4-氯喹唑啉-6-甲酸乙酯 | 155960-94-4

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 4-氯喹唑啉-6-甲酸乙酯
• 中文别名: 4-氯喹唑啉-6-羧酸乙酯
• 英文名称: 4-chloro-quinazoline-6-formic ether
• 英文别名: ethyl 4-chloroquinazoline-6-carboxylate；4-chloro-quinazoline-6-carboxylic acid ethyl ester
• CAS: 155960-94-4
• 化学式: C₁₁H₉ClN₂O₂
• 分子量: 236.658
• InChiKey: ADKCJHRCXSXELJ-UHFFFAOYSA-N

物化性质

• 沸点：
  366.5±22.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-氯喹唑啉-6-甲酸乙酯 在 sodium hydroxide 、 氨 、 sodium carbonate 、 焦碳酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 3.0h， 生成 6-carbamoyl-4-<<3,4-(methylenedioxy)benzyl>amino>quinazoline
  参考文献：
  名称：

  Cyclic GMP Phosphodiesterase Inhibitors. 2. Requirement of 6-Substitution of Quinazoline Derivatives for Potent and Selective Inhibitory Activity

  摘要：

  We synthesized various 4-[[3,4-(methylenedioxy)benzyl]amino]quinazolines substituted at the 5-to 8-positions and evaluated their inhibitory activities toward cyclic GMP phosphodiesterase (cGMP-PDE) from porcine aorta, Monosubstitution at the 6-position was essential for the inhibitory activity, and the preferred substituents were compact and hydrophobic: methoxy (3b, IC50 = 0.23 mu M), methyl (3c, 0.10 mu M), chloro (3d, 0.019 mu M), thiomethyl (3f, 0.031 mu M), and cyano (3p, 0.090 mu M) groups. Compounds 3b-d,f,p lacked inhibitory activity toward other PDE isozymes (all IC50 values > 100 mu M), and their relaxing activities in porcine coronary arteries were well correlated with the inhibitory activities toward cGMP-PDE (r = 0.88, p < 0.05). One of these compounds, 3b, elevated the intracellular cGMP level in isolated porcine coronary arteries without causing any change in the cAMP level. We consider that this series of compounds dilates coronary arteries via potent and specific inhibition of cGMP-PDE,

  DOI：

  10.1021/jm00039a024
• 作为产物：
  描述：

  4-氧代-3,4-二氢喹唑啉-6-羧酸乙酯 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以100%的产率得到4-氯喹唑啉-6-甲酸乙酯
  参考文献：
  名称：

  氧杂环丁烷的分子内开环：获得官能化羟甲基 2,3-二氢咪唑并[1,2-c]喹唑啉

  摘要：

  开发了分子内氧杂环丁烷开环，在温和条件下由 N-(3-甲基氧杂环丁烷-3-基)喹唑啉-4-胺提供新型 2-(羟甲基)-2,3-二氢咪唑并[1,2-c]喹唑啉. 以良好的收率合成了具有多种取代基的具有医学相关性的三环支架。此外，反应优化导致了一锅法的发展。

  DOI：

  10.1055/s-0039-1691578

文献信息

• POLYCYCLIC QUINAZOLINES, PREPARATION THEREOF, AND USE THEREOF
  申请人：Li Jianqi

  公开号：US20110288086A1

  公开（公告）日：2011-11-24

  At least one active pharmaceutical ingredient is chosen from polycyclic quinazolines of formula V, pharmaceutically acceptable salts thereof, and hydrates of the pharmaceutically acceptable salts. The active pharmaceutical ingredients disclosed may be inhibitors of protein tyrosine kinase inhibitors and/or aurora kinase. The active pharmaceutical ingredients can be used for treating cancers susceptible to treatment with protein tyrosine kinase inhibitors and/or aurora kinase inhibitors.

  至少选择一种活性药用成分来自公式V的多环喹唑啉，其药学上可接受的盐，以及药学上可接受的盐的水合物。所披露的活性药用成分可能是蛋白酪氨酸激酶抑制剂和/或极化激酶的抑制剂。这些活性药用成分可用于治疗对蛋白酪氨酸激酶抑制剂和/或极化激酶抑制剂治疗敏感的癌症。
• Novel antifungal agent containing heterocyclic compound
  申请人：Nakamoto Kazutaka

  公开号：US20070105943A1

  公开（公告）日：2007-05-10

  The present invention provides an antifungal agent represented by the formula: [wherein A 1 represents a 3-pyridyl group which may have a substituent, a quinolyl group which may have a substituent, or the like; X 1 represents a group represented by the formula —NH—C(═O)—, a group represented by the formula —C(═O)—NH—, or the like; E represents a furyl group, a thienyl group, a pyrrolyl group, a phenyl group, a pyridyl group, a tetrazolyl group, a thiazolyl group or a pyrazolyl group; with the proviso that A 1 may have 1 to 3 substituents, and E has one or two substituents].

  本发明提供了一种抗真菌剂，其表示为以下式子： [其中A1表示一个3-吡啶基团，可能具有取代基，喹啉基团，可能具有取代基或类似物；X1表示由公式—NH—C（═O）—，由公式—C（═O）—NH—或类似物表示的基团；E表示呋喃基团，噻吩基团，吡咯基团，苯基团，吡啶基团，四唑基团，噻唑基团或吡唑基团；但A1可能具有1到3个取代基，E具有一个或两个取代基。]
• Novel Antimalarial Agent Containing Heterocyclic Compound
  申请人：Nakamoto Kazutaka

  公开号：US20090227799A1

  公开（公告）日：2009-09-10

  Disclosed is an antimalarial agent containing a compound represented by the formula: [wherein A 1 represents a 3-pyridyl group that may have a substituent, a 6-quinolyl group that may have a substituent, or the like; X 1 represents a group represented by the formula —C(═O)—NH— or the like; E represents a furyl group, a thienyl group or a phenyl group; with the proviso that A 1 may have one to three substituents, and E has one of two substituents] or a salt thereof or hydrates thereof.

  揭示了一种抗疟疾剂，其包含由下式表示的化合物： [其中A1表示一个3-吡啶基团，可以有取代基，一个6-喹啉基团，可以有取代基或类似物；X1表示一个由公式-C（═O）-NH-或类似物表示的基团；E表示一个呋喃基团，噻吩基团或苯基团；但前提是A1可以有1到3个取代基，E有两个取代基之一]或其盐或水合物。
• NOVEL ANTIFUNGAL AGENT CONTAINING HETEROCYCLIC COMPOUND
  申请人：NAKAMOTO Kazutaka

  公开号：US20110195999A1

  公开（公告）日：2011-08-11

  The present invention provides an antifungal agent represented by the formula: wherein A 1 represents a 3-pyridyl group which may have a substituent, a quinolyl group which may have a substituent, or the like; X 1 represents a group represented by the formula —NH—C(═O)—, a group represented by the formula —C(═O)—NH—, or the like; E represents a furyl group, a thienyl group, a pyrrolyl group, a phenyl group, a pyridyl group, a tetrazolyl group, a thiazolyl group or a pyrazolyl group; with the proviso that A 1 may have 1 to 3 substituents, and E has one or two substituents.

  本发明提供一种抗真菌剂，其化学式如下： 其中，A1代表3-吡啶基，可以有取代基，喹啉基，也可以有取代基等；X1代表由公式—NH—C（═O）—，由公式—C（═O）—NH—等表示的基团；E代表呋喃基，噻吩基，吡咯基，苯基，吡啶基，四唑基，噻唑基或吡唑基；但要求A1可能有1到3个取代基，E有1或2个取代基。
• NOVEL ANTIFUNGAL AGENT COMPRISING HETEROCYCLIC COMPOUND
  申请人：Eisai Co., Ltd.

  公开号：EP1669348A1

  公开（公告）日：2006-06-14

  The present invention provides an antifungal agent represented by the formula: [wherein A1 represents a 3-pyridyl group which may have a substituent, a quinolyl group which may have a substituent, or the like; X1 represents a group represented by the formula -NH-C(=O)-, a group represented by the formula -C(=O)-NH-, or the like; E represents a furyl group, a thienyl group, a pyrrolyl group, a phenyl group, a pyridyl group, a tetrazolyl group, a thiazolyl group or a pyrazolyl group; with the proviso that A1 may have 1 to 3 substituents, and E has one or two substituents].

  本发明提供了一种由式表示的抗真菌剂： [其中A1代表可具有取代基的3-吡啶基、可具有取代基的喹啉基或类似基团；X1代表由式-NH-C(＝O)-代表的基团、由式-C(＝O)-NH-代表的基团或类似基团；E 代表呋喃基、噻吩基、吡咯基、苯基、吡啶基、四唑基、噻唑基或吡唑基；但 A1 可具有 1 至 3 个取代基，E 具有 1 或 2 个取代基]。