5-trifluoromethylquinazoline-2,4(1H,3H)-dione | 959236-92-1

• 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: 5-trifluoromethylquinazoline-2,4(1H,3H)-dione
• 英文别名: 5-trifluoromethylquinazolin-2,4(1H,3H)-dione；5-(Trifluoromethyl)quinazoline-2,4(1H,3H)-dione；5-(trifluoromethyl)-1H-quinazoline-2,4-dione
• CAS: 959236-92-1
• 化学式: C₉H₅F₃N₂O₂
• 分子量: 230.146
• InChiKey: MSAVDWKURUSWSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-trifluoromethylquinazoline-2,4(1H,3H)-dione 在 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以80%的产率得到2,4-二氯-5-(三氟甲基)喹唑啉
  参考文献：
  名称：

  Synthesis and QSAR of Quinazoline Sulfonamides As Highly Potent Human Histamine H₄ Receptor Inverse Agonists

  摘要：

  Hit optimization of the class of quinazoline containing histamine H-4 receptor (H4R) ligands resulted in a sulfonamide substituted analogue with high affinity for the H4R. This moiety leads to improved physicochemical properties and is believed to probe a distinct H4R binding pocket that was previously identified using pharmacophore modeling. By introducing a variety of sulfonamide substituents, the H4R affinity was optimized. The interaction of the new ligands, in combination with a set of previously published quinazoline compounds, was described by a QSAR equation. Pharmacological studies revealed that the sulfonamide analogues have excellent H4R affinity and behave as inverse agonists at the human H4R. In vivo evaluation of the potent 2-(6-chloro-2-(4-methylpiperazin-1-yl)quinazoline-4-amino)-N-phenylethanesulfonamide (54) (pK(i) = 8.31 +/- 0.10) revealed it to have anti-inflammatory activity in an animal model of acute inflammation.

  DOI：

  10.1021/jm901379s
• 作为产物：
  描述：

  在 氨 作用下， 以 甲醇 为溶剂， 以64 %的产率得到5-trifluoromethylquinazoline-2,4(1H,3H)-dione
  参考文献：
  名称：

  CN116178284

  摘要：

  公开号：

文献信息

• Quinazolines and related heterocyclic compounds and their therapeutic use
  申请人：Vereniging voor Christelijk Hoger Onderwijs, Wetenschappelijk Onderzoek en Patiëntenzorg

  公开号：EP2077263A1

  公开（公告）日：2009-07-08

  A compound of the formula wherein X is CR1 or N; Y is CR3 or N; R1, R3, R4, R5 and R6 are independently H, F, Cl, Br, I, or a hydrocarbon group which optionally contains one or more heteroatoms; R7 is a heterocyclic group including one or more N atoms; R' is Rx or NRyRz wherein Rx, Ry and Rz are each H or the same or different groups, including cyclic groups formed by Ry and Rz with the N atom, of up to 20 C atoms and optionally including up to 3 further heteroatoms selected from N, O and S; or a pharmaceutically acceptable salt, ester or solvate thereof, has therapeutic utility.

  该化合物的公式为X是CR1或N；Y是CR3或N；R1、R3、R4、R5和R6分别独立地为H、F、Cl、Br、I或一个可能含有一个或多个杂原子的碳氢基团；R7是一个包括一个或多个N原子的杂环基团；R'是Rx或NRyRz，其中Rx、Ry和Rz分别为H或相同或不同的基团，包括由Ry和Rz与N原子形成的环基团，最多包含20个碳原子，且可选地包含最多3个进一步从N、O和S中选择的杂原子；或其药用盐、酯或溶剂化合物具有治疗用途。
• Quinazolines and related heterocyclic compounds, and their therapeutic use
  申请人：Smits Rogier Adriaan

  公开号：US08530486B2

  公开（公告）日：2013-09-10

  A compound of the formula (I) wherein X is CR1 or N; Y is CR3 or N; R1, R3, R4, R5 and R6 are independently H, F, Cl, Br, I, or a hydrocarbon group which optionally contains one or more heteroatoms; R7 is a heterocyclic group including one or more N atoms; R′ is Rx or NRyRz wherein Rx, Ry and Rz are each H or the same or different groups, including cyclic groups formed by Ry and Rz with the N atom, of up to 20 C atoms and optionally including up to 3 further heteroatoms selected from N, O and S; or a pharmaceutically acceptable salt, ester or solvate thereof.

  化合物的公式（I），其中X是CR1或N; Y是CR3或N; R1、R3、R4、R5和R6独立地为H、F、Cl、Br、I或含有一个或多个杂原子的碳氢基团; R7是包括一个或多个N原子的杂环基团; R′是Rx或NRyRz，其中Rx、Ry和Rz分别为H或相同或不同的基团，包括由Ry和Rz与N原子形成的环状基团，长度最长可达20个C原子，并且可选地包括最多3个从N、O和S中选择的进一步杂原子; 或其药学上可接受的盐、酯或溶剂化物。
• Quinazolines and Related Heterocyclic Compounds, and Their Therapeutic Use
  申请人：Smits Rogier Adriaan

  公开号：US20100298322A1

  公开（公告）日：2010-11-25

  A compound of the formula (I) wherein X is CR 1 or N; Y is CR 3 or N; R 1 , R 3 , R 4 , R 5 and R 6 are independently H, F, Cl, Br, I, or a hydrocarbon group which optionally contains one or more heteroatoms; R 7 is a heterocyclic group including one or more N atoms; R′ is R x or NR y R z wherein R x , R y and R z are each H or the same or different groups, including cyclic groups formed by R y and R z with the N atom, of up to 20 C atoms and optionally including up to 3 further heteroatoms selected from N, O and S; or a pharmaceutically acceptable salt, ester or solvate thereof.

  化合物的式子 (I)，其中 X 是 CR1 或 N；Y 是 CR3 或 N；R1、R3、R4、R5 和 R6 分别是 H、F、Cl、Br、I 或一个含有一个或多个杂原子的碳氢基团；R7 是一个含有一个或多个 N 原子的杂环基团；R′ 是 Rx 或 NRyRz，其中 Rx、Ry 和 Rz 分别是 H 或相同或不同的基团，包括由 Ry 和 Rz 与 N 原子形成的环状基团，具有高达 20 个 C 原子并且可选地包括最多 3 个来自 N、O 和 S 的进一步杂原子；或其药学上可接受的盐、酯或溶剂化物。
• QUINAZOLINES AND RELATED HETEROCYCLIC COMPOUNDS, AND THEIR THERAPEUTIC USE
  申请人：Vereniging voor Christelijk Hoger Onderwijs, Wetenschappelijk Onderzoek en Patiëntenzorg

  公开号：EP2238119A1

  公开（公告）日：2010-10-13
• US8530486B2
  申请人：——

  公开号：US8530486B2

  公开（公告）日：2013-09-10