Synthesis and biological evaluation of novel series of aminopyrimidine derivatives as urease inhibitors and antimicrobial agents

References

• Onoda Y, Takido M, Magaribuchi T, Tamaki H. Effects of 12-sulfodehydroabietic acid monosodium salt (TA-2711), a new anti-ulcer agent, on gastric mucosal lesions induced by necrotizing agents and gastric mucosal defensive factors in rats. Jpn J Pharmacol 1990;52:631–638.
   PubMedGoogle Scholar
• Mobley HL, Island MD, Hausinger RP. Molecular biology of microbial ureases. Microbiol Rev 1995;59:451–480.
   PubMedGoogle Scholar
• Montecucco C, Rappuoli R. Living dangerously: how Helicobacter pylori survives in the human stomach. Nat Rev Mol Cell Biol 2001;2:457–466.
   PubMed Web of Science ®Google Scholar
• Mobley HL, Hausinger RP. Microbial ureases: significance, regulation, and molecular characterization. Microbiol Rev 1989;53:85–108.
   PubMedGoogle Scholar
• Hauck RD. (1984). Nitrogen in Crop Production. In: Hauck RD, ed. Madison, WI: American Society of Agronomy, 551.
   Google Scholar
• Andrews RK, Dexter A, Blakeley RL, Zerner B. Jack bean urease (EC 3.5.1.5) VIII. On the inhibition of urease by amides and esters of phosphoric acid. J Am Chem Soc 1986;108:7124–7125.
   Web of Science ®Google Scholar
• McCarty GW, Bremner JM, Lee JS. Inhibition of plant and microbial ureases by phosphoroamides. Plant Soil 1990;127:269–283.
   Web of Science ®Google Scholar
• Khan KM, Iqbal S, Lodhi MA, Maharvi GM, Ullah Z, Choudhary MI et al. Biscoumarin: new class of urease inhibitors; economical synthesis and activity. Bioorg Med Chem 2004;12:1963–1968.
   PubMed Web of Science ®Google Scholar
• Amtul Z, Rahman AU, Siddiqui RA, Choudhary MI. Chemistry and mechanism of urease inhibition. Curr Med Chem 2002;9:1323–1348.
   PubMed Web of Science ®Google Scholar
• Kosikowska P, Berlicki L. Urease inhibitors as potential drugs for gastric and urinary tract infections: a patent review. Expert Opin Ther Pat 2011;21:945–957.
   PubMed Web of Science ®Google Scholar
• You ZL, Xian DM, Zhang M, Cheng XS, Li XF. Synthesis, biological evaluation, and molecular docking studies of 2,5-substituted-1,4-benzoquinone as novel urease inhibitors. Bioorg Med Chem 2012;20:4889–4894.
   PubMed Web of Science ®Google Scholar
• Akhtar T, Hameed S, Khan KM, Choudhary MI. Syntheses, urease inhibition, and antimicrobial studies of some chiral 3-substituted-4-amino-5-thioxo-1H,4H-1,2,4-triazoles. Med Chem 2008;4:539–543.
   PubMed Web of Science ®Google Scholar
• Rauf A, Ahmed F, Qureshi AM, Rehman A-U, Khan A, Qadir MI et al. Synthesis and urease inhibition studies of barbituric and thiobarbituric acid derived sulphonamides. J Chin Chem Soc 2011;58:528–537.
   Web of Science ®Google Scholar
• Khan KM, Ali M, Wadood A, Zaheer-ul-Haq, Khan M, Lodhi MA et al. Molecular modeling-based antioxidant arylidene barbiturates as urease inhibitors. J Mol Graph Model 2011;30:153–156.
   PubMedGoogle Scholar
• Li HQ, Xiao ZP, Yin-Luo, Yan T, Lv PC, Zhu HL. Amines and oximes derived from deoxybenzoins as Helicobacter pylori urease inhibitors. Eur J Med Chem 2009;44:2246–2251.
   PubMed Web of Science ®Google Scholar
• Lagoja IM. Pyrimidine as constituent of natural biologically active compounds. Chem Biodivers 2005;2:1–50.
   PubMed Web of Science ®Google Scholar
• Mishra R, Tomar I. Pyrimidine: The molecule of diverse biological and medicinal importance. Internat J Pharma Sci Res 2011;2:758–771.
   Google Scholar
• Patel R, Desai K, Chikhalia K. Synthesis and biological activity of some 2,4,6-trisubstituted-1,3,5-s–triazines. J Ind Chem Soc 2003;80:138–140.
   Google Scholar
• Chaudhary A, Sharma PK, Verma P, Kumar N, Dudhe R. Microwave assisted synthesis of novel pyrimidine derivatives and investigation of their analgesic and ulcerogenic activity. Med Chem Res 2012;21:3629–3645.
   Web of Science ®Google Scholar
• Rangappa KS, Kallappa MH, Ramya VS, Mallinath HH. Analgesic, anti-pyretic and DNA cleavage studies of novel pyrimidine derivatives of coumarin moiety. Euro J Med Chem 2010;45:2597–2605.
   PubMedGoogle Scholar
• Amr AE, Nermien MS, Abdulla MM. Synthesis, reactions, and anti-inflammatory activity of heterocyclic systems fused to a thiophene moiety using citrazinic acid as synthon. Monatsh Chem 2007;138:699–707.
   Web of Science ®Google Scholar
• Fujiwara N, Nakajima T, Ueda Y, Fujita H, Kawakami H. Novel piperidinylpyrimidine derivatives as inhibitors of HIV-1 LTR activation. Bioorg Med Chem 2008;16:9804–9816.
   PubMed Web of Science ®Google Scholar
• Ballell L, Field RA, Chung GA, Young RJ. New thiopyrazolo[3,4-d]pyrimidine derivatives as anti-mycobacterial agents. Bioorg Med Chem Lett 2007;17:1736–1740.
   PubMed Web of Science ®Google Scholar
• Wagner E, Al-Kadasi K, Zimecki M, Sawka-Dobrowolska W. Synthesis and pharmacological screening of derivatives of isoxazolo[4,5-d]pyrimidine. Eur J Med Chem 2008;43:2498–2504.
   PubMed Web of Science ®Google Scholar
• Jean-Damien C, David B, Ronald K, Julian G, Pan L, Robert D. Vertex Pharmaceuticals Incorporated, USA, PCT. Int Appl 2002;WO 0222608.
   Google Scholar
• Gorlitzer K, Herbig S, Walter RD. Indeno[1,2-d]pyrimidin-4-yl-amine. Pharmazie 1997;52:670–672.
   Web of Science ®Google Scholar
• Kashyap SJ, Sharma PK, Garg VK, Dudhe R, Kumar N. Review on synthesis and various biological potential of thiazolopyrimidine derivatives. J Adv Sci Res 2011;2:18–24.
   Google Scholar
• Giridhar R, Tamboli RS, Ramajayam R, Prajapati DG, Yadav MR. Assessment of antiplatelet activity of 2-aminopyrimidines. Eur J Med Chem 2012;50:428–432.
   PubMed Web of Science ®Google Scholar
• Knölker HJ, Reddy KR. Isolation and synthesis of biologically active carbazole alkaloids. Chem Rev 2002;102:4303–4427.
   PubMed Web of Science ®Google Scholar
• Noguchi N, Nishino K, Niki E. Antioxidant action of the antihypertensive drug, carvedilol, against lipid peroxidation. Biochem Pharmacol 2000;59:1069–1076.
   PubMed Web of Science ®Google Scholar
• Zall A, Kieser D, Höttecke N, Naumann EC, Thomaszewski B, Schneider K et al. NSAID-derived γ-secretase modulation requires an acidic moiety on the carbazole scaffold. Bioorg Med Chem 2011;19:4903–4909.
   PubMedGoogle Scholar
• Routier S, Mérour JY, Dias N, Lansiaux A, Bailly C, Lozach O et al. Synthesis and biological evaluation of novel phenylcarbazoles as potential anticancer agents. J Med Chem 2006;49:789–799.
   PubMed Web of Science ®Google Scholar
• Hu L, Li ZR, Li Y, Qu J, Ling YH, Jiang JD et al. Synthesis and structure-activity relationships of carbazole sulfonamides as a novel class of antimitotic agents against solid tumors. J Med Chem 2006;49:6273–6282.
   PubMed Web of Science ®Google Scholar
• Syutkin RV, Abashev GG, Shklyaeva EV, Kudryavtsev PG. New carbazole-containing chalcones and pyrimidines based thereon: synthesis and electrochemical study. Russ J Org Chem 2011;47:530–536.
   Google Scholar
• Bandgar BP, Sarangdhar RJ, Viswakarma S, Ahamed FA. Synthesis and biological evaluation of orally active prodrugs of indomethacin. J Med Chem 2011;54:1191–1201.
   PubMed Web of Science ®Google Scholar
• Bandgar BP, Jalde SS, Korbad BL, Patil SA, Chavan HV, Kinkar SN et al. Synthesis and antioxidant, cytotoxicity and antimicrobial activities of novel curcumin mimics. J Enzyme Inhib Med Chem 2012;27:267–274.
   PubMed Web of Science ®Google Scholar
• Bandgar BP, Adsul LK, Lonikar SV, Chavan HV, Shringare SN, Patil SA et al. Synthesis of novel carbazole chalcones as radical scavenger, antimicrobial and cancer chemopreventive agents. J Enzyme Inhib Med Chem 2012. DOI: 10.3109/14756366.2012.663365.
   Google Scholar
• Khan I, Ali S, Hameed S, Rama NH, Hussain MT, Wadood A et al. Synthesis, antioxidant activities and urease inhibition of some new 1,2,4-triazole and 1,3,4-thiadiazole derivatives. Eur J Med Chem 2010;45:5200–5207.
   PubMed Web of Science ®Google Scholar
• Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 1997;23:3–25.
   Web of Science ®Google Scholar
• Hou T, Wang J, Zhang W, Xu X. ADME evaluation in drug discovery. 6. Can oral bioavailability in humans be effectively predicted by simple molecular property-based rules? J Chem Inf Model 2007;47:460–463.
   PubMed Web of Science ®Google Scholar
• Bandgar BP, Patil SA, Korbad BL, Nile SH, Khobragade CN. Synthesis and biological evaluation of β-chloro vinyl chalcones as inhibitors of TNF-α and IL-6 with antimicrobial activity. Eur J Med Chem 2010;45:2629–2633.
   PubMed Web of Science ®Google Scholar
• Drug-likeness and molecular property prediction. Available at: http://molsoft.com/mprop/.
   Google Scholar