3-(4-methoxybenzyl)-6-nitroquinazolin-4-(3H)-one | 900513-13-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-(4-methoxybenzyl)-6-nitroquinazolin-4-(3H)-one
• 英文别名: 3-[(4-Methoxyphenyl)methyl]-6-nitroquinazolin-4-one
• CAS: 900513-13-5
• 化学式: C₁₆H₁₃N₃O₄
• 分子量: 311.297
• InChiKey: BNXSTBPULBXDAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  87.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-methoxybenzyl)-6-nitroquinazolin-4-(3H)-one 在 palladium on activated charcoal 吡啶 、 copper(l) iodide 、 溴 、 甲酸铵 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.75h， 生成 8-(4-Methoxy-benzyl)-9-oxo-8,9-dihydro-thiazolo[5,4-f]quinazoline-2-carbonitrile
  参考文献：
  名称：

  Thiazolo[5,4-f]quinazolin-9-ones, inhibitors of glycogen synthase kinase-3

  摘要：

  In an effort to identify new protein kinase inhibitors with increased potency and selectivity, we have developed the microwave-assisted synthesis of thiazolo[5,4-f]quinazolin-9-ones. The effects of eighteen derivatives on CDK1/cyclin B, CDK5/p25, and GSK-3 were investigated. Several turned out to inhibit GSK-3 in the micromolar range. Molecular modeling studies suggest that the most selective GSK-3 inhibitors 7a-d bind into the ATP-binding site through a key hydrogen bond interaction with Val135 and target the specific hydrophobic backpocket of the enzyme. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.006
• 作为产物：
  描述：

  6-硝基喹唑啉-4(3H)-酮 、 4-甲氧基氯苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 3-(4-methoxybenzyl)-6-nitroquinazolin-4-(3H)-one
  参考文献：
  名称：

  Thiazolo[5,4-f]quinazolin-9-ones, inhibitors of glycogen synthase kinase-3

  摘要：

  In an effort to identify new protein kinase inhibitors with increased potency and selectivity, we have developed the microwave-assisted synthesis of thiazolo[5,4-f]quinazolin-9-ones. The effects of eighteen derivatives on CDK1/cyclin B, CDK5/p25, and GSK-3 were investigated. Several turned out to inhibit GSK-3 in the micromolar range. Molecular modeling studies suggest that the most selective GSK-3 inhibitors 7a-d bind into the ATP-binding site through a key hydrogen bond interaction with Val135 and target the specific hydrophobic backpocket of the enzyme. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.006

文献信息

• [EN] 3-HYDROQUINAZOLIN-4-ONE DERIVATIVES FOR USE AS STEAROYL COA DESATURASE INHIBITORS<br/>[FR] DÉRIVÉS DE 3-HYDROQUINAZOLINE-4-ONE UTILISÉS COMME INHIBITEURS DE STÉARYL-ACP DÉSATURASE
  申请人：CV THERAPEUTICS INC

  公开号：WO2010056230A1

  公开（公告）日：2010-05-20

  The present invention discloses 3-hydroquinazolm-4-one derivatives for use as inhibitors of stearoyl-CoA desaturase. The compounds are useful in treating and/or preventing various human diseases, mediated by stearoyl-CoA desaturase (SCD) enzymes, especially diseases related to abnormal lipid levels, cancer, cardiovascular disease, diabetes, obesity, metabolic syndrome and the like.

  本发明公开了3-羟基喹唑烷-4-酮衍生物，用作硬脂酰辅酶A去饱和酶的抑制剂。这些化合物在治疗和/或预防各种由硬脂酰辅酶A去饱和酶（SCD）酶介导的人类疾病方面具有用途，特别是与异常脂质水平、癌症、心血管疾病、糖尿病、肥胖、代谢综合征等相关的疾病。
• 3-HYDROQUINAZOLIN-4-ONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS
  申请人：Koltun Dmitry

  公开号：US20080255161A1

  公开（公告）日：2008-10-16

  The present invention discloses 3-hydroquinazolin-4-one derivatives for use as inhibitors of stearoyl-CoA desaturase. The compounds are useful in treating and/or preventing various human diseases, mediated by stearoyl-CoA desaturase (SCD) enzymes, especially diseases related to abnormal lipid levels, cancer, cardiovascular disease, diabetes, obesity, metabolic syndrome and the like.

  本发明揭示了3-羟基喹唑啉-4-酮衍生物，用作硬脂酰辅酶A去饱和酶的抑制剂。这些化合物在治疗和/或预防由硬脂酰辅酶A去饱和酶（SCD）酶介导的各种人类疾病方面具有用途，特别是与异常脂质水平、癌症、心血管疾病、糖尿病、肥胖、代谢综合征等相关的疾病。
• 3-HYDROQUINAZOLIN-4-ONE DERIVATIVES FOR USE AS STEAROYL COA DESATURASE INHIBITORS
  申请人：Gilead Sciences, Inc.

  公开号：EP2350029A1

  公开（公告）日：2011-08-03
• Thiazolo[5,4-f]quinazolin-9-ones, inhibitors of glycogen synthase kinase-3
  作者：Alexandra Testard、Cédric Logé、Benoît Léger、Jean-Michel Robert、Olivier Lozach、Mélina Blairvacq、Laurent Meijer、Valérie Thiéry、Thierry Besson

  DOI：10.1016/j.bmcl.2006.04.006

  日期：2006.7

  In an effort to identify new protein kinase inhibitors with increased potency and selectivity, we have developed the microwave-assisted synthesis of thiazolo[5,4-f]quinazolin-9-ones. The effects of eighteen derivatives on CDK1/cyclin B, CDK5/p25, and GSK-3 were investigated. Several turned out to inhibit GSK-3 in the micromolar range. Molecular modeling studies suggest that the most selective GSK-3 inhibitors 7a-d bind into the ATP-binding site through a key hydrogen bond interaction with Val135 and target the specific hydrophobic backpocket of the enzyme. (c) 2006 Elsevier Ltd. All rights reserved.