toward a New Genetic System with Expanded Dimensions:  Size-Expanded Analogues of Deoxyadenosine and Thymidine
  作者：Haibo Liu、Jianmin Gao、Lystranne Maynard、Y. David Saito、Eric T. Kool

  DOI：10.1021/ja038384r

  日期：2004.2.1

  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.