7-[(2,4-dichloro-5-methoxyphenyl)amino]-2-iodothieno[3,2-b]pyridine-6-carbonitrile | 700844-36-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: 7-[(2,4-dichloro-5-methoxyphenyl)amino]-2-iodothieno[3,2-b]pyridine-6-carbonitrile
• 英文别名: 7-(2,4-dichloro-5-methoxyanilino)-2-iodothieno[3,2-b]pyridine-6-carbonitrile
• CAS: 700844-36-6
• 化学式: C₁₅H₈Cl₂IN₃OS
• 分子量: 476.125
• InChiKey: YFEHAXRUHDBVER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  86.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-[(2,4-dichloro-5-methoxyphenyl)amino]-2-iodothieno[3,2-b]pyridine-6-carbonitrile 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 7-[(2,4-dichloro-5-methoxyphenyl)amino]-2-(5-formylthien-2-yl)thieno[3,2-b]pyridine-6-carbonitrile
  参考文献：
  名称：

  Synthesis and Src Kinase Inhibitory Activity of 2-Phenyl- and 2-Thienyl-7-phenylaminothieno[3,2-b]pyridine-6-carbonitriles

  摘要：

  2-Phenyl-7-phenylaminothieno[3,2-b]pyridine-6-carbonitriles were recently reported to be inhibitors of Src kinase activity. In this study we present structure-activity relationships for additional thieno[3,2-b]pyridine-6-carbonitriles, modifying the substituents on the C-2 phenyl and C-7 phenylamino groups. Derivatives with various aminomethyl and aminoethyl substituents on the para position of the C-2 phenyl group retained the activity of the initial analogues. However, direct attachment of an amino group led to decreased activity. A 2,4-dichloro-5-methoxyphenylamino group at C-7 provided superior inhibition of Src enzymatic activity. Replacement of the C-2 phenyl group with a 3,5-substituted thiophene led to improved Src inhibitory activity compared to the parent compound, but other thiophene isomers were less active. One of the analogues reported here exhibited in vivo activity comparable to that of SKI-606, a related 3-quinolinecarbonitrile currently in clinical trials.

  DOI：

  10.1021/jm050175p
• 作为产物：
  描述：

  7-二甲基氨基-4-甲基香豆素-3-异硫氰酸酯 在 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 为溶剂， 反应 6.33h， 生成 7-[(2,4-dichloro-5-methoxyphenyl)amino]-2-iodothieno[3,2-b]pyridine-6-carbonitrile
  参考文献：
  名称：

  Identification of 7-Phenylaminothieno- [3,2-b]pyridine-6-carbonitriles as a New Class of Src Kinase Inhibitors

  摘要：

  We disclose here a new class of kinase inhibitors, obtained by replacing the phenyl ring of a 3-quinoline-carbonitrile system with a thiophene ring. When suitably substituted, the resultant 7-phenylaminothieno[3,2-b]pyridine-6-carbonitrile analogues show potent inhibition of Src kinase activity.

  DOI：

  10.1021/jm049237m

文献信息

• Thieno[3,2-b]pyridine-6-carbonitriles and thieno[2,3-b]pyridine-5-carbonitriles as protein kinase inhibitors
  申请人：Wyeth

  公开号：US20040242883A1

  公开（公告）日：2004-12-02

  This invention provides compounds of Formula (1a)-(1f), II 1 wherein: X, m, n, q, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Y, Q, Z, Z′, Z′″, Z″ and J are defined hereinbefore in the specification, which are useful in the treatment of cancer, stroke, myocardial infarction, neuropathic pain, osteoporosis, polycystic kidney disease, autoimmune disease, rheumatoid arthritis, and transplant rejection and process for producing said compounds.

  这项发明提供了式（1a）-（1f）的化合物，II1，其中：X、m、n、q、R1、R2、R3、R4、R5、R6、R7、R8、R9、Y、Q、Z、Z′、Z′″、Z″和J在本说明书中有定义，这些化合物在治疗癌症、中风、心肌梗死、神经病痛、骨质疏松症、多囊性肾脏病、自身免疫疾病、类风湿关节炎和移植排斥方面具有用途，并提供了生产这些化合物的方法。
• Thieno [ 3,2-b] pyridine-6-carbonitriles and thieno [2,3-b] pyridine-5-carbonitriles as protein kinase inhibitors
  申请人：Boschelli Harris Diane

  公开号：US20080070913A1

  公开（公告）日：2008-03-20

  This invention provides compounds of Formula (1a)-(1f), II wherein: X, m, n, q, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Y, Q, Z, Z′, Z′″, Z″ and J are defined hereinbefore in the specification, which are useful in the treatment of cancer, stroke, myocardial infarction, neuropathic pain, osteoporosis, polycystic kidney disease, autoimmune disease, rheumatoid arthritis, and transplant rejection and process for producing said compounds.

  本发明提供了以下公式（1a）-（1f），II的化合物： 其中，X，m，n，q，R1，R2，R3，R4，R5，R6，R7，R8，R9，Y，Q，Z，Z′，Z′″，Z″和J在说明书中已定义，这些化合物在癌症、中风、心肌梗死、神经病性疼痛、骨质疏松症、多囊肾病、自身免疫性疾病、类风湿性关节炎和移植排斥等疾病的治疗中有用，并提供了制备这些化合物的方法。
• [EN] THIENO[3,2-b]PYRIDINE-6-CARBONITRILES AND THIENO[2,3-b]PYRIDINE-5-CARBONITRILES AS PROTEIN KINASE INHIBITORS<br/>[FR] THIENO[3,2-B]PYRIDINE-6-CARBONITRILES ET THIENO[2,3-B]PYRIDINE-5-CARBONITRILES EN TANT QU'INHIBITEURS DE PROTEINE KINASE
  申请人：WYETH CORP

  公开号：WO2004048386A3

  公开（公告）日：2004-10-07
• Inhibition of Src kinase activity by 7-[(2,4-dichloro-5-methoxyphenyl)amino]-2-heteroaryl-thieno[3,2-b]pyridine-6-carbonitriles
  作者：Diane H. Boschelli、Biqi Wu、Ana Carolina Barrios Sosa、Joan J. Chen、Jennifer M. Golas、Frank Boschelli

  DOI：10.1016/j.bmcl.2005.07.061

  日期：2005.11

  7-[(2,4-Dichloro-5-methoxyphenyl)aminolthieno[3,2-b]pyridine-6-carbonitriles with various heteroaryl groups at C-2 are inhibitors of Src kinase activity. Of these new analogs, compounds substituted at C-2 by a 3,5-furan or a 2,5-pyridine had the best activity in the Src enzyme and cell assays. (c) 2005 Elsevier Ltd. All rights reserved.
• THIENO[3,2-B]PYRIDINE-6-CARBONITRILES AND THIENO[2,3-B]PYRIDINE-5-CARBONITRILES AS PROTEIN KINASE INHIBITORS
  申请人：Wyeth

  公开号：EP1565474A2

  公开（公告）日：2005-08-24