[4-(Butylthio)-1H-pyrazolo[3,4-b]pyridin-5-yl]phenylmethanone | 227617-11-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [4-(Butylthio)-1H-pyrazolo[3,4-b]pyridin-5-yl]phenylmethanone
• 英文别名: 5-benzoyl-4-(butylsulfanyl)-1H-pyrazolo[3,4-b]pyridine；(4-butylsulfanyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-phenylmethanone
• CAS: 227617-11-0
• 化学式: C₁₇H₁₇N₃OS
• 分子量: 311.407
• InChiKey: FACHZFAWMXYQIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [4-(Butylthio)-1H-pyrazolo[3,4-b]pyridin-5-yl]phenylmethanone 在 Oxone 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 15.0h， 以60%的产率得到[4-(Butylsulfinyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]phenylmethanone
  参考文献：
  名称：

  USE OF PYRAZOLO [3,4-b] PYRIDINE AS CYCLIN DEPENDANT KINASE INHIBITORS

  摘要：

  公开号：

  EP1043998B1
• 作为产物：
  描述：

  5-benzoyl-1-[(4-methoxyphenyl)methyl]-7H-pyrazolo[3,4-b]pyridin-4-one 在 三氟乙酸 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 8.5h， 生成 [4-(Butylthio)-1H-pyrazolo[3,4-b]pyridin-5-yl]phenylmethanone
  参考文献：
  名称：

  1H-Pyrazolo[3,4-b]pyridine Inhibitors of Cyclin-Dependent Kinases

  摘要：

  1H-Pyrazolo[3,4-b]pyridine 3 (SQ-67563) has been shown to be a potent, selective inhibitor of CDK1/CDK2 in vitro. In cells 3 acts as a cytotoxic agent with the ability to block cell cycle progression and/or induce apoptosis. The solid state structure of 3 bound to CDK2 shows 3 resides coincident with the ATP purine binding site and forms important H-bonding interactions with Leu83 on the protein backbone. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00034-9

文献信息

• Use of pyrazolo [3,4-b] pyridine as cyclin dependent kinase inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US06107305A1

  公开（公告）日：2000-08-22

  Compounds of the formula ##STR1## and pharmaceutically acceptable salts thereof for use as inhibitors of cyclin dependent kinases, wherein: X is O, S(O).sub.m ; Y is alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl; R.sub.1 is hydrogen or lower alkyl; R.sub.2 is alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, --O-alkyl, --O-aryl, --NR.sub.4 R.sub.5 ; R.sub.3 is hydrogen or lower alkyl; R.sub.4 is hydrogen, alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, --O-alkyl, --O-aryl; R.sub.5 is hydrogen, alkyl, aryl, alkylaryl, heteroaryl, alkylheteroaryl, cycloalkyl, alkylcycloalkyl, heterocycloalkyl, alkylheterocycloalkyl, --O-alkyl, --O-aryl; and m is 0, 1 or 2. The compounds of formula I are protein kinase inhibitors and are useful in the treatment and prevention of proliferative diseases, for example, cancer, inflammation and arthritis. They may also be useful in the treatment of neurodegenerative diseases such as Alzheimer's disease, cardiovascular diseases, viral diseases and fungal diseases.

  公式##STR1##中的化合物及其药用盐可用作细胞周期依赖性激酶的抑制剂，其中：X为O，S(O).sub.m；Y为烷基，芳基，芳基烷基，杂芳基，杂芳基烷基，环烷基，环烷基烷基，杂环烷基，杂环烷基烷基；R.sub.1为氢或较低烷基；R.sub.2为烷基，芳基，芳基烷基，杂芳基，杂芳基烷基，环烷基，环烷基烷基，杂环烷基，杂环烷基烷基，--O-烷基，--O-芳基，--NR.sub.4 R.sub.5；R.sub.3为氢或较低烷基；R.sub.4为氢，烷基，芳基，芳基烷基，杂芳基，杂芳基烷基，环烷基，环烷基烷基，杂环烷基，杂环烷基烷基，--O-烷基，--O-芳基；R.sub.5为氢，烷基，芳基，烷基芳基，杂芳基，烷基杂芳基，环烷基，烷基环烷基，杂环烷基，烷基杂环烷基，--O-烷基，--O-芳基；m为0，1或2。公式I的化合物是蛋白激酶抑制剂，可用于治疗和预防增生性疾病，例如癌症，炎症和关节炎。它们也可能在治疗神经退行性疾病如阿尔茨海默病，心血管疾病，病毒性疾病和真菌性疾病方面有用。
• EP1043998A4
  申请人：——

  公开号：EP1043998A4

  公开（公告）日：2004-02-04
• USE OF PYRAZOLO 3,4-b] PYRIDINE AS CYCLIN DEPENDENT KINASE INHIBITORS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP1043998A1

  公开（公告）日：2000-10-18
• US6107305A
  申请人：——

  公开号：US6107305A

  公开（公告）日：2000-08-22
• [EN] USE OF PYRAZOLO [3,4-b] PYRIDINE AS CYCLIN DEPENDENT KINASE INHIBITORS<br/>[FR] UTILISATION DE PYRAZOLO[3,4-b]PYRIDINE EN TANT QU'INHIBITEURS DE KINASE DEPENDANT DE LA CYCLINE
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：WO1999030710A1

  公开（公告）日：1999-06-24

  (EN) Compounds of formula (I) and pharmaceutically acceptable salts thereof for use as inhibitors of cyclin dependent kinases, wherein: X is O, S(O)m; Y is alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl; R1 is hydrogen or lower alkyl; R2 is alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocloalkylalkyl, -O-alkyl, -O-aryl, -NR4R5; R3 is hydrogen or lower alkyl; R4 is hydrogen, alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, -O-alkyl, -O-aryl; R5 is hydrogen, alkyl, aryl, alkylaryl, heteroaryl, alkylheteroaryl, cycloalkyl, alkylcycloalkyl, heterocycloalkyl, alkylheterocycloalkyl, -O-alkyl, -O-aryl; and m is 0, 1 or 2. The compounds of formula (I) are proteinkinase inhibitors and are useful in the treatment and prevention of proliferative diseases, for example, cancer, inflammation and arthritis. They may also be useful in the treatment of neurodegenerative diseases such as Alzheimer's disease, cardiovascular diseases, viral diseases and fungal diseases.(FR) L'invention concerne des composés de formule (I), ainsi que des sels pharmaceutiquement acceptables de ceux-ci, destinés à être utilisés en tant qu'inhibiteurs de kinase dépendant de la cycline. Dans cette formule: X représente O, S(O)m; Y représentant alkyle, aryle, arylalkyle, hétéroaryle, hétéroarylalkyle, cycloalkyle, cycloalkylalkyle, hétérocycloalkyle, hétérocycloalkylalkyle; R1 représente hydrogène ou alkyle inférieur; R2 représente alkyle, aryle, arylalkyle, hétéroaryle, hétéroarylalkyle, cycloalkyle, cycloalkylalkyle, hétérocycloalkyle, hétérocycloalkylalkyle, -O-alkyle, -O-aryle, -NR4R5; R3 représente hydrogène ou alkyle inférieur; R4 représente hydrogène, alkyle, aryle, arylalkyle, hétéroaryle, hétéroarylalkyle, cycloalkyle, cycloalkylalkyle, hétérocycloalkyle, hétérocycloalkylalkyle, -O-alkyle, -O-aryle; R5 représente hydrogène, alkyle, aryle, alkylaryle, hétéroaryle, alkylhétéroaryle, cycloalkyle, alkylcycloalkyle, hétérocycloalkyle, alkylhétérocycloalkyle, -O-alkyle, -O-aryle; et m est égal à 0, 1, ou 2. Ces composés de formule I constituent des inhibiteurs de la protéine kinase et sont utiles au traitement et à la prévention de maladies prolifératives, par exemple le cancer, les inflammations, et l'arthrite. Ces composés peuvent en outre être utiles au traitement des maladies neurodégénératives telles que la maladie d'Alzheimer et les maladies cardiovasculaires, virales et fongiques.