European Journal of Chemistry

Synthesis, reactions and applications of pyranotriazolopyrimidines



Main Article Content

Ashraf Hassan Fekry Abd El-Wahab
Ibrahim Ali Radini
Hany Mostafa Mohamed

Abstract

This review deals with synthesis, reactions and their applications of pyrano triazolo pyrimidines. The main purpose of this review is present a survey of literatures on the reactivity of amino imino derivatives and carboxylic acid derivatives. Some of these reactions have been applied successfully to the synthesis of biological important compounds.


icon graph This Abstract was viewed 2060 times | icon graph Article PDF downloaded 788 times

How to Cite
(1)
El-Wahab, A. H. F. A.; Radini, I. A.; Mohamed, H. M. Synthesis, Reactions and Applications of Pyranotriazolopyrimidines. Eur. J. Chem. 2014, 5, 681-694.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Bloxham, J.; Dell, C. P.; Smith, C. W. Heterocycles 1994, 38, 339-408.

[2]. Nawawar, G. A.; Abdelrazek, F. M.; Swellam, R. H. Arch. Pharm. 1991, 342, 875-877.
http://dx.doi.org/10.1002/ardp.2503241110

[3]. Zamocka, J.; Misikova, E.; Durinida, J. Pharmazie 1991, 46, 610-613.

[4]. Hong, J. W.; Xiao, Q. R.; Yan, Y. Z; Zhan, H. Z. J. Braz. Chem. Soc. 2009, 20, 1939-1943.
http://dx.doi.org/10.1590/S0103-50532009001000025

[5]. Saman, D.; Reza, S.; Majid, V.; Hamid, R. M. Chinese Chem. Lett. 2012, 23, 253-256.
http://dx.doi.org/10.1016/j.cclet.2011.11.025

[6]. Hossein, E.; Gholam, H. Z.; Reza, S.; Saman, D. Heterocycl. Commun. 2012, 18(2), 67-70.

[7]. Mogilaiah, K.; Sharath, B. H.; Vidya, K.; Shiva, K. K. Indian J. Chem. B 2010, 49, 390-393.

[8]. Wang, X. S.; Yang, G. S.; Zhao, G. Tetrahedron Asymmetr. 2008, 19, 709-714.
http://dx.doi.org/10.1016/j.tetasy.2008.02.018

[9]. Itokawa, H.; Mihar, T.; Takeya, K. Chem. Pharm. Bull. 1983, 31, 2353-2358.
http://dx.doi.org/10.1248/cpb.31.2353

[10]. Martinez, A. G.; Marco, L. J. Bioorg. Med. Chem. Lett. 1997, 7, 3165-3170.
http://dx.doi.org/10.1016/S0960-894X(97)10165-2

[11]. Dell, C. P.; Smith, C. W. Eur. Pat. 537, 94, 9 21Apr 1993; ref. Chem. Abstr. 1993, 119, 139102d.

[12]. Bianchi, G.; Tava, A. Agric. Biol. Chem. 1987, 51, 2001-2002.
http://dx.doi.org/10.1271/bbb1961.51.2001

[13]. Marec, F.; Kollarova, I.; Jegorov, A. Planta Med. 2001, 67, 127-131.
http://dx.doi.org/10.1055/s-2001-11498

[14]. Gil, S. J.; Dong, S. L.; Dong, C K. .; Yurngdong, J.; Jong, K. S.; Seung, H. L; Youn, C. K. Eur. J. Pharmacol. 2011, 654, 226-234.

[15]. Fischer, G. Adv. Heterocycl. Chem. 1993, 57, 81-138.
http://dx.doi.org/10.1016/S0065-2725(08)60887-9

[16]. Shaban, M. A. E.; Morgan, A. E. A. Adv. Heterocycl. Chem. 2000, 77, 345-394.
http://dx.doi.org/10.1016/S0065-2725(00)77009-7

[17]. Shaban, M. A. E.; Morgan, A. E. A. Adv. Heterocycl. Chem. 2000, 73, 131-176.
http://dx.doi.org/10.1016/S0065-2725(08)60942-3

[18]. Shaban, M. A. E.; Morgan, A. E. A. Adv. Heterocycl. Chem. 2000, 75, 243-281.
http://dx.doi.org/10.1016/S0065-2725(08)60986-1

[19]. Zhang, N.; Ayral-Kaloustian, S.; Nguyen, T.; Afragola, J.; Hernandez, R.; Lucas, J.; Gibbons, J.; Beyer, C. J. Med. Chem. 2007, 50, 319-327
http://dx.doi.org/10.1021/jm060717i

[20]. Havlicek, L.; Fuksova, K.; Krystof, V.; Orsag, M.; Vojtesek, B.; Strnad, M. Bioorg. Med. Chem. 2005, 13, 5399-5403.
http://dx.doi.org/10.1016/j.bmc.2005.06.007

[21]. Fraley, M. E.; Hoffman W. F.; Rubino R. S. Bioorg. Med. Chem. Lett. 2002, 12, 2767-2770.
http://dx.doi.org/10.1016/S0960-894X(02)00525-5

[22]. Chen, Q.; Zhu, X. L.; Jiang, L. L.; Liu, Z. M.; Yang, G. F. Eur. J. Med. Chem. 2008, 43, 595-603.
http://dx.doi.org/10.1016/j.ejmech.2007.04.021

[23]. Shigeko, U.; Shinya, T.; Takako, M.; Tomiichiro, O. Brain Res. 2002, 946, 298-306.
http://dx.doi.org/10.1016/S0006-8993(02)02898-6

[24]. Abdel-Rahman, H. M.; El-Koussi, N. A.; Hassan, H. Y. Arch Pharm. 2009, 342(2), 94-99.
http://dx.doi.org/10.1002/ardp.200800113

[25]. Fathy, A. E.; Ashraf, H. F.; Gameel, A. M. E.; Mostafa, M. K. Acta Pharm. 2004, 54, 13-26.

[26]. Ashraf, H. F. A. Pharmaceuticals 2012, 5, 745-757.
http://dx.doi.org/10.3390/ph5070745

[27]. Ashraf, H. F. A. J. Al-Azhar Bull. Sci. 2012, 1, 13-27.

[28]. Ahmed, Z. S.; Nagwa, A. E.; Ahmed, M. E. J. Chem. Res. 2000, 164-166.

[29]. Ahmed, H. B.; Hussien, A. E.; Nagwa, A. E.; Kamal, A. R.; Ahmed, M. E. Il Farmaco 2001, 56, 968-973.

[30]. El-Agrody, A. M.; El-Hakim, M. H.; Abd El-Latif, M. S.; Fakery, A. H.; El-Sayed, E. M.; El-Ghareab, K. A. Acta Pharm. 2000, 50, 111-120

[31]. Kamar, M.; Fakher, C.; Abdelouahid, S.; Jose, M. C.; Mansour, S. Heteroletters. Org. 2011, 1, 95-105.

[32]. Fakher, C.; Mehdi, M.; Hedi, B. M.; Leila, C. G.; Mansour, S. Eur. J. Med. Chem. 2007, 42, 715-718.
http://dx.doi.org/10.1016/j.ejmech.2006.12.002

[33]. Giudice, M. R. D.; Borioni, A.; Gatta, F. J. Heterocycl. Chem. 1994, 13, 1503-1507.
http://dx.doi.org/10.1002/jhet.5570310637

[34]. Zaki, M. E. A.; Fawzy, N. M.; Swelam, S. A. Molecules 1999, 3, 1-8.
http://dx.doi.org/10.1007/s007830050070

[35]. Hafidh, A.; Baccar, B. J. Soc. Alg. Chim. 2002, 12, 89-97.

[36]. Zuming, L.; Guangfu, Y.; Xianghua, Q. J. Chem. Technol. Biotechnol. 2001, 76, 1154-115.8

[37]. Messaad, M.; Chabchoub, F.; Salem, M. Heterocycl. Commun, 2005, 11, 139-144.
http://dx.doi.org/10.1515/HC.2005.11.2.139

[38]. El-Agrody, A. M.; Emam, H. A.; El-Hakim, M. H.; Abd El-Latif, M. S.; Fakery, A. H. J. Chem. Res. (S) 1997, 320-321.

[39]. Manal, M. K.; Aliaa, M. K.; Eman, K. A.; Heba A. H. Eur. J. Med. Chem. 2013, 59, 183-193.
http://dx.doi.org/10.1016/j.ejmech.2012.11.011

[40]. Mohammed, F. K.; Badrey, M. G. J. Korean Chem. Soc. 2011, 55(2), 218-229.
http://dx.doi.org/10.5012/jkcs.2011.55.2.218

[41]. El-Agrody, M. A.; Abd El-Latif, S. M.; Fakery, H. A.; Bedair, H.; A. J. Chem. Res. 2000, 26-27.

[42]. Bedair, H.; A.; El-Hady, A. N.; Abd El-Latif, S. M.; Fakery, H. A.; El-Agrody, M. A. Il Farmaco 2000, 55, 708-714.
http://dx.doi.org/10.1016/S0014-827X(00)00097-5

[43]. El-Hady, A. N.; El-Agrody M. A.; Abd El-Latif, S. M.; Fakery, H. A.; Bedair, H. A. Molecules 2001, 6, 519-521.
http://dx.doi.org/10.3390/60600519

[44]. Ashraf, H. F. A. Acta Pham. 2003, 58, 701-720.

[45]. Aly, H. A.; Ibraheim, I. A.; El-Saied H. E.; Nashwa, M. M. Oriental J. Chem. 2008, 24(3), 801-806.

[46]. Ahmed, H. S.; Magdi, E. A. Z; Eman, M. H. M.; Faiza M. A.;Farouk, M. E. A. Arch. Pharm. Chem. Life Sci. 2007, 340, 345-351.
http://dx.doi.org/10.1002/ardp.200700007

[47]. Magdi, E. A. Z.; Eman, M. H. M.; Faiza, M. A. Heterocycl. Comm. 2004, 10, 97-102.

[48]. Ahmed, H. S.; Magdi, E. A. Z; Eman, M. H. M.; Faiza, M. A.; Farouk, M. E. A. Arch. Pharm. 2007, 340, 236-243.
http://dx.doi.org/10.1002/ardp.200700005

[49]. Zaki, M. E. A. Molecules 1998, 3, 71-79.
http://dx.doi.org/10.3390/30300071

[50]. Kurbatov, E. S.; Starikova, Z. A.; Krasnikov, V. V.; Mezheritskii, V. V. Chem. Heterocyc. Compd. 2006, 42 (10), 1366-1367.
http://dx.doi.org/10.1007/s10593-006-0250-8

[51]. Musial, R.; Jampilek, J.; Buchta, V.; Silva, L.; Niedbala, H.; Podezwa, B.; Palka, A.; Majerz, M. K.; Oleksyn, B.; Polansk, J. Bioorg Med. Chem. 2006, 14, 3592-3598
http://dx.doi.org/10.1016/j.bmc.2006.01.016

[52]. Abdullah, M. A.; Ashraf, H. F. A.; Hany, M. M; Ahmed, M. E. Lett. Drug Des. Discov. 2012, 9, 459-470.

[53]. Nermien, N. S.; Hany, M. M.; Esaam, S. A.; Shymaa, S. A.; Ahmed, M. E. Eur. J. Med. Chem. 2011, 46, 765-772.
http://dx.doi.org/10.1016/j.ejmech.2010.12.015

[54]. El-Agrody, A. M.; Sabry, N. M.; Motlaq, S. S. J. Chem. Res. 2011, 2, 77-83.
http://dx.doi.org/10.3184/174751911X12964930076728

[55]. Hassanien, A. A.; Zahran, M. A.; El-gaby, M. S. A.; Ghorab, M. M. J. Indian Chem. Soc. 1999, 76(7), 350-354.

[56]. Ben, S. A.; Romdhane, A.; Elie, N.; Touboul, D.; Ben, H. Lett. Org. Chem. 2013, 10(3), 185-190.
http://dx.doi.org/10.2174/1570178611310030007

[57]. Anis, R.; Jean, F. G.; M`hamed, A. H.; Hichem, B. J. Phosphorus Sulfur 2012, 187, 612-618.
http://dx.doi.org/10.1080/10426507.2011.636109

[58]. Georgiadis, M. p.; Cauladouros, E. A.; Delitheos, A. K. J. Pharm. Sci. 1992, 81, 1126-1131.
http://dx.doi.org/10.1002/jps.2600811117

[59]. Zamocka, J.; Misikova, E.; J. Durinda, J. Cesk. Slov. Farm. 1992, 41, 170-172.

[60]. Ohira, T.; Yatagai, M. J. Jpn. Wood Res. Soc. 1993, 39, 237-242

[61]. Mohr, S. J.; Chirigos, M. A.; Fuhrman, F. S.; Pryor, J. W. Cancer Res. 1975, 35, 3750-3754.

[62]. Eiden, F.; Denk, F. Arch Pharm. Weinheim Ger. (Arch. Pharm.) 1991, 324, 353-354.
http://dx.doi.org/10.1002/ardp.19913240606

[63]. Tandon, V. K.; Vaish, M.; Jain, S.; Bhakuni, D. S.; R. C. Srimal, R. C. Indian J. Pharm. Sci. 1991, 53, 22-23.

[64]. Bargagna, A.; Longobardi, M.; Mariani, E.; Schenone, P.; Marmo, E. Farmaco 1990, 45, 405-413.

[65]. Bargagna, A.; Longobardi, M.; Mariani, E.; Schenone, P.; Marmo, E. Farmaco 1991, 46, 461-475.

[66]. Bargagna, A.; Longobardi, M.; Mariani, E.; Schenone, P.; Marmo, E. Farmaco 1992, 47, 345-355.

[67]. Gorlitzer, K.; Dehre, A.; Engler, E. Arch Pharm. Weinheim Ger. (Arch. Pharm.) 1983, 316, 264-270.

[68]. Ermili, A.; Roma, G.; Buonamici, M.; Cuttica, A.; Galante, M. Farmaco Ed. Sci. 1979, 34, 535-544.

[69]. Dell, C. P.; Smith, C. W. European Patent Appl. EP 537949, Chem. Abstr. 119 (1993) 139102d

[70]. Brunavs, M.; Dell, C. P.; Gallagher, P. T.; Owton, W. M.; Smith, C. W. European Patent Appl. EP 557075. Chem. Abstr. 120 (1994) 106768t.

[71]. Mohamed, G. B.; Sobhi M. G. Molecules 2012, 17, 11538-11553.
http://dx.doi.org/10.3390/molecules171011538

[72]. Anis, R.; Marie, T. M.; Abderrahim, B. S.; Aymen, J.; Hichem, B. J. J. Soc. Chim. Tunisie 2012, 14, 1277-1280.

Supporting Agencies

Chemistry Department, Faculty of Science, Al-Azhar University, 11884, Nasr City, Cairo, Egypt
Most read articles by the same author(s)

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 © 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).