Design, synthesis, and biological evaluation of novel quinazoline derivatives as anti-inflammatory agents against lipopolysaccharide-induced acute lung injury in rats

Chemical Biology and Drug Design

Volumn 85, Issue 6, 2015, Pages 672-684

  Hu, Jie ^a   Zhang, Yali ^a   Dong, Lili ^b   Wang, Zhe ^a   Chen, Lingfeng ^a   Liang, Dandan ^a   Shi, Dengjian ^a   Shan, Xiaoou ^b   Liang, Guang ^a  

^a WENZHOU MEDICAL UNIVERSITY   (China)

^b THE SECOND AFFILIATED HOSPITAL AND YUYING CHILDREN S HOSPITAL OF WENZHOU MEDICAL UNIVERSITY   (China)

Author keywords

acute lung injury; anti inflammation; IL 6; quinazoline derivatives; TNF

Indexed keywords

ANTIINFLAMMATORY AGENT; CYCLOOXYGENASE 2; INTERLEUKIN 1BETA; INTERLEUKIN 6; LIPOPOLYSACCHARIDE; MESSENGER RNA; N 4 (3 BROMOPHENYL) N 4 (3 METHYLBUT 2 EN 1 YL)QUINAZOLINE 4,6 DIAMINE; N 4 (QUINOLIN 6 YL)QUINZOLINE 4,6 DIAMINE; QUINAZOLINE DERIVATIVE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ACUTE LUNG INJURY; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOKINE RELEASE; DOSE RESPONSE; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; GENE EXPRESSION; HISTOPATHOLOGY; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; INFLAMMATORY CELL; INFLAMMATORY INFILTRATE; MACROPHAGE; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT; STRUCTURE ACTIVITY RELATION; ANIMAL; CHEMISTRY; DRUG EFFECTS; IMMUNOLOGY; LUNG; PATHOLOGY; SPRAGUE DAWLEY RAT; SYNTHESIS;

RATTUS;

ACUTE LUNG INJURY; ANIMALS; ANTI-INFLAMMATORY AGENTS; DRUG DESIGN; INTERLEUKIN-6; LIPOPOLYSACCHARIDES; LUNG; MALE; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; QUINAZOLINES; RATS; RATS, SPRAGUE-DAWLEY; TUMOR NECROSIS FACTOR-ALPHA;

EID: 84929301562     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/cbdd.12454     Document Type: Article

References (35)

1. Ware L.B., Matthay M.A., (2000) The acute respiratory distress syndrome. N Engl J Med; 342: 1334-1349.
2. Musumeci F., Radi M., Brullo C., Schenone S., (2012) Vascular endothelial growth factor (VEGF) receptors: drugs and new inhibitors. J Med Chem; 55: 10797-10822.
3. Hemmila M.R., Napolitano L.M., (2006) Severe respiratory failure: advanced treatment options. Crit Care Med; 34: S278-S290.
4. Lee W.L., Downey G.P., (2001) Neutrophil activation and acute lung injury. Curr Opin Crit Care; 7: 1-7.
5. Goodman R.B., Pugin J., Lee J.S., Matthay M.A., (2003) Cytokine-mediated inflammation in acute lung injury. Cytokine Growth Factor Rev; 14: 523-535.
6. Meduri G.U., Kohler G., Headley S., Tolley E., Stentz F., Postlethwaite A., (1995) Inflammatory cytokines in the BAL of patients with ARDS. Persistent elevation over time predicts poor outcome. Chest; 108: 1303-1314.
7. Wang Y.L., Malik A.B., Sun Y., Hu S., Reynolds A.B., Minshall R.D., Hu G., (2011) Innate immune function of the adherens junction protein p120-catenin in endothelial response to endotoxin. J Immunol; 186: 3180-3187.
8. Schrader L.I., Kinzenbaw D.A., Johnson A.W., Faraci F.M., Didion S.P., (2007) IL-6 deficiency protects against angiotensin II induced endothelial dysfunction and hypertrophy. Arterioscler Thromb Vasc Biol; 27: 2576-2581.
9. Ito H., Koide N., Hassan F., Islam S., Tumurkhuu G., Mori I., Yoshida T., Kakumu S., Moriwaki H., Yokochi T., (2006) Lethal endotoxic shock using alpha-galactosylceramide sensitization as a new experimental model of septic shock. Lab Invest; 86: 254-261.
10. Mukhopadhyay S., Hoidal J.R., Mukherjee T.K., (2006) Role of TNFalpha in pulmonary pathophysiology. Respir Res; 7: 125.
11. Rudolph J., Esler W.P., O'Connor S., Coish P.D., Wickens P.L., Brands M., Bierer D.E., et al,. (2007) Quinazolinone derivatives as orally available ghrelin receptor antagonists for the treatment of diabetes and obesity. J Med Chem; 50: 5202-5216.
12. Iwashita A., Yamazaki S., Mihara K., Hattori K., Yamamoto H., Ishida J., Matsuoka N., Mutoh S., (2004) Neuroprotective effects of a novel poly(ADP-ribose) polymerase-1 inhibitor, 2-[3-[4-(4-chlorophenyl)-1-piperazinyl] propyl]-4(3H)-quinazolinone (FR255595), in an in vitro model of cell death and in mouse 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine model of Parkinson's disease. J Pharmacol Exp Ther; 309: 1067-1078.
13. Tamaoki S., Yamauchi Y., Nakano Y., Sakano S., Asagarasu A., Sato M., (2007) Pharmacological properties of 3-amino-5,6,7,8-tetrahydro-2-[4-[4-(quinolin-2-yl)piperazin-1-yl]butyl]quinazolin-4(3H)-one (TZB-30878), a novel therapeutic agent for diarrhea-predominant irritable bowel syndrome (IBS) and its effects on an experimental IBS model. J Pharmacol Exp Ther; 322: 1315-1323.
14. Tobe M., Isobe Y., Tomizawa H., Nagasaki T., Takahashi H., Hayashi H., (2003) A novel structural class of potent inhibitors of NF-κB activation: structure-activity relationships and biological effects of 6-aminoquinazoline derivatives. Bioorg Med Chem; 11: 3869-3878.
15. Qian L., Shen Y., Chen J.-C., Wang Y.-X., Wu X.-T., Chen T.-J., Zheng K.-C., (2008) 3D-QSAR and docking studies of quinazoline derivatives with the inhibitory activity toward NF-κB. QSAR Comb Sci; 27: 984-995.
16. Rajput C.S., Singhal S., (2013) Synthesis, characterization, and anti-inflammatory activity of newer quinazolinone analogs. J Pharm; 2013: 1-7.
17. Madapa S., Tusi Z., Sridhar D., Kumar A., Siddiqi M.I., Srivastava K., Rizvi A., Tripathi R., Puri S.K., Shiva Keshava G.B., Shukla P.K., Batra S., (2009) Search for new pharmacophores for antimalarial activity. Part I: synthesis and antimalarial activity of new 2-methyl-6-ureido-4-quinolinamides. Bioorg Med Chem; 17: 203-221.
18. Domarkas J., Dudouit F., Williams C., Qiyu Q., Banerjee R., Brahimi F., Jean-Claude B.J., (2006) The combi-targeting concept: synthesis of stable nitrosoureas designed to inhibit the epidermal growth factor receptor (EGFR). J Med Chem; 49: 3544-3552.
19. Tsou H.R., Mamuya N., Johnson B.D., Reich M.F., Gruber B.C., Ye F., Nilakantan R., Shen R., Discafani C., DeBlanc R., Davis R., Koehn F.E., Greenberger L.M., Wang Y.F., Wissner A., (2001) 6-Substituted-4-(3-bromophenylamino)quinazolines as putative irreversible inhibitors of the epidermal growth factor receptor (EGFR) and human epidermal growth factor receptor (HER-2) tyrosine kinases with enhanced antitumor activity. J Med Chem; 44: 2719-2734.
20. Marvania B., Lee P.C., Chaniyara R., Dong H., Suman S., Kakadiya R., Chou T.C., Lee T.C., Shah A., Su T.L., (2011) Design, synthesis and antitumor evaluation of phenyl N-mustard-quinazoline conjugates. Bioorg Med Chem; 19: 1987-1998.
21. Smaill J.B., Palmer B.D., Rewcastle G.W., Denny W.A., McNamara D.J., Dobrusin E.M., Bridges A.J., et al,. (1999) Tyrosine kinase inhibitors. 15. 4-(Phenylamino)quinazoline and 4-(phenylamino)pyrido[d]pyrimidine acrylamides as irreversible inhibitors of the ATP binding site of the epidermal growth factor receptor. J Med Chem; 42: 1803-1815.
22. Barnes M.C., Chana S.S., Dennison H., Mathews N., Spencer K.C., (2005) Morpholinylanilinoquinazoline derivatives for use as antiviral agents, 2005, US Patent number: US20080311076.
23. Botros S., (1972) Synthesis of certain nitro-quinazoline derivatives structurally related to some chemotherapeutic agents. Egypt J Pharm Sci; 13: 11-21.
24. Saad S.M., Khan I., Perveen S., Khan K.M., Yousuf S., (2013) N-(2,5-Dimeth-oxy-phen-yl)-6-nitro-quinazolin-4-amine. Acta Crystallogr Sect E Struct Rep Online; 69: o8.
25. Foucourt A., Dubouilh-Benard C., Chosson E., Corbière C., Buquet C., Iannelli M., Leblond B., Marsais F., Besson T., (2010) Microwave-accelerated Dimroth rearrangement for the synthesis of 4-anilino-6-nitroquinazolines. Application to an efficient synthesis of a microtubule destabilizing agent. Tetrahedron; 66: 4495-4502.
26. Morley J., Simpson J., (1949) 215. The chemistry of simple heterocyclic systems. Part II. Condensations of 4-chloro-6-and 4-chloro-7-nitroquinazoline with amines. J Chem Soc; 1014-1017.
27. Smaill J.B., Showalter H.D., Zhou H., Bridges A.J., McNamara D.J., Fry D.W., Nelson J.M., Sherwood V., Vincent P.W., Roberts B.J., Elliott W.L., Denny W.A., (2001) Tyrosine kinase inhibitors. 18. 6-Substituted 4-anilinoquinazolines and 4-anilinopyrido[3,4-d]pyrimidines as soluble, irreversible inhibitors of the epidermal growth factor receptor. J Med Chem; 44: 429-440.
28. Madapa S., Tusi Z., Mishra A., Srivastava K., Pandey S.K., Tripathi R., Puri S.K., Batra S., (2009a) Search for new pharmacophores for antimalarial activity. Part II: synthesis and antimalarial activity of new 6-ureido-4-anilinoquinazolines. Bioorg Med Chem; 17: 222-234.
29. Schnur R., Arnold L,. (1996) Preparation of N-phenylquinazoline-4-amines as neoplasm inhibitors. US Patent number: WO9630347.
30. Boyce J., Brown M., Fitzner J., Kowski T., (2006) Kinase-directed, activity-based probes US Patent number: WO2006076463
31. Pan Y., Wang Y., Cai L., Cai Y., Hu J., Yu C., Li J., Feng Z., Yang S., Li X., Liang G., (2012) Inhibition of high glucose-induced inflammatory response and macrophage infiltration by a novel curcumin derivative prevents renal injury in diabetic rats. Br J Pharmacol; 166: 1169-1182.
32. Wu J., Li J., Cai Y., Pan Y., Ye F., Zhang Y., Zhao Y., Yang S., Li X., Liang G., (2011) Evaluation and discovery of novel synthetic chalcone derivatives as anti-inflammatory agents. J Med Chem; 54: 8110-8123.
33. Gasparotto V., Castagliuolo I., Ferlin M.G., (2007). 3-substituted 7-phenyl-pyrroloquinolinones show potent cytotoxic activity in human cancer cell lines. J Med Chem; 50: 5509-5513.
34. Marshall H.E., Potts E.N., Kelleher Z.T., Stamler J.S., Foster W.M., Auten R.L., (2009) Protection from lipopolysaccharide-induced lung injury by augmentation of airway S-nitrosothiols. Am J Respir Crit Care Med; 180: 11-18.
35. Minamino T., Komuro I., (2006) Regeneration of the endothelium as a novel therapeutic strategy for acute lung injury. J Clin Invest; 116: 2316-2319.