European Journal of Chemistry 2014, 5(4), 681-694. doi:10.5155/eurjchem.5.4.681-694.1087

Synthesis, reactions and applications of pyranotriazolopyrimidines


Ashraf Hassan Fekry Abd El-Wahab (1,*) , Ibrahim Ali Radini (2) , Hany Mostafa Mohamed (3)

(1) Chemistry Department, Faculty of Science, Al-Azhar University, 11884, Nasr City, Cairo, Egypt
(2) Chemistry Department, Faculty of Science, Jazan University, 2097, Jazan, Saudi Arabia
(3) Chemistry Department, Faculty of Science, Al-Azhar University, 11884, Nasr City, Cairo, Egypt
(*) Corresponding Author

Received: 30 Apr 2014, Accepted: 27 May 2014, Published: 31 Dec 2014

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.


Keywords


Naphthols; Pyrimidine; Biological activity; Pyranopyrimidines; α-Cyanocinnamonitriles; Carboxylic acid derivatives

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.5.4.681-694.1087

Get Citation | Scilit | GrowKudos | ResearchGate | Publons | Microsoft Academic

WorldCat | Dimensions | SemanticScholar | PlumX Metrics | Kopernio | Zotero | Mendeley

Article Metrics


This Abstract was viewed 933 times | PDF Article downloaded 301 times


Citations

/


[1]. Ashraf Hassan Fekry Abd El-Wahab, Ibrahim Ali Radini, Hany Mostafa Mohamed
ChemInform Abstract: Synthesis, Reactions and Applications of Pyranotriazolopyrimidines
ChemInform  46(20), no, 2015
DOI: 10.1002/chin.201520307
/


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.


How to cite


El-Wahab, A.; Radini, I.; Mohamed, H. Eur. J. Chem. 2014, 5(4), 681-694. doi:10.5155/eurjchem.5.4.681-694.1087
El-Wahab, A.; Radini, I.; Mohamed, H. Synthesis, reactions and applications of pyranotriazolopyrimidines. Eur. J. Chem. 2014, 5(4), 681-694. doi:10.5155/eurjchem.5.4.681-694.1087
El-Wahab, A., Radini, I., & Mohamed, H. (2014). Synthesis, reactions and applications of pyranotriazolopyrimidines. European Journal of Chemistry, 5(4), 681-694. doi:10.5155/eurjchem.5.4.681-694.1087
El-Wahab, Ashraf, Ibrahim Ali Radini, & Hany Mostafa Mohamed. "Synthesis, reactions and applications of pyranotriazolopyrimidines." European Journal of Chemistry [Online], 5.4 (2014): 681-694. Web. 7 Dec. 2019
El-Wahab, Ashraf, Radini, Ibrahim, AND Mohamed, Hany. "Synthesis, reactions and applications of pyranotriazolopyrimidines" European Journal of Chemistry [Online], Volume 5 Number 4 (31 December 2014)

DOI Link: https://doi.org/10.5155/eurjchem.5.4.681-694.1087

| | | | |

| | | | | |

.

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.