6-methoxy-2-(thiophen-2-yl)quinazolin-4(3H)-one | 219773-58-7

• 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: 6-methoxy-2-(thiophen-2-yl)quinazolin-4(3H)-one
• 英文别名: 6-methoxy-2-thiophen-2-yl-3H-quinazolin-4-one
• CAS: 219773-58-7
• 化学式: C₁₃H₁₀N₂O₂S
• 分子量: 258.301
• InChiKey: CQVKPTHNMUEXDC-UHFFFAOYSA-N

物化性质

• 熔点：
  261-262 °C
• 沸点：
  459.5±51.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  78.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-methoxy-2-(thiophen-2-yl)quinazolin-4(3H)-one 在 肼 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (6-methoxy-2-thiophen-2-yl-quinazolin-4-yl)-hydrazine
  参考文献：
  名称：

  The design and synthesis of novel orally active inhibitors of AP-1 and NF-κB mediated transcriptional activation. SAR of In vitro and In vivo studies

  摘要：

  We have developed novel orally active quinazoline analogues as inhibitors of AP-1 and NF-kappaB mediated transcriptional activation. Among the derivatives prepared, 1-[2-(2-thienyl)quinazolin-4-ylamino]-3-methyl-3-pyrroline-2,5-dione (10) showed significant activity in an adjuvant-induced arthritis rat model by reducing the swelling by 65% in the non-injected foot. The synthesis, structure-activity relationship, and in vivo activity are described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.047
• 作为产物：
  描述：

  2-氨基-5-甲氧基苯甲酸 在 ammonium acetate 、 乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 6-methoxy-2-(thiophen-2-yl)quinazolin-4(3H)-one
  参考文献：
  名称：

  The design and synthesis of novel orally active inhibitors of AP-1 and NF-κB mediated transcriptional activation. SAR of In vitro and In vivo studies

  摘要：

  We have developed novel orally active quinazoline analogues as inhibitors of AP-1 and NF-kappaB mediated transcriptional activation. Among the derivatives prepared, 1-[2-(2-thienyl)quinazolin-4-ylamino]-3-methyl-3-pyrroline-2,5-dione (10) showed significant activity in an adjuvant-induced arthritis rat model by reducing the swelling by 65% in the non-injected foot. The synthesis, structure-activity relationship, and in vivo activity are described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.047

文献信息

• A highly efficient heterogeneous palladium-catalyzed carbonylative annulation of 2-aminobenzamides with aryl iodides leading to quinazolinones
  作者：Shengyong You、Bin Huang、Tao Yan、Mingzhong Cai

  DOI：10.1016/j.jorganchem.2018.09.003

  日期：2018.11

  The first heterogeneous carbonylative annulation of 2-aminobenzamides with aryl iodides was achieved in N,N-dimethylformamide (DMF) at 120 °C under 10 bar of carbon monoxide by using an MCM-41-immobilized bidentate phosphine palladium(II) complex [MCM-41-2P-Pd(OAc)2] as catalyst and 1,8-diazabicycloundec-7-ene (DBU) as base, yielding a wide variety of quinazolinone derivatives in good to excellent

  通过使用MCM-41固定的二齿膦膦钯（II）络合物[MCM] ，在N，N-二甲基甲酰胺（DMF）中于120°C，10 bar一氧化碳的条件下，首次实现了2-氨基苯甲酰胺与芳基碘的羰基环化反应。-41-2P-Pd（OAc）2 ]作为催化剂，1,8-二氮杂双环十一碳烯-7（DBU）作为碱，可产生多种喹唑啉酮衍生物，收率良好至极佳。新的多相钯催化剂可以通过简单的方法容易地由市售试剂制备，并通过过滤反应溶液进行回收，并循环使用八次而不会显着降低活性。
• A practical synthesis of quinazolinones via intermolecular cyclization between 2-halobenzamides and benzylamines catalyzed by copper(I) immobilized on MCM-41
  作者：Nan Yan、Chongren You、Mingzhong Cai

  DOI：10.1016/j.jorganchem.2019.07.003

  日期：2019.10

  using an MCM-41-immobilized l-proline copper(I) complex [MCM-41-l-Proline-CuBr] as the catalyst and air as the oxidant, yielding a variety of quinazolinone derivatives in good yields. The new MCM-41-l-Proline-CuBr catalyst can easily be prepared from commercially readily available and inexpensive reagents and recovered by filtration of the reaction mixture, and reused up to seven times with almost consistent

  该非均相串联Ñ -arylation /氧化C-H的2-卤代苯甲酰胺和苄胺的酰胺化在DMSO，在110或120℃下通过使用MCM-41固定来实现升-脯氨酸铜（I）配合物[MCM-41-升-脯氨酸-CuBr]作催化剂，空气作氧化剂，以高收率得到各种喹唑啉酮衍生物。新MCM-41-升-脯氨酸-溴化亚铜催化剂可容易地从市场上容易获得且廉价的试剂和制备通过将反应混合物的过滤回收，并用几乎一致的活性重复使用7次。
• Copper-Catalyzed Domino Synthesis of Quinazolinones via Ullmann-Type Coupling and Aerobic Oxidative C−H Amidation
  作者：Wei Xu、Yibao Jin、Hongxia Liu、Yuyang Jiang、and Hua Fu

  DOI：10.1021/ol1030266

  日期：2011.3.18

  starting materials as well as economical and environmentally friendly air as the oxidant. This can be the first example of constructing N-heterocycles via sequential Ullmann-type coupling under air and aerobic oxidative C−H amidation.

  已经开发了一种高效的铜催化的喹唑啉酮衍生物的方法，该方案使用廉价且容易获得的取代的2-卤代苯甲酰胺和（芳基）甲胺作为起始原料，以及经济和环境友好的空气作为氧化剂。这可能是在空气和好氧氧化CH-H酰胺化作用下通过顺序Ullmann型偶联构建N-杂环的第一个例子。
• Quinazoline analogs and related compounds and methods for treating
  申请人：Signal Pharmaceuticals, Inc.

  公开号：US05939421A1

  公开（公告）日：1999-08-17

  Compounds having utility as anti-inflammatory agents in general and, more specifically, for the prevention and/or treatment of immunoinflammatory and autoimmune diseases are disclosed. The compounds are quinazoline-containing compounds. Methods are also disclosed for preventing and/or treating inflammatory conditions by administering to an animal in need thereof an effective amount of a compound of this invention, preferably in the form of a pharmaceutical composition.

  本发明涉及具有抗炎作用的化合物，通常用于预防和/或治疗免疫炎症和自身免疫性疾病。这些化合物是喹唑啉类化合物。本发明还揭示了通过向需要的动物施用该化合物的有效量，优选地以药物组合物的形式，来预防和/或治疗炎症病况的方法。
• [EN] QUINAZOLINE ANALOGS AND RELATED COMPOUNDS AND METHODS FOR TREATING INFLAMMATORY CONDITIONS<br/>[FR] ANALOGUES DE QUINAZOLINE ET COMPOSES ASSOCIES ET METHODES POUR TRAITER LES TROUBLES INFLAMMATOIRES
  申请人：SIGNAL PHARMACEUTICALS, INC.

  公开号：WO1999001441A1

  公开（公告）日：1999-01-14

  (EN) Compounds having utility as anti-inflammatory agents in general and, more specifically, for the prevention and/or treatment of immunoinflammatory and autoimmune diseases are disclosed. The compounds are quinazoline-containing compounds. Methods are also disclosed for preventing and/or treating inflammatory conditions by administering to an animal in need thereof an effective amount of a compound of this invention, preferably in the form of a pharmaceutical composition.(FR) L'invention concerne des composés utiles de manière générale comme agents anti-inflammatoires et plus spécifiquement comme agents préventifs et/ou thérapeutiques pour les maladies immuno-inflammatoires et auto-immunes. Ces composés contiennent de la quinazoline. L'invention concerne également de méthodes pour prévenir et/ou traiter les états inflammatoires en administrant à un animal nécessitant un tel traitement une quantité efficace d'un des composés décrits, de préférence sous forme d'une composition pharmaceutique.

  该发明涉及一种具有抗炎作用的化合物，可用于预防和/或治疗免疫炎症和自身免疫疾病。这些化合物含有喹唑啉。本发明还揭示了通过向需要治疗的动物施用本发明的化合物的有效量，尤其是以药物组成物的形式，以预防和/或治疗炎症状况的方法。