3-(3-溴-4-氯苯基)-1H-哒嗪-6-酮 | 62902-74-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 3-(3-溴-4-氯苯基)-1H-哒嗪-6-酮
• 英文名称: 6-(3-Bromo-4-chlorophenyl)-3(2H)pyridazinone
• 英文别名: 6-(3-Bromo-4-chlorophenyl)pyridazin-3(2H)-one；3-(3-bromo-4-chlorophenyl)-1H-pyridazin-6-one
• CAS: 62902-74-3
• 化学式: C₁₀H₆BrClN₂O
• 分子量: 285.527
• InChiKey: ZNTBDXYCXDIVMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  zinc(II) cyanide 、 3-(3-溴-4-氯苯基)-1H-哒嗪-6-酮 在 1,1'-双(二苯基膦)二茂铁 、 tris-(dibenzylideneacetone)dipalladium(0) 、 zinc diacetate 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以91%的产率得到
  参考文献：
  名称：

  Diazinones as P2 replacements for pyrazole-based cathepsin S inhibitors

  摘要：

  A pyridazin-4-one fragment 4 (hCatS IC(50) = 170 mu M) discovered through Tethering was modeled into cathepsin S and predicted to overlap in S2 with the tetrahydropyridinepyrazole core of a previously disclosed series of CatS inhibitors. This fragment served as a template to design pyridazin-3-one 12 (hCatS IC(50) = 430 nM), which also incorporates P3 and P5 binding elements. A crystal structure of 12 bound to Cys25Ser CatS led to the synthesis of the potent diazinone isomers 22 (hCatS IC(50) = 60 nM) and 27 (hCatS IC(50) = 40 nM). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.086
• 作为产物：
  描述：

  在 ammonium hydroxide 、 肼 作用下， 以 水 为溶剂， 生成 3-(3-溴-4-氯苯基)-1H-哒嗪-6-酮
  参考文献：
  名称：

  Diazinones as P2 replacements for pyrazole-based cathepsin S inhibitors

  摘要：

  A pyridazin-4-one fragment 4 (hCatS IC(50) = 170 mu M) discovered through Tethering was modeled into cathepsin S and predicted to overlap in S2 with the tetrahydropyridinepyrazole core of a previously disclosed series of CatS inhibitors. This fragment served as a template to design pyridazin-3-one 12 (hCatS IC(50) = 430 nM), which also incorporates P3 and P5 binding elements. A crystal structure of 12 bound to Cys25Ser CatS led to the synthesis of the potent diazinone isomers 22 (hCatS IC(50) = 60 nM) and 27 (hCatS IC(50) = 40 nM). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.086

文献信息

• Process for producing antifungal pyridazinone derivatives and certain novel compounds produced by such a process
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0089650A1

  公开（公告）日：1983-09-28

  Compounds of formula (I): [wherein R' and R3 represent hydrogen or halogen atoms, R2 represents a hydrogen or halogen atom or a lower alkyl or alkoxy group (provided R', R2 and R3 are not simultaneously hydrogen), ...... represents a single or double carbon-carbon bond and, where it is a single bond, R4 represents a group of formula -SR5 (wherein R5 represents an optionally substituted alkyl, phenyl, aralkyl or pyridyl group or a lower alkenyl group) and, where it is a double bond, R4 represents hydrogen] can be prepared by reacting a compound of formula (II): with a compound of formula R6H [where R6 represents a group -SR5, a group -SR7 (where R7 represents a group of formula and Y represents oxygen or sulphur, R8 and R9 represent lower alkoxy groups and R10 represents a lower alkoxy, lower alkyl or phenyl group), a methoxy group or a halogen atom) to give a compound of formula (IV): or, where R6 represents a methoxy group, a methyl ester thereof; reacting this compound with hydrazine to give a compound of formula (V): or (VI): and if necessary, treating the compound of formula (V) with an acid or a base to produce the compound of formula (VI). All of the compounds of formula (I) are valuable antifungal agents and compounds of formula (V) where R6 represents a group of formula -SR5 are novel compounds.

  式(I)化合物： 其中 R' 和 R3 代表氢原子或卤素原子，R2 代表氢原子或卤素原子或低级烷基或烷氧基（条件是 R'、R2 和 R3 不同时为氢），...... 代表单碳碳键或双碳碳键，如果是单键，R4 代表式-SR5 的基团（其中 R5 代表任选取代的烷基、苯基、芳烷基或吡啶基或低级烯基），如果是双键，R4 代表氢]可通过式（II）化合物与式 R6H[其中 R6 代表基团-SR5、基团-SR7（其中 R7 代表基团-SR7）、基团-R6H]反应制备： 与式 R6H[其中 R6 代表一个基团-SR5、一个基团-SR7（其中 R7 代表一个式基团 和 Y 代表氧或硫，R8 和 R9 代表低级烷氧基，R10 代表低级烷氧基、低级烷基或苯基）、甲氧基或卤原子)，得到式(IV)化合物： 或（其中 R6 代表甲氧基）其甲酯；将该化合物与肼反应，得到式（V）化合物： 或 (VI)： 必要时，用酸或碱处理式（V）化合物，生成式（VI）化合物。所有式（I）化合物都是有价值的抗真菌剂，而式（V）化合物（其中 R6 代表式-SR5 的基团）则是新型化合物。
• US4052395A
  申请人：——

  公开号：US4052395A

  公开（公告）日：1977-10-04
• US4603201A
  申请人：——

  公开号：US4603201A

  公开（公告）日：1986-07-29
• Diazinones as P2 replacements for pyrazole-based cathepsin S inhibitors
  作者：Michael K. Ameriks、Scott D. Bembenek、Matthew T. Burdett、Ingrid C. Choong、James P. Edwards、Damara Gebauer、Yin Gu、Lars Karlsson、Hans E. Purkey、Bart L. Staker、Siquan Sun、Robin L. Thurmond、Jian Zhu

  DOI：10.1016/j.bmcl.2010.05.086

  日期：2010.7

  A pyridazin-4-one fragment 4 (hCatS IC(50) = 170 mu M) discovered through Tethering was modeled into cathepsin S and predicted to overlap in S2 with the tetrahydropyridinepyrazole core of a previously disclosed series of CatS inhibitors. This fragment served as a template to design pyridazin-3-one 12 (hCatS IC(50) = 430 nM), which also incorporates P3 and P5 binding elements. A crystal structure of 12 bound to Cys25Ser CatS led to the synthesis of the potent diazinone isomers 22 (hCatS IC(50) = 60 nM) and 27 (hCatS IC(50) = 40 nM). (C) 2010 Elsevier Ltd. All rights reserved.