Synthesis and bioactivity of some new 1-tolyl-3-aryl-4-methylimidazole-2- thiones

Medicinal Chemistry Research

Volumn 16, Issue 3, 2007, Pages 143-154

  Saeed, Aamer ^a   Batool, Mahira ^a  

^a QUAID I AZAM UNIVERSITY   (Pakistan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; BROMINE; THIONINE; THIOUREA;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; FRAGMENTATION REACTION; INSECTICIDAL ACTIVITY; MASS FRAGMENTOGRAPHY; NONHUMAN; POLYMERIZATION; SPECTROSCOPY;

EID: 38949142306     PISSN: 10542523     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00044-007-9017-8     Document Type: Article

References (29)

1. Al-Masoudi AI, Khodair AI, Al-Soud YA, Al-Masoudi NA (2003) Synthesis of N-Substituted 1-Amino-2,3-dihydro-1H-imidazole-2-thione-N-nucleosides and S-Glycosylated Derivatives, Nucleosides. Nucleotides and Nucleic Acids 22:299-307
2. 2. J. Am. Chem. Soc. 124:45388-45389
3. Arduengo AJ, Moran JR, Rodriguez-Parada J, Ward MD (1990) Molecular control of self-assembled monolayer films of imidazole-2-thiones: adsorption and reactivity, J. Am. Chem. Soc. 112:6153-6154
4. Atta-ur-Rahman, Choudhary MI, Thomsen J (2001) In Bioassay Techniques for Drug Development, Harwood Academic Publishers, The Netherlands, pp.16, 22, 67
5. Chow K, Heidelbaugh T, Gil D, Garst M, Micheal LA, Nguyen PX, Gomex DG (2003) Preparation of 4-substitued imidazole-2-thiones and imidazol-2-ones as agonists of alpha-2B and alpha -2C adrenergic receptors, PCT Int. Appl.WO 03 99,795 (2002). Chem. Abstr. 140:5050k
6. Dage RC, Schnettler RA (1989) Reducing reperfusion injury with imidazole-2-thiones, Eur.Pat. Appl.EP 284,925 (1987). Chem. Abstr. 110:88630d
7. Doerge DR, Decker CJ, Takazawall RS (1993) Chemical and enzymic oxidation of benzimidazoline-2-thiones: a dichotomy in the mechanism of peroxides inhibition Biochemistry 32:58-65
8. Du Mont W-W, Mugesh G, Wismach C, Jones PG (2001) Reactions of Organo-selenenyl Iodides with Thiouracil Drugs: An Enzyme Mimetic Study on the Inhibition of Iodothyronine Deiodinase, Angew. Chem., Int. Ed. 40:2486-2489
9. Engler H, Taurog A, Nakashima T (1982) Mechanism of inactivation of thyroid peroxidase by thioureylene drugs. Biochem. Pharmacol. 31:3801-3806
10. Fuentes J, Angulo M, Pradera MA (2002) Fluoronucleosides, Isothiocyanato C Nucleosides, and Thioureylene Di-C-nucleosides via Cyclic Sulfates. J. Org. Chem. 67:2577-2587
11. Gasch C, Pradera MA, Salameh BAB, Molina JL, Fuentes J (2000) Chiral thioxohydroimidazoles with two sugar moieties. N-, C-, and spironucleosides Tetrahedron Asymmetry 11:435-452
12. Harris NV, Smith C, Ashton MJ, Bridge W, Bush RC, Coffee ECJ, Dron DI, Harper MF, Lythgoe DJ, Newton CG, Riddell D (1992) Acyl-CoA:cholesterol O-Acyl Transferase (ACAT) Inhibitors. 1. 2-(Alkylthio)-4,5-diphenyl-1H-imidazoles as Potent Inhibitors of ACAT J. Med. Chem. 35:4384-3492
13. Kruse LI, Kaiser C, DeWolf WE, Walter E, Finkelstein JA, Frazee JS, James S, Hilbert EL, Ross ST, Stephen T, Flaim KE, Sawyer JL (1990) Substrate inhibitors of dopamine-β-hydrolase. 4. Structure activity relationships at the copper binding site. J. Med. Chem. 33:781-789
14. Kruse HP, Matthias Heydenreich M, Engst W, Schilde W, Krolla J (2005) The identification of 1,3-oxazolidine-2-thiones and 1,3-thiazolidine-2-thiones from the reaction of glucose with benzyl isothiocyanate, Carbohyd. Res. 340:203-210
15. Lagoja IM, Pannecouque C, Aerschot AV, Myriam W, Debyser Z, Alzarini JB, Herdewijin P, Clercq ED (2003) N-Aminoimidazole Derivatives Inhibiting Retroviral Replication via a Yet Unidentified Mode of Action, J. Med. Chem. 46:1546-1553
16. Loksha YM, El-Badawi MA, El-Barbary AA, Pedersen EB, Nielsen C (2003) Synthesis of 2-methylsulfanyl-1H-imidazoles as novel non-nucleoside reverse transcriptase inhibitors (NNRTIs), Arch. Pharm. 336:175-180
17. Matsuda K, Yanagisawa I, Isomura Y, Mase T, Shibanuma T (1997) One-Pot Preparation of 1-Substituted Imidazole-2-thione from Isothiocyanate and Amino Acetal, Synth. Commun 27:3565-3569
18. Mukkamala R (2003) Lubricating oil anticorrosion-antiwear additives consisting of alkylated imidazolidinethiones and zinc diththiophosphates, U.S. Pat. Appl. Publ. US 2002 198,115 (2002). Chem. Abstr. 138:58652y
19. Ren J, Nichols C, Bird LE, Fujiwara T, Sugimoto H, Stuart DI, Stammers DK (2000) Binding of the second generation non-nucleoside inhibitor S-1153 to HIV-1 reverse transcriptase involves extensive main chain hydrogen bonding. J. Biol. Chem. 275:14316-14320
20. Ross ST, Kruse LI, Ohlstein EH, Erickson R, Ezekiel RW, Flaim M, Sawyer KE, Berkowitzi BA (1987) Inhibitors of dopamine beta-hydroxylase. Some 1-(pyridylmethyl)imidazole-2-thiones. J. Med. Chem. 30:1309-1313
21. Saeed A, Florke U (2006) 1-(2-Chlorophenyl)-3-(4-methylbenzoyl)thiourea, Acta Cryst. E.62:2403-2405
22. Saeed A, Parvez M (2005) The Crystal Structure of 1-(4-Chlorophenyl)-3- (4-methyl benzoyl) thiourea. Cent. Eur. J. Chem. 3: 780-791
23. Schantl JG, Lagoja IM (1997) Direct Synthetic Approach to N-substitued 1-Amino-2,4-dihydro-1H-imidazole-2-thiones, Heterocycles 45:691-700
24. Schnettler RA, Dage RC, Grisar JM, Palpoloi FP (1990) Reducing reperfusion injury with 1,3-dihydro-4-methyl-5-[4-(methylthio)benzoyl]-2H- imdazole-2-thione, U.S. US 4,868,187 (1989). Chem. Abstr. 112:70022p
25. Smith RC, Gore JZ (1990) 2-Imidazolethiones Protect Ascorbic Acid From Oxidation Induced by Copper, Biochim. Biophys. Acta. 1034:263-267
26. Wang X-C, Wang F, Quan Z-J, Wang M-G, Z Li (2005) An efficient and clean synthesis of 1-aroyl-3-aryl-4-substituted imidazole-2-thiones in water. J. Chem. Res. 61:689-690
27. Xu J, Yadan J-C (1995) A new and convenient synthesis of imidazol-2-thiones from imidazoles, Synlett. 239-241
28. Xue J, Yadan JC (1995) Synthesis of L-(+)-Ergothioneine, J. Org. Chem. 60:6296-6301
29. Zeng RS, Zou J-P, Zhi S-J, Chen J, Shen Q (2003) Novel Synthesis of 1-Aroyl-3-aryl-4-substituted Imidazole-2-thiones. Organic Lett. 61:1657-1659