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Synthesis and antimicrobial activities of some novel bis-pyrazole derivatives containing a hydrophosphoryl unit
Salah Abdel-Ghaffar Abdel-Aziz (1)
, Tarik El-Sayed Ali (2,*) , Kamilia Mohamed El-Mahdy (3) , Somaia Mohamed Abdel-Karim (4) (1) Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Cairo, EG-11711, Egypt
(2) Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Cairo, EG-11711, Egypt
(3) Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Cairo, EG-11711, Egypt
(4) Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Cairo, EG-11711, Egypt
(*) Corresponding Author
Received: 15 Jul 2010 | Revised: 10 Aug 2010 | Accepted: 16 Aug 2010 | Published: 28 Mar 2011 | Issue Date: March 2011
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.
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DOI: 10.5155/eurjchem.2.1.25-35.208
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Synthetic Communications 43(24), 3329, 2013
DOI: 10.1080/00397911.2013.783074
[2]. R. Chauhan, A. A. Siddiqi, J. Dwivedi
An approach to regioselective synthesis of pyrazole and isoxazole derivatives and study of their antimicrobial effect
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[7]. W F. Rodhan, S S. Kadhium, Z Z M Ali, A G Eleiwi, R F Abbas, I R Mohamed, Z A Hussein
Chemistry and synthesis of Bis Pyrazole derivatives and their biological activity: a review
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DOI: 10.1080/00397911.2014.948965
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DOI: 10.5155/eurjchem.10.4.367-375.1915
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DOI: 10.1080/10426507.2021.1960833
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DOI: 10.1080/00397911.2021.2024574
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DOI: 10.1515/ncrs-2016-0046
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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.
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