全部 标题 作者
关键词 摘要

OALib Journal期刊
ISSN: 2333-9721
费用:99美元

查看量下载量

相关文章

更多...

Chemical Characteristics, Synthetic Methods, and Biological Potential of Quinazoline and Quinazolinone Derivatives

DOI: 10.1155/2014/395637

Full-Text   Cite this paper   Add to My Lib

Abstract:

The heterocyclic fused rings quinazoline and quinazolinone have drawn a huge consideration owing to their expanded applications in the field of pharmaceutical chemistry. Quinazoline and quinazolinone are reported for their diversified biological activities and compounds with different substitutions bring together to knowledge of a target with understanding of the molecule types that might interact with the target receptors. Quinazolines and quinazolinones are considered as an important chemical for the synthesis of various physiological significance and pharmacological utilized molecules. Quinazolines and quinazolinone are a large class of biologically active compounds that exhibited broad spectrum of biological activities such as anti-HIV, anticancer, antifungal, antibacterial, antimutagenic, anticoccidial, anticonvulsant, anti-inflammatory, antidepressant, antimalarial, antioxidant, antileukemic, and antileishmanial activities and other activities. Being considered as advantaged scaffold, the alteration is made with different substituent. 1. Introduction Quinazolines and quinazolinones are classes of fused heterocycles that are of considerable interest because of the diverse range of their biological properties [1]. Many substituted quinazoline and quinazolinone derivatives possess a wide range of bioactivities such as antimalarial, anticancer, antimicrobial, antifungal, antiviral, antiprotozoan, anti-inflammatory, diuretic, muscle relaxant, antitubercular, antidepressant, anticonvulsant, acaricidal, weedicide, and many other biological activities. Quinazoline and quinazolinone compounds are also used in preparation of various functional materials for synthetic chemistry and also present in various drugs molecules (Figure 1). This review is an attempt to expand the huge potentiality and focused on the various biological activities of quinazolines and quinazolinones [2]. Figure 1: Some marketed available drugs contain quinazoline and quinazolinone moiety [2]. Quinazolinones will be classified into the following five categories, based on the substitution patterns of the ring system [3]. These are 2-substituted-4(3H)-quinazolinones, 3-substituted-4(3H)-quinazolinones, 4-substituted-quinazolines, 2,3-disubstituted-4(3H)-quinazolinones, and 2,4-disubstituted-4(3H)-quinazolinones. Depending upon the position of the keto or oxo group, these compounds may be classified into three types [4]. Out of the three (2(1H)quinazolinones, 4(3H)quinazolinones and 2,4(1H,3H)quinazolinedione) quinazolinone structures, 4(3H)-quinazolinones are most prevalent, either as

References

[1]  D. J. Connolly, D. Cusack, T. P. O’Sullivan, and P. J. Guiry, “Synthesis of quinazolinones and quinazolines,” Tetrahedron, vol. 61, no. 43, pp. 10153–10202, 2005.
[2]  Abida, P. Nayyar, and M. Arpanarana, “An updated review: newer quinazoline derivatives under clinical trial,” International Journal of Pharmaceutical & Biological Archive, vol. 2, no. 6, pp. 1651–1657, 2011.
[3]  S. B. Mhaske and N. P. Argade, “The chemistry of recently isolated naturally occurring quinazolinone alkaloids,” Tetrahedron, vol. 62, no. 42, pp. 9787–9826, 2006.
[4]  A. K. Mahato, B. Srivastava, and S. Nithya, “Chemistry structure activity relationship and biological activity of quinazoline-4(3H)-one derivatives,” Inventi Rapid: MedChem, vol. 2, no. 1, 2011.
[5]  W. L. F. Armarego, A Text Book of Quinazolines, 1963.
[6]  R. Rajput and A. P. Mishra, “A review on biological activity of quinazolinones,” International Journal of Pharmacy and Pharmaceutical Sciences, vol. 4, no. 2, pp. 66–70, 2012.
[7]  B. Pati and S. Banerjee, “Quinazolines: an illustrated review,” Journal of Advanced Pharmacy. Education & Research, vol. 3, no. 3, pp. 136–151, 2013.
[8]  B. Vijayakumar, P. Prasanthi, K. M. Teja et al., “Quinazoline derivatives and pharmacological activities: a review,” International Journal of Medicinal Chemistry & Analysis, vol. 3, no. 1, pp. 10–21, 2013.
[9]  X. Yang, H. Liu, H. Futa, R. Qiao, Y. Jiang, and Y. Zhao, “Efficient copper-catalyzed synthesis of 4-aminoquinazoline and 2,4-diaminoquinazoline derivatives,” Synlett, no. 1, pp. 101–106, 2010.
[10]  V. L. Truong and M. Morrow, “Mild and efficient ligand-free copper-catalyzed condensation for the synthesis of quinazolines,” Tetrahedron Letters, vol. 51, no. 4, pp. 758–760, 2010.
[11]  S. Shweta, S. Chirag, T. Bhawana, and J. Talesara, “Synthesis of phthalimido or succinimido[2-aryl-4-oxo-3-{2-phenyl-4(3H)- quinazolinon-3-yl}-1,3-thiazolidin-5-yl]ethanoate,” Journal of the Indian Chemical Society, vol. 86, no. 4, pp. 397–401, 2009.
[12]  O. O. Ajani, C. A. Obafemi, C. O. Ikpo, K. O. Ajanaku, K. O. Ogunniran, and O. O. James, “Comparative study of microwave assisted and conventional synthesis of novel 2-quinoxalinone-3- hydrazone derivatives and its spectroscopic properties,” International Journal of Physical Sciences, vol. 4, no. 4, pp. 156–164, 2009.
[13]  H. Mutlu and G. Irez, “Synthesis and characterization of new tridentate iminooxime ligands and their Co(III) complexes,” Turkish Journal of Chemistry, vol. 32, no. 6, pp. 731–741, 2008.
[14]  G. Abdel and H. A. W. Mohammed, “Design and synthesis of some new derivatives of 3H-quinazolin-4-one with promising anticonvulsant activity,” Acta Pharmaceutica, vol. 53, no. 2, pp. 127–138, 2003.
[15]  A.-F. E. Mourad, A. A. Aly, H. H. Farag, and E. A. Beshr, “Microwave assisted synthesis of triazoloquinazolinones and benzimidazoquinazolinones,” Beilstein Journal of Organic Chemistry, vol. 3, article 11, 2007.
[16]  N. M. Abdel Gawad, H. H. Georgey, R. M. Youssef, and N. A. El-Sayed, “Synthesis and antitumor activity of some 2, 3-disubstituted quinazolin-4(3H)-ones and 4, 6-disubstituted- 1, 2, 3, 4-tetrahydroquinazolin- 2H-ones,” European Journal of Medicinal Chemistry, vol. 45, no. 12, pp. 6058–6067, 2010.
[17]  J. He, X. Wang, X. Zhao, Y. Liang, H. He, and L. Fu, “Synthesis and antitumor activity of novel quinazoline derivatives containing thiosemicarbazide moiety,” European Journal of Medicinal Chemistry, vol. 54, pp. 925–930, 2012.
[18]  B. Marvania, P.-C. Lee, R. Chaniyara et al., “Design, synthesis and antitumor evaluation of phenyl N-mustard-quinazoline conjugates,” Bioorganic and Medicinal Chemistry, vol. 19, no. 6, pp. 1987–1998, 2011.
[19]  H.-Q. Li, D.-D. Li, X. Lu, Y.-Y. Xu, and H.-L. Zhu, “Design and synthesis of 4,6-substituted-(diaphenylamino)quinazolines as potent EGFR inhibitors with antitumor activity,” Bioorganic and Medicinal Chemistry, vol. 20, no. 1, pp. 317–323, 2012.
[20]  C. Fernandes, C. Oliveira, L. Gano, A. Bourkoula, I. Pirmettis, and I. Santos, “Radioiodination of new EGFR inhibitors as potential SPECT agents for molecular imaging of breast cancer,” Bioorganic and Medicinal Chemistry, vol. 15, no. 12, pp. 3974–3980, 2007.
[21]  K. G. Petrov, Y.-M. Zhang, M. Carter et al., “Optimization and SAR for dual ErbB-1/ErbB-2 tyrosine kinase inhibition in the 6-furanylquinazoline series,” Bioorganic and Medicinal Chemistry Letters, vol. 16, no. 17, pp. 4686–4691, 2006.
[22]  A. S. Rosenthal, C. Tanega, M. Shen et al., “Potent and selective small molecule inhibitors of specific isoforms of Cdc2-like kinases (Clk) and dual specificity tyrosine-phosphorylation-regulated kinases (Dyrk),” Bioorganic and Medicinal Chemistry Letters, vol. 21, no. 10, pp. 3152–3158, 2011.
[23]  F. Gellibert, M. H. Fouchet, V. L. Nguyen et al., “Design of novel quinazoline derivatives and related analogues as potent and selective ALK5 inhibitors,” Bioorganic and Medicinal Chemistry Letters, vol. 19, no. 8, pp. 2277–2281, 2009.
[24]  A. Wissner, H. L. Fraser, C. L. Ingalls et al., “Dual irreversible kinase inhibitors: quinazoline-based inhibitors incorporating two independent reactive centers with each targeting different cysteine residues in the kinase domains of EGFR and VEGFR-2,” Bioorganic and Medicinal Chemistry, vol. 15, no. 11, pp. 3635–3648, 2007.
[25]  M. N. Noolvi and H. M. Patel, “A comparative QSAR analysis and molecular docking studies of quinazoline derivatives as tyrosine kinase (EGFR) inhibitors: a rational approach to anticancer drug design,” Journal of Saudi Chemical Society, vol. 17, no. 4, pp. 361–379, 2013.
[26]  J. A. Heath, M. M. Mehrotra, S. Chi et al., “Identification of 4-piperazin-1-yl-quinazoline template based aryl and benzyl thioureas as potent, selective, and orally bioavailable inhibitors of platelet-derived growth factor (PDGF) receptor,” Bioorganic and Medicinal Chemistry Letters, vol. 14, no. 19, pp. 4867–4872, 2004.
[27]  K. Matsuno, T. Seishi, T. Nakajima et al., “Potent and selective inhibitors of platelet-derived growth factor receptor phosphorylation, part 4: structure-activity relationships for substituents on the quinazoline moiety of 4-[4-(N-substituted(thio)carbamoyl)-1-piperazinyl]-6,7-dimethoxyquinazoline derivatives,” Bioorganic and Medicinal Chemistry Letters, vol. 13, no. 18, pp. 3001–3004, 2003.
[28]  N. M. Heron, M. Anderson, D. P. Blowers et al., “SAR and inhibitor complex structure determination of a novel class of potent and specific Aurora kinase inhibitors,” Bioorganic and Medicinal Chemistry Letters, vol. 16, no. 5, pp. 1320–1323, 2006.
[29]  K. M. Foote, A. A. Mortlock, N. M. Heron et al., “Synthesis and SAR of 1-acetanilide-4-aminopyrazole-substituted quinazolines: Selective inhibitors of Aurora B kinase with potent anti-tumor activity,” Bioorganic and Medicinal Chemistry Letters, vol. 18, no. 6, pp. 1904–1909, 2008.
[30]  Z. Chen, X. Huang, H. Yang et al., “Anti-tumor effects of B-2, a novel 2,3-disubstituted 8-arylamino-3H-imidazo[4,5-g]quinazoline derivative, on the human lung adenocarcinoma A549 cell line in vitro and in vivo,” Chemico-Biological Interactions, vol. 189, no. 1-2, pp. 90–99, 2011.
[31]  P. Ballard, R. H. Bradbury, C. S. Harris et al., “Inhibitors of epidermal growth factor receptor tyrosine kinase: Novel C-5 substituted anilinoquinazolines designed to target the ribose pocket,” Bioorganic and Medicinal Chemistry Letters, vol. 16, no. 6, pp. 1633–1637, 2006.
[32]  P. M. Chandrika, T. Yakaiah, A. R. R. Rao et al., “Synthesis of novel 4,6-disubstituted quinazoline derivatives, their anti-inflammatory and anti-cancer activity (cytotoxic) against U937 leukemia cell lines,” European Journal of Medicinal Chemistry, vol. 43, no. 4, pp. 846–852, 2008.
[33]  L. Zhu, J. Jin, C. Liu et al., “Synthesis and biological evaluation of novel quinazoline-derived human Pin1 inhibitors,” Bioorganic and Medicinal Chemistry, vol. 19, no. 9, pp. 2797–2807, 2011.
[34]  A. S. El-Azab, M. A. Al-Omar, A. A. M. Abdel-Aziz et al., “Design, synthesis and biological evaluation of novel quinazoline derivatives as potential antitumor agents: Molecular docking study,” European Journal of Medicinal Chemistry, vol. 45, no. 9, pp. 4188–4198, 2010.
[35]  L. Cedric, T. Alexandra, T. Valerie et al., “Synthesis, biological evaluation and molecular modeling studies of quinazoline derivatives,” European Journal of Medicinal Chemistry, vol. 43, pp. 1469–1477, 2008.
[36]  P. Selvam, P. Vijayalakshimi, D. F. Smee et al., “Novel 3-sulphonamido-quinazolin-4(3H)-one derivatives: Microwave-assisted synthesis and evaluation of antiviral activities against respiratory and biodefense viruses,” Antiviral Chemistry and Chemotherapy, vol. 18, no. 5, pp. 301–305, 2007.
[37]  G. D. Galarce, R. E. Foncea, A. M. Edwards, H. Pessoa-Mahana, C. D. Pessoa-Mahana, and R. A. Ebensperger, “Biological evaluation of novel 6-Arylbenzimidazo [1,2-c]quinazoline derivatives as inhibitors of LPS-induced TNF-alpha secretion,” Biological Research, vol. 41, no. 1, pp. 43–50, 2008.
[38]  K. S. Hatti, V. Chandregowda, G. Venkateswara Rao, A. Kush, and G. Chandrasekara Reddy, “In-silico interaction studies of quinazoline derivatives for their inhibitory action on both wild and mutant EGFRs,” Journal of Proteomics and Bioinformatics, vol. 2, no. 3, pp. 126–130, 2009.
[39]  D. Raffa, G. Daidone, B. Maggio, S. Cascioferro, F. Plescia, and D. Schillaci, “Synthesis and antileukemic activity of new 3-(5-methylisoxazol-3-yl) and 3-(pyrimidin-2-yl)-2-styrylquinazolin-4(3H)-ones,” Farmaco, vol. 59, no. 6, pp. 451–455, 2004.
[40]  N. B. Patel and J. C. Patel, “Synthesis and antimicrobial activity of Schiff bases and 2-azetidinones derived from quinazolin-4(3H)-one,” Arabian Journal of Chemistry, vol. 4, no. 4, pp. 403–411, 2011.
[41]  M. Cakici, M. Catir, S. Karabuga et al., “Synthesis and biological evaluation of (S)-4-aminoquinazoline alcohols,” Tetrahedron Asymmetry, vol. 21, no. 16, pp. 2027–2031, 2010.
[42]  P. M. S. Bedi, V. Kumar, and M. P. Mahajan, “Synthesis and biological activity of novel antibacterial quinazolines,” Bioorganic and Medicinal Chemistry Letters, vol. 14, no. 20, pp. 5211–5213, 2004.
[43]  A. M. Alafeefy, A. S. El-Azab, M. A. Mohamed, M. A. Bakhat, and S. G. Abdel-Hamid, “Synthesis of some new substituted iodoquinazoline derivatives and their antimicrobial screening,” Journal of Saudi Chemical Society, vol. 15, no. 4, pp. 319–325, 2011.
[44]  V. Jatav, S. Kashaw, and P. Mishra, “Synthesis, antibacterial and antifungal activity of some novel 3-[5-(4-substituted phenyl) 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones,” Medicinal Chemistry Research, vol. 17, no. 2–7, pp. 169–181, 2008.
[45]  P. Praveen Kumar, Y. Rajendra Prasad, N. R. Kumar, and S. Sridhar, “Synthesis and antimicrobial activity of 6,7,8,9-tetrahydro-5(H)-5- nitrophenylthiazolo[2,3-b]-quinazoline-3(2H)-one derivatives,” Asian Journal of Chemistry, vol. 20, no. 7, pp. 5161–5165, 2008.
[46]  K. Siddappa, T. Reddy, M. Mallikarjun, and C. V. Reddy, “Synthesis, characterization and antimicrobial studies of 3-[(2-hydroxy-quinolin-3-ylmethylene)-amino]-2-phenyl-3H-quinazolin-4-one and its metal(II) complexes,” E-Journal of Chemistry, vol. 5, no. 1, pp. 155–162, 2008.
[47]  N. C. Desai, P. N. Shihora, and D. L. Moradia, “Synthesis and characterization of new quinazolines as potential antimicrobial agents,” Indian Journal of Chemistry, vol. 46, no. 3, pp. 550–553, 2007.
[48]  R. Suthakaran, S. Kavimani, P. Venkaiaiah, and K. Suganthi, “Synthesis and antimicrobial activity of 3-(2-(4z)-4-substituted benzylidene-4,5-dihydro-5-oxo-2-phenylimidazol-1-yl)ethyl)-6,8-un/dibromo subtituted-2-substituted quinazoline-(3H)-one,” Rasāyan Journal of Chemistry, vol. 1, no. 1, pp. 22–29, 2008.
[49]  S. Jantová, ?. Stankovsky, and K. ?pirková, “In vitro antibacterial activity of ten series of substituted quinazolines,” Biologia, vol. 59, no. 6, pp. 741–752, 2004.
[50]  J. A. Patel, B. D. Mistry, and K. R. Desai, “Synthesis and antimicrobial activity of newer quinazolinones,” E-Journal of Chemistry, vol. 3, no. 2, pp. 97–102, 2006.
[51]  M. M. Ghorab, S. M. Abdel-Gawad, and M. S. A. El-Gaby, “Synthesis and evaluation of some new fluorinated hydroquinazoline derivatives as antifungal agents,” Farmaco, vol. 55, no. 4, pp. 249–255, 2000.
[52]  G.-F. Xu, B.-A. Song, P. S. Bhadury et al., “Synthesis and antifungal activity of novel s-substituted 6-fluoro-4-alkyl(aryl)thioquinazoline derivatives,” Bioorganic and Medicinal Chemistry, vol. 15, no. 11, pp. 3768–3774, 2007.
[53]  A. Omar and M. A. Ahmed, “Synthesis of some new 3H-quinazolin-4-one derivatives as potential Antitubercular agents,” World Applied Sciences Journal, vol. 5, no. 1, pp. 94–99, 2008.
[54]  J. í Kune, B. Jaroslav, M. Pour, K. Waisser, M. Iosárek, and J. í Janota, “Quinazoline derivatives with antitubercular activity,” Farmaco, vol. 55, no. 11-12, pp. 725–729, 2000.
[55]  V. K. Srivastava and A. Kumar, “Synthesis of newer thiadiazolyl and thiazolidinonyl quinazolin-4(3H)-ones as potential anticonvulsant agents,” European Journal of Medicinal Chemistry, vol. 37, no. 11, pp. 873–882, 2003.
[56]  P. Kumar, K. N. Dhawan, S. Vrat, K. P. Bhargava, and K. Kishore, “Synthesis of 6-substituted 2-phenyl-3-(5-substituted mercapto-1,3,4,thiadiazol-2-yl)quinazolin-4-(3H)-ones as antitubercular agents,” Archiv der Pharmazie, vol. 316, no. 9, pp. 759–763, 1983.
[57]  K. S. Kumar, S. Ganguly, R. Veerasamy, and E. De Clercq, “Synthesis, antiviral activity and cytotoxicity evaluation of Schiff bases of some 2-phenyl quinazoline-4(3)H-ones,” European Journal of Medicinal Chemistry, vol. 45, no. 11, pp. 5474–5479, 2010.
[58]  M. Schleiss, J. Eickhoff, S. Auerochs et al., “Protein kinase inhibitors of the quinazoline class exert anti-cytomegaloviral activity in vitro and in vivo,” Antiviral Research, vol. 79, no. 1, pp. 49–61, 2008.
[59]  S. N. Pandeya, D. Sriram, G. Nath, and E. de Clercq, “Synthesis, antibacterial, antifungal and anti-HIV evaluation of Schiff and Mannich bases of isatin derivatives with 3-amino-2-methylmercapto quinazolin-4(3H)-one,” Pharmaceutica Acta Helvetiae, vol. 74, no. 1, pp. 11–17, 1999.
[60]  D. Kohli, S. R. Hashim, S. Vishal, M. Sharma, and A. K. Singh, “Synthesis and antibacterial activity of quinazolinone derivatives,” International Journal of Pharmacy and Pharmaceutical Sciences, vol. 1, no. 1, pp. 163–169, 2009.
[61]  C. Ye, J. You, X. F. Li et al., “Design, synthesis and anticoccidial activity of a series of 3-(2-(2-methoxyphenyl)-2-oxoethyl) quinazolinone derivatives,” Pesticide Biochemistry and Physiology, vol. 97, no. 3, pp. 194–198, 2010.
[62]  J. You, C. Ye, Y. Weng, X. Mo, and Y. Wang, “Synthesis and anticoccidial activity of 4-(2-methoxyphenyl)-2- oxobutylquinazolinone derivatives,” Arkivoc, vol. 2008, no. 17, pp. 1–11, 2008.
[63]  A. M. Alafeefy, A. A. Kadi, O. A. Al-Deeb, K. E. H. El-Tahir, and N. A. Al-Jaber, “Synthesis, analgesic and anti-inflammatory evaluation of some novel quinazoline derivatives,” European Journal of Medicinal Chemistry, vol. 45, no. 11, pp. 4947–4952, 2010.
[64]  R. S. Giri, H. M. Thaker, T. Giordano et al., “Design, synthesis and characterization of novel 2-(2,4-disubstituted-thiazole-5-yl)-3-aryl-3H-quinazoline-4-one derivatives as inhibitors of NF-κB and AP-1 mediated transcription activation and as potential anti-inflammatory agents,” European Journal of Medicinal Chemistry, vol. 44, no. 5, pp. 2184–2189, 2009.
[65]  V. Alagarsamy, V. Raja Solomon, and K. Dhanabal, “Synthesis and pharmacological evaluation of some 3-phenyl-2-substituted-3H-quinazolin-4-one as analgesic, anti-inflammatory agents,” Bioorganic and Medicinal Chemistry, vol. 15, no. 1, pp. 235–241, 2007.
[66]  K. Hemalatha and K. Girija, “Synthesis of some novel 2, 3-disubstituted quinazolinone derivatives as analgesic and anti-inflammatory agents,” International Journal of Pharmacy and Pharmaceutical Sciences, vol. 3, no. 2, pp. 103–106, 2011.
[67]  A. Kumar, S. Sharma, K. Bajaj et al., “Some new 2,3,6-trisubstituted quinazolinones as potent anti-inflammatory, analgesic and COX-II inhibitors,” Bioorganic and Medicinal Chemistry, vol. 11, no. 23, pp. 5293–5299, 2003.
[68]  C. Balakumar, P. Lamba, D. Pran Kishore et al., “Synthesis, anti-inflammatory evaluation and docking studies of some new fluorinated fused quinazolines,” European Journal of Medicinal Chemistry, vol. 45, no. 11, pp. 4904–4913, 2010.
[69]  S. M. Mosaad, K. I. Mohamed, M. A. Ahmed, G. A. Sami, and M. M. Adel, “Synthesis and anti-inflammatory evaluation of some quinazoline derivatives,” International Journal of Pharmacology, vol. 1, no. 3, pp. 261–266, 2005.
[70]  C. H. Rajver, C. H. Swarnalatha, R. Stephen, and Sudharshini, “Synthesis of 6-bromo-oxo quinazoline derivatives and their pharmacological activities,” International Journal of Chemical Research, vol. 1, no. 1, pp. 21–24, 2010.
[71]  M. Srivastav and S. M. Shantakumar, “Synthesis and Anti-inflammatory activity of some novel 3-(6-substituted-1,3-benzothiazole-2-yl)-2-[{(4-substituted phenyl) amino} methyl] quinazolines-4 (3H)-ones,” E-Journal of Chemistry, vol. 6, no. 4, pp. 1055–1062, 2009.
[72]  A. Omar, M. F. Fattah, M. M. Emad, M. I. Neama, and M. K. Mohsen, “Synthesis of some new quinazolin-4-one derivatives and evaluation of their antimicrobial and antiinflammatory effects,” Acta Poloniae Pharmaceutica: Drug Research, vol. 65, no. 1, pp. 11–20, 2008.
[73]  V. Jatav, P. Mishra, S. Kashaw, and J. P. Stables, “Synthesis and CNS depressant activity of some novel 3-[5-substituted 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones,” European Journal of Medicinal Chemistry, vol. 43, no. 1, pp. 135–141, 2008.
[74]  V. Jatav, P. Mishra, S. Kashaw, and J. P. Stables, “CNS depressant and anticonvulsant activities of some novel 3-[5-substituted 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones,” European Journal of Medicinal Chemistry, vol. 43, no. 9, pp. 1945–1954, 2008.
[75]  M. M. Aly, Y. A. Mohamed, K. A. M. El-Bayouki, W. M. Basyouni, and S. Y. Abbas, “Synthesis of some new 4(3H)-quinazolinone-2-carboxaldehyde thiosemicarbazones and their metal complexes and a study on their anticonvulsant,analgesic,cytotoxic and antimicrobial activities,” European Journal of Medicinal Chemistry, vol. 45, no. 8, pp. 3365–3373, 2010.
[76]  S. K. Kashaw, V. Kashaw, P. Mishra, N. K. Jain, and J. P. Stables, “Synthesis, anticonvulsant and CNS depressant activity of some new bioactive 1-(4-substituted-phenyl)-3-(4-oxo-2-phenyl/ethyl-4H-quinazolin-3-yl)-urea,” European Journal of Medicinal Chemistry, vol. 44, no. 11, pp. 4335–4343, 2009.
[77]  A. Gürsoy and N. Terzio?lu, “Synthesis and isolation of new regioisomeric 4-thiazolidinones and their anticonvulsant activity,” Turkish Journal of Chemistry, vol. 29, no. 3, pp. 247–254, 2005.
[78]  V. K. Pandey, S. Tusi, Z. Tusi et al., “Thiadiazolyl quinazolones as potential antiviral and antihypertensive agents,” Indian Journal of Chemistry Section B: Organic and Medicinal Chemistry, vol. 43, no. 1, pp. 180–183, 2004.
[79]  V. K. Srivastava and A. Kumar, “Synthesis of some newer derivatives of substituted quinazolinonyl-2-oxo/thiobarbituric acid as potent anticonvulsant agents,” Bioorganic and Medicinal Chemistry, vol. 12, no. 5, pp. 1257–1264, 2004.
[80]  R. Chioua, F. Benabdelouahab, M. Chioua, R. Martínez-Alvarez, and A. Herrera Fernández, “Synthesis of novel quinazoline derivatives via pyrimidine ortho-quinodimethane,” Molecules, vol. 7, no. 7, pp. 507–510, 2002.
[81]  L. M. Werbel and M. J. Degnan, “Synthesis and antimalarial and antitumor effects of 2-amino-4-(hydrazino and hydroxyamino)-6-[(aryl)thio]quinazolines,” Journal of Medicinal Chemistry, vol. 30, no. 11, pp. 2151–2154, 1987.
[82]  Y. Kabri, N. Azas, A. Dumètre et al., “Original quinazoline derivatives displaying antiplasmodial properties,” European Journal of Medicinal Chemistry, vol. 45, no. 2, pp. 616–622, 2010.
[83]  S. Madapa, Z. Tusi, A. Mishra et al., “Search for new pharmacophores for antimalarial activity. Part II. Synthesis and antimalarial activity of new 6-ureido-4-anilinoquinazolines,” Bioorganic and Medicinal Chemistry, vol. 17, no. 1, pp. 222–234, 2009.
[84]  P. Verhaeghe, A. Dumtre, C. Castera-Ducros et al., “4-Thiophenoxy-2-trichloromethyquinazolines display in vitro selective antiplasmodial activity against the human malaria parasite Plasmodium falciparum,” Bioorganic and Medicinal Chemistry Letters, vol. 21, no. 19, pp. 6003–6006, 2011.
[85]  P. Verhaeghe, N. Azas, M. Gasquet et al., “Synthesis and antiplasmodial activity of new 4-aryl-2-trichloromethylquinazolines,” Bioorganic and Medicinal Chemistry Letters, vol. 18, no. 1, pp. 396–401, 2008.
[86]  T. P. Selvam, P. V. Kumar, and A. S. Kumar, “Synthesis and anti-oxidant activity of novel 6,7,8,9 tetra hydro- 5H-5-(2′-hydroxy phenyl)-2-(4′-substituted benzylidine)- 3-(4-nitrophenyl amino) thiazolo quinazoline derivatives,” Research in Biotechnology, vol. 1, no. 1, pp. 38–48, 2010.
[87]  W. L. Armarego, The Chemistry of Heterocyclic Compound Fused Pyrimidines, vol. 11, part-1, 1967.
[88]  K. C. Agarwal, V. Sharma, N. Shakya, and S. Gupta, “Design and synthesis of novel substituted quinazoline derivatives as antileishmanial agents,” Bioorganic and Medicinal Chemistry Letters, vol. 19, no. 18, pp. 5474–5477, 2009.
[89]  Y. H. Kim, H. Choi, J. Lee et al., “Quinazolines as potent and highly selective PDE5 inhibitors as potential therapeutics for male erectile dysfunction,” Bioorganic and Medicinal Chemistry Letters, vol. 18, no. 23, pp. 6279–6282, 2008.
[90]  S. Sasmal, D. Balasubrahmanyam, H. R. Kanna Reddy et al., “Design and optimization of quinazoline derivatives as melanin concentrating hormone receptor 1 (MCHR1) antagonists: part 2,” Bioorganic and Medicinal Chemistry Letters, vol. 22, no. 9, pp. 3163–3167, 2012.
[91]  V. Alagarsamy and U. S. Pathak, “Synthesis and antihypertensive activity of novel 3-benzyl-2-substituted-3H-[1,2,4]triazolo[5,1-b]quinazolin-9-ones,” Bioorganic and Medicinal Chemistry, vol. 15, no. 10, pp. 3457–3462, 2007.
[92]  V. Alagarsamy, V. R. Solomon, and M. Murugan, “Synthesis and pharmacological investigation of novel 4-benzyl-1-substituted-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-ones as new class of H1-antihistaminic agents,” Bioorganic and Medicinal Chemistry, vol. 15, no. 12, pp. 4009–4015, 2007.
[93]  N. Schormann, S. E. Velu, S. Murugesan et al., “Synthesis and characterization of potent inhibitors of Trypanosoma cruzi dihydrofolate reductase,” Bioorganic and Medicinal Chemistry, vol. 18, no. 11, pp. 4056–4066, 2010.
[94]  J. P. Patil, S. V. Amrutkar, and M. S. Ranawat, “Microwave assisted synthesis of quinazolinone using different bases,” Journal of Pharmaceutical Sciences and Research, vol. 1, no. 3, pp. 52–54, 2009.
[95]  E. Georgescu, F. Georgescu, M. R. Caira et al., “A new synthesis of pyrrolo[1,2-c]quinazoline from quinazolinium N-ylides: a re-investigation,” Arkivoc, vol. 2009, no. 12, pp. 232–241, 2009.
[96]  Z. Rachid, M. MacPhee, C. Williams, M. Todorova, and B. J. Jean-Claude, “Design and synthesis of new stabilized combi-triazenes for targeting solid tumors expressing the epidermal growth factor receptor (EGFR) or its closest homologue HER2,” Bioorganic and Medicinal Chemistry Letters, vol. 19, no. 18, pp. 5505–5509, 2009.
[97]  S. H. Yang, D. B. Khadka, S. H. Cho et al., “Virtual screening and synthesis of quinazolines as novel JAK2 inhibitors,” Bioorganic and Medicinal Chemistry, vol. 19, no. 2, pp. 968–977, 2011.
[98]  D. Kohli, S. R. Hashim, S. Vishal, M. Sharma, and A. K. Singh, “Synthesis and antibacterial activity of quinazolinone derivatives,” International Journal of Pharmacy and Pharmaceutical Sciences, vol. 1, pp. 163–169, 2009.
[99]  I. P. Jung, H. L. So, S. C. Chan, and S. K. Kwan, “Study on the selective reduction of 1H-quinazoline-2,4-diones,” Bulletin of the Korean Chemical Society, vol. 29, no. 6, pp. 1256–1258, 2008.

Full-Text

Contact Us

[email protected]

QQ:3279437679

WhatsApp +8615387084133