tert-butyl 2-amino-3-cyano-5,6-dihydro-4H-thieno[2,3-b]pyridine-7-carboxylate | 675572-66-4

• 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: tert-butyl 2-amino-3-cyano-5,6-dihydro-4H-thieno[2,3-b]pyridine-7-carboxylate
• CAS: 675572-66-4
• 化学式: C₁₃H₁₇N₃O₂S
• 分子量: 279.363
• InChiKey: NWOCAXBKQTXZPP-UHFFFAOYSA-N

物化性质

• 沸点：
  482.9±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-amino-3-cyano-5,6-dihydro-4H-thieno[2,3-b]pyridine-7-carboxylate 在 吡啶 、 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 N-[7-(benzenesulfonyl)-3-cyano-5,6-dihydro-4H-thieno[2,3-b]pyridin-2-yl]naphthalene-1-carboxamide
  参考文献：
  名称：

  N-(3-Cyano-4,5,6,7-tetrahydro-1-benzothien-2-yl)amides as potent, selective, inhibitors of JNK2 and JNK3

  摘要：

  The identification and exploration of a novel, potent and selective series of N-(3-cyano-4,5,6,7-tetrahydro-1-benzothien2-yl)amide inhibitors of JNK2 and JNK3 kinases is described. Compounds 5a and 11a were identified as potent inhibitors of JNK3 (pIC(50) 6.7 and 6.6, respectively), with essentially equal potency against JNK2 (pIC(50) 6.5). Selectivity within the mitogen-activated protein kinase (MAPK) family, against JNK1, p38 alpha and ERK2, was observed for the series. X-ray crystallography of 5e and 8a in JNK3 revealed a unique binding mode, with the 3-cyano substituent forming an H-bond acceptor interaction with the hinge region of the ATP-binding site. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.003
• 作为产物：
  描述：

  N-叔丁氧羰基-3-哌啶酮 、 丙二腈 在 sulfur 、 二乙胺 作用下， 以 乙醇 为溶剂， 生成 tert-butyl 2-amino-3-cyano-5,6-dihydro-4H-thieno[2,3-b]pyridine-7-carboxylate
  参考文献：
  名称：

  N-(3-Cyano-4,5,6,7-tetrahydro-1-benzothien-2-yl)amides as potent, selective, inhibitors of JNK2 and JNK3

  摘要：

  The identification and exploration of a novel, potent and selective series of N-(3-cyano-4,5,6,7-tetrahydro-1-benzothien2-yl)amide inhibitors of JNK2 and JNK3 kinases is described. Compounds 5a and 11a were identified as potent inhibitors of JNK3 (pIC(50) 6.7 and 6.6, respectively), with essentially equal potency against JNK2 (pIC(50) 6.5). Selectivity within the mitogen-activated protein kinase (MAPK) family, against JNK1, p38 alpha and ERK2, was observed for the series. X-ray crystallography of 5e and 8a in JNK3 revealed a unique binding mode, with the 3-cyano substituent forming an H-bond acceptor interaction with the hinge region of the ATP-binding site. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.003

文献信息

• US7273876B2
  申请人：——

  公开号：US7273876B2

  公开（公告）日：2007-09-25
• N-(3-Cyano-4,5,6,7-tetrahydro-1-benzothien-2-yl)amides as potent, selective, inhibitors of JNK2 and JNK3
  作者：Richard M. Angell、Francis L. Atkinson、Murray J. Brown、Tsu Tshen Chuang、John A. Christopher、Maria Cichy-Knight、Allison K. Dunn、Kendra E. Hightower、Susanna Malkakorpi、James R. Musgrave、Margarete Neu、Paul Rowland、Robyn L. Shea、Jeffery L. Smith、Donald O. Somers、Sonia A. Thomas、Gladstone Thompson、Ruolan Wang

  DOI：10.1016/j.bmcl.2006.12.003

  日期：2007.3

  The identification and exploration of a novel, potent and selective series of N-(3-cyano-4,5,6,7-tetrahydro-1-benzothien2-yl)amide inhibitors of JNK2 and JNK3 kinases is described. Compounds 5a and 11a were identified as potent inhibitors of JNK3 (pIC(50) 6.7 and 6.6, respectively), with essentially equal potency against JNK2 (pIC(50) 6.5). Selectivity within the mitogen-activated protein kinase (MAPK) family, against JNK1, p38 alpha and ERK2, was observed for the series. X-ray crystallography of 5e and 8a in JNK3 revealed a unique binding mode, with the 3-cyano substituent forming an H-bond acceptor interaction with the hinge region of the ATP-binding site. (c) 2006 Elsevier Ltd. All rights reserved.