1,1-Dimethylethyl 4-(5-bromo-2-carbamoylbenzofuran-3-ylcarbamoyl)piperidine-1-carboxylate | 1169562-29-1

• 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: 1,1-Dimethylethyl 4-(5-bromo-2-carbamoylbenzofuran-3-ylcarbamoyl)piperidine-1-carboxylate
• 英文别名: tert-butyl 4-[(5-bromo-2-carbamoyl-1-benzofuran-3-yl)carbamoyl]piperidine-1-carboxylate
• CAS: 1169562-29-1
• 化学式: C₂₀H₂₄BrN₃O₅
• 分子量: 466.332
• InChiKey: RRSVKAGASPNYDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,1-Dimethylethyl 4-(5-bromo-2-carbamoylbenzofuran-3-ylcarbamoyl)piperidine-1-carboxylate 在 盐酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 生成 8-bromo-2-piperidin-4-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
• 作为产物：
  描述：

  5-溴-2-羟基苯甲腈 在 三聚氯氰 、 potassium carbonate 、 potassium hydroxide 作用下， 以 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 生成 1,1-Dimethylethyl 4-(5-bromo-2-carbamoylbenzofuran-3-ylcarbamoyl)piperidine-1-carboxylate
  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
• 作为试剂：
  描述：

  4-氯羰基-哌啶-1-羧酸叔丁酯 、 tert-butyl 2-(5-bromo-2-carbamoylbenzofuran-3-ylcarbamoyl)pyrrolidine-1-carboxylate 、 吡啶 在 盐酸 、 水 、 碳酸氢钠 、 氯化钠 、 二氯甲烷 、 magnesium sulfate 、 1,1-Dimethylethyl 4-(5-bromo-2-carbamoylbenzofuran-3-ylcarbamoyl)piperidine-1-carboxylate 作用下， 以 二氯甲烷 为溶剂， 以to give a 3.45 g of white solid as crude 1,1-dimethylethyl 4-(5-bromo-2-carbamoylbenzofuran-3-ylcarbamoyl)piperidine-1-carboxylate which的产率得到1,1-Dimethylethyl 4-(5-bromo-2-carbamoylbenzofuran-3-ylcarbamoyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Benzofuropyrimidinones

  摘要：

  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。

  公开号：

  US20090247559A1

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 AS PROTEIN KINASE INHIBITORS
  申请人：Exelixis, Inc.

  公开号：EP2097419A1

  公开（公告）日：2009-09-09