1,2-二氢-4-苯基喹唑啉-2-羧酸 | 153681-81-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 1,2-二氢-4-苯基喹唑啉-2-羧酸
• 英文名称: 1,2-dihydro-4-phenylquinazoline-2-carboxylic acid
• 英文别名: 4-Phenyl-1,2-dihydroquinazoline-2-carboxylic acid；4-phenyl-1,2-dihydroquinazoline-2-carboxylic acid
• CAS: 153681-81-3
• 化学式: C₁₅H₁₂N₂O₂
• 分子量: 252.272
• InChiKey: XAEOJMCFZWPJAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-二氢-4-苯基喹唑啉-2-羧酸 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 azepan-1-yl(4-phenylquinazolin-2-yl)methanone
  参考文献：
  名称：

  被设计为新型的转运蛋白强配体的4-苯基喹唑啉-2-羧酰胺的合成与生物学评价

  摘要：

  一系列新的4-苯基喹唑啉-2-羧酰胺（1 - 58）被设计为PK11195，公知的18 kDa的转运蛋白（TSPO）参考配体，的氮杂等排并合成由一个非常简单和有效的程序的装置。这些衍生物中的许多与TSPO结合的K i值在纳摩尔/亚纳摩尔范围内，对中央苯并二氮杂receptor受体（BzR）表现出选择性，并显示出结构亲和力关系，与先前公布的配体-TSPO相互作用的药效团/拓扑模型一致。

  DOI：

  10.1021/jm201703k
• 作为产物：
  描述：

  乙醛酸 、 2-氨基二苯甲酮 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 1,2-二氢-4-苯基喹唑啉-2-羧酸
  参考文献：
  名称：

  被设计为新型的转运蛋白强配体的4-苯基喹唑啉-2-羧酰胺的合成与生物学评价

  摘要：

  一系列新的4-苯基喹唑啉-2-羧酰胺（1 - 58）被设计为PK11195，公知的18 kDa的转运蛋白（TSPO）参考配体，的氮杂等排并合成由一个非常简单和有效的程序的装置。这些衍生物中的许多与TSPO结合的K i值在纳摩尔/亚纳摩尔范围内，对中央苯并二氮杂receptor受体（BzR）表现出选择性，并显示出结构亲和力关系，与先前公布的配体-TSPO相互作用的药效团/拓扑模型一致。

  DOI：

  10.1021/jm201703k

文献信息

• Reactions of hydroxyglycines. New synthetic routes to 4-phenylquinazoline derivatives
  作者：Anthonius J. Hoefnagel、Henk van Koningsveld、Frank van Meurs、Joop A. Peters、Anton Sinnema、Herman van Bekkum

  DOI：10.1016/s0040-4020(01)80432-4

  日期：1993.7

  Reaction of hydroxyglycine with 2-aminobenzophenones gives 1,2-dihydro-4-phenyl-quinazoline-2-carboxylic acids in high yields and under mild conditions. These can be smoothly converted into the corresponding 3,4-dihydro isomers and into quinazoline derivatives via rearrangement and oxidation by air, respectively. The X-ray crystallographic structure of 6-chloro-1,2-dihydro-1-methyl-4-phenylquinazoline-2-carboxylic

  羟基甘氨酸与2-氨基二苯甲酮的反应以高收率和在温和的条件下得到1,2-二氢-4-苯基-喹唑啉-2-羧酸。它们可以分别通过重排和通过空气氧化而平滑地转化为相应的3，4-二氢异构体和喹唑啉衍生物。6-氯-1,2-二氢-1-甲基-4-苯基喹唑啉-2-羧酸的X射线晶体结构显示C（2）处的羧酸根和N（1）处的甲基位于轴向位置。
• FACILE PREPARATION OF 4-SUBSTITUTED QUINAZOLINES AND RELATED HETEROCYCLES
  申请人：Wang Zerong Daniel

  公开号：US20120283436A1

  公开（公告）日：2012-11-08

  A straightforward single step method for the preparation and/or production of substituted quinazolines is disclosed, wherein said quinazolines preferably contain one substituent at position 4, and may contain other functional groups at various positions, such as 5, 6, 7, and/or 8 of quinazolines. In addition, the extension of this new method leads to the formation of different type of heterocyclic aromatic compounds, that include but are not limited to perimidines, anthrapyrimidin-7-ones (also known as anthrapyrimidinones), anthra[1,9:5,10]dipyrimidines (also known as quinazoline[5,4-ef]perimidines) and benzo[e]-pyrimido[4,5,6-gh]pyrimidines.

  本发明揭示了一种制备和/或生产取代喹唑啉的简单单步方法，其中所述喹唑啉优选在位置4处含有一个取代基，并且可能在喹唑啉的各种位置，例如5、6、7和/或8处含有其他官能团。此外，这种新方法的扩展还导致不同类型的杂环芳香化合物的形成，包括但不限于咪唑啉、蒽吡咯啉-7-酮（也称为蒽吡咯啉酮）、蒽[1,9:5,10]二咪唑啉（也称为喹唑啉[5,4-ef]咪唑啉）和苯并[e]-嘧啶[4,5,6-gh]嘧啶。
• Structure–Activity Relationship Refinement and Further Assessment of 4-Phenylquinazoline-2-carboxamide Translocator Protein Ligands as Antiproliferative Agents in Human Glioblastoma Tumors
  作者：Sabrina Castellano、Sabrina Taliani、Monica Viviano、Ciro Milite、Eleonora Da Pozzo、Barbara Costa、Elisabetta Barresi、Agostino Bruno、Sandro Cosconati、Luciana Marinelli、Giovanni Greco、Ettore Novellino、Gianluca Sbardella、Federico Da Settimo、Claudia Martini

  DOI：10.1021/jm401721h

  日期：2014.3.27

  Structure-activity relationships (SARs) within the 4-phenylquinazoline-2-carboxamide series of translocator protein (TSPO) ligands have been explored further by the synthesis and TSPO binding affinity evaluation of N-benzyl-N-ethyl/methyl derivatives variously decorated at the 6-, 2'-, 4'-, and 4″-positions. Most of the compounds showed high affinity with K(i) values in the nanomolar/subnanomolar range. A pharmacophore model was developed and employed to better address SAR data presented by the new TSPO ligands. A subset of the new compounds (5, 8, 12, and 19) were tested for their ability to inhibit the viability of human glioblastoma cell line U343. The observed antiproliferative effect was demonstrated to be specific for compound 19, endowed with the best combination of binding affinity and efficacy. Furthermore, the ability of 19 to induce mitochondrial membrane dissipation (Δψ(m)) substantiated the intracellular pro-apoptotic mechanism activated by the binding of this class of ligands to TSPO.
• US9273012B2
  申请人：——

  公开号：US9273012B2

  公开（公告）日：2016-03-01
• [EN] A FACILE PREPARATION OF 4-SUBSTITUTED QUINAZOLINES AND RELATED HETEROCYCLES<br/>[FR] PRÉPARATION AISÉE DE QUINAZOLINES 4-SUBSTITUÉES ET HÉTÉROCYCLES ASSOCIÉS
  申请人：UNIV HOUSTON SYSTEM

  公开号：WO2012151141A2

  公开（公告）日：2012-11-08

  A straightforward single step method for the preparation and/or production of substituted quinazolines is disclosed, wherein said quinazolines preferably contain one substituent at position 4, and may contain other functional groups at various positions, such as 5, 6, 7, and/or 8 of quinazolines. In addition, the extension of this new method leads to the formation of different type of heterocyclic aromatic compounds, that include but are not limited to perimidines, anthrapyrimidin-7-ones (also known as anthrapyrimidinones), anthra[1,9:5, 10]dipyrimidines (also known as quinazoline[5,4-ef]perimidines) and benzo[e]- pyrimido[4,5,6-gh]pyrimidines.