5-bromo-2-cyclobutylmethoxybenzonitrile | 1419747-72-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-bromo-2-cyclobutylmethoxybenzonitrile
• 英文别名: 5-Bromo-2-(cyclobutylmethoxy)benzonitrile；5-bromo-2-(cyclobutylmethoxy)benzonitrile
• CAS: 1419747-72-0
• 化学式: C₁₂H₁₂BrNO
• 分子量: 266.137
• InChiKey: FSQWQTPXOXDPHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-2-cyclobutylmethoxybenzonitrile 在 四(三苯基膦)钯 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 5-(2-Aminopyrimidin-4-yl)-2-(cyclobutylmethoxy)benzonitrile
  参考文献：
  名称：

  Lead optimization of isocytosine-derived xanthine oxidase inhibitors

  摘要：

  We report our attempts at improving the oral efficacy of low-nanomolar inhibitors of xanthine oxidase from isocytosine series through chemical modifications. Our lead compound had earlier shown good in vivo efficacy when administered intraperitoneally but not orally. Several modifications are reported here which achieved more than twofold improvement in exposure. A compound with significant improvement in oral efficacy was also obtained. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.057

文献信息

• BENZONITRILE DERIVATIVES AS KINASE INHIBITORS
  申请人：Hoelzemann Guenter

  公开号：US20140228340A1

  公开（公告）日：2014-08-14

  Compounds of the formula I, in which R 1 , R 2 , X and Y have the meanings indicated in Claim 1 , are inhibitors of TBK1 and IKKε and can be employed, inter alia, for the treatment of cancer and inflammatory diseases.

  式I中的化合物，其中R1、R2、X和Y具有权利要求1中指示的含义，是TBK1和IKKε的抑制剂，可用于治疗癌症和炎症性疾病。
• Benzonitrile derivatives as kinase inhibitors
  申请人：Hoelzemann Guenter

  公开号：US08969335B2

  公开（公告）日：2015-03-03

  Compounds of the formula I, in which R1, R2, X and Y have the meanings indicated in Claim 1, are inhibitors of TBK1 and IKKε and can be employed, inter alia, for the treatment of cancer and inflammatory diseases.

  公式I中的化合物，其中R1，R2，X和Y具有声明1中指示的含义，是TBK1和IKKε的抑制剂，可用于治疗癌症和炎症性疾病等。
• US8969335B2
  申请人：——

  公开号：US8969335B2

  公开（公告）日：2015-03-03
• [DE] BENZONITRILDERIVATE ALS KINASEHEMMER<br/>[EN] BENZONITRILE DERIVATIVES AS KINASE INHIBITORS<br/>[FR] DÉRIVÉS DE BENZONITRILE EN TANT QU'INHIBITEURS DE KINASES
  申请人：MERCK PATENT GMBH

  公开号：WO2013034238A1

  公开（公告）日：2013-03-14

  Verbindungen der Formel I worin R1, R2, X und Y die in Anspruch 1 angegebenen Bedeutungen haben, sind Hemmer von TBK1 und ΙΚΚε und können unter anderem für die Behandlung von Krebs und Entzündungskrankheiten eingesetzt werden.
• Lead optimization of isocytosine-derived xanthine oxidase inhibitors
  作者：Komal Bajaj、Sandeep Burudkar、Pranay Shah、Ashish Keche、Usha Ghosh、Prashant Tannu、Smriti Khanna、Ankita Srivastava、Nitin J. Deshmukh、Amol Dixit、Yogesh Ahire、Anagha Damre、Kumar V.S. Nemmani、Asha Kulkarni-Almeida、Chandrika B-Rao、Rajiv Sharma、H. Sivaramakrishnan

  DOI：10.1016/j.bmcl.2012.11.057

  日期：2013.2

  We report our attempts at improving the oral efficacy of low-nanomolar inhibitors of xanthine oxidase from isocytosine series through chemical modifications. Our lead compound had earlier shown good in vivo efficacy when administered intraperitoneally but not orally. Several modifications are reported here which achieved more than twofold improvement in exposure. A compound with significant improvement in oral efficacy was also obtained. (c) 2012 Elsevier Ltd. All rights reserved.