

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 (1,*)



(1) Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah-21589, Saudi Arabia
(2) Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah-21589, Saudi Arabia
(3) Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah-21589, Saudi Arabia
(*) Corresponding Author
Received: 19 Aug 2010 | Revised: 24 Feb 2011 | Accepted: 04 Nov 2010 | Published: 30 Jun 2011 | Issue Date: June 2011
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.
Announcements
Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.
1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).
2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).
3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).
Editor-in-Chief
European Journal of Chemistry
Keywords
Full Text:
PDF

DOI: 10.5155/eurjchem.2.2.243-250.257
Links for Article
| | | | | | |
| | | | | | |
| | | |
Related Articles
Article Metrics


Citations
[1]. Wanhe Wang, Zhen-Zhen Dong, Chao Yang, Guodong Li, Yam-Chi Tse, Chung-Hang Leung, Dik-Lung Ma
An iridium(III) complex-based chemosensor for the detection of thiourea in living cells
Sensors and Actuators B: Chemical 251, 374, 2017
DOI: 10.1016/j.snb.2017.05.100

[2]. Hassan M. Faidallah, Sherif A. F. Rostom, Khalid A. Khan, Salem A. Basaif
Synthesis and characterization of some hydroxypyridone derivatives and their evaluation as antimicrobial agents
Journal of Enzyme Inhibition and Medicinal Chemistry 28(5), 926, 2013
DOI: 10.3109/14756366.2012.694880

[3]. Monika Jangir, Ritika Pathak, Satyawati Sharma, Shilpi Sharma
Biocontrol mechanisms of Bacillus sp., isolated from tomato rhizosphere, against Fusarium oxysporum f. sp. lycopersici
Biological Control 123, 60, 2018
DOI: 10.1016/j.biocontrol.2018.04.018

[4]. Ahmed H. Moustafa, Hassan A. El-Sayed, Abd El-Fattah Z. Haikal, Rasha A. Abd El-Hady
Synthesis and Antimicrobial Activity of Some 2-Pyridone Nucleosides Containing a Sulfonamide Moiety
Nucleosides, Nucleotides and Nucleic Acids 32(5), 221, 2013
DOI: 10.1080/15257770.2013.775449

[5]. Ranjana Aggarwal, Swati Walia, Chinu Rani
Dehydroacetic Acid and Its Derivatives as Starting Synthons for Synthesis of Heterocyclic Compounds
HETEROCYCLES 94(7), 1197, 2017
DOI: 10.3987/REV-17-860

[6]. Galal H. Elgemeie, Rasha A. Azzam, Rasha E. Elsayed
Sulfa drug analogs: new classes of N-sulfonyl aminated azines and their biological and preclinical importance in medicinal chemistry (2000–2018)
Medicinal Chemistry Research 28(8), 1099, 2019
DOI: 10.1007/s00044-019-02378-6

[7]. Monika Jangir, Ritika Pathak, Abhishek Sharma, Shilpi Sharma, Satyawati Sharma
Volatiles as strong markers for antifungal activity against Fusarium oxysporum f. sp. lycopersici
Indian Phytopathology 72(4), 681, 2019
DOI: 10.1007/s42360-018-0073-4

[8]. Kamal Mohamed Dawood, Hussein Khalaf-Allah Abu-Deif
Synthesis and antimicrobial activity of some new 1,2-bis-[1,3-thiazolidin-3-yl]ethane derivatives
European Journal of Chemistry 4(3), 277, 2013
DOI: 10.5155/eurjchem.4.3.277-284.837

[9]. Samia M. Sayed, Mohamed A. Raslan, Kamal M. Dawood
Synthesis and Reactivity of Phenylthiourea Derivatives: An Efficient Synthesis of New Thiazole-Based Heterocycles
Journal of Heterocyclic Chemistry 53(2), 508, 2016
DOI: 10.1002/jhet.2327

[10]. Mohamed Ahmed Mahmoud Abdel Reheim, Ibrahim Saad Abdel Hafiz, Ahmed Adel Mohamed Sarhan, Hala Mohamed Reffat
Synthesis and Biological Studies of Some New Pyrazole, Dihydropyridinethione, Pyrimidine, Thiophene and 4H-Pyran Derivatives
HETEROCYCLES 102(2), 291, 2021
DOI: 10.3987/COM-20-14354

[11]. Jonnie N. Asegbeloyin, Oguejiofo T. Ujam, Chizoba M. Ngige, Valentine I. Onwukeme, Tania Groutso
Crystal structure ofN′-[(1E)-1-(6-methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ylidene)ethyl]benzenesulfonohydrazide
Acta Crystallographica Section E Structure Reports Online 70(11), o1179, 2014
DOI: 10.1107/S1600536814022648

[12]. Zainab Ngaini, Ainaa Nadiah Abd Halim, Ferlicia Rasin, Wan Sharifatun Handayani Wan Zullkiplee
Synthesis and structure–activity relationship studies of mono- and bis-thiourea derivatives featuring halogenated azo dyes with antimicrobial properties
Phosphorus, Sulfur, and Silicon and the Related Elements 197(9), 909, 2022
DOI: 10.1080/10426507.2022.2046577

[13]. O. T. Ujam, O. C. Ogbonna, A. Oliver, J. I. Ume, E. Janusson, C. C. Chime
Crystal structure of 4-hydroxy-6-methyl-3-[(1E)-1-(2-phenylhydrazinylidene)ethyl]-2H-pyran-2-one
Journal of Structural Chemistry 58(3), 636, 2017
DOI: 10.1134/S0022476617030325

[14]. Richa Sharma, Laurent Gal, Dominique Garmyn, V. S. Bisaria, Shilpi Sharma, Pascal Piveteau
Evidence of Biocontrol Activity of Bioinoculants Against a Human Pathogen, Listeria monocytogenes
Frontiers in Microbiology 11, , 2020
DOI: 10.3389/fmicb.2020.00350

[15]. Mohamed Ahmed Mahmoud Abdel Reheim, Ibrahim Saad Abdel Hafiz, Hend Saad Eldin Abdel Rady
Microwave assisted the short time clean synthesis of 1,3-diketones as building blocks in heterocyclic synthesis: a facile synthesis and antimicrobial evaluation of new dihydropyridine, 4H-pyrane, dihydropyridazine, pyrimidine and pyrazole derivatives
Molecular Diversity 26(2), 741, 2022
DOI: 10.1007/s11030-020-10152-9

[16]. Malliga R. Iyer, Pinaki Bhattacharjee, Biswajit Kundu, Nicholas Rutland, Casey M. Wood
One-Pot Synthesis of Thio-Augmented Sulfonylureas via a Modified Bunte’s Reaction
ACS Omega 7(35), 31612, 2022
DOI: 10.1021/acsomega.2c04816

[17]. Abbas Ali Esmaeili, Fariba Mesbah, Abbas Moradi, Amir Khojastehnezhad, Maryam Khalili
Straightforward and simple synthesis of novel pyranodipyrimidine derivatives via reaction of aromatic aldehydes and heterocyclic-1,3-dicarbonyl compound
Phosphorus, Sulfur, and Silicon and the Related Elements 196(9), 819, 2021
DOI: 10.1080/10426507.2021.1921775

References
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.
How to cite
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.2.2.243-250.257

















European Journal of Chemistry 2011, 2(2), 243-250 | doi: https://doi.org/10.5155/eurjchem.2.2.243-250.257 | Get rights and content
Refbacks
- There are currently no refbacks.
Copyright (c)
© Copyright 2010 - 2023 • Atlanta Publishing House LLC • All Right Reserved.
The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.
Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.