8-bromo-2-[(2S)-pyrrolidin-2-yl][1]benzofuro[3,2-d]pyrimidin-4(3H)-one | 1169557-85-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 8-bromo-2-[(2S)-pyrrolidin-2-yl][1]benzofuro[3,2-d]pyrimidin-4(3H)-one
• 英文别名: 8-bromo-2-[(2S)-pyrrolidin-2-yl]-3H-[1]benzofuro[3,2-d]pyrimidin-4-one
• CAS: 1169557-85-0
• 化学式: C₁₄H₁₂BrN₃O₂
• 分子量: 334.172
• InChiKey: IFSZNNCMCGMAHD-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 8-bromo-2-[(2S)-pyrrolidin-2-yl][1]benzofuro[3,2-d]pyrimidin-4(3H)-one 在 sodium cyanoborohydride 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成 8-bromo-2-[(2S)-1-methylpyrrolidin-2-yl]-3H-[1]benzofuro[3,2-d]pyrimidin-4-one
  参考文献：
  名称：

  Discovery of XL413, a potent and selective CDC7 inhibitor

  摘要：

  CDC7 is a serine/threonine kinase that has been shown to be required for the initiation and maintenance of DNA replication. Up-regulation of CDC7 is detected in multiple tumor cell lines, with inhibition of CDC7 resulting in cell cycle arrest. In this paper, we disclose the discovery of a potent and selective CDC7 inhibitor, XL413 (14), which was advanced into Phase 1 clinical trials. Starting from advanced lead 3, described in a preceding communication, we optimized the CDC7 potency and selectivity to demonstrate in vitro CDC7 dependent cell cycle arrest and in vivo tumor growth inhibition in a Colo-205 xenograft model. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.024
• 作为产物：
  描述：

  (2S)-N-(5-bromo-2-carbamoyl-1-benzofuran-3-yl)pyrrolidine-2-carboxamide 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以95%的产率得到8-bromo-2-[(2S)-pyrrolidin-2-yl][1]benzofuro[3,2-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  Discovery of XL413, a potent and selective CDC7 inhibitor

  摘要：

  CDC7 is a serine/threonine kinase that has been shown to be required for the initiation and maintenance of DNA replication. Up-regulation of CDC7 is detected in multiple tumor cell lines, with inhibition of CDC7 resulting in cell cycle arrest. In this paper, we disclose the discovery of a potent and selective CDC7 inhibitor, XL413 (14), which was advanced into Phase 1 clinical trials. Starting from advanced lead 3, described in a preceding communication, we optimized the CDC7 potency and selectivity to demonstrate in vitro CDC7 dependent cell cycle arrest and in vivo tumor growth inhibition in a Colo-205 xenograft model. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.024

文献信息

• [EN] BENZOFUROPYRIMIDINONES AS PROTEIN KINASE INHIBITORS<br/>[FR] BENZOFUROPYRIMIDINONES EN TANT QU'INHIBITEURS DE PROTÉINE KINASE
  申请人：EXELIXIS INC

  公开号：WO2009086264A1

  公开（公告）日：2009-07-09

  A compound according to formula I: or a pharmaceutically acceptable salt thereof; wherein R1, R2, R3a, R3b, R3c and R3d are as defined in the specification, pharmaceutical compositions thereof, and methods of use thereof.

  根据公式I的化合物：或其药用可接受盐；其中R1、R2、R3a、R3b、R3c和R3d如规范中所定义，以及其药物组合物和使用方法。
• Benzofuropyrimidinones
  申请人：Brown S. David

  公开号：US20090247559A1

  公开（公告）日：2009-10-01

  A compound according to formula I: or a pharmaceutically acceptable salt thereof; wherein R 1 , R 2 , R 3a , R 3b , R 3c and R 3d are as defined in the specification, pharmaceutical compositions thereof, and methods of use thereof.

  公式I所示的化合物或其药学上可接受的盐；其中R1、R2、R3a、R3b、R3c和R3d如规范中所定义，以及其药物组合物和使用方法。
• BENZOFUROPYRIMIDINONES AS PROTEIN KINASE INHIBITORS
  申请人：Exelixis, Inc.

  公开号：EP2097419A1

  公开（公告）日：2009-09-09