Synthesis and characterization of a novel series of benzenesulfonylurea and thiourea derivatives of 2H-pyran and 2H-pyridine-2-ones as antibacterial, antimycobacterial and antifungal agents

Hassan Mostafa Faidallah; Khalid Ali Khan; Abdullah Mohammad Asiri

doi:10.5155/eurjchem.2.2.243-250.257

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Published: Jun 30, 2011

DOI: https://doi.org/10.5155/eurjchem.2.2.243-250.257

Keywords:

2H-pyran-2-one hydrazones, 1-Amino-2H-pyridin-2-ones, Benzenesulfonylurea derivatives, Thiourea derivatives, Antimicrobial activity, Antimycobacterial activity

Section

Research Article

Issue

Vol. 2 No. 2 (2011): June 2011

Dates

Received 2010-08-19
Accepted 2010-11-04
Published 2011-06-30

Hassan Mostafa Faidallah

Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah-21589, Saudi Arabia

Khalid Ali Khan

Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah-21589, Saudi Arabia

Abdullah Mohammad Asiri

Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah-21589, Saudi Arabia

Abstract

Arylhydrazines reacted with dehydroacetic acid (1) to give the corresponding 2H-pyran-2-one hydrazones (2), which on treatment with hydrazine hydrate afforded the corresponding 1-amino-2H-pyridin-2-ones (3). Reaction of 3 with nitrous acid, aromatic aldehyde and substituted benzenesulfonyl chlorides yielded the corresponding 2H-pyridine-2-one derivatives. A series of urea and thiourea derivatives were also prepared. Some of these compounds have shown significant antibacterial and mild to moderate antimycobacterial and antifungal activities. 2_2_243_250_800

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Faidallah, H. M.; Khan, K. A.; Asiri, A. M. Synthesis and Characterization of a Novel Series of Benzenesulfonylurea and Thiourea Derivatives of 2H-Pyran and 2H-Pyridine-2-Ones As Antibacterial, Antimycobacterial and Antifungal Agents. Eur. J. Chem. 2011, 2, 243-250.

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References

[1]. Dickinson, J. M. Nat. Prod. Rep. 1993, 10(1), 71-98.
doi:10.1039/np9931000071
PMid:8451032

[2]. Douglas, C. J.; Sklenika, H. M.; Shen, H. C.; Mathias, D. S.; Degen, S. J.; Golding, G. M.; Morgan, C. D.; Shin, R. A.; Mueller, K. L.; Scurer, L. M.; Johnson, E. W.; Hsung, R. P. Tetrahedron 1999, 55, 13683-13696.
doi:10.1016/S0040-4020(99)00847-9

[3]. Hatch, M. S.; Brown, W. M.; Deck, J. A.; Hunsaker, L. A.; Deck, L. M.; Vander Jagt, D. L. B. B. A. -Protein Struct. M. 2002, 1596, 381-391.

[4]. Tuchinda, P.; Reutrakul, V.; Claeson, P.; Pongprayoon, U.; Sematong, T.; Santisuk, T.; Taylor, W. C. Phytochemistry 2002, 59, 169-173.
doi:10.1016/S0031-9422(01)00451-4

[5]. Rao, P. N. P.; Uddin, J.; Knaus, E. E. J. Med. Chem. 2004, 47, 3972-3990.
doi:10.1021/jm049939b
PMid:15267236

[6]. Fujimoto, H.; Okamoto, Y.; Sone, E.; Maeda, S.; Akiyama, K.; Ishibashi, M. Chem. Pharm. Bull. 2005, 53, 923-929.
doi:10.1248/cpb.53.923

[7]. Marrison, L. R.; Dickinson, J. M.; Fairlamb, I. J. S. Bioorg. Med. Chem. Lett. 2002, 12, 3509-3515.
doi:10.1016/S0960-894X(02)00824-7

[8]. Marrison, L. R.; Dickinson, J. M.; Fairlamb, I. J. S. Bioorg. Med. Chem. Lett. 2003, 13, 2667-2671.
doi:10.1016/S0960-894X(03)00546-8

[9]. De Clercq, E. J. Med. Chem. 1995, 38, 2491-2517.
doi:10.1021/jm00014a001
PMid:7543152

[10]. De Clercq, E. B. B. A. - Mol. Basis Dis. 2002, 1587, 258-275.

[11]. Fairlamb, I. J. S.; Marrison, L. R.; Dickinson, J. M.; Lu, F. J.; Schmidt, J. P. Bioorg. Med. Chem. 2004, 12, 4285-4299.
doi:10.1016/j.bmc.2004.01.051

[12]. McGlacken, G. P.; Fairlamb, I. J. S. Nat. Prod. Rep. 2005, 22, 369-385.
doi:10.1039/b416651p
PMid:16010346

[13]. Fossa, P.; Menozzi, G.; Dorigo, P.; Floreani, M.; Mosti, L. Bioorg. Med. Chem. 2003, 11, 4749-4759.
doi:10.1016/S0968-0896(03)00528-5

[14]. Krauze, A.; Vitolina, R.; Garaliene, V.; Sile, L.; Kluša, V.; Duburs, G. Eur. J. Med. Chem. 2005, 40, 1163-1167.
doi:10.1016/j.ejmech.2005.04.004
PMid:15927309

[15]. Ochoa, E.; Suarez, M.; Verdecia, Y.; Pita, B.; Martin, N.; Quinteiro, M.; Seoane, C.; Soto, J. L.; Duque, J.; Pomes, R. Tetrahedron 1998, 54, 12409-12420.
doi:10.1016/S0040-4020(98)00760-1

[16]. Parlow, J. J.; South, M. S. Tetrahedron 2003, 59, 7695-7701.
doi:10.1016/S0040-4020(03)01239-0

[17]. Abdel-Aziz, A. A.; El-Subbagh, H. I.; Kunieda, T. Bioorg. Med. Chem. 2005, 13, 4929-4935.
doi:10.1016/j.bmc.2005.05.027

[18]. Srivastava, B. K.; Solanki, M.; Mishra, B.; Soni, R.; Jayadev, S.; Valani, D.; Jain, M.; Patel, P. R. Bioorg. Med. Chem. 2007, 15, 1924-1929.
doi:10.1016/j.bmc.2006.09.034

[19]. Aanandhi, M. V.; George, S.; Vaidhyalingam, V. Arkivoc 2008, 11, 187-194.

[20]. Narayana, B. L.; Rao, A. R. R.; Rao, P. S. Eur. J. Med. Chem. 2009, 44, 1369-1376.
doi:10.1016/j.ejmech.2008.05.025
PMid:18603332

[21]. Ranft, D.; Seyfarth, T.; Schaper, K. J.; Lehwark-Yvetot, G.; Bruhn, C.; Buege, A. Arch. Pharm. Pharm. Med. Chem. 1999, 332, 427-430.
doi:10.1002/(SICI)1521-4184(199912)332:12<427::AID-ARDP427>3.0.CO;2-H

[22]. Khoshneviszadeh, M.; Edraki, N.; Javidnia, K.; Alborzi, A.; Pourabbas, B.; Mardaneh, J.; Miri, R. Bioorg. Med. Chem. 2009, 17, 1579-1586.
doi:10.1016/j.bmc.2008.12.070

[23]. Abid, M.; Kakul Husain, K.; Azam, A. Bioorg. Med. Chem. Lett. 2005, 15, 4375- 4379.
doi:10.1016/j.bmcl.2005.06.029

[24]. Goebel, T.; Ulmer, D.; Projahn, H.; Kloeckner, J.; Heller, E.; Glaser, M.; Ponte-Sucre, A.; Specht, S.; Sarite, S. R.; Hoerauf, A.; Kaiser, A.; Hauber, I.; Hauber, J.; Holzgrabe, U. J. Med. Chem. 2008, 51, 238-250.
doi:10.1021/jm070763y
PMid:18159921

[25]. Rodrigues, T.; Guedes, R. C.; dos Santos, D. J. V. A.; Carrasco, M.; Gut, J.; Rosenthal, P. J.; Moreira, R.; Lopes, F. Bioorg. Med. Chem. Lett. 2009, 19, 3476-3480.
doi:10.1016/j.bmcl.2009.05.017

[26]. Tiwari, A. K.; Mishra, A. K.; Bajpai, A.; Mishra, P.; Sharma, R. K.; Pandey, V. K.; Singh, V. K. Bioorg. Med. Chem. Lett. 2006, 16, 4581-4585.
doi:10.1016/j.bmcl.2006.06.015

[27]. Gudmundsson, K. S.; Johns, B. A.; Wang, Z.; Turner, E. M.; Allen, S. H.; Freeman, G. A.; Boyd, F. L. Jr.; Sexton, C. J.; Selleseth, D. W.; Moniri, K. R.; Creech, K. L. Bioorg. Med. Chem. 2005, 13, 5346-5361.
doi:10.1016/j.bmc.2005.05.043

[28]. Allen, S. H.; Johns, B. A.; Gudmundsson, K. S.; Freeman, G. A.; Boyd, F. L. Jr.; Sexton, C. H.; Selleseth, D. W.; Creech, K. L.; Moniri, K. R. Bioorg. Med. Chem. 2006, 14, 944-954.
doi:10.1016/j.bmc.2005.09.015

[29]. Croitoru, M.; Pintilie, L.; Tanase, C.; Caproiu, M. T.; Draghici, C. Rev. Chem. -Bucharest 2004, 55(12), 993-997.

[30]. Limban, C.; Misisir, A.; Chirita, I.; Ilie, C.; Caproiu, M. T. Rev. Chem. -Bucharest 2008, 59(10), 1136-1139.

[31]. Limban, C.; Misisir, A.; Chirita, I.; Niculescu, G. M.; Ilie, C.; Caproiu, M. T. Rev. Chem. -Bucharest 2008, 59(11), 1245-1249.

[32]. Limban, C.; Misisir, A.; Chirita, I.; Niculescu, G. M.; Ilie, C.; Caproiu, M. T. Rev. Chem. -Bucharest 2009, 60(7), 657-661.

[33]. Morusceag, L.; Misisir, A.; Ilie, C.; Guta, R.; Andreescu, D. N.; Caproiu, M. T. Rev. Chem. -Bucharest 2009, 60(8), 805-809.

[34]. Dogruer, D. S.; Urlu, S.; Onkol, T.; Ozcelik, B.; Sahin, M. F. Turk. J. Chem. 2010, 34, 57-65.

[35]. Conte, J. E.; Barriere, S. L. Manual of Antibiotics and Infectious Disease. 1st ed., Lea and Febiger, USA, 1988, 135-38.

[36]. Mamolo, M. G.; Vio, L. Il Farmaco 1992, 47, 1055-1066.
PMid:1445613

[37]. Ait-Baziz, N.; Rachedi, Y.; Silva, A. M. S. Arkivoc 2010, 10, 86-97.

[38]. Akhrem, A. A.; Moiseenkov, A. M.; Lakhvich, F.A. Smul’Skii, S. P. Izy. Akad. N. SSR Ser.1971, 5, 1098-1100.

[39]. Habart, M. H.; Pene, C.; Royer, R. Chim. Ther. 1973, 8, 314-318.

[40]. Cantos, A.; De March, P.; Manas, M. M.; Pla, A.; Ferrando, F. S.; Vergili, A. Bull. Chem. Soc. Japan. 1987, 60, 4425-4431.
doi:10.1246/bcsj.60.4425

[41]. Susnik, I.; Furak, J. V.; Durakovic, S.; Kopuvanoc, S.; Lasniger, J. Monatsch. Chem. 1992, 123, 817-822.
doi:10.1007/BF00812331

[42]. Bendaas, A.; Hamdi, M.; Sellier, N. J. Heterocylic Chem. 1999, 36, 1291-1294.
doi:10.1002/jhet.5570360529

[43]. Djerrari, B.; Essasi, E.; Fifani, J. Bull. Soc. Chim. France 1991, 128, 521-524.

[44]. Perkin, Jr., W. H.; Bernhart, C. Ber. 1884, 17, 1522-1527.

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