Pub Date : 2020-04-15DOI: 10.5772/intechopen.89180
H. Hashem
Active heterocyclic compounds are one of the main topics of interest for the medicinal chemists as they display a number of pharmacological activities. Nitrogen, sulfur, and oxygen containing five- and six-membered heterocyclic compounds have occupied enormous significance in the field of medicinal chemistry. The most important six-membered heterocyclic compounds are quinazoline and quinazolinone derivatives for their biological activities. The current chapter outlined the different methods for synthesis of quinazoline and quinazolinone derivatives that possess broad spectrum of biological activities.
{"title":"Synthesis of Quinazoline and Quinazolinone Derivatives","authors":"H. Hashem","doi":"10.5772/intechopen.89180","DOIUrl":"https://doi.org/10.5772/intechopen.89180","url":null,"abstract":"Active heterocyclic compounds are one of the main topics of interest for the medicinal chemists as they display a number of pharmacological activities. Nitrogen, sulfur, and oxygen containing five- and six-membered heterocyclic compounds have occupied enormous significance in the field of medicinal chemistry. The most important six-membered heterocyclic compounds are quinazoline and quinazolinone derivatives for their biological activities. The current chapter outlined the different methods for synthesis of quinazoline and quinazolinone derivatives that possess broad spectrum of biological activities.","PeriodicalId":138118,"journal":{"name":"Quinazolinone and Quinazoline Derivatives","volume":"16 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2020-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"123380089","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2020-01-29DOI: 10.5772/intechopen.90621
A. Radwan, F. Alanazi
The chemical structure of quinazolinones includes benzene ring fused with 2-pyrimidinone (1), 4-pyrimidinone (2) or 2,4-pyrimidinedione (3) ring, and are named as quinazolin-2(1H)-one, quinazolin-4(3H)-one or quinazolin-2,4(1H, 3H)-one, respectively. The chemical structure of quinazolinones constitutes a crucial scaffold of natural and synthetic compounds with various therapeutic and biological activities. Quinazolinones are first synthesized by Stefan Niementowski (1866–1925) and named after Niementowski quinazolinone synthesis. Quinazolinones have strongly attracted the interest of medicinal chemist as they constitute a large class of compounds that exhibited broad spectrum of biological activities including antimicrobial, antimalarial, anticonvulsant, anticancer, anti-leishmanial, anti-inflammatory, etc. This chapter provides a brief overview on the recent advances on chemical and pharmacological aspects of quinazolinone derivatives published in the last decade. inhibitions by ovine COX and carrageenan-induced rat paw oedema methods. Four compounds showed potent anti-inflammatory activity with oedema inhibition percentage of 49 ± 1.16, 45 ± 0.82, 46 ± 1.36 and 54 ± 1.83 using indomethacin drug as reference.
{"title":"Biological Activity of Quinazolinones","authors":"A. Radwan, F. Alanazi","doi":"10.5772/intechopen.90621","DOIUrl":"https://doi.org/10.5772/intechopen.90621","url":null,"abstract":"The chemical structure of quinazolinones includes benzene ring fused with 2-pyrimidinone (1), 4-pyrimidinone (2) or 2,4-pyrimidinedione (3) ring, and are named as quinazolin-2(1H)-one, quinazolin-4(3H)-one or quinazolin-2,4(1H, 3H)-one, respectively. The chemical structure of quinazolinones constitutes a crucial scaffold of natural and synthetic compounds with various therapeutic and biological activities. Quinazolinones are first synthesized by Stefan Niementowski (1866–1925) and named after Niementowski quinazolinone synthesis. Quinazolinones have strongly attracted the interest of medicinal chemist as they constitute a large class of compounds that exhibited broad spectrum of biological activities including antimicrobial, antimalarial, anticonvulsant, anticancer, anti-leishmanial, anti-inflammatory, etc. This chapter provides a brief overview on the recent advances on chemical and pharmacological aspects of quinazolinone derivatives published in the last decade. inhibitions by ovine COX and carrageenan-induced rat paw oedema methods. Four compounds showed potent anti-inflammatory activity with oedema inhibition percentage of 49 ± 1.16, 45 ± 0.82, 46 ± 1.36 and 54 ± 1.83 using indomethacin drug as reference.","PeriodicalId":138118,"journal":{"name":"Quinazolinone and Quinazoline Derivatives","volume":"28 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2020-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134413408","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2020-01-22DOI: 10.5772/intechopen.90104
S. Abbas
4(3 H )-Quinazolinone derivatives have considerable great interesting due to the diverse range of their biological properties. This review summarized the methods of preparation of 2-substituted-4(3 H )-quinazolinone, 3-substituted-4(3 H )-quinazoli-none and 2,3-disubstituted-4(3 H )-quinazolinone derivatives. Chemical reaction of 4(3 H )-quinazolinone derivatives and the reactivity of the 2-methyl group, reactivity of the 3-amino group, electrophilic substitution, oxidation, reduction, reaction of 4(3 H )-quinazolinones with metal ions, Mannich reaction, cycloaddition reaction as well as other reagents were discussed. Also, biological properties of 4(3 H )-quinazolinone derivatives were given herein.
{"title":"4(3H)-Quinazolinone Derivatives: Syntheses, Physical Properties, Chemical Reaction, and Biological Properties","authors":"S. Abbas","doi":"10.5772/intechopen.90104","DOIUrl":"https://doi.org/10.5772/intechopen.90104","url":null,"abstract":"4(3 H )-Quinazolinone derivatives have considerable great interesting due to the diverse range of their biological properties. This review summarized the methods of preparation of 2-substituted-4(3 H )-quinazolinone, 3-substituted-4(3 H )-quinazoli-none and 2,3-disubstituted-4(3 H )-quinazolinone derivatives. Chemical reaction of 4(3 H )-quinazolinone derivatives and the reactivity of the 2-methyl group, reactivity of the 3-amino group, electrophilic substitution, oxidation, reduction, reaction of 4(3 H )-quinazolinones with metal ions, Mannich reaction, cycloaddition reaction as well as other reagents were discussed. Also, biological properties of 4(3 H )-quinazolinone derivatives were given herein.","PeriodicalId":138118,"journal":{"name":"Quinazolinone and Quinazoline Derivatives","volume":"22 19","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2020-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"120862897","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-12-13DOI: 10.5772/intechopen.89203
Satyendra Mishra
Drug discovery and optimization comprise one of the most significant targets in medicinal chemistry. Quinazoline and quinazolinone derivatives and nitrogen-containing heterocycles have received significant attention due to their widely and distinct biopharmaceutical activities. Quinazolines and quinazolinones are considered as noteworthy chemical for the synthesis of diverse physiological significance and pharmacological utilized molecules. Quinazolines are building blocks for about 150 naturally occurring alkaloids with a broad range of biological activity. The various substituted quinazolines and quinazolinones displayed important, for example, sedative hypnotics, antibacterial, anti-inflammatory, analgesic, antipsychotic, antifungal, antimalarial, anticonvulsant, anti-Parkinsonism, cancer, and other activities. This chapter aims to highlight the latest evidence of quinazolinone and quinazoline derivatives as a privileged scaffold in medicinal chemistry.
{"title":"Quinazolinone and Quinazoline Derivatives: Synthesis and Biological Application","authors":"Satyendra Mishra","doi":"10.5772/intechopen.89203","DOIUrl":"https://doi.org/10.5772/intechopen.89203","url":null,"abstract":"Drug discovery and optimization comprise one of the most significant targets in medicinal chemistry. Quinazoline and quinazolinone derivatives and nitrogen-containing heterocycles have received significant attention due to their widely and distinct biopharmaceutical activities. Quinazolines and quinazolinones are considered as noteworthy chemical for the synthesis of diverse physiological significance and pharmacological utilized molecules. Quinazolines are building blocks for about 150 naturally occurring alkaloids with a broad range of biological activity. The various substituted quinazolines and quinazolinones displayed important, for example, sedative hypnotics, antibacterial, anti-inflammatory, analgesic, antipsychotic, antifungal, antimalarial, anticonvulsant, anti-Parkinsonism, cancer, and other activities. This chapter aims to highlight the latest evidence of quinazolinone and quinazoline derivatives as a privileged scaffold in medicinal chemistry.","PeriodicalId":138118,"journal":{"name":"Quinazolinone and Quinazoline Derivatives","volume":"20 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2019-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"133608376","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-09-12DOI: 10.5772/INTECHOPEN.89164
C. Chiriță, Carmen Limban, D. Nuță, Emil Ștefănescu, S. Negreș, C. E. Zbârcea, C. D. Marineci, O. Șeremet, Mihaela M. Trandafir, A. Missir, I. Chiriţă
The quinazoline scaffold is found in the chemical structure of many marketed drugs used in CNS disorders as antidepressants, anxiolytics, or hypnotics. Also, the carbamate ester derivatives have different certain therapeutic actions, such as hyp-notic or parasympathomimetic ones. We have obtained new 4(3H)-quinazolinones by bringing together in the same structure the quinazoline nucleus and carbamate ester group. The compounds named Q1–Q5 were characterized by measuring the melting points, by determining the infrared and NMR spectra, and by elemental analysis. The pharmacological tests evidenced that the compounds have a very low acute toxicity, lethal doses being >2000 mg/kg bw. The compounds had different actions observed in forced swimming test (FST), tail suspension test (TST), or elevated plus maze (EPM), probably influenced by the presence of different radicals on the nucleus. Thus, Q1 with a nitro group in structure manifested the highest antidepressant effect, showing a reduction of immobilization time in FST and TST. On the other hand, Q3 and Q5, with two groups methoxy, respective ethoxy, had a slight anxiolytic effect, highlighted by an increase of the time spent in open arms and a decrease of the time spent in closed arms of EPM.
{"title":"Synthesis and Pharmacological Research Regarding New Compounds with Quinazolin-4-One Structure","authors":"C. Chiriță, Carmen Limban, D. Nuță, Emil Ștefănescu, S. Negreș, C. E. Zbârcea, C. D. Marineci, O. Șeremet, Mihaela M. Trandafir, A. Missir, I. Chiriţă","doi":"10.5772/INTECHOPEN.89164","DOIUrl":"https://doi.org/10.5772/INTECHOPEN.89164","url":null,"abstract":"The quinazoline scaffold is found in the chemical structure of many marketed drugs used in CNS disorders as antidepressants, anxiolytics, or hypnotics. Also, the carbamate ester derivatives have different certain therapeutic actions, such as hyp-notic or parasympathomimetic ones. We have obtained new 4(3H)-quinazolinones by bringing together in the same structure the quinazoline nucleus and carbamate ester group. The compounds named Q1–Q5 were characterized by measuring the melting points, by determining the infrared and NMR spectra, and by elemental analysis. The pharmacological tests evidenced that the compounds have a very low acute toxicity, lethal doses being >2000 mg/kg bw. The compounds had different actions observed in forced swimming test (FST), tail suspension test (TST), or elevated plus maze (EPM), probably influenced by the presence of different radicals on the nucleus. Thus, Q1 with a nitro group in structure manifested the highest antidepressant effect, showing a reduction of immobilization time in FST and TST. On the other hand, Q3 and Q5, with two groups methoxy, respective ethoxy, had a slight anxiolytic effect, highlighted by an increase of the time spent in open arms and a decrease of the time spent in closed arms of EPM.","PeriodicalId":138118,"journal":{"name":"Quinazolinone and Quinazoline Derivatives","volume":"26 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2019-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"131982897","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2015-12-24DOI: 10.5772/INTECHOPEN.89871
V. Navale, R. Shinde, S. Patil, A. Vibhute, S. Zangade
3-Amino-2-methyl-3H-quinazolin-4-one on condensation with different substituted acetophenones in presence of acetic acid under classical procedure to affords novel series of Schiff bases containing quanzoline moiety. The newly synthesized imines are confirmed on the basis of spectral technique, 1H NMR, IR and mass spectroscopy.
3-氨基-2-甲基-3 - h -喹唑啉-4- 1与不同取代的苯乙酮在乙酸存在下经经典反应制得一系列新的含喹唑啉部分的希夫碱。通过光谱技术、核磁共振氢谱、红外光谱和质谱对新合成的亚胺进行了确证。
{"title":"Quinazoline Based Synthesis of some Heterocyclic Schiff Bases","authors":"V. Navale, R. Shinde, S. Patil, A. Vibhute, S. Zangade","doi":"10.5772/INTECHOPEN.89871","DOIUrl":"https://doi.org/10.5772/INTECHOPEN.89871","url":null,"abstract":"3-Amino-2-methyl-3H-quinazolin-4-one on condensation with different substituted acetophenones in presence of acetic acid under classical procedure to affords novel series of Schiff bases containing quanzoline moiety. The newly synthesized imines are confirmed on the basis of spectral technique, 1H NMR, IR and mass spectroscopy.","PeriodicalId":138118,"journal":{"name":"Quinazolinone and Quinazoline Derivatives","volume":"27 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2015-12-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"127876114","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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