2-氯-N-(2-甲基-4-氧喹唑啉-3-基)乙酰胺 | 6761-07-5

• 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-氯-N-(2-甲基-4-氧喹唑啉-3-基)乙酰胺
• 英文名称: 2-chloro-N-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
• 英文别名: Acetamide, 2-chloro-N-(2-methyl-4-oxo-3(4H)-quinazolinyl)-；2-chloro-N-(2-methyl-4-oxoquinazolin-3-yl)acetamide
• CAS: 6761-07-5
• 化学式: C₁₁H₁₀ClN₃O₂
• mdl: MFCD00446679
• 分子量: 251.672
• InChiKey: VCMWUZCYIYMJBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氯-N-(2-甲基-4-氧喹唑啉-3-基)乙酰胺 在 ammonium acetate 、 溶剂黄146 作用下， 反应 8.0h， 以75%的产率得到6-methyl-2,4-dihydro-[1,2,4]triazino[2,3-c]quinazolin-3-one
  参考文献：
  名称：

  Ibrahim, S. S.; Abdel-Halim, A. M.; Gabr, Y., Journal of Chemical Research, Miniprint, 1997, # 5, p. 1041 - 1063

  摘要：

  DOI：
• 作为产物：
  描述：

  邻乙酰氨基苯甲酸 在 hydrazine hydrate 、 三乙胺 作用下， 以 甲苯 为溶剂， 生成 2-氯-N-(2-甲基-4-氧喹唑啉-3-基)乙酰胺
  参考文献：
  名称：

  Molecular modeling study and synthesis of quinazolinone-arylpiperazine derivatives as α1-adrenoreceptor antagonists

  摘要：

  Three series of new 2-[(4-substituted piperazin-1-yl) methyliquinazolin-4(3H)-ones 4a-c, Ethyl 6,7-dimethoxy-4-oxo-3-[2-(4-substituted piperazin-1-yl)acetamido/propanamido]-3,4-dihydroquinazoline-2-carboxylates 9a-f and their 2-methyl analogues 13a-I were designed and synthesized as promising alpha(1)-adrenoceptor antagonists. The final compounds were evaluated for their in vivo hypotensive activity in normotensive cats. The most potent hypotensive quinazolinone derivatives 4b, 9e, 13i, 13j were further tested on isolated thoracic aortic rings of male Wister rats. All the tested compounds displayed alpha(1)-blocking activity with IC50 ranging from 0.2 to 0.4 mM less than prazosin. Furthermore, in the present work, molecular modeling study using Accelrys Discovery Studio 2.1 software was performed by mapping the synthesized compounds to the alpha(1)-adrenoceptor antagonist hypothesis in order to predict their mechanism of action. Compound 13j which has the best-fitting score displayed the highest in vivo and in vitro activity among the tested compounds. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.045

文献信息

• Synthesis, anticorrosion, antibacterial, and antifungal activity of new amphiphilic compounds possessing quinazolin-4(3H)-one scaffold
  作者：S. Öztürk、S. Okay、A. Yıldırım

  DOI：10.1007/s11172-020-3023-0

  日期：2020.11

  determined. Antibacterial and antifungal activities of the synthesized compounds were investigated. N,N-Dimethyl-N-2-[(2-methyl-4-oxoquinazolin-3(4H)-yl)amino]-2-oxoethyl}tetradecan-1-aminium chloride (4a) showed the highest antibacterial activity against five human pathogens. Antifungal activity against Candida albicans was shown only by surfactant 4a.

  首次制备了基于喹唑啉-4(3H)-one 的阳离子表面活性剂，并通过红外和核磁共振光谱技术和元素分析对其进行了充分表征。测定了它们的一些物理化学性质，例如密度、临界胶束浓度、表面张力、降低表面张力的有效性、胶束化的吉布斯自由能、泡沫和乳液稳定性以及抗腐蚀活性。研究了合成化合物的抗菌和抗真菌活性。N,N-二甲基-N-2-[(2-methyl-4-oxoquinazolin-3(4H)-yl)amino]-2-oxoethyl}tetradecan-1-aminium chloride (4a) 显示出最高的抗菌活性五种人类病原体。对白色念珠菌的抗真菌活性仅由表面活性剂 4a 显示。
• Synthesis ofN‐Heteryl‐β‐[(2‐alkoxyethyl)oxy]/β[[2‐(N,N‐dialkyamino)ethyl]oxy]acetamide as Possible H,-Ant ihistaminics 1
  作者：A. Raghu Ram Rao、V. Malla Reddy

  DOI：10.1002/jps.2600830707

  日期：1994.7

  The synthesis of beta-[2-(alkoxyethyl)oxy]- and beta-[[2-(N,N-dialkylamino)ethyl]oxy]acetamides containing an N-heteryl moiety is reported. Three heteryl systems, 2-phenyl/methyl-3,4-dihydro-4-oxoquinazolin-3- yl, 5-aryl-1,3,4-oxadiazol-2-yl, and 5-alkyl-1,3,4-thiadiazol-2-yl, were employed. Appropriate heterylamines were first converted into their respective chloroacetamides and then reacted with

  报道了含有N-杂基部分的β-[2-（烷氧基乙基）氧基]-和β-[[2-（N，N-二烷基氨基）乙基]氧基]乙酰胺的合成。三个杂基系统，2-苯基/甲基-3,4-二氢-4-氧喹唑啉-3-基，5-芳基-1,3,4-恶二唑-2-基和5-烷基-1,3,4使用了噻二唑-2-基。首先将适当的杂胺转化为它们各自的氯乙酰胺，然后在无水碳酸钾存在下，在无水丙酮中与2-烷氧基乙醇/ 2-（N，N-二烷基氨基）乙醇反应，得到标题化合物。合成并表征了来自每个系列的十个这种新的乙酰胺。使用分离的豚鼠回肠法测定了它们的体外抗组胺活性。化合物的IC50值表明与其结构和电子特征相关。
• Quinazolinones, 13.Comm. Synthesis of 3-[2-(2,3-Dihydro-5-phenyl-4-substituted-3H-1,2,4-triazole-3-thione-2-yl)-acetylamino]-2-methyl-4(3H)-quinazolinones and their pharmacological activities
  作者：Servet Büyüktimkin、Nadir Büyüktimkin、Osman Özdemir、Sevim Rollas

  DOI：10.1002/ardp.19893220112

  日期：——

  Some 2‐methyl‐3‐triazole‐substituted‐4(3H)‐quinazolinones 3a–f were prepared and tested for their H1‐ and H2‐ antihistaminic activities. In addition these compounds are central nervous system depressants and anticonvulsants. 3e shows highly significant decrease of locomotor activity.

  制备了一些 2-甲基-3-三唑-取代的-4(3H)-喹唑啉酮3a-f，并测试了它们的H1-和H2-抗组胺活性。此外，这些化合物是中枢神经系统抑制剂和抗惊厥药。图 3e 显示了自发活动的高度显着降低。
• Chinazolinone, 5. Mitt. Synthese von 3-Chloracylamino-2-methyl-4(3H)-chinazolinon-Derivaten mit antikonvulsiver und hypnotischer Wirkung
  作者：Servet Büyüktimkin

  DOI：10.1002/ardp.19863191011

  日期：——

  Ausgehend von den 3-Amino-2-methyl-4(3H)-chinazolinonen 1 wurden durch Acylierung die Amide 3a–h erhalten. Kondensation mit Imidazol bzw. 4-Methylimidazol ergab die Imidazolderivate 4a–h bzw. die 2-Pyrrolidone 5a,b. Die meisten dieser Verbindungen zeigen signifikante antikonvulsive und hypnotische Wirkungen. Quinazolinones, V: Syntheses of 3-(Choroacylamino)-2-methyl-4(3H)-quinazolinone Derivatives

  Ausgehend von den 3-Amino-2-methyl-4(3H)-chinazolinonen 1 wurden durch Acylierung die Amide 3a-h erhalten。缩聚 mit 咪唑 bzw。4-Methylimidazol ergab die Imidazolderivate 4a–h bzw。2-吡咯烷酮 5a,b。Die meisten dieser Verbindungen zeigen signifikante anticonvul​​sive und hypnotische Wirkungen。喹唑啉酮，V：从 3-氨基-2-甲基-4(3H)-喹唑啉酮 1、酰胺 3a– 开始合成具有抗惊厥和催眠活性的 3-(Chrooacylamino)-2-methyl-4(3H)-quinazolinone 衍生物h 是通过酰化得到的。与咪唑或
• Antitumor and antileishmanial evaluation of novel heterocycles derived from quinazoline scaffold: a molecular modeling approach
  作者：Daisy H. Fleita、Rafat M. Mohareb、Ola K. Sakka

  DOI：10.1007/s00044-012-0213-9

  日期：2013.5

  Novel thiazole, pyrimidine and benzylidene derivatives derived from quinazoline scaffold have been synthesized. The antitumor evaluation of the newly synthesized products against three cancer cell lines namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460), and CNS cancer (SF-268) showed that the benzylidene-quinazoline derivative 12a showed remarkable activity against all three cell lines. The thiazolo-quinazoline derivative 10 showed greater activity than the control against breast adenocarcinoma (MCF-7) with a concentration of 0.01 mu M. Moreover, the antileishmanial activity of the newly synthesized products tested on Leishmania donovani amastigotes showed that compounds 4, 14, and 18 had very promising activity.