Biological importance of imidazole nucleus in the new millennium

Medicinal Chemistry Research

Volumn 20, Issue 8, 2011, Pages 1119-1140

  Narasimhan, Balasubramanian ^a   Sharma, Deepika ^b   Kumar, Pradeep ^a  

^a MAHARSHI DAYANAND UNIVERSITY   (India)

^b PANJAB UNIVERSITY   (India)

Author keywords

Analgesic; Anti bacterial activity; Anti cancer; Imidazole

Indexed keywords

(3,4 DIMETHOXYPHENYL) [5 [3 METHYL 5 [(PYRIDIN 4 YLMETHYL) AMINO] 3H IMIDAZOL 4 YL][1,3,4]OXADIA ZOL 2 YL]AMINE; 1 (4 CHLOROPHENYL) 4 (3,4,5 TRIMETHOXYPHENYL) 1,3 DIHYDROIMIDAZOL 2 ONE; 1 (6,7 DIMETHOXY 2 NAPHTHYL) 1 (1H IMIDAZOL 4 YL) 2 METHYLPROPAN 1 OL; 2 (1H IMIDAZOL 1 YL) 7 METHOXY 3 PHENYL 4H 1 BENZO PYRAN 4 ONE; 2 (PIPERIDINE 1 YL)N[2 (PIPERIDINE 1 YLMETHYL) 11 OXO 1H,11H XANTHENO[1,2 D]IMIDAZOL 5 YL]ACETAMIDE; 4 (3 FLUORO 4 METHOXYPHENYL) 1 (3,4,5 TRIMETHOXYPHENYL) 1H IMIDAZOLE; 4 [1 (4 CYANOPHENYL) 4 (4 FLUOROPHENYL) 1 BUTENYL] 1H IMIDAZOLE; 4 METHYL N [4 METHYL 3 [4 (PYRIDIN 3 YL) 1H IMIDAZOL 2 YLAMINO]PHENYL]BENZIMIDAZOLE; 6 [(2 DIMETHYLAMINO)ETHYL] 2 (4 METHOXYPHENYL) 9 METHYL 3,8 DIHYDRO 1,3,6 TRIAZACYCLOPENTA[B]NAPHTHALENE 5,7 DIONE; 9 (3,4 DIMETHOXYPHENYL) 5 (2 DIMETHYL AMINOETHYL) 8H 5,8,10 TRIAZACYCLOPENTA[A]PHENALENE 4,6 DIONE; [IMIDAZO(1,2 ALPHA)PYRIDINE](AMINE)DICHLOROPLATINUM; ANTICOAGULANT AGENT; ANTIDIABETIC AGENT; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ANTIMALARIAL AGENT; ANTINEOPLASTIC AGENT; ANTIOBESITY AGENT; ANTITRYPANOSOMAL AGENT; ANTIVIRUS AGENT; BIS PYRROLE[2,1][1,4]BENZODIAZEPINE IMIDAZOLE POLYAMIDE; ENZYME ACTIVATOR; ENZYME INHIBITOR; HEME OXYGENASE INHIBITOR; HISTAMINE H3 RECEPTOR ANTAGONIST; IMIDAZOFURIN; IMIDAZOLE DERIVATIVE; N METHYL 3 [1 METHYL 4 [1 METHYL 4[4(ALPHA BROMOACRYLAMIDO)IMIDAZOLE 2 CARBOXAMIDO]PYRROLE 2 CARBOXAMIDO]]PROPION AMIDINE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANALGESIC ACTIVITY; ANTIBACTERIAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIPROTOZOAL ACTIVITY; ANTIVIRAL ACTIVITY; BIOLOGICAL ACTIVITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; NONHUMAN; REVIEW; TRANQUILIZING ACTIVITY;

EID: 80054762439     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-010-9472-5     Document Type: Review

References (71)

1. Abraham G, Solyom S, Csuzdi E, Berzsenyi P, Ling I, Tarnawa I, Hamori T, Pallagi I, Horvath K, Andrasi F, Kapus G, Harsing LG, Kiraly I, Patthy M, Horvath G (2000) New non competitive AMPA antagonists. Bioorg Med Chem 8:2127-2143 (Pubitemid 30612504)
2. Adams JL, Boehm JC, Gallagher TF, Kassis S, Webb EF, Hall R, Sorenson M, Garigipati R, Griswold DE, Lee JC (2001) Pyrimidinylimidazole inhibitors of p38: Cyclic N-1 imidazole substituents enhance p38 kinase inhibition and oral activity. Bioorg Med Chem Lett 11:2867-2870
3. Angibaud P, Saha AK, Bourdrez X, End DW, Frenye E, Lezouret P, Mannens G, Mevellec L, Meyer C, Pilatte I, Poncelet V, Roux B, Smets G, Dun JV, Venet M, Wouters W (2003) 4-Methyl-1,2, 4-triazol-3-yl heterocycle as an alternative to the 1-methylimidazol- 5-yl moiety in the Farnesyltransferase inhibitor ZARNESTRA TM. Bioorg Med Chem Lett 13:4361-4364 (Pubitemid 37490818)
4. Babizhayev MA (2006) Biological activities of the natural imidazolecontaining peptidomimetics N-acetylcarnosine, carcinine and L-carnosine in ophthalmic and skincare products. Life Sci 78:2343-2357
5. Baraldi PG, Beria I, Cozzi P, Bianchi N, Gambari R, Romagnoli R (2003) Synthesis and growth inhibition activity of a-bromoacrylic heterocyclic and benzoheterocyclic derivatives of distamycin A modified on the amidino moiety. Bioorg Med Chem 11: 965-975 (Pubitemid 36287055)
6. Bellina F, Cauteruccio S, Monti SM, Rossi R (2006) Novel imidazole-based combretastatin A-4 analogues: Evaluation of their in vitro antitumor activity and molecular modeling study of their binding to the colchicine site of tubulin. Bioorg Med Chem Lett 16:5757-5762 (Pubitemid 44486746)
7. Bhandari K, Srinivas N, Keshava GBS, Shukla PK (2009) Tetrahydronaphthyl azole oxime ethers: The conformationally rigid analogues of oxiconazole as antibacterials. Eur J Med Chem 44: 437-447
8. Bolos CA, Papazisis KT, Kortasaris AH, Voyatzi S, Zamboli D, Kyriakidis DA (2002) Antiproliferative activity of mixed-ligand dien-Cu(II) complexes with thiazole, thiazoline and imidazole derivatives. J Inorg Biochem 88:25-36 (Pubitemid 34003047)
9. Congiu C, Cocco MT, Onnis V (2008) Design, synthesis and in vitro antitumor activity of new 1,4-diarylimidazole-2-ones and their 2- thione analogues. Bioorg Med Chem Lett 18:989-993 (Pubitemid 351179344)
10. Crane L, Anastassiadour M, Hage SE, Stigliani JL, Baeiard-Mouysset G, Payard M, Leger JM, Bizot-Espiard J, Ktorza A, Caignard D, Renard P (2006) Design and synthesis of novel imidazoline derivatives with potent antihyperglycemic activity in a rat model of type 2 diabetes. Bioorg Med Chem 14:7419-7433 (Pubitemid 44486807)
11. Emami S, Foroumadi A, Falahati M, Lotfali E, Rajabalian S, Ebrahimi S, Farahyar S, Shafiee A (2004) Stereoselective synthesis and antifungal activity of (Z)-trans-3-azolyl-2-methylchromanone oxime ethers, synthesis of 2-(aminocarbonylmethylthio)- 1H-imidazoles as novel Capravirine analogues. Bioorg Med Chem 12:5881-5889 (Pubitemid 39388187)
12. Emami S, Foroumadi A, Falahati M, Lotfali E, Rajabalian S, Ebrahimi S, Farahyar S, Shafiee A (2008) 2-Hydroxyphenacyl azoles and related azolium derivatives as antifungal agents. Bioorg Med Chem Lett 18:141-146
13. Ferreira SB, Costa MS, Boechat N, Bezerra RJS, Genestra MS, Canto-Cavalheiro MM, Kover WB, Ferreira VF (2007) Synthesis and evaluation of new difluoromethyl azoles as antileishmanial agents. Eur J Med Chem 42:1388-1395 (Pubitemid 350137573)
14. Foroumadi A, Emami S, Pournourmohammadi S, Kharazmi A, Shafiee A (2005) Synthesis and in vitro leishmanicidal activity of 2-(1-methyl-5-nitro-1H- imidazol-2-yl)-5-substituted-1, 3, 4- thiadiazole derivatives. Eur J Med Chem 40:1346-1350 (Pubitemid 41618277)
15. Franchetti P, Marchetti LS, Cappaellaci JA, Yalowitz HN, Jayaram BM, Glodstein M, Grafantini A (2001) New C-nucleoside analogue of tiazofurin: Synthesis and biological evaluation of 2- b-ribofuranosylimidazole-4-carboxamide (imidazofurin). Bioorg Med Chem Lett 11:67-69 (Pubitemid 32006126)
16. Geronikaki A, Babaev E, Dearden J, Dehaen W, Filimonov D, Galabeva I, Krajneva V, Lagunin A, Macaev F, Molodavkin G, Poroikov V, Pogrebnoi S, Saloutin V, Stepanchikova A, Stingaci E, Tkach N, Vlad L, Voronina T (2004) Design, synthesis, computational and biological evaluation of new anxiolytics. Bioorg Med Chem 12:6559-6568 (Pubitemid 39535178)
17. Gore VK, Ma VV, Tamir R, Gavva NR, Treanor JJS, Norman MH (2007) Structure-activity relationship (SAR) investigations of substituted imidazole analogs as TRPV1 antagonists. Bioorg Med Chem Lett 17:5825-5830 (Pubitemid 47446224)
18. Grabmann S, Apelt J, Sippl W, Ligneau X, Pertz HH, Zhao YH, Arrang J, Ganellin CR, Schwartz J, Schunack W, Stark H (2003) Imidazole derivatives as a novel class of hybrid compounds with inhibitory histamine N-methyltransferase potencies and histamine hH3 receptor affinities. Bioorg Med Chem 11:2163-2174 (Pubitemid 36457843)
19. Gupta P, Hameed S, Jain R (2004) Ring-substituted imidazoles as a new class of anti-tuberculosis agents. Inhibition of PDGFR tyrosine kinase activity by a series of novel N-(3-(4-(pyridin-3- yl)-1H-imidazol-2-ylamino)phenyl) amides-A SAR study on the bioisosterism of pyrimidine and imidazole. Eur J Med Chem 39:805-814
20. Hackett JC, Kim Y, Su B, Brueggemeier RW (2005) Synthesis and characterization of azole isoflavone inhibitors of aromatase. Bioorg Med Chem 13:4063-4070 (Pubitemid 40725038)
21. Han MS, Kim DH (2001) Effect of zinc ion on the inhibition of carboxypeptidase A by imidazole-bearing substrate analogues. Bioorg Med Chem Lett 11:1425-1427 (Pubitemid 32510835)
22. Huq F, Daghriri H, Yu JQ, Beale P, Fisher K (2004a) Studies on the synthesis and characterization of four trans-planaramineplatinum( II) complexes of the form trans-PtL(NH3)CL2 where L = 2-hydroxypyridine, 3-hydroxypyridine, imidazole and imidazo( 1, 2-a)pyridine. Eur J Med Chem 39:691-697 (Pubitemid 38970083)
23. Huq F, Yu JQ, Daghriri H, Beale P (2004b) Studies on activities, cell uptake and DNA binding of four trans-planaramineplatinum(II) complexes of the form: Trans-PtL(NH3)Cl2, where L =2-hydroxypyridine, imidazole, 3-hydroxypyridine and imidazo( 1, 2-a)pyridine. J Inorg Biochem 98:1261-1270 (Pubitemid 38951046)
24. Karjalainer A, Kalapudas A, Saodervall M, Pelkonen O, Lammintausta R (2000) Synthesis of new potent and selective aromatase inhibitors based on long-chained diarylalkylimidazole and diarylalkyltriazole molecule skeletons. Eur J Pharm Sci 11:109-131 (Pubitemid 30479854)
25. Kawanishi M, Kotoku N, Itagaki S, Horii T, Kobayashi M (2004) Structure-activity relationship of anti-malarial spongean peroxides having a 3-methoxy-1, 2-dioxane structure. Bioorg Med Chem 12:5297-5307 (Pubitemid 39243950)
26. Kennedy DC, Wu A, Patrick BO, James BR (2006) Ruthenium (III) maltolato-nitroimidazole complexes: Synthesis and biological activity. J Inorg Biochem 100:1974-1982 (Pubitemid 44738035)
27. Khabnadideh S, Rezaei Z, Khalafi-Nezhad A, Bahrinajafi R, Mohamadi R, Farrokhroz AA (2003) Synthesis of N-alkylated derivatives of imidazole as antibacterial agents. Bioorg Med Chem Lett 13:2863-2865 (Pubitemid 37386239)
28. Khalafi-Nezhad A, Rad MSN, Mohabatkar H, Asrari Z, Hemmateenejad B (2005) Design, synthesis, antibacterial and QSAR studies of benzimidazole and imidazole chloroaryloxyalkyl derivatives. Bioorg Med Chem 13:1931-1938 (Pubitemid 40261116)
29. Kiselyov AS, Semenova M, Semenov VV (2006) Hetaryl imidazoles: A novel dual inhibitors of VEGF receptors I and II. Bioorg Med Chem Lett 16:1440-1444 (Pubitemid 43143038)
30. Kostakis IK, Pouli N, Marakos P, Kousidou OC, Roussidis A, Tzanakakis GN, Karamanos NK (2008) Design, synthesis and cell growth inhibitory activity of a series of novel aminosubstituted xantheno[1, 2-d]imidazoles in breast cancer cells. Bioorg Med Chem 16:3445-3455 (Pubitemid 351444818)
31. Kumar R, Lown JW (2005) Design, synthesis and in vitro cytotoxic studies of novel bis-pyrrolo[2, 1][1, 4] benzodiazepine-pyrrole and imidazole polyamide conjugates. Eur J Med Chem 40:641-654 (Pubitemid 40797560)
32. Li Q, Claiborne A, Li T, Hasvold L, Stoll VS, Muchmore S, Jakob CG, Gu W, Cohen J, Hutchins C, Frost D, Rosenberg SH, Sham HL (2004a) Design, synthesis and activity of 4-quinolone and pyridone compounds as nonthiol-containing farnesyltransferase inhibitors. Bioorg Med Chem Lett 14:5367-5370 (Pubitemid 39348929)
33. Li Q, Wang GT, Li T, Gwaltney SL, Woods KW, Claiborne A, Wang X, Gu W, Cohen J, Stoll VS, Hutchins C, Frost D, Rosenberg SH, Sham HL (2004b) Synthesis and activity of 1-aryl-1- imidazolyl methyl ethers as non-thiol farnesyltransferase inhibitors. Bioorg Med Chem Lett 14:5371-5376 (Pubitemid 39348930)
34. Li F, Cui J, Guo Le, Qian X, Ren W, Wang K, Liu F (2007) Molecular design, chemical synthesis and biological evaluation of '4-1' pentacyclic aryl/heteroaryl-imidazonaphthalimides. Bioorg Med Chem 15:5114-5121 (Pubitemid 46880380)
35. Lin N, Wang L, Wang X, Wang GT, Cohen J, Gu W, Zhang H, Rosenberg SH, Sham HL (2004) Synthesis and biological evaluation of 1-benzyl-5-(3-biphenyl-2- yl-propyl)-1H-imidazole as novel farnesyltransferase inhibitor. Bioorg Med Chem Lett 14:5057-5062 (Pubitemid 39233365)
36. Loksha YM, El-Barbary AA, El-Badawi MA, Nielsen C, Pedersen EB (2005) Synthesis of 2-(aminocarbonylmethylthio)-1H-imidazoles as novel Capravirine analogues. Bioorg Med Chem 13:4209-4220 (Pubitemid 40779390)
37. Mader M, Dios A, Shih C, Bonjouklian R, Li T, White W, Uralde BL, Sanchez-Martinez C, Prado M, Jaramillo C, Diego E, Cabrejas LMM, Dominguez C, Montero C, Shepherd T, Dally R, Toth JE, Chatterjee A, Pleite S, Blanco-Urgoiti J, Perez L, Barberis M, Lorite MJ, Jambrina E, Nevill CR, Lee PA, Schultz RC, Wolos JA, Li LC, Campbell RM, Anderson BD (2008) Imidazolyl benzimidazoles and imidazo[4, 5-b]pyridines as potent p38a MAP kinase inhibitors with excellent in vivo antiinflammatory properties. Bioorg Med Chem Lett 18:179-183
38. Mahbootri S, Sellmer A, Esayah A, Elz S, Uecker A, Bohmer F (2008) Inhibition of PDGFR tyrosine kinase activity by a series of novel N-(3-(4-(pyridin-3-yl)-1H-imidazol-2-ylamino)phenyl) amides-A SAR study on the bioisosterism of pyrimidine and imidazole. Eur J Med Chem 43:1444-1453 (Pubitemid 351885215)
39. Mano T, Stevens RW, Ando K, Nakao K, Okumura T, Sakakibara M, Okumura T, Tamura T, Miyamoto K (2003) Novel imidazole compounds as a new series of potent, orally active inhibitors of 5-lipoxygenase. Bioorg Med Chem 11:3879-3887 (Pubitemid 36970114)
40. Matsunagu N, Kaku T, Ojida A, Tanaka T (2004) C17, 20-lyase inhibitors. Part 2: Design, synthesis and structure-activity relationships of (2-naphthylmethyl)-1H-imidazoles as novel C17, 20-lyase inhibitors. Bioorg Med Chem 12:4313-4336 (Pubitemid 39055637)
41. Mayer G, Taberner PV (2002) Effects of the imidazoline ligands efaroxan and KU14R on blood glucose homeostasis in the mouse. Eur J Pharmacol 454:95-102 (Pubitemid 35284371)
42. McLay LM, Halley F, Souness JE, Mckenna J, Benning V, Birrell M, Burton B, Belvisi M, Collis A, Constan A, Foster M, Hele D, Jayyosi Z, Kelle M, Maslen C, Miller G, Ouldelhkim M, Page K, Phipps S, Pollock K, Porter B, Ratcliffe AJ, Redford EJ, Webber S, Slater B, Thybaud V, Wilsher N (2001) The discovery of RPR 200765A, a p38 MAP kinase inhibitor displaying a good oral anti-arthritic efficacy. Bioorg Med Chem 9:537-554 (Pubitemid 32244051)
43. Mor M, Bordi F, Silva C, Rivara S, Zuliani V, Vocondio F, Rivara M, Barocelli E, Bertoni S, Ballabeni V, Magnanini F, Impicciatore M, Plazzi PV (2004) Synthesis, biological activity, QSAR and QSPR study of 2-aminobenzimidazole derivatives as potent H3- antagonists. Bioorg Med Chem 12:663-674 (Pubitemid 38169256)
44. Moura KCG, Salomao K, Menna-Barreto RFS, Emery FS, Pinto MCFR, Pinto AV, Castro SL (2004) Studies on the trypanocidal activity of semi-synthetic pyran[b-4, 3]naphtho[1, 2-d]imidazoles from b-lapachone. Eur J Med Chem 39:639-645 (Pubitemid 38962500)
45. Na YJ, Baek HS, Ahn SM, Shin HJ, Chang I, Hwang JS (2007) [4-t- Butylphenyl]-N-(4-imidazol-1-yl phenyl)sulfonamide (ISCK03) inhibits SCF/c-kit signaling in 501mel human melanoma cells and abolishes melanin production in mice and brownish guinea pigs. Biochem Pharmacol 74:780-786 (Pubitemid 47087757)
46. Nagarapu L, Satyender A, Rajashaker B, Srinivas K, Rani PR, Radhika K, Subhashini G (2008) Synthesis and antimicrobial activity of novel C-linked imidazole glycoconjugates. Bioorg Med Chem Lett 18:1167-1171 (Pubitemid 351193006)
47. Nakamura T, Kakinuma H, Umemiya H, Amada H, Miyata N, Taniguchi K, Bando K, Sato M (2004) Imidazole derivatives as new potent and selective 20-HETE synthase inhibitors. Bioorg Med Chem Lett 14:333-336 (Pubitemid 38045117)
48. Nantermet PG, Barrow JC, Lindsley SR, Young M, Mao S, Carroll S, Bailey C, Bosserman M, Colussi D, McMasters DR, Vacca JP, Selnick HG (2004) Imidazole acetic acid TAFIa inhibitors: SAR studies centered around the basic P1 group. Bioorg Med Chem Lett 14:2141-2145 (Pubitemid 38481378)
49. Navidpour L, Shadnia H, Shafaroodi H, Amini M, Dehpour AR, Shafiee A (2007) Design, synthesis and biological evaluation of substituted 2-alkylthio-1, 5-diarylimidazoles as selective COX-2 inhibitors. Bioorg Med Chem 15:1976-1982 (Pubitemid 46176633)
50. Plummer CW, Finke PE, Mills SG, Wang J, Tong XL, Doss GA, Fong TM, Lao JZ, Schaffer M, Chen J, Shen C, Stribling DS, Shearman LP, Strack AM, Ploeg LHTV (2005) Synthesis and activity of 4,5-diarylimidazoles as human CB1 receptor inverse agonists. Bioorg Med Chem Lett 15:1441-1446 (Pubitemid 40269008)
51. Power EC, Ganellin CR, Benton DCH (2006) Partial structures of ketoconazole as modulators of the large conductance calciumactivated potassium channel (BKCa). Bioorg Med Chem Lett 16:887-890 (Pubitemid 43059845)
52. Rodrignez-argulles MC, Lopez-Silva EC, Sanmartin J, Pelagatti P, Zani F (2005) Copper complexes of imidazole-2-, pyrrole-2- and indol-3-carbaldehyde thiosemicarbazones: Inhibitory activity against fungi and bacteria. J Inorg Biochem 99:2231-2239 (Pubitemid 41562862)
53. Roman G, Riley JG, Vlahakis JZ, Kinobe RT, Brien JF, Nakatsu K, Szarek WA (2007) Heme oxygenase inhibition by 2-oxy-substituted 1-(1H-imidazol-1-yl)-4- phenylbutanes: Effect of halogen substitution in the phenyl ring. Bioorg Med Chem 15:3225-3234 (Pubitemid 46484332)
54. Saha AK, Liu L, Marichal P, Odds F (2000a) Novel antifungals based on 4-substituted imidazole: Solid-phase synthesis of substituted aryl sulfonamides towards optimization of in vitro activity. Bioorg Med Chem Lett 10:2735-2739
55. Saha AK, Liu L, Simoneaux RL, Kukla MJ, Marichal P, Odds F (2000b) Novel antifungals based on 4-substituted imidazole: A combinatorial chemistry approach to lead discovery and optimization. Bioorg Med Chem Lett 10:2175-2178
56. Sandbhor U, Pritchard R (2004) Antimelanomal activity of the copper (II) complexes of 1-substituted 5-amino-imidazole ligands against B16F10 mouse melanoma cells. Bioorg Med Chem Lett 14:2877-2882 (Pubitemid 38569755)
57. Scozzafava A, Supuran CT (2000) Carbonic anhydrase activators: Part 24. High affinity isozymes I, II and IV activators, derivatives of 4-(4-chlorophenylsulfonylureido-amino acyl) ethyl-1H-imidazole. Eur J Pharm Sci 10:29-41 (Pubitemid 30123142)
58. Sondhi SM, Singh N, Johar M, Kumar A (2005) Synthesis, antiinflammatory and analgesic activities evaluation of some mono, bi and tricyclic pyrimidine derivatives. Bioorg Med Chem 13:6158-6166 (Pubitemid 41400137)
59. Sorrenti V, Salerno L, Giacomo CD, Acquaviva R, Siracusa MA, Vanella A (2006) Imidazole derivatives as antioxidants and selective inhibitors of nNOS. Nitric Oxide 14:45-50 (Pubitemid 43063507)
60. Starcevic K, Kralj M, Ester K, Sabol I, Grce M, Pavelic K, Karminski-Zamola G (2007) Synthesis, antiviral and antitumor activity of 2-substituted-5-amidino-benzimidazoles. Bioorg Med Chem 15:4419-4426 (Pubitemid 46777296)
61. Tanitame A, Oyamada Y, Ofuji K, Fujimoto M, Suzuki K, Ueda T, Terauchi H, Kawasaki M, Nagai K, Wach M, Yamagishi J (2004) Synthesis and antibacterial activity of novel and potent DNA gyrase inhibitors with azole ring. Bioorg Med Chem 12:5515-5524 (Pubitemid 39304051)
62. Uchida K, Nishiyama Y, Tanaka T, Yamaguchi H (2003) In vitro activity of novel imidazole antifungal agent NND-502 against Malassezia species. Int J Antimicrob Agents 21:234-238 (Pubitemid 36299184)
63. Ujjinamatada RK, Baier A, Borowski P, Hosmane RS (2007) An analogue of AICAR with dual inhibitory activity against WNV and HCV NTPase/helicase: Synthesis and in vitro screening of 4-carbamoyl-5-(4, 6-diamino-2,5-dihydro-1, 3, 5-triazin-2-yl) imidazole-1-b-d-ribofuranoside. Bioorg Med Chem Lett 17: 2285-2288 (Pubitemid 46505262)
64. Venkatesan AM, Agarwal A, Abe T, Ushirogochi H, Yamamura I, Kumagai T, Petersen PJ, Weiss WJ, Lenoy E, Yang Y, Shales DM, Ryan JL, Mansour TS (2004) Novel imidazole substituted 6-methylidene-penems as broad-spectrum b-lactamase inhibitors. Bioorg Med Chem 12:5807-5817 (Pubitemid 39388180)
65. Venkatesan AM, Agarwal A, Abe T, Ushirogochi H, Santos OD, Mihira A, Takasaki T, Li Z, Francisco G, Lin YI, Peterson PJ, Yang Y, Weiss WJ, Shales DM, Mansour TS (2008) 5,5,6-Fused tricycles bearing imidazole and pyrazole 6-methylidene penems as broad-spectrum inhibitors of b-lactamases. Bioorg Med Chem 16:1890-1902 (Pubitemid 351226578)
66. Vlahakis JZ, Kinobe RT, Nakatsu K, Szarek WA, Crandall IE (2006) Anti-Plasmodium activity of imidazole-dioxolane compounds. Bioorg Med Chem Lett 16:2396-2406
67. Volke V, Wegener G, Bourin M, Vasar E (2003) Antidepressant- and anxiolytic-like effects of selective neuronal NOS inhibitor 1-(2- trifluoromethylphenyl)-imidazole in mice. Behav Brain Res 140:141-147 (Pubitemid 36313249)
68. Wang C, Wang Y, Di A, Magnuson MA, Ye H, Roe MW, Nelson DJ, Bell GI, Philison LH (2005) 5-Amino-imidazole carboxamide riboside acutely potentiates glucose-stimulated insulin secretion from mouse pancreatic islets by KATP channel-dependent and - independent pathways. Biochem Biophys Res Commun 330: 1073-1079
69. Zampieri D, Mamolo MG, Vio L, Banfti E, Scialino G, Fermeglia M, Ferrone M, Pricl S (2007) Synthesis, antifungal and antimycobacterial activities of new bis-imidazole derivatives and prediction of their binding to P45014DM by molecular docking and MM/PBSA method. Bioorg Med Chem 15:7444-7458 (Pubitemid 47554513)
70. Zampieri D, Mamolo MG, Laurini E, Scialino G, Banfti E, Vio L (2008) Antifungal and antimycobacterial activity of 1-(3,5- diaryl-4,5-dihydro-1H- pyrazol-4-yl)-1H-imidazole derivatives. Bioorg Med Chem 16:4516-4522 (Pubitemid 351545839)
71. Zhang N, Chen H, Sood R, Kalicharran K, Fattom AI, Naso RB, Barnard DL, Sidwell RW, Hosmane RS (2002) In vitro inhibition of the measles virus by novel ring-expanded ('fat') nucleoside analogues containing the imidazo[4,5-e][and] diazepine ring system. Bioorg Med Chem Lett 12:3391-3394 (Pubitemid 35292454)