European Journal of Chemistry 2011, 2(2), 243-250. doi:10.5155/eurjchem.2.2.243-250.257

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,*) , Khalid Ali Khan (2) , Abdullah Mohammad Asiri (3)

(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, Accepted: 04 Nov 2010, Published: 30 Jun 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.2_2_243_250_800


Keywords


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

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.2.2.243-250.257

Article Metrics


This Abstract was viewed 1030 times | PDF Article downloaded 428 times

Citations

/


[1]. 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
/


[2]. 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
/


[3]. 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
/


[4]. 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
/


[5]. 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
/


[6]. 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
/


[7]. 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
/


[8]. 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
/


[9]. 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
/


[10]. 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
/


[11]. 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  , , 2018
DOI: 10.1007/s42360-018-0073-4
/


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.


How to cite


Faidallah, H.; Khan, K.; Asiri, A. Eur. J. Chem. 2011, 2(2), 243-250. doi:10.5155/eurjchem.2.2.243-250.257
Faidallah, H.; Khan, K.; Asiri, A. 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(2), 243-250. doi:10.5155/eurjchem.2.2.243-250.257
Faidallah, H., Khan, K., & Asiri, A. (2011). 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. European Journal of Chemistry, 2(2), 243-250. doi:10.5155/eurjchem.2.2.243-250.257
Faidallah, Hassan, Khalid Ali Khan, & Abdullah Mohammad Asiri. "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." European Journal of Chemistry [Online], 2.2 (2011): 243-250. Web. 14 Nov. 2019
Faidallah, Hassan, Khan, Khalid, AND Asiri, Abdullah. "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" European Journal of Chemistry [Online], Volume 2 Number 2 (30 June 2011)

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

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2019  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 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.