European Journal of Chemistry

Synthesis and antimicrobial activities of some novel bis-pyrazole derivatives containing a hydrophosphoryl unit



Main Article Content

Salah Abdel-Ghaffar Abdel-Aziz
Tarik El-Sayed Ali
Kamilia Mohamed El-Mahdy
Somaia Mohamed Abdel-Karim

Abstract

Vilsmeier-Haack reaction conditions were applied on some methyl ketone aryl phosphonicdihydrazones to yield some interesting bis-pyrazole derivatives containing a hydro-phosphoryl unit. Bis-{4-formyl-3-aryl-1H-pyrazol-1-yl}phosphine oxides (4a,b) were condensed with some nucleophiles such as aniline, phenacyltriphenylphosphonium bromide and 4-phenylthiosemicarbazide followed by treatment with thioglycolic acid, diethyl phosphite and/or acetic anhydride to yield a novel class of bis-pyrazoles containing sulfur and phosphorus derivatives. Most of the newly synthesized compounds were evaluated for their in vitro antimicrobial activities.

2_1_25_35_800


icon graph This Abstract was viewed 2614 times | icon graph Article PDF downloaded 1022 times

How to Cite
(1)
Abdel-Aziz, S. A.-G.; Ali, T. E.-S.; El-Mahdy, K. M.; Abdel-Karim, S. M. Synthesis and Antimicrobial Activities of Some Novel Bis-Pyrazole Derivatives Containing a Hydrophosphoryl Unit. Eur. J. Chem. 2011, 2, 25-35.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Mitchell, R. E.; Greenwood, D. R.; Sarojini, V. Phytochemistry 2008, 69, 2704-2707.
doi:10.1016/j.phytochem.2008.08.013
PMid:18834606

[2]. Abdel-Hafez, E. M. N.; Abuo-Rahma, G. A. A.; Abdel-Aziz, M.; Radwan, M. F.; Farag, H. H. Bioorg. Med. Chem. 2009, 17, 3829-3837.
doi:10.1016/j.bmc.2009.04.037

[3]. Ali, T. E. Eur. J. Med. Chem. 2009, 44, 4385-4392.
doi:10.1016/j.ejmech.2009.06.022
PMid:19615792

[4]. Rai, N. S.; Kalluraya, B.; Lingappa, B.; Shenoy, S.; Puranic, V. G. Eur. J. Med. Chem. 2008, 43, 1715-1720.
doi:10.1016/j.ejmech.2007.08.002
PMid:17923171

[5]. Witschel, M. Bioorg. Med. Chem. 2009, 17, 4221-4229.
doi:10.1016/j.bmc.2008.11.006

[6]. Lahm, G. P.; Stevenson, T. M.; Selby, T. P.; Freudenberger, J. H.; Cordova, D.; Flexner, L.; Bellin, C. A.; Dubas, C. M.; Smith, B. K.; Hughes, K. A.; Hollingshaus, J. G.; Clark, C. E.; Benner, E. A. Bioorg. Med. Chem. Lett. 2007, 17, 6274-6279.
doi:10.1016/j.bmcl.2007.09.012

[7]. Kopp, M.; Lancelot, J. C.; Dallemagne, P.; Rault, S. J. Heterocycl. Chem. 2001, 38, 1045-1050.
doi:10.1002/jhet.5570380506

[8]. Colliot, F.; Kukorowski, K. A.; Hawkins, D. W.; Roberts, D. A. Brighton Crop Prot. Conf. Pests Dis. 1992, 1, 29-34.

[9]. Miura, Y.; Ohnishi, M.; Mabuchi, T.; Yanai, I. Brighton Crop Prot. Conf. Weeds 1993, 1, 35-41.

[10]. Konotsune, T.; Kawakubo, K.; Honma, T. Jap. Pat. 1980, 8035035; Chem. Abstr. 1980, 93, 20750.

[11]. Sengupta, S. K.; Pandey, O. P.; Rao, G. P.; Dwivedi, A.; Singh, P. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 839-849.
doi:10.1080/10426500307813

[12]. Sengupta, S. K.; Pandey, O. P.; Rao, G. P.; Singh, P. Metal-Based Drugs 2002, 8, 293-302.
doi:10.1155/MBD.2002.293
PMid:18476009 PMCid:2365282

[13]. Ali, T. E.; Abdel-Rahman, R. M.; Hanafy, F. I.; El-Edfawy, S. M. Phosphorus, Sulfur Silicon Relat. Elem. 2008, 183, 2565-2577.
doi:10.1080/10426500801967864

[14]. Pareek, S.; Vyas, S.; Seth, G.; Vyas, P. C. Heteroatom Chem. 2009, 20, 246-249.
doi:10.1002/hc.20533

[15]. Ali, T. E. Eur. J. Med. Chem. 2009, 44, 4539-4546.
doi:10.1016/j.ejmech.2009.06.022
PMid:19615792

[16]. Fest, C.; Schmidt, K. J. Chemistry of Organophosphorus Compounds; Springer-Verlag: Berlin, 1973.

[17]. Troev, K. D. Chemistry and Applications of H-phosphonate; Elsevier, Amsterdam, 2006, pp. 253-261.
doi:10.1016/B978-044452737-0/50006-5

[18]. Katcyuba, S. A.; Monakhova, N. I.; Ashrafullina, L. K.; Shagidulin, R. R. J. Mol. Struct. 1992, 269, 1-21.
doi:10.1016/0022-2860(92)80001-X

[19]. Shagidulin, R. R.; Ashrafullina, L. K.; Monakhova, N. I.; Katcyuba, S. A. Russ. J. Gen. Chem.1997, 67, 567-578.

[20]. Ali, T. E. Arkivoc 2008, 2, 71-79.

[21]. Ali, T. E.; Halacheva, S. S. Heteroatom Chem. 2009, 20, 117-122.
doi:10.1002/hc.20520

[22]. Ali, T. E. Phosphorus, Sulfur Silicon and Relat. Elem. 2010, 185, 88-96.
doi:10.1080/10426500802713309

[23]. Shukla, J. S.; Zaidi, Mohd. G. H. Asian J. Chem. 1993, 5, 253-258.

[24]. Corbridge, D. E. C. Phosphorus: An outline of its chemistry, Biohemistry and uses, 5th Edn., Elsevier, Amsterdam, 1995, p. 336.

[25]. Babin, Y. V.; Gavrikov, A. V.; Ustynyuk, Y. A. Mendeleev Commun. 2008, 18, 12-13.
doi:10.1016/j.mencom.2008.01.005

[26]. Mamaev, V. M.; Prisyajnuk, A. V.; Laikov, D. N.; Logutenko, L. S.; Babin, Y. V. Russ. J. Phys. Chem. 2001, 75, 581-588.

[27]. Mamaev, V. M.; Prisyajnuk, A. V.; Logutenko, L. S.; Babin, Y. V. Mendeleev Commun. 2001, 11, 221-222.
doi:10.1070/MC2001v011n06ABEH001418

[28]. Maffei, M.; Buono, G. Tetrahedron 2003, 59, 8821-8825.
doi:10.1016/j.tet.2003.08.067

[29]. Brehme, R.; Grundemann, E.; Schneider, M. J. Prakt. Chem. 2000, 342, 700-706.
doi:10.1002/1521-3897(200009)342:7<700::AID-PRAC700>3.0.CO;2-U

[30]. Rathelot, P.; Azas, N.; El-Kashef, H.; Delmas, F.; Di Giorgio, C.; Timon-David, P.; Maldonado, J.; Vanelle, P. Eur. J. Med. Chem. 2002, 37, 671-679.
doi:10.1016/S0223-5234(02)01388-0

[31]. Abadi, A. H.; Eissa, A. A. H.; Hassan, G. S. Chem. Pharm. Bull. 2003, 51, 838-844.
doi:10.1248/cpb.51.838

[32]. De Luca, L.; Giaocomelli, G.; Masala, S.; Porcheddu, A. A. Synlett.2004, 13, 2299-2302.

[33]. Kumar, A.; Prakash, O.; Kinger, M.; Singh, S. P. Can. J. Chem. 2006, 84, 438-442.
doi:10.1139/V06-015

[34]. Sosnovskikh, V. Y.; Kutsenko, V. A.; Ovsyannikov, I. S. Russ. Chem. Bull. 2000, 49, 478-481.
doi:10.1007/BF02494778

[35]. Abdel-Khalik, M. M.; Negm, A. M.; Elkhouly, A. I., Elnagdi, M. H. Heteroatom Chem. 2004, 15, 502-507.
doi:10.1002/hc.20047

[36]. Ghosh, C. K.; Sahana, S. Tetrahedron 1993, 49, 4127-4134.
doi:10.1016/S0040-4020(01)89924-5

[37]. Rakitin, O. A. Arkivoc 2009, 1, 129-149.

[38]. Hudson, H. R.; Keglevich, G. Phosphorus, Sulfur Silicon and Relat. Elem. 2008, 183, 2256-2261.
doi:10.1080/10426500801938592

[39]. Babu, B. H.; Sirinivasulu, K.; Babu, B. V.; Sirinivas, R.; Raju, C. N. Synth. Commun.2008, 38, 2941-2949.
doi:10.1080/00397910802005273

[40]. Petteren, D.; Marcolini, M.; Bernardi, L.; Fini, F.; Herrera, R.; Sgarzani, V.; Ricci, A. J. Org. Chem. 2006, 71, 6269-6272.
doi:10.1021/jo060708h
PMid:16872218

[41]. Failla, S.; Finocchiaro, P.; Hagele, G.; Rapisardi, R. Phosphorus, Sulfur Silicon and Relat. Elem. 1993, 82, 79-89.
doi:10.1080/10426509308047411

[42]. Kumar, S. K.; Hager, E.; Pettit, C.; Gurulingappa, H.; Davidson, N. E.; Khan, S. R. J. Med. Chem. 2003, 46, 2813-2815.
doi:10.1021/jm030213+
PMid:12825923

[43]. Wu, J. H.; Wang, X. H.; Yi, Y. H.; Lee, K. H. Bioorg. Med. Chem. Lett. 2003, 13, 1813-1815.
doi:10.1016/S0960-894X(03)00197-5

[44]. Taber, D. F.; Nelson, C. G. J. Org. Chem. 2006, 71, 8973-8974.
doi:10.1021/jo061420v
PMid:17081034

[45]. Dominguez, J. N.; Leon, C.; Rodrigues, J.; Domínguez, N. G.; Gut, J.; Rosenthal, P. J. IL Farmaco 2005, 60, 307-311.
doi:10.1016/j.farmac.2005.01.005
PMid:15848205

[46]. Bardone, F.; Mladenova, M.; Gaudemar, M. Synthesis 1988, 611-614.
doi:10.1055/s-1988-27652

[47]. Martins Alho, M. A.; D`Accorso, N. B. J. Heterocycl. Chem.2000, 37, 811-814.
doi:10.1002/jhet.5570370423

[48]. Martins Alho, M. A.; Moglioni, A. G.; Brousse, B. N.; Moltrasio, G. Y.; D`Accorso, N. B. Arkivoc 2000, 4, 627-640.

[49]. Brousse, B. N.; Moglioni, A. G.; Martins Alho, M. A.; Larena, A. A.; Moltrasio, G. Y.; D`Accorso, N. B. Arkivoc 2002, 10, 14-23.

[50]. Rahman, A. U.; Choudhary, M. I.; Thomsen, W. J. Bioassay Techniques for drug development, Netherlands: Harwood Academic Publishers 2001.
doi:10.4324/9780203304532

[51]. Khan, K. M.; Saify, Z. S.; Zeesha, A. K.; Ahmed, M.; Saeed, M.; Schick, M.; Bkohlbau, H. J.; Voelter, W. Arzneim-Forsch/Drug Res. 2000, 50, 915-922.

Supporting Agencies

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 © 2024 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).