Generic placeholder image

Current Drug Research Reviews

Editor-in-Chief

ISSN (Print): 2589-9775
ISSN (Online): 2589-9783

Review Article

Imidazole: An Emerging Scaffold Showing its Therapeutic Voyage to Develop Valuable Molecular Entities

Author(s): Bhawna Chopra*, Ashwani K. Dhingra and Deo Nandan Prasad

Volume 12, Issue 2, 2020

Page: [103 - 117] Pages: 15

DOI: 10.2174/2589977511666191129152038

Abstract

Objective: Imidazole is a heterocyclic moiety having immense biological importance. Since ancient times, the imidazole nucleus is considered to be a promising moiety in the field of chemistry. Preliminary in vitro and in vivo studies have provided valuable scientific evidence for its use. Subsequently, imidazole constitutes a new class of compounds for new drug development as the presence of this nucleus in diverse therapeutic categories viz; antimicrobial, anti-inflammatory, anticancer, immunomodulator, antiviral etc. has made it an interesting moiety for the design and development of new pharmacological agents. Thus, this review aims to summarize the reported molecular entities which were synthesized by using conventional as well as microwave processes, chemistry and biological potential of imidazole containing heterocyclic molecules while identifying potential areas of further research on imidazole.

Results: The review comprises literature pertaining to the evidence-based pharmacological or therapeutic potential of imidazole using published articles and worldwide databases. Various pharmacological experiments using different models exclusively proved the potential of imidazole.

Summary: Focusing on the discovery and development of new imidazole nucleus based molecules at a faster rate, there is a need to search previous information available in the market in the field of medicinal chemistry. Therefore, the present review aims to elaborate the therapeutic worth of imidazole and its analogs.

Keywords: Imidazole, imidazolones, biological activity, microwave, discovery, heterocyclic.

Next »
Graphical Abstract
[1]
Eicher T, Hauptmann S, Speicher A. The chemistry of heterocycles: structures, reactions, synthesis, and applications. Wiley 2003.
[http://dx.doi.org/10.1002/352760183X]
[2]
Abernethy JL. Organic chemistry, Vol. II: Stereochemistry and the chemistry of natural products (Finar, I.L.). J Chem Educ 1957; 34(8): A352.
[http://dx.doi.org/10.1021/ed034pA352]]
[3]
Obot IB, Obi-Egbedi NO, Umoren SA. Adsorption characteristics and corrosion inhibitive properties of clotrimazole for aluminium corrosion in hydrochloric acidInt. J Electrochem Soc 2009; 4: 863-77.
[4]
Bhatnagar A, Sharma PK, Kumar N. review on imidazoles: their chemistry and pharmacological potentialsinter. J PharmTech Res 2011; 3(1): 268-82.
[5]
Singh H, Kapoor VK. Medicinal and pharmaceutical chemistry. J Med Chem 1997; 40: 3990.
[6]
Chawla A, Sharma A, Sharma AK. Review: A convenient approach for the synthesis of imidazole derivatives using microwaves. Der Pharma Chem 2012; 4(1): 116-40.
[7]
Debus H. Ueber die Einwirkung des Ammoniaks auf GlyoxalAnnalen. Der Chemieund Pharmacie 1858; 107(2): 199-208.
[http://dx.doi.org/10.1002/jlac.18581070209]
[8]
Aaglawe MJ, Dhule SS, Bahekar SS, Wakte PS, Shinde DB. Synthesis and antibacterial activity of some oxazolone derivatives J. Korean Chem Soc 2003; 47: 133-6.
[http://dx.doi.org/10.5012/jkcs.2003.47.2.133]
[9]
Grimmett MR. Comprehensive heterocyclic chemistry II; Katritsky 3rd Ed USA; Oxford. 1996.
[10]
Boiani M, González M. Imidazole and benzimidazole derivatives as chemotherapeutic agents. Mini Rev Med Chem 2005; 5(4): 409-24.
[http://dx.doi.org/10.2174/1389557053544047] [PMID: 15853629]
[11]
Wright SW, Harris RR, Collins RJ, et al. Novel 1-(pyridylphenyl)-1-phenyl-2-imidazolylethanols with topical antiinflammatory activity. J Med Chem 1992; 35(17): 3148-55.
[http://dx.doi.org/10.1021/jm00095a009] [PMID: 1507204]
[12]
Chen J, Wang Z, Lu Y, Dalton JT, Miller DD, Li W. Synthesis and antiproliferative activity of imidazole and imidazoline analogs for melanoma. Bioorg Med Chem Lett 2008; 18(11): 3183-7.
[http://dx.doi.org/10.1016/j.bmcl.2008.04.073] [PMID: 18477505]
[13]
Das P, Himaja M. Design and synthesis of 4-[2′-(5′- Nitro)]imidazolylbenzoyl(N-methyl) aminoacids and peptides Int. J. Drug Develop. Res 2010; 2(2): 364-70.
[14]
Ferreira SB, Costa MS, Boechat N, et al. Synthesis and evaluation of new difluoromethyl azoles as antileishmanial agents. Eur J Med Chem 2007; 42(11-12): 1388-95.
[http://dx.doi.org/10.1016/j.ejmech.2007.02.020] [PMID: 17445951]
[15]
Valdez CA, Tripp JC, Miyamoto Y, Kalisiak J, Hruz P, Andersen YS, et al. Synthesis and electrochemistry of 2-ethenyl and 2-ethanyl derivatives of 5-nitroimidazole and antimicrobial activity against Giardia lamblia. J Med Chem 2009; 52(13): 4038-53.
[http://dx.doi.org/10.1021/jm900356n] [PMID: 19480409]
[16]
Dominianni SJ, Yen TT. Oral hypoglycemic agents. Discovery and structure-activity relationships of phenacylimidazolium halides. J Med Chem 1989; 32(10): 2301-6.
[http://dx.doi.org/10.1021/jm00130a013] [PMID: 2795602]
[17]
Grassmann S, Sadek B, Ligneau X, et al. Progress in the proxifan class: heterocyclic congeners as novel potent and selective histamine H(3)-receptor antagonists. Eur J Pharm Sci 2002; 15(4): 367-78.
[http://dx.doi.org/10.1016/S0928-0987(02)00024-6 PMID: 11988398]
[18]
Soujanya Y, Sastry GN. Theoretical elucidation of the antioxidant mechanism of 1,3-dihydro-1-methyl-2H-imidazole-2- selenol (MSeI). Tetrahedron Lett 2007; 482109-12.
[http://dx.doi.org/10.1016/j.tetlet.2007.01.131]
[19]
Nguyen DN, Stump CA, Walsh ES, et al. Potent inhibitors of farnesyltransferase and geranylgeranyltransferase-I. Bioorg Med Chem Lett 2002; 12(9): 1269-73.
[http://dx.doi.org/10.1016/S0960-894X(02)00154-3 PMID: 11965368]
[20]
Kortiwala N, Patel J, Desai VA. Imidazolone and its Various Biological Activities –A Review J. Chem Chem Sci 2016; 6(1): 25-32.
[21]
Lunt E, Newton CG, Smith C, et al. Antitumor imidazotetrazines. 14. Synthesis and antitumor activity of 6- and 8-substituted imidazo[5,1-d]-1,2,3,5-tetrazinones and 8-substituted pyrazolo[5,1-d]-1,2,3,5-tetrazinones. J Med Chem 1987; 30(2): 357-66.
[http://dx.doi.org/10.1021/jm00385a018] [PMID: 3806616]
[22]
Hoffman K. Imidazoles and its derivatives Interscience 1953; 143-5.
[23]
Bredereck H, Gompper R, Hayer D. Formamid-reaktionen, xiii. imidazole aus α-diketonen. Chem Ber 1959 Feb; 92(2): 338-43.
[http://dx.doi.org/10.1002/cber.19590920214]
[24]
Robert CE. 5- membered heterocycles combining two heteroatoms & their benzo derivativesHeterocyc. Compound 1957; V-5: 744.
[25]
Wallach S. Ber 1881; 14: 420-3.
[http://dx.doi.org/10.1002/cber.18810140195]
[26]
Stamova AYA, Georgieva SF, Georgieva MB. Reaction strategies for synthesis of imidazole derivatives: a review. Ber 1876; 184: 33-5.
[27]
Wallach, (1881), Ber, 14, pp 735; Wallach, Stricker, (1880), Ber, 13, pp 51; Wallach, Schulze, (1880), Ber, 13, pp 1514
[28]
Sarasin W. Helv Chim Acta 1924; 7: 720.
[http://dx.doi.org/10.1002/hlca.19240070188]
[29]
Robert C E. 1957; 5- membered heterocycles combining two heteroatoms & their benzo derivatives," Heterocyclic compound 5: 744.
[30]
Rogoski JM, Nagornyy PA. Stereoselective Synthesis of Piperine via a Horner Wadsworth-Emmons Reaction http://www.geocities. ws/justin_m_r/papers/piperine.pdf
[31]
Sheth AH, Prajapati PM, Shah YR, Sen DJ. Synthesis of bispyrimido imidazole fused ring heterocyclic adductwithureas of mannich base for CNS depression. Int J Drug Dev Res 2009; 1(1): 75-80.
[32]
Shaabani A, Maleki A, Behnam M. Tandem oxidation process using cerric ammonium nitrate: three-component synthesis of trisubstitutedimidazoles under aerobic oxidation conditions. Synth Commun 2009; 39(1): 102-10.
[http://dx.doi.org/10.1080/00397910802369661]
[33]
Xu Y, Guo QX. Synthesis of heterocyclic compounds under Microwave irradiation. Heterocycles 2004; 63(4): 903-74.
[http://dx.doi.org/10.3987/REV-03-574]
[34]
Romanova NN, Kudan PV, Gravis AG, Bundel YG. The use of Microwave activation in the chemistry of heterocyclic compounds. Chem Heterocycl Compd 2000; 36(10): 1130-40.
[http://dx.doi.org/10.1023/A:1002898029145]
[35]
Hoz A, Diaz-Ortiz A, Mateo MC, et al. Microwave assisted synthesis and crystal structures of 2-imidazolines and imidazoles. Tetrahedron 2006; 62: 5868-74.
[http://dx.doi.org/10.1016/j.tet.2006.04.020]
[36]
Maruthikumar TV, Reddy VP, Rao PH. Microwave induced solvent free synthesis of 1-aryl-2-(1E)-arylvinyl-4-arylmethylene-2-imidazolin-5-ones. Indian J Chem 2005; 44B: 1931-2.
[37]
Kerneur G, Lerestif JM, Bazureau JP, Hamelin J. Convenient preparation of 4-alkylidene-1H-imidazol-5(4H)-one derivatives from imidate and aldehydes by a solvent free cycloaddition under microwaves. Synthesis 1997; 3: 287-9.
[http://dx.doi.org/10.1055/s-1997-1177]
[38]
Lerestif JM, Perrocheau J, Tonnard F, Bazureau JP, Hamelin J. 1,3- Dipolar cycloaddition of imidateylides on imino-alcohols: Synthesis of new imidazolones using solvent free conditions. Tetrahedron 1995; 51: 6757-74.
[http://dx.doi.org/10.1016/0040-4020(95)00321-X]
[39]
Al-Masoudi NA, Saeed BA, Essa AH, Al-Soud YA. Microwave-assisted synthesis of acyclic C-nucleosides from 1,2- and 1,3-diketones. Nucleosides Nucleotides Nucleic Acids 2009; 28(3): 175-83.
[http://dx.doi.org/10.1080/15257770902830997] [PMID: 19333856]
[40]
Khan KM, Mughal UR, Khan S, Khan S, Perveen S, Choudhary MI. Synthesis and antibacterial and antifungal activity of 5-substituted imidazolones. Lett Drug Des Discov 2009; 6: 69-77.
[http://dx.doi.org/10.2174/157018009787158553]
[41]
Greenwald I. Journal of the chemical society. Chem Abstr 1925; 19: 1853.
[42]
Granacher C. Über anhydride von aminosäurederivaten. HCA 1925; 8(1): 865-73.
[43]
Devasia GM. Tetrahedron letters. Chem Abstr 1976; 46: 4051.
[44]
Ladenburg A, Scholtz M. Synthese der piperinsäure und des piperins. Ber Dtsch Chem Ges 1894; 27(3): 2958-60.
[45]
Mustafa A, Harhash AHE. Action of grignard reagents ix action of organomagnesium compounds on 2-phenyl-4-arylidene-2-oxazolin-5-ones and 2--phenyl-4-benzylidene-2-imidazolin-5-one. J Org Chem 1956; 21(5): 575-6.
[http://dx.doi.org/10.1021/jo01111a023]
[46]
Misra VS and , Prakash S. Pyrimidine: the molecule of diverse biological and medicinal importance. Indiun J Phurm 1974; 36: 142.
[47]
Fahmy AFM, Okabi MOA. Reaction of 4-arylidene-2-styryl-5(4)-oxazolones and related compounds. Indian J Chem 1972; 10: 961-4.
[48]
Chatrabhuji PM, Zala AP, Undavia NK. Synthesis of 5-oxo-imidazolines derivatives as anti-microbial agents. Int J Chemtech Appl 2015; 4(1): 44-8.
[49]
Kortiwala N, Patel J, Desai VA. Imidazolone and its various biological activities – A review. J Chem Chem Sci 2016; 6(1): 25-32.
[50]
Pringsheim A. Elementare theorie der ganzen transcendenten funktionen von endlicher ordnung. Math Ann 1904; 58: 257-342.
[http://dx.doi.org/10.1007/BF01444962]
[51]
Erlenmeyer E, Wittenberg M. Zur synthese der phenylbrenztraubensäuren, 3 mitt. Ann Chem 1904; 92: 343-51.
[52]
Wines WA, Napier NK. Toward an understanding of cross-cultural ethics: A tentative model. J Bus Ethics 1992; 11(11): 831-41.
[53]
Behrens OK, Bergmann M. Cosubstrates in proteolysis. Journal of Biological Chemistry 1939; 129(2): 587-602.
[54]
Chatrabhuji PM, Zala AP, Undavia NK. Antimicrobial studies of newly synthesized 1-[(4-methoxycinnamoyl) amino]-2-methyl-4-aryl methine-5-oxo-imidazolines Org chem 2015; 11(7): 267-72.
[55]
Mohr E, Stroschein F. Mitteilung über lactonähnliche anhydride acylierter aminosäuren. über das lacton des racemischen benzoylphenylalanins. J. für Prakt Chem 1910; 82(1): 322-35.
[56]
Misra S, Satsangi RK, Tiwari SS. Synthesis and CNS activities of some 2-alkyl-3(2-substituted indol-3-yl)-methyl, 6-substituted-qui-nazolin-4(3H)-ones. Pol J Pharmacol Pharm 1982; 34(5-6): 441-7.
[57]
Lokhandwala S, Parekh NM. Synthesis and microbial studies of imidazolone based azetidinone analogues. Pharma Chem 2014; 6(6): 139-42.
[58]
Solankee A, Kapadia K, Patel J, Thakor I. Synthesis and antimicrobial activity of 1-phenyl/substituted phenyl/benzyl/naphthyl-2-phenyl-4-(3′-phenoxy benzylidene)-imidazoline-5-ones. Asian J Chem 2002; 14(2): 699.
[59]
Rao VM, Reddy VM. Synthesis and biological activities of derivatives of mercaptobenzimidazoles. part-ii: some reactions of 2-mercapto-5 (or 6)-nitro-and 2-mercapto-4 (or 7)-nitrobenzimi dazoles. ChemInform 1984; 15(41): 245.
[60]
Botta M, Corelli F, Gasparrini F, Messina F, Mugnaini C. Chiral azole derivatives. 4. Enantiomers of bifonazole and related antifungal agents: synthesis, configuration assignment, and biological evaluation. J Org Chem 2000; 65(15): 4736-9.
[http://dx.doi.org/10.1021/jo991937p] [PMID: 10959884]
[61]
Wright WB Jr, Brabander HJ, Hardy RA Jr, Osterberg AC. Central nervous system depressants. I. 1-aminoalkyl-3-aryl derivatives of 2-imidazolidinone, 2-imidazolidinethione, and tetrahydro-2(1H)-pyrimidinone. J Med Chem 1966; 9(6): 852-7.
[http://dx.doi.org/10.1021/jm00324a017] [PMID: 5972045]
[62]
Verma M, Chaturvedi AK, Chaudhari A, Parmar SS. Monoamine oxidase inhibitory and anticonvulsant properties of 1,2,4-trisubstituted 5-imidazolones. J Pharm Sci 1974; 63(11): 1740-4.
[http://dx.doi.org/10.1002/jps.2600631115] [PMID: 4427234]
[63]
Upadhyay P, Pandya A, Parekh H. Possible anticonvulsant imidazloinones. synthesis and anticonvulsant activity of 1N-(ϒ′-Picolinyl)-4-subsituted-benzylidene-2-methyl/phenyl-5-imidazolinone. J Indian Chem Soc 1991; 68: 296.
[64]
Nath N, Giri S, Prasad R, Salem ML, Singh AK, Singh I. 5-aminoimidazole-4-carboxamide ribonucleoside: a novel immunomodulator with therapeutic efficacy in experimental autoimmune encephalomyelitis. J Immunol 2005; 175(1): 566-74.
[http://dx.doi.org/10.4049/jimmunol.175.1.566] [PMID: 15972693]
[65]
Dahiya R, Kumar A. Synthesis, Spectral and Anthelmintic Activity Studies on Some Novel Imidazole Derivatives. E-J Chem 2008; 5(S2): 1133-43.
[http://dx.doi.org/10.1155/2008/161783]
[66]
Erhardt PW, Hagedorn AA III, Davey D, et al. Cardiotonic agents. 5. Fragments from the heterocycle-phenyl-imidazole pharmacophore. J Med Chem 1989; 32(6): 1173-6.
[http://dx.doi.org/10.1021/jm00126a005] [PMID: 2542552]
[67]
Johnson RA, Huong SM, Huang ES. Inhibitory effect of 4-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)1H - imidazole on HCMV DNA replication and permissive infection. Antiviral Res 1999; 41(3): 101-11.
[http://dx.doi.org/10.1016/S0166-3542(99)00002-9 PMID: 10320043]
[68]
Bishnol A, Pandey V, Saxena R. Potential antibacterial agents: 5-imidazolones derivatives J Indian Chem Soc 1978; 41(B): 89.
[69]
Sennequier N, Wolan D, Stuehr DJ. Antifungal imidazoles block assembly of inducible NO synthase into an active dimer. J Biol Chem 1999; 274(2): 930-8.
[http://dx.doi.org/10.1074/jbc.274.2.930] [PMID: 9873034]
[70]
Brogden RN, Heel RC, Speight TM, Avery GS. Metronidazole in anaerobic infections: A review of its activity, pharmacokinetics and therapeutic use. Drugs 1978; 16(5): 387-417.
[http://dx.doi.org/10.2165/00003495-197816050-00002 PMID: 363399]
[71]
Jain R, Vangapandu S, Jain M, Kaur N, Singh S, Singh PP. Antimalarial activities of ring-substituted bioimidazoles. Bioorg Med Chem Lett 2002; 12(13): 1701-4.
[http://dx.doi.org/10.1016/S0960-894X(02)00289-5 PMID: 12067541]
[72]
Brimblecombe RW, Duncan WAM, Durant GJ, Emmett JC, Gannellin CR, Parsons ME. J Int Med Res 1975; 3: 86-92.
[http://dx.doi.org/10.1177/030006057500300205]
[73]
Jackson PF, Bullington JL. Pyridinylimidazole based p38 MAP kinase inhibitors. Curr Top Med Chem 2002; 2(9): 1011-20.
[http://dx.doi.org/10.2174/1568026023393372] [PMID: 12171568]
[74]
Wilson KP, McCaffrey PG, Hsiao K, et al. The structural basis for the specificity of pyridinylimidazole inhibitors of p38 MAP kinase. Chem Biol 1997; 4(6): 423-31.
[http://dx.doi.org/10.1016/S1074-5521(97)90194-0] [PMID: 9224565]
[75]
Bolós J. Structure-activity relationships of p38 mitogen-activated protein kinase inhibitors. Mini Rev Med Chem 2005; 5(9): 857-68.
[http://dx.doi.org/10.2174/1389557054867048] [PMID: 16178727]
[76]
Diller DJ, Lin TH, Metzger A. The discovery of novel chemotypes of p38 kinase inhibitors. Curr Top Med Chem 2005; 5(10): 953-65.
[http://dx.doi.org/10.2174/1568026054985948] [PMID: 16178740]
[77]
Delgado JN, Remers WA. Wilson and Gisvold’s textbook of organic medicinal and pharmaceutical chemistry. 11th ed. 1998.
[78]
Rodriques Coura J, de Castro SL, Mem SL. A critical review on Chagas disease chemotherapy. Mem Inst Oswaldo Cruz 2002; 97(1): 3-24.
[http://dx.doi.org/10.1590/S0074-02762002000100001 PMID: 11992141]
[79]
Rani N, Sharma A, Gupta GK, Singh R. Imidazoles as potential antifungal agents: a review. Mini Rev Med Chem 2013; 13(11): 1626-55.
[http://dx.doi.org/10.2174/13895575113139990069 PMID: 23815583]
[80]
Kleeman A, Engel J, Kutscher B, Reichert D. 4th ed Pharmaceutical Substances New Jersey 1999; 3.
[81]
Ding M, Chen Y, Huang N. Synthesis and fungicidal activities of derivatives of 2-alkylthio-3-amino-4h-imidazol-4-one. Phosphorus Sulfur Silicon Relat Elem 2004; 179(11): 2287-96.
[http://dx.doi.org/10.1080/10426500490484977]
[82]
Sun Y, Ding MW. Synthesis of terminal vinylphosphonates via dbu-promoted tandem phospha-michael/elimination reactions. Phosphorus Sulfur Silicon Relat Elem 2004; 179: 2465.
[http://dx.doi.org/10.1080/10426500490485363]
[83]
Hu Y, Yang S, Ding M. Synthesis and fungicidal activities of 2-benzothiazolylthio-substituted 4h-imidazol-4-ones and 4(3h)-quina-zolinones. Phosphorus Sulfur Silicon Relat Elem 2004; 179(10): 1933-9.
[http://dx.doi.org/10.1080/10426500490466913]
[84]
Sun Y, Fu BQ, Ding MW. One-Pot Synthesis and Fungicidal Activities of Derivatives of Imidazo [2, 1-b]-1, 3, 4-thiadiazol-5 (6 H)-one. Phosphorus Sulfur Silicon Relat Elem 2006; 181(6): 1437-43.
[http://dx.doi.org/10.1080/10426500500328954]
[85]
Huang X, Liu Z, Yang F, Ding M. Synthesis and properties of novel imidazolone derivatives containing a sulfur atom. Phosphorus Sulfur Silicon Relat Elem 2007; 182(5): 939-50.
[http://dx.doi.org/10.1080/10426500601088762]
[86]
Yang WC, Li J, Li J, Chen Q, Yang GF. Novel synthetic methods for N-cyano-1H-imidazole-4-carboxamides and their fungicidal activity. Bioorg Med Chem Lett 2012; 22(3): 1455-8.
[http://dx.doi.org/10.1016/j.bmcl.2011.11.115] [PMID: 22189134]
[87]
Puratchikody A, Doble M. Antinociceptive and antiinflammatory activities and QSAR studies on 2-substituted-4, 5-diphenyl-1H-imidazoles. Bioorg Med Chem 2007; 15(2): 1083-90.
[http://dx.doi.org/10.1016/j.bmc.2006.10.025] [PMID: 17079151]
[88]
Achar KCS, Hosamani KM, Seetharamareddy HR. In-vivo analgesic and anti-inflammatory activities of newly synthesized benzimidazole derivatives. Eur J Med Chem 2010; 45(5): 2048-54.
[http://dx.doi.org/10.1016/j.ejmech.2010.01.029] [PMID: 20133024]
[89]
El-Araby M, Omar A, Hassanein HH, El-Helby AG, Abdel-Rahman AA. Design, synthesis and in vivo anti-inflammatory activities of 2, 4-diaryl-5-4H-imidazolone derivatives. Molecules 2012; 17(10): 12262-75.
[http://dx.doi.org/10.3390/molecules171012262] [PMID: 23079497]
[90]
Singh IP, Saxena AK, Sinha JN, Shanker K. Synthesis and anti-inflammatory activity of thiazolidinones and imidazolidinones derived from thiosemicarbazones. Eur J Med Chem 1985; 20: 283-6.
[91]
Ming WD, Jing Z. New facile synthesis of 2-aryloxy-5-(2-furfurylidene)-4H-imidazoline-4-ones. Chin Chem Lett 2002; 13: 942-4.
[92]
Tandon M, Kumar P, Pande K, Bhalla TN, Barthwal JP. Novel thiazolidinones as potent anti-inflammatory and analgesic agents. Pharmacology 1985; 31(5): 260-7.
[http://dx.doi.org/10.1159/000138130] [PMID: 3877940]
[93]
Sawhney SN, Vir D, Gupta A. Synthesis of some 2-(5-aryl-4, 5-dihydropyrazol-3-yl) and 2-(2-amino-6-arylpyrimidin-4-yl)benzimi dazoles as potential anti-inflammatory agents. Indian J Chem 1990; 29B: 1107-12.
[94]
Sawhney SN, Bhutani S, Vir D. Synthesis of some 2-(2-benzothiazolyl)-and-2-(2-benzoimidazolyl)-6-aryl-4,5 dihydro-3(2H)-pyridazinones as potential anti-inflammatory agents. Indian J Chem 1987; 26B: 348-50.
[95]
Trivedi GK, Vora J, Singh P, Hingorani LL. Synthesis, anti-inflammatory, antibacterial and antifungal activities of benzimidazoles. Indian J Chem 1990; 29B: 596-7.
[96]
Raghavendra P, Veena G, Kumar GA, et al. Microwave synthesis and anti-inflammatory evaluation of some new imidazolo quinoline analogs. RASAYAN Journal of Chemistry 2011; 4(1): 91-102.
[97]
Sathe BS, Jagtap VA, Deshmukh SD, Jain BV. Screening of in-vitro anti-inflammatory activity of some newly synthesized fluorinated benzothiazolo imidazole compounds. Int J Pharm Pharm Sci 2011; 3(3): 220-2.
[98]
Husain A, Drabu S, Kumar N, Alam MM, Bawa S. Synthesis and biological evaluation of di- and tri-substituted imidazoles as safer anti-inflammatory-antifungal agents. J Pharm Bioallied Sci 2013; 5(2): 154-61.
[http://dx.doi.org/10.4103/0975-7406.111822] [PMID: 23833522]
[99]
Desai NC, Bhavsar AM, Baldaniya BB. Synthesis and antimicrobial activity of 5-imidazolinone derivatives. Indian J Pharm Sci 2009; 71(1): 90-4.
[http://dx.doi.org/10.4103/0250-474X.51953] [PMID: 20177470]
[100]
Benkli K, Karaburun AC, Gündoğdu-Karaburun N, Demirayak S, Güven K. Synthesis and antimicrobial activities of some new nitroimidazole derivatives. Arch Pharm Res 2003; 26(10): 773-7.
[http://dx.doi.org/10.1007/BF02980019] [PMID: 14609122]
[101]
Patel A, Bari S, Talele G, Patel J, Sarangapani M. Iran. Synthesis and antimicrobial activity of some new isatin derivatives. J Pharma Res 2006; 4: 249.
[102]
Suthakaran R, Kavimani S, Venkaiaiah P, Suganthi K. Synthesis and antimicrobial activity of 3 -(2- (4z) - 4 - substituted benzylidene-4,5-dihydro-5- oxo-2-phenyl imidazol-1-yl)ethyl)-6,8- un/dibromo subtituted-2-substituted quinazoline-(3h)-one. Rasayan J Chem 2008; 1(1): 22.
[103]
Khan KM, Khan M, Ali M, et al. Synthesis of bis-Schiff bases of isatins and their antiglycation activity. Bioorg Med Chem 2009 Nov 15; 17(22): 7795-801.
[http://dx.doi.org/10.1016/j.bmc.2009.09.028] [PMID: 19837595]
[104]
Baldaniya BB. Synthesis, characterization and biological activity of 5-arylidene-3-(6,7-dicloro-1,3-benzothiazol-2-yl)-phenyl-3,5-dihydro-4h-imidazol-4-ones. E-J Chem 2010; 7(1): 81-4.
[http://dx.doi.org/10.1155/2010/264036]
[105]
Shah RA, Patel PS, Trivedi DK, Vyas PJ. Synthesis, characterization and antimicrobial activities of 4-benzylidene-1-4-[3-(substituted phenyl)prop-2-enoyl]phenyl-2-phenyl-imidazol-5-one. Pharma Chem 2010; 2(1): 117-20.
[106]
Bhanat K, Parashar N, Jain K, Sharma VK. synthesis and antimicrobial study of 4-benzylidene-2-phenyl-1-(5-phenylthiazole-2-yl)-1h-imidazol-5(4h)-one. Asian J Biochem Pharm Res 2011; 1(1): 83-90.
[107]
Sah P, Saraswat N, Seth M. Mechanisms of nucleation and growth of nanoparticles in solution. E-J Chem 2011; 8(1): 427.
[http://dx.doi.org/10.1155/2011/726315]
[108]
Bharadwaj S, Rathore DK, Parashar B, Sharma VK. Review: A convenient approach for the synthesis of imidazole derivatives using microwaves. J Chem Pharm Res 2010; 2(5): 392.
[109]
Lokhandwala S, Rai S. “Synthesis and in vitro Microbial Evaluation of Some Novel Imidozol-5-one Derivatives,” Inter. J ChemTech Res 2013; 5(5): 2609-13.
[110]
Synthesis, Characterization and Antimicrobial Studies of Transition Metal Complexes of Imidazole Derivative. Bull Chem Soc Ethiop 2010; 24(2): 201-7.
[111]
Atia AJ, Khan A. Synthesis and antibacterial activities of new metronidazole and imidazole derivatives. Molecules 2009; 14(7): 2431-46.
[http://dx.doi.org/10.3390/molecules14072431] [PMID: 19633614]
[112]
De B, Gupta JK, Saravanan VS. Synthesis of some oxazolinones and imidazolinones and their antimicrobial screening. Acta Pharm 2005; 55(3): 287-96.
[PMID: 16375839]
[113]
Mistry RN, Desai KR. Studies on synthesis of some novel heterocyclic azalactone derivatives and their anti-microbial activity. Eur J Chem 2005; 2(6): 42-51.
[114]
Joshi H, Upadhyay P, Karia D, Baxi AJ. Synthesis of some novel imidazolinones as potent anticonvulsant agents. Eur J Med Chem 2003; 38(9): 837-40.
[http://dx.doi.org/10.1016/S0223-5234(03)00117-X PMID: 14561482]
[115]
Siddiqui SA, Bhusare SR. New novel synthesis and anti-bacterial activity of 1-(substituted phenyl)-2-phenyl-4-(3′-halo, 4′-hydroxy 5′-methoxy benzylidene)-imidazole-5-one. Bull Korean Chem Soc 2001; 22(9): 1033-6.
[116]
Solankee A, Solankee S, Patel G. Potential anti-bacterial agents: 5-imidazolone Derivatives. Rasayan J Chem 2008; 2: 228-31.
[117]
Taunk A, Pandey R, Taunk A. Disciplined Reactions - A facile one-flask synthesis of 2-substituted-4-m-methoxy -p-hydroxy bezylidene-1-phenyl-2-imidazolin-5-ones and its biological evaluation research and reviews. J Chem 2013; 2013: 24.
[118]
Antolini M, Bozzoli A, Ghiron C, Kennedy G, Rossi T, Ursini A. analogues of 4,5-bis(3,5-dichlorophenyl)-2-trifluoromethyl-1H-imidazole as potential antibacterial agents. Bioorg Med Chem Lett 1999; 9(7): 1023-8.
[http://dx.doi.org/10.1016/S0960-894X(99)00112-2 PMID: 10230632]
[119]
Saravanan S, Selvan PS, Gopal N, Gupta JK, De B. Synthesis and antibacterial activity of some imidazole-5-(4H)one derivatives. Arch Pharm (Weinheim) 2005; 338(10): 488-92.
[http://dx.doi.org/10.1002/ardp.200400944] [PMID: 16211653]
[120]
Vijesh AM, Isloor AM, Telkar S, Peethambar SK, Rai S, Isloor N, et al. Synthesis, characterization and antimicrobial studies of some new pyrazole incorporated imidazole derivatives. Eur J Med Chem 2011; 46(8): 3531-6.
[http://dx.doi.org/10.1016/j.ejmech.2011.05.005] [PMID: 21620535]
[121]
Lu X, Liu X, Wan B, Franzblau SG, Chen L, Zhou C, et al. Synthesis and evaluation of anti-tubercular and antibacterial activities of new 4-(2,6-dichlorobenzyloxy)phenyl thiazole, oxazole and imidazole derivatives. Part 2. Eur J Med Chem 2012 Mar; 49: 164-71.
[http://dx.doi.org/10.1016/j.ejmech.2012.01.007] [PMID: 22264895]
[122]
Jain AK, Ravichandran V, Sisodiya M, Agrawal RK. Synthesis and antibacterial evaluation of 2-substituted-4,5-diphenyl- N-alkyl imidazole derivatives. Asian Pac J Trop Med 2010; 471-4.
[http://dx.doi.org/10.1016/S1995-7645(10)60113-7]
[123]
Ramachandran R, Rani M, Senthan S, Jeong YT, Kabilan S. Synthesis, spectral, crystal structure and in vitro antimicrobial evaluation of imidazole/benzotriazole substituted piperidin-4-one derivatives. Eur J Med Chem 2011; 46(5): 1926-34.
[http://dx.doi.org/10.1016/j.ejmech.2011.02.036] [PMID: 21397368]
[124]
Padmavathi V, Prema Kumari C, Venkatesh BC, Padmaja A. Synthesis and antimicrobial activity of amido linked pyrrolyl and pyrazolyl-oxazoles, thiazoles and imidazoles. Eur J Med Chem 2011; 46(11): 5317-26.
[http://dx.doi.org/10.1016/j.ejmech.2011.08.032] [PMID: 21906854]
[125]
Ali TE, Aziz SAA, El-Shaaer HM, Hanafy FI, El-Fauomy AZ. A review on the biological applications of imidazole, thiazole and their derivatives. Turk J Chem 2008; 32: 365.
[126]
Voosala C, Yarla NS, Nakka MR, Voosala SV, et al. Facile Synthesis of 1-(substituted phenyl)-2-phenyl-4-(substitutedbenzyli-dine)-imidazole-5-ones and Antifungal Activity Studies against Phytopathogens. Med Chem 2013; 4: 1.
[127]
De Vita D, Scipione L, Tortorella S, et al. Synthesis and antifungal activity of a new series of 2-(1H-imidazol-1-yl)-1-phenylethanol derivatives. Eur J Med Chem 2012; 49: 334-42.
[http://dx.doi.org/10.1016/j.ejmech.2012.01.034] [PMID: 22321993]
[128]
Yang XD, Wan WC, Deng XY, Li Y, Yang LJ, Li L, et al. Design, synthesis and cytotoxic activities of novel hybrid compounds between 2-phenylbenzofuran and imidazole. Bioorg Med Chem Lett 2012 Apr 15; 22(8): 2726-9.
[http://dx.doi.org/10.1016/j.bmcl.2012.02.094] [PMID: 22440627]
[129]
El-Gendy Z, Morsy JM, Allimony HA, Abdel-Monem WR, Abdel-Rahman RM. Phosphorus Sulfur Silicon Relat Elem 2003; 178: 2055.
[http://dx.doi.org/10.1080/10426500390228738]
[130]
Congiu C, Cocco MT, Onnis V. Design, synthesis, and in vitro antitumor activity of new 1,4-diarylimidazole-2-ones and their 2-thione analogues. Bioorg Med Chem Lett 2008; 18(3): 989-93.
[http://dx.doi.org/10.1016/j.bmcl.2007.12.023] [PMID: 18164978]
[131]
Mesaik MA, Khan KM. Immunomodulatory properties of synthetic imidazolone derivatives. Lett Drug Des Discov 2005; 2: 490-6.
[http://dx.doi.org/10.2174/1570180054771554]
[132]
Wadia DN, Patel PM. Synthesis and application of acid dyes based on 3-(4-aminophenyl)-5-benzylidene-2-substituted phenyl-3, 5-dihydroimidazol-4-one. E-Journal of Chemistry 2008; 5(s1): S987-96.
[http://dx.doi.org/10.1155/2008/470490]
[133]
Fujimoto T, Tobisu M, Konishi N, et al. Synthesis and biological evaluation of the metabolites of 2-(1-3-[(6-chloronaphthalen-2-yl) sulfonyl]propanoylpiperidin-4-yl)-5-methyl-1,2-dihydro-3H-imida zo[1,5-c]imidazol-3-one. Bioorg Med Chem 2009; 17(23): 7993-8002.
[http://dx.doi.org/10.1016/j.bmc.2009.10.009] [PMID: 19861238]
[134]
Patel K, Jayachandran E, Shah R, Javali V, Sreenivasa GM. Int J Pharma Bio Sci 2010; 1(3): 1.
[135]
Zhan P, Liu X, Zhu J, et al. Synthesis and biological evaluation of imidazole thioacetanilides as novel non-nucleoside HIV-1 reverse transcriptase inhibitors. Bioorg Med Chem 2009; 17(16): 5775-81.
[http://dx.doi.org/10.1016/j.bmc.2009.07.028] [PMID: 19643613]
[136]
Hadizadeh F, Hosseinzadeh H, Motamed-Shariaty VS, Seifi M, Kazemi S. 3‐Formylchromones as diverse building blocks in heterocycles synthesis.i Iran J. Pharm Res 2008; 7(1): 29-33.

© 2024 Bentham Science Publishers | Privacy Policy