[KSCI] Korea Science Citation Index Service

http://dx.doi.org/10.5012/bkcs.2004.25.7.991

Synthesis of Certain 6-(Arylthio)uracils and Related Derivatives as Potential Antiviral Agents

El-Emam, Ali A. (Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University)
Massoud, Mohamed A.M. (Departments of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, University of Mansoura)
El-Bendary, Eman R. (Departments of Meducinal Chemistry, Faculty of Pharmacy, University of Mansoura)
El-Sayed, Magda A. (Departments of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, University of Mansoura)

Publication Information

Bulletin of the Korean Chemical Society / v.25, no.7, 2004 , pp. 991-996 More about this Journal

Abstract

New series of 6-(arylthio)uracils, 6-(4-substituted-1-piperazinyl)uracils, 2,4,5-trioxo-1H,3H-benzothiopyrano[2,3-d]pyrimidine and 5-aryl-2,4-dioxo-1H,3H-pyrimido[5,4-f]benzo[1,4]thiazepines have been prepared and screened for their in vitro activity against herpes simplex-1 virus (HSV-1) and human immunodeficiency virus-1 (HIV-1). The in vitro cytotoxic activity was also evaluated. The results of biological testing revealed that compound 5b showed marginal activity against HSV-1, while compounds 5b and 5f exhibited marginal activity against HIV-1. The rest of the tested compounds were found devoid of antiviral activity against both HSV-1 and HIV-1.

Keywords

Substituted uracils; Benzothiopyrano[2,3-d]pyrimidine; Pyrimido[5,4-f]benzo[1,4]thiazepines; Antiviral activity; Cytotoxicity;

Citations & Related Records

Times Cited By Web Of Science : 5 (Related Records In Web of Science)
Times Cited By SCOPUS : 5

Reference
Cited By SCOPUS

1	Choo, H.; Chong, Y.; Choi, Y.; Mathew, J.; Schinazi, R. F.; Chu, C. K. J. Med. Chem. 2003, 46, 389. DOI ScienceOn
2	Balzarini, J.; Pannecouque, C.; De Clercq, E.; Aquaro, S.; Perno, C.-F.; Egberink, H.; Holy, A. Antimicrob. Agents Chemother. 2002, 46, 2185. DOI
3	Miyasaka, T.; Tanaka, H.; Baba, M.; Miyakawa, H.; Walker, R. T.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1989, 32, 2507. DOI
4	Klunder, J. M.; Hargrave, K. D.; West, M.; Cullen, E.; Pal, K.; Behnke, M.; Kapadia, S. R.; McNeil, D. W.; Wu, J. C.; Chow, G. C.; Adams, J. J. Med. Chem. 1992, 35, 1887. DOI
5	Maruenda, H.; Johnson, F. J. Med. Chem. 1995, 38, 2145. DOI ScienceOn
6	Rontikis, R.; Benhida, R.; Aubertin, A.-M.; Greirson, D. S.; Monneret, C. J. Med. Chem. 1996, 39, 2427. DOI ScienceOn
7	Glynn, S. L.; Yazdanian, M. J. Pharm. Sci. 1998, 87, 306. DOI ScienceOn
8	Mai, A.; Sbardella, G.; Artico, M.; Ragno, R.; Massa, S.; Novellino, E.; Greco, G.; Lavecchia, A.; Musiu, C.; La Colla, M.; Murgioni, C.; La Colla, P.; Loddo, R. J. Med. Chem. 2001, 44, 2544. DOI ScienceOn
9	Tanaka, H.; Takashima, H.; Ubasawa, M.; Sekiya, K.; Inouye, N.; Baba, M.; Shigeta, S.; Walker, R. T.; De Clercq, E.; Miyasaka, T. J. Med. Chem. 1995, 38, 2860. DOI ScienceOn
10	Heinisch, G.; Huber, E.; Matuszczak, B.; Maurer, A.; Prillinger, U. Arch. Pharm. 1997, 330, 29. DOI ScienceOn
11	Mitsuya, H.; Weinhold, K. J.; Furman, P. A.; St. Clair, M. H.; Nusinoff-Lehrman, S.; Gallo, R. C.; Bolognesi, D. P.; Barry, D. W.; Broder, S. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 7096. DOI ScienceOn
12	Tantillo, C.; Ding, J.; Jacobo-Molina, A.; Nanni, R. G.; Boyer, P. L.; Hughes, S. H.; Pauwels, R.; Andries, K.; Janssen, P. A. J.; Arnold, E. J. Mol. Biol. 1994, 243, 369. DOI ScienceOn
13	El-Emam, A. A.; Nasr, M N.; Pedersen, E. B.; Fouad, T.; Nielsen, C. Phosphorus, Sulfur & Silicone and Rel. Elements 2001, 174, 25. DOI ScienceOn
14	Pedersen, O. S.; Pedersen, E. B. Antiviral Chem. Chemother. 1999, 10, 285.
15	Barth, B.; Dierich, G.; Heinisch, G.; Jenny, V.; Matuszczak, B.; Mereiter, K.; Planer, R.; Schoepf, I.; Stoiber, H.; Traugott, T.; Aufschnaiter, P. V. Antimicrob. Agents Chemother. 1996, 7, 300.
16	El-Emam, A. A.; Pedersen, E. B.; Jacobsen, J. P.; Nielsen, C. Bull. Soc. Chim. France 1993, 130, 817.
17	Cresswell, M.; Wood, H. C. S. J. Chem. Soc. 1960, 4768. DOI
18	Zahran, M. A.; Abdel-Megeid, A. E.-S.; Abdel-Rahman, A. A.; El-Emam, A. A.; Pedersen, E. B.; Nielsen, C. Heterocycles 1995, 41, 2507. DOI
19	Hufford, C. D.; Badria, F. A.; Abou-Karam, M.; Shier, W. T.; Rogers, R. D. J. Nat. Prod. 1991, 54, 1543. DOI
20	Kelly, T. A.; Proudfoot, J. R.; McNeil, D. W.; Patel, U. R.; David, E.; Hargrave, K. D.; Grob, P. M.; Cardozo, M.; Agarwal, A.; Adams, J. J. Med. Chem. 1995, 38, 4839. DOI
21	Yarchoan, R.; Mitsuya, H.; Thomas, R. V.; Pluda, J. M.; Hartman, N. R.; Perno, C.-F.; Marczyk, K. S.; Allain, J.-P.; Johns, D. G.; Broder, S. Science 1989, 245, 412. DOI ScienceOn
22	Cywin, C. L.; Klunder, J. M.; Hoermann, M.; Brickwood, J. R.; David, E.; Grob, P. M.; Schwartz, R.; Pauletti, D.; Barringer, K. J.; Shih, C.-K.; Sorge, C. L.; Erickson, D. A.; Joseph, D. P.; Hattox, S. E. J. Med. Chem. 1998, 41, 2972. DOI ScienceOn
23	Davoll, J.; Evans, D. D. J. Chem. Soc. 1960, 5041. DOI
24	Weinslow, O. S.; Kiser, O. S.; Fine, D.; Bader, J.; Shoemaker, R. H.; Boyd, M. R. J. Natl. Cancer Inst. 1989, 81, 577. DOI
25	Hiramitsu, T.; Maki, Y. Synth. Commun. 1977, 177.
26	Larsen, E.; Daniel, K.; Vaaben, G. B.; El-Emam, A. A.; Pedersen, E. B.; Nielsen, C. Acta Chem. Scand. 1996, 50, 417. DOI
27	Abou-Karam, M.; Shier, W. T. J. Nat. Prod. 1990, 53, 340. DOI
28	Danel, K.; Larsen, E.; Pedersen, E. B.; Vestergaard, B. F.; Nielsen, C. J. Med. Chem. 1997, 40, 1845. DOI ScienceOn
29	Klunder, J. M.; Hoermann, M.; Cywin, C. L.; David, E.; Brickwood, J. R.; Schwartz, R.; Barringer, K. J.; Pauletti, D.; Shih, C.-K.; Erickson, D. A.; Sorge, C. L.; Joseph, D. P.; Hattox, S. E.; Adams, J.; Grob, P. M. J. Med. Chem. 1998, 41, 2960. DOI ScienceOn
30	Romero, D. L.; Olmsted, R. A.; Poel, T. J.; Morge, R. A.; Biles, C.; Keiser, B. J.; Kopta, L. A.; Friis, J. M.; Hosley, J. D.; Stefanski, K. J.; Wishka, D. G.; Evans, D. B.; Morris, J.; Stehle, R. G.; Sharma, S. K.; Yagi, Y.; Voorman, R. L.; Adam, W. J.; Tarpley, W. G.; Thomas, R. C. J. Med. Chem. 1996, 39, 3769. DOI ScienceOn
31	Ishikawa, I.; Ito, T.; Melik-Ohanjanian, R. G.; Takayanagi, H.; Mizuno, Y.; Ogura, H.; Kawahara, N. Heterocycles 1990, 31, 1641. DOI
32	Nugent, R. A.; Schlachter, S. T.; Murphy, M. J.; Cleek, G. J.; Poel, T. J.; Wishka, D. R.; Yagi, Y.; Keiser, B. J.; Olmsted, R. A.; Kopta, L. A.; Swaney, S. M.; Poppe, S. M.; Morris, J.; Tarpley, G.; Thomas, R. C. J. Med. Chem. 1998, 41, 3793. DOI ScienceOn
33	Proudfoot, J. R.; Hargrave, K. D.; Kapadia, S. R.; Patel, U. R.; Grozinger, K. G.; McNeil, D. W.; Cullen, E.; Cardozo, M.; Tong, L.; Rose, J.; David, E.; Mauldin, S. C.; Fuchs, V. U.; Vitous, J.; Hoermann, M.; Klunder, J. M.; Raghaven, P.; Skiles, J. W.; Mui, P.; Richman, D. D.; Sulivan, J. L.; Shih, C.-K.; Grob, P. M.; Adams, J. J. Med. Chem. 1995, 38, 4830. DOI
34	Kelly, T. A.; McNeil, D. W.; Rose, J. M.; David, E.; Shih, C.-K.; Grob, P. M. J. Med. Chem. 1997, 40, 2430. DOI ScienceOn
35	Romero, D. L.; Morge, R. A.; Biles, C.; Berrios-Pena, N.; May, P. D.; Palmer, J. R.; Johnson, P. D.; Smith, H. W.; Busso, M.; Tan, C.-K.; Voorman, R. L.; Reusser, F.; Althaus, I. W.; So, A. G.; Resnick, L.; Tarpley, W. G.; Aristoff, P. A. J. Med. Chem. 1994, 37, 999. DOI

11	Nadia G. Haress. (2014) Acta Crystallographica Section E Structure Reports Online )-dione / 70 (11) , o1144
2	Fatmah A. M. Al-Omary. (2014) Acta Crystallographica Section E Structure Reports Online )-dione / 70 (2) , o179
3	Fatmah A. M. Al-Omary. (2014) Acta Crystallographica Section E Structure Reports Online 4-(2-Methoxyphenyl)piperazin-1-ium 6-chloro-5-isopropyl-2,4-dioxopyrimidin-1-ide / 70 (3) , o245
7	Nadia G. Haress. (2014) Acta Crystallographica Section E Structure Reports Online )-dione / 70 (7) , o768
1	(2017) Chemistry Central Journal One pot synthesis, antimicrobial and antioxidant activities of fused uracils: pyrimidodiazepines, lumazines, triazolouracil and xanthines / 11 (1)
6	(2011) Molecules Synthesis and Antimicrobial Activity of Some Novel 5-Alkyl-6-Substituted Uracils and Related Derivatives / 16 (6) , 4764
6	(2004) Heterocyclic communications EFFICIENT SYNTHESIS OF NOVEL 6-PHENYLTHIO-2,4- DISUBSTITUTED PYRIMIDINES / 14 (6) , None
2	(2018) HETEROCYCLES Synthesis of 6,7-Dihydro-5H-thiopyrano[2,3-d]pyrimidin-5-one Derivatives Starting with 4,6-Dichloro-2-(methylsulfanyl)pyrimidine / 96 (2) , 287
6	(2004) 대한화학회지 담배조직을 이용한 바이오센서의 과산화수소 환원 최적 산도 / 48 (6) , 654
2	Ali A. El-Emam. (2004) Chem Inform Synthesis of Certain 6-(Arylthio)uracils and Related Derivatives as Potential Antiviral Agents. / 36 (2) , None
10	Mohamed A. Al-Omar. (2004) Synthetic communications Some Observations on the Base-Catalyzed Cyclocondensation of 2,6-Dihalobenzaldehydes, Ethyl Cyanoacetate, and Thiourea / 40 (10) , 1530
6	Khairy A.M. El-Bayouki. (2011) Journal of sulfur chemistry Synthesis, reactions, and biological activity of 1,4-thiazepines and their fused aryl and heteroaryl derivatives: a review / 32 (6) , 623
9	Ebtehal S. Al-Abdullah. (2011) European journal of medicinal chemistry Synthesis of novel 6-phenyl-2,4-disubstituted pyrimidine-5-carbonitriles as potential antimicrobial agents / 46 (9) , 4642
6	(2004) Heterocyclic communications Pyrimidine-5-carbonitriles - part III: synthesis and antimicrobial activity of novel 6-(2-substituted propyl)-2,4-disubstituted pyrimidine-5-carbonitriles / 19 (6) , None
6	(2004) Heterocyclic communications Pyrimidine-5-carbonitriles - part III: synthesis and antimicrobial activity of novel 6-(2-substituted propyl)-2,4-disubstituted pyrimidine-5-carbonitriles / 19 (6) , None
6	(2004) Journal of porphyrins and phthalocyanines Synthesis, antiviral, cytotoxicity and antitumor evaluations of A<SUB>4</SUB> type of porphyrin derivatives / 19 (6) , 753
None	Mirsada Salihović. (2004) Journal of molecular structure Synthesis, structural, conformational and DFT studies of N-3 and O-4 alkylated regioisomers of 5-(hydroxypropyl)pyrimidine / 1091 (None) , 170
3	(2004) ACS omega 6-(Ar)Alkylamino-Substituted Uracil Derivatives: Lipid Mimetics with Potent Activity at the Orphan G Protein-Coupled Receptor 84 (GPR84) / 3 (3) , 3365
3	(2004) Letters in drug design & discovery Cytotoxicity and Molecular Targeting Study of Novel 2-Chloro-3- substituted Quinoline Derivatives as Antitumor Agents / 16 (3) , 273
11	(2020) Asian journal of chemistry Synthesis of Diverse Fused Tetracyclic Thiazepine-Chalcone Derivatives by Claisen-Schmidt Condensation Reaction and their Antimicrobial Activity / 32 (11) , 2860
None	(2021) Bioorganic & medicinal chemistry letters Dioxotriazine derivatives as a new class of P2X<SUB>3</SUB> receptor antagonists: Identification of a lead and initial SAR studies / 37 (None) , 127833

1	/ Synthetic Communications
2	/ Tetrahedron Letters
3	/ Molecules
4	/ European Journal of Medicinal Chemistry