6-chloro-2-methoxy-1H-quinazolin-4-one | 246231-74-3

• 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: 6-chloro-2-methoxy-1H-quinazolin-4-one
• 英文别名: 6-chloro-2-methoxy-3H-quinazolin-4-one
• CAS: 246231-74-3
• 化学式: C₉H₇ClN₂O₂
• 分子量: 210.62
• InChiKey: UENLPJFXBBOOFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-2-methoxy-1H-quinazolin-4-one 、 (3S-trans)-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile 以 甲苯 为溶剂， 反应 4.0h， 以41%的产率得到(3S,4R)-4-(6-chloro-4-oxo-1,4-dihydroquinazolin-2-ylamino)-3-hydroxy-2,2-dimethylchroman-6-carbonitrile
  参考文献：
  名称：

  Discovery and structure–activity relationships of a novel series of benzopyran-based KATP openers for urge urinary incontinence

  摘要：

  A novel series of benzopyran derivatives were synthesized and evaluated as K(ATP) channel openers. Structure-activity relationships were investigated around 4-position of the benzopyran nucleus. Optimization of 4-substituent with some heterocyclic rings led to compound 13b bearing a benzo[d] isoxazol-3-one moiety as a potent and selective KATP channel opener in vitro. In two anesthetized rat models of myogenic bladder overactivity, compound 13b was found to inhibit spontaneous bladder contractions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.055
• 作为产物：
  描述：

  5-(3-chlorophenyl)-3-methoxy-1,2,4-oxadiazole 在 二苯基乙炔 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以24%的产率得到2-methoxy-8-chloroquinazolin-4-one
  参考文献：
  名称：

  Photoinduced Single Electron Transfer on 5-Aryl-1,2,4-oxadiazoles:  Some Mechanistic Investigations in the Synthesis of Quinazolin-4-ones

  摘要：

  The photochemistry of some 5-aryl-3-methoxy- (or 5-aryl-3-phenyl-) 1,2,4-oxadiazoles irradiated in the presence of different sensitizers [such as diphenylacetylene (DAC), 9,10-diphenylanthracene (DAN), or triphenylene (TPH)] or ground-state donors such as triethylamine (TEA) has been investigated. Intermediates arising from breaking of the ring O-N bond develop both into quinazolin-4-ones (by a heterocyclization reaction involving the aryl at the C-5 of the oxadiazole nucleus) and into open-chain products (corresponding to a reduction at the ring O-N bond), in different ratios depending on their structures and photoreaction conditions. A reasonable explanation considers sensitization by photoinduced electron transfer either from the sensitizer in its excited state to the oxadiazole in its ground state or from the electron donor reagent (TEA) to the excited oxadiazole; in both cases an oxadiazole radical anion is formed as a key species from which breaking of the ring O-N bond takes place. Reduction potentials of representative oxadiazoles confirm this hypothesis. Possible applications in the synthesis of variously substituted quinazolin-4-ones are recognized.

  DOI：

  10.1021/jo990298f

文献信息

• NOVEL BENZOPYRAN DERIVATIVES AS POTASSIUM CHANNEL OPENERS
  申请人：Zhang Xuqing

  公开号：US20070049556A1

  公开（公告）日：2007-03-01

  The present invention is directed to novel benzopyran derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders related to potassium channel.

  本发明涉及新型苯并吡喃衍生物，含有它们的药物组合物以及它们在治疗与钾通道相关的疾病中的应用。
• Benzopyran derivatives as potassium channel openers
  申请人：Janssen Pharmaceutica NV

  公开号：US07812183B2

  公开（公告）日：2010-10-12

  The present invention is directed to novel benzopyran derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders related to potassium channel.

  本发明涉及新型苯并吡喃衍生物，包含它们的药物组合物以及它们在治疗与钾通道相关的疾病中的应用。
• BENZOPYRAN AND PYRANOPYRIDINE DERIVATIVES AS POTASSIUM CHANNEL OPENERS
  申请人：Janssen Pharmaceutica, N.V.

  公开号：EP1940516A2

  公开（公告）日：2008-07-09
• US7812183B2
  申请人：——

  公开号：US7812183B2

  公开（公告）日：2010-10-12
• US7838553B2
  申请人：——

  公开号：US7838553B2

  公开（公告）日：2010-11-23