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

PDF

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

This Abstract was viewed 2747 times |

Article PDF downloaded 1157 times

How to Cite

(1)

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.

Links for Article

Crossref - Scopus - Google - European PMC

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.

Supporting Agencies

Most read articles by the same author(s)

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

License Terms

License Terms

by-nc

Copyright © 2025 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).

Article Sidebar

Main Article Content

Abstract

Article Details

Downloads

Metrics