2-三氯甲基-4(3H)-喹唑啉酮 | 5558-95-2

• 物质功能分类: 有机原料 - 酮类化合物
• 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: 2-三氯甲基-4(3H)-喹唑啉酮
• 中文别名: 2-(三氯甲基)喹唑啉-4(3H)-酮
• 英文名称: 2-trichloromethyl-3H-quinazoline-4-one
• 英文别名: 2-trichloromethyl-4(3H)-quinazolinone；2-trichloromethylquinazolin-4(3H)-one；2-trichloromethyl-3H-4-quinazolinone；2-trichloromethyl-4-quinazolone；2-trichloromethyl-3H-quinazolin-4-one；2-Trichlormethyl-3H-chinazolin-4-on；2-(Trichloromethyl)quinazolin-4(1H)-one；2-(trichloromethyl)-3H-quinazolin-4-one
• CAS: 5558-95-2
• 化学式: C₉H₅Cl₃N₂O
• mdl: MFCD00006886
• 分子量: 263.51
• InChiKey: BFLBZZSGIIUGIX-UHFFFAOYSA-N

物化性质

• 熔点：
  211-213 °C(lit.)
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，未有已知危险发生。

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-三氯甲基-4(3H)-喹唑啉酮 在 盐酸 、 草酰氯 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 生成 [2-[[2-(Trichloromethyl)quinazolin-4-yl]amino]phenyl]arsonic acid
  参考文献：
  名称：

  具有强抗白血病活性的有机苯基砷酸化合物。

  摘要：

  合成了一系列12种有机砷酸化合物，并针对人B谱系（NALM-6）和T谱系（MOLT-3）急性淋巴细胞白血病（ALL）细胞系进行了评估。铅化合物2-三氯甲基-4- [4'-（4“-苯基偶氮）苯基ar磺酸]氨基喹唑啉（化合物19，PHI-P518; IC（50）=针对NALM-6和2.0 + / 1.1 microM -0.8 microM（针对MOLT-3）和2-甲硫基-4-（2'-苯基砷酸）氨基嘧啶（化合物15，PHI-P381; IC（50）= 1.5 +/- 0.3 microM（针对NALM-6和2.3 + / -0.5 microM（针对MOLT-3）在低微摩尔浓度下表现出强大的抗白血病活性。

  DOI：

  10.1016/s0960-894x(02)00928-9
• 作为产物：
  描述：

  2,2,2-Trichloro-N-phenyl-acetimidoyl isocyanate 以 苯 为溶剂， 反应 1.0h， 生成 2-三氯甲基-4(3H)-喹唑啉酮
  参考文献：
  名称：

  Simple method for the synthesis of 2-trichloromethyl-4-quinazolones

  摘要：

  DOI：

  10.1007/bf00474013

文献信息

• QUINAZOLINE DERIVATIVES FOR THE TREATMENT AND PREVENTION OF DIABETES AND OBESITY
  申请人：Lee Nam Kyu

  公开号：US20080207614A1

  公开（公告）日：2008-08-28

  The present invention relates to novel quinazoline derivatives effective in lowering blood glucose level and body weight, and a medicine for treatment and/or prevention of diabetes and/or obesity, which comprises the compound as an active ingredient.

  本发明涉及一种新型喹唑啉衍生物，能够有效降低血糖水平和体重，以及一种用于治疗和/或预防糖尿病和/或肥胖的药物，其中该化合物作为活性成分。
• Durch sichtbares Licht polymerisierbares Gemisch
  申请人：HOECHST CELANESE CORPORATION

  公开号：EP0313007A2

  公开（公告）日：1989-04-26

  Es wird ein photopolymerisierbares Gemisch sowie ein daraus hergestelltes Aufzeichnungsmaterial beschrieben, das eine ethylenisch ungesättigte polymerisierbare Verbindung, insbesondere einen Acryl- oder Methacryl­säureester, ggf. ein polymeres Bindemittel und eine Kombination aus einer basischen Acridinverbindung und einem durch Halogenmethylgruppen substituiertem Triazin oder Chinazolinon enthält. Das Gemisch hat eine beson­ders hohe Lichtempfindlichkeit im sichtbaren Spektral­bereich und ist zur Belichtung durch Laser oder durch Projektion geeignet.

  本文描述了一种可光聚合的混合物及其制成的记录材料，该混合物含有一种乙烯不饱和可聚合化合物，特别是丙烯酸酯或甲基丙烯酸酯，可选的还有一种聚合物粘合剂以及一种碱性吖啶化合物和一种被卤素甲基取代的三嗪或喹唑啉酮的组合。这种混合物在可见光谱范围内具有特别高的光敏性，适合用激光或投影进行曝光。
• Targeting the human malaria parasite Plasmodium falciparum: In vitro identification of a new antiplasmodial hit in 4-phenoxy-2-trichloromethylquinazoline series
  作者：Caroline Castera-Ducros、Nadine Azas、Pierre Verhaeghe、Sébastien Hutter、Philippe Garrigue、Aurélien Dumètre、Litaty Mbatchi、Michèle Laget、Vincent Remusat、France Sifredi、Sylvain Rault、Pascal Rathelot、Patrice Vanelle

  DOI：10.1016/j.ejmech.2011.06.021

  日期：2011.9

  From the promising results we previously obtained in quinazoline series and to complete the evaluation of the in vitro antiplasmodial activity of original 2-trichloromethylquinazolines, we synthesized new quinazolines possessing a variously substituted phenoxy group at position 4 through a simple and efficient two-step-synthesis approach. The studies of their activity toward the multi-resistant W2 Plasmodium falciparum strain and of their cytotoxicity on the human hepatocyte HepG2 cell line highlighted a hit compound (molecule 7) displaying a W2 IC(50) value of 1.1 mu M and a HepG2 CC(50) value of 50 mu M, comparable to chloroquine and doxycycline. Structure-activity- and toxicity relationships indicate that the trichloromethyl group plays a key role in the antiplasmodial activity of such chemical scaffold and also that the phenoxy group substitution as a direct influence on the molecules selectivity. Moreover, molecule 7 displays significant specific activity against the Plasmodium genus in comparison with Toxoplasma and does not show any mutagenic property at the Ames test. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synthesis and evaluation of quinazoline derivatives as phosphodiesterase 7 inhibitors
  作者：Ana I. Sánchez、Valentín Martínez-Barrasa、Carolina Burgos、Juan J. Vaquero、Julio Alvarez-Builla、Emma Terricabras、Víctor Segarra

  DOI：10.1016/j.bmc.2013.01.067

  日期：2013.4

  The latest scientific findings concerning PDE7 and PDE4 inhibition suggest that selective small-molecule inhibitors of both enzymes could provide a novel approach to treat a variety of immunological diseases. In this context, we describe a new series of quinazoline derivatives from quinazolin-4-thiones which include a substituted biphenyl fragment. Some of these compounds show inhibitory potencies at sub-micromolar levels against the catalytic domain of PDE7. (C) 2013 Elsevier Ltd. All rights reserved.
• Sonogashira cross-coupling reaction in 4-chloro-2-trichloromethylquinazoline series is possible despite a side dimerization reaction
  作者：Charline Kieffer、Pierre Verhaeghe、Nicolas Primas、Caroline Castera-Ducros、Armand Gellis、Roselyne Rosas、Sylvain Rault、Pascal Rathelot、Patrice Vanelle

  DOI：10.1016/j.tet.2013.01.094

  日期：2013.4

  We studied the Sonogashira coupling reaction between 4-chloro-2-trichloromethylquinazoline and various terminal alkynes, mainly in phenylacetylene series. A brief review of the literature shows that mono- or polybromo/chloromethylated substrates, especially in aromatic series, are very rarely compatible with the achievement of Sonogashira reactions. Thus, although the 4-chloroquinazoline scaffold is a very good substrate for this palladium-catalyzed reaction, the typical behavior of the trichloromethyl group in reductive media leads to the competitive formation of undesirable reduced homodimers in high yields. However, by closely examining all the Sonogashira reaction parameters, we developed a specific operating procedure, using Pd(OAc)(2), Cs2CO3, and DMF, which resulted in the synthesis of 14 original coupling products in 10-70% yield, depending on the alkyne used. (C) 2013 Elsevier Ltd. All rights reserved.