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Mini-Reviews in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-193X
ISSN (Online): 1875-6298

Mini-Review Article

Synthetic and Reactions Routes to Tetrahydrothieno[3,2-b]Quinoline Derivatives (Part IV)

Author(s): Ameen A. Abu-Hashem*, Ahmed A. M. Abdelgawad, Hoda A. R. Hussein and Moustafa A. Gouda*

Volume 19, Issue 1, 2022

Published on: 18 February, 2021

Page: [74 - 91] Pages: 18

DOI: 10.2174/1570193X18666210218212719

Price: $65

Abstract

This review describes the synthesis and chemical reactivity of tetrahydrothieno[3,2-b] quinoline derivatives through many reagents such as; 1, 2-dihydropyridine-3-carbonitrile; 1,6-dihydropyrimidine- 5-carbonitrile; 2,3-dihydropyridazine-4-carbonitrile; 3-amino-thiophene-2-carboxylate; 3- amino-thiophene-2-carbonitrile; 3,4-diaminothieno[2,3-b] thiophene-2,5-dicarbo- nitrile; 2-(3-bromo-1- iodoisoquinolin-8-yl) benzonitrile and 3-mercapto-benzo[g]quinolin-4(1H)-one derivatives. The synthesis of tetrahydrothieno [3, 2-b] quinoline derivatives was explained through the following chemical reactions: Aldol condensation, alkylation, cyclocondensation, dehydration, chlorination, Wolff-Kishner reduction, acylation, Friedlander reaction and intramolecular cyclization

Keywords: Pyridine-3-carbonitrile, pyrimidine-5-carbonitrile, 3-aminothiophene-2-carbonitrile, iodoisoquinolines, mercaptobenzoquinolinones, synthesis, reactivity

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[1]
Hill, M.D. Recent strategies for the synthesis of pyridine derivatives. Chemistry, 2010, 16(40), 12052-12062.
[http://dx.doi.org/10.1002/chem.201001100] [PMID: 20827696]
[2]
El-Hashash, M.A.; Sherif, S.M.; Badawy, A.A.; Rashdan, H.R. Synthesis of some new antimicrobial of 5, 6, 7, 8-tetrahydro-pyrimido[4, 5-b]quinolone derivatives. Der Pharma. Chem., 2014, 6(4), 23-29.
[3]
Elkholy, Y.M.; Morsy, M.A. Facile synthesis of 5, 6, 7, 8-tetra-hydropyrimido [4, 5-b]-quinoline derivatives. Molecules, 2006, 11(11), 890-903.
[http://dx.doi.org/10.3390/11110890] [PMID: 18007394]
[4]
Gholap, A.R.; Toti, K.S.; Shirazi, F.; Kumari, R.; Bhat, M.K.; Deshpande, M.V.; Srinivasan, K.V. Synthesis and evaluation of antifungal properties of a series of the novel 2-amino-5-oxo-4-phenyl-5,6,7,8-tetrahydroquinoline-3-carbonitrile and its analogues. Bioorg. Med. Chem., 2007, 15(21), 6705-6715.
[http://dx.doi.org/10.1016/j.bmc.2007.08.009] [PMID: 17765545]
[5]
Dodiya, D.K.; Ram, H.K.; Trivedi, A.R.; Shah, V.H. An efficient, microwave-assisted, one-pot synthesis of novel 5, 6, 7, 8-tetra-hydroquinoline-3-carbonitriles. J. Serb. Chem. Soc., 2011, 76(6), 823-830.
[http://dx.doi.org/10.2298/JSC100702071D]]
[6]
Gudmundsson, K.S.; Boggs, S.D.; Catalano, J.G.; Svolto, A.; Spaltenstein, A.; Thomson, M.; Wheelan, P.; Jenkinson, S. Imidazopyridine-5,6,7,8-tetrahydro-8-quinolinamine derivatives with potent activity against HIV-1. Bioorg. Med. Chem. Lett., 2009, 19(22), 6399-6403.
[http://dx.doi.org/10.1016/j.bmcl.2009.09.056] [PMID: 19818609]
[7]
Crawford, J.B.; Chen, G.; Gauthier, D.; Wilson, T.; Carpenter, B.; Baird, I.R.; McEachern, E.; Kaller, A.; Harwig, C.; Atsma, B.; Skerlj, R.T.; Bridger, G.J. AMD070, a CXCR4 chemokine receptor antagonist: practical large-scale laboratory synthesis. Org. Process Res. Dev., 2008, 12(5), 823-830.
[http://dx.doi.org/10.1021/op8000993]]
[8]
Gavrilov, M.Y.; Mardanova, L.G.; Kolla, V.E.; Konshin, M.E. Synthesis, anti-inflammatory and analgesic activities of 2-aryl-amino-5, 6, 7, 8-tetrahydroquinoline-3-carboxamides. Pharm. Chem. J., 1988, 22(7), 554-556.
[http://dx.doi.org/10.1007/BF00763528]]
[9]
Brandt, W.; Mologni, L.; Preu, L.; Lemcke, T.; Gambacorti-Passerini, C.; Kunick, C. Inhibitors of the RET tyrosine kinase based on a 2-(alkylsulfanyl)-4-(3-thienyl)nicotinonitrile scaffold. Eur. J. Med. Chem., 2010, 45(7), 2919-2927.
[http://dx.doi.org/10.1016/j.ejmech.2010.03.017] [PMID: 20409618]
[10]
Barbay, J.K.; Gong, Y.; Buntinx, M.; Li, J.; Claes, C.; Hornby, P.J.; Van Lommen, G.; Van Wauwe, J.; He, W. Synthesis and characterization of 5,6,7,8-tetrahydroquinoline C5a receptor antagonists. Bioorg. Med. Chem. Lett., 2008, 18(8), 2544-2548.
[http://dx.doi.org/10.1016/j.bmcl.2008.03.049] [PMID: 18378452]
[11]
Marella, A.; Tanwar, O.P.; Saha, R.; Ali, M.R.; Srivastava, S.; Akhter, M.; Shaquiquzzaman, M.; Alam, M.M. Quinoline: A versatile heterocyclic. Saudi Pharm. J., 2013, 21(1), 1-12.
[http://dx.doi.org/10.1016/j.jsps.2012.03.002] [PMID: 23960814]
[12]
Abu-Hashem, A.A.; Abdelgawad, A.A.M.; Gouda, M.A. Vilsmeier-Haack cyclisation as a facile synthetic route to thieno[2, 3- b]quinolines (Part I). Lett. Org. Chem., 2020. E-pub Ahead of Print
[13]
Teja, C.; Nawaz Khan, F.R. Recent advances in the synthesis of thienoquinolines (Quinoline‐fused heterocycle). Asian J. Org. Chem., 2020, 9(12), 1889-1900.
[http://dx.doi.org/10.1002/ajoc.202000427]]
[14]
Bhagat, S.; Sharma, R.; Sawant, D.M.; Sharma, L.; Chakraborti, A.K. LiOH_H2O As a novel dual activation catalyst for highly efficient and easy synthesis of 1,3-diaryl-2-propenones by Claisen-Schmidt condensation under mild conditions. J. Mol. Catal. Chem., 2006, 244, 20-24.
[http://dx.doi.org/10.1016/j.molcata.2005.08.039]]
[15]
Krauze, A.A.; Bomika, Z.A.; Shestopalov, A.M.; Rodinovskaya, L.A.; Pelcher, Y.E.; Dubur, G.Y.; Sharanin, Y.A.; Promonenkov, V.K. Synthesis and some reactions of 3-cyanopyridine-2-thiones. Chem. Heterocycl. Compd., 1981, 17(3), 279-284.
[http://dx.doi.org/10.1007/BF00505994]]
[16]
Attaby, F.A. Reactions of styrylthienyl ketone, styryl furyl ketone with thiocyanoacetamide: synthesis of several new pyridines, thieno[2, 3-b]pyridines, pyrido[2′, 3′: 4, 5]thieno[3, 2-c]pyridazines and pyrido-[3′, 2′: 4, 5] thieno[3, 2-d]pyrimidin one derivatives. Phosphorus Sulfur Silicon Relat. Elem., 1998, 139(1), 1-12.
[http://dx.doi.org/10.1080/10426509808035673]]
[17]
Buryi, D.S.; Dotsenko, V.V.; Levashov, A.S.; Lukina, D.Y.; Strelkov, V.D.; Aksenov, N.A.; Aksenova, I.V.; Netreba, E.E. Synthesis of 4, 6-disubstituted 2-thioxo-1, 2-dihydropyridine-3-carbo-nitriles by the reaction of acetylenic ketones with cyanothioacetamide. Russ. J. Gen. Chem., 2019, 89(5), 886-895.
[http://dx.doi.org/10.1134/S1070363219050050]]
[18]
Dai, D.; Burgeson, J.R.; Tyavanagimatt, S.R.; Byrd, C.M.; Hruby, D.E. Thienopyridine derivatives for the a 6lx3/5377 (2006.01) treatment and prevention of A6II 45/00 (2006.01) dengue virus infections. U.S. Patent Appl. 13708,224 2013.
[19]
Kamel, M.M.; El-Deen, E.M. New tetracyclic compounds including thieno [2, 3-b: 4, 5-b′] dipyridines of possible antimicrobial activity. Bull. Fac. Pharm. Cairo Univ., 2003, 41(1), 197-206.
[20]
El-Deen, E.M.M.; Anwar, M.M.; Kotb, E.R. Synthesis and cytotoxic evaluation of new 6,7,8,9-tetrahydropyrido[3′,2′:4,5]thieno[3,2-b] quinoline derivatives. Res. J. Pharm. Biol. Chem. Sci., 2014, 5(6), 1535-1549.
[21]
Mohi El-Deen, E.M.; Abd El-Hameed, E.K. Synthesis and in vitro biological evaluation of new tetracyclic pyridothienoquinolines as potential antimicrobial agents. Acta Pol. Pharm., 2017, 74(3), 837-847.
[PMID: 29513953]
[22]
Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J.T.; Bokesch, H.; Kenney, S.; Boyd, M.R. New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst., 1990, 82(13), 1107-1112.
[http://dx.doi.org/10.1093/jnci/82.13.1107] [PMID: 2359136]
[23]
Taher, A.; Lumbiny, B.J.; Lee, I.M. A facile microwave-assisted Knoevenagel condensation of various aldehydes and ketones using amine-functionalized metal organic frameworks. Inorg. Chem. Commun., 2020, 119108092
[http://dx.doi.org/10.1016/j.inoche.2020.108092]]
[24]
Abdel-Mohsen, S.A.; Geies, A.A. A convenient synthesis of pyrrolo [2, 3-b] pyridines and pyrido [2′, 3′: 5, 4] pyrrolo [2, 3-d] pyrimidines. Monatsh. Chem., 2008, 139(10), 1233-1240.
[http://dx.doi.org/10.1007/s00706-007-0839-3]]
[25]
Peinador, C.; Ojea, V.; Quintela, J.M. A convenient synthesis for some new pyrido [3′, 2′: 4, 5] thieno‐ [3, 2‐d] pyrimidine derivatives with potential biological activity. J. Heterocycl. Chem., 1992, 29(7), 1693-1702.
[http://dx.doi.org/10.1002/jhet.5570290704]]
[26]
Peinador, C.; Moreira, M.J.; Quintela, J.M. An efficient iminophosphorane-mediated synthesis for pyrido [3′, 2′: 4, 5] thieno [3, 2-d] pyrimidine derivatives. Tetrahedron, 1994, 50(22), 6705-6714.
[http://dx.doi.org/10.1016/S0040-4020(01)89699-X]]
[27]
Zhao, Y.; Li, M.; Li, B.; Zhang, S.; Su, A.; Xing, Y.; Ge, Z.; Li, R.; Yang, B. Discovery and optimization of thienopyridine derivatives as novel urea transporter inhibitors. Eur. J. Med. Chem., 2019, 172, 131-142.
[http://dx.doi.org/10.1016/j.ejmech.2019.03.060] [PMID: 30959323]
[28]
Kamal El-Dean, A.M.; Micky, G.A.A.; Ahmed, A.B.A-H.; Ahmed, R.H. Convenient synthesis and reactions of some 7,9-dimethylthieno-[2,3-b:4,5-b′]dipyridines. J. Chem. Res., 2009, 10, 649-652.
[http://dx.doi.org/10.3184/030823409X12532880131016]]
[29]
Ho, Y.W. Facile synthesis and properties of new (4-Substituted-phehyl) azo-pyrido [2′, 3′: 4, 5] thieno [2, 3-d] pyrimidin-6-(5H)-one dyes derived from thioxopyrimidine. J. Chem. Soc. Pak., 2014, 36(1), 123-130.
[30]
Abdel-Mohsen, S.A.; Geies, A.A. Synthesis of pyrido[2‘,3‘:4,5]thieno[2,3-d]pyrimidines through Friedländer reactions. J. Chem. Res., 2007, 12, 689-692.
[http://dx.doi.org/10.3184/030823407X269961]]
[31]
Loidreau, Y.; Marchand, P.; Dubouilh-Benard, C.; Nourrisson, M.R.; Duflos, M.; Lozach, O.; Loaëc, N.; Meijer, L.; Besson, T. Synthesis and biological evaluation of N-arylbenzo[b]thieno[3,2-d]pyrimidin-4-amines and their pyrido and pyrazino analogues as Ser/Thr kinase inhibitors. Eur. J. Med. Chem., 2012, 58, 171-183.
[http://dx.doi.org/10.1016/j.ejmech.2012.10.006] [PMID: 23124214]
[32]
Blanco, G.; Fernandez-Mato, A.; Quintela, J.M.; Peinador, C. One-pot three-step synthesis of pyrazinothienopyrimidines using tandem Aza-Wittig/electrocyclic ring closure. Synthesis, 2009, 03, 438-444.
[33]
Fernández-Mato, A.; Quintela, J.M.; Peinador, C.; Platas-Iglesias, C. Preparation and study of pyridothienopyrazines and their Ruthenium (II) complexes: a new family of bidentate ligands. Tetrahedron, 2011, 67(11), 2035-2043.
[http://dx.doi.org/10.1016/j.tet.2011.01.066]]
[34]
Amin, M.A.; Ismail, M.M.; Barakat, S.E.; Abdul-Rahman, A.A.; Bayomi, A.H.; El-Gamal, K. Synthesis and antimicrobial activity of some new quinoline and 1H-pyrazolo[3,4-b] quinoline derivatives. Bull. Pharm. Sci., 2004, 27(2), 237-245.
[http://dx.doi.org/10.21608/bfsa.2004.65452]]
[35]
Luo, L.; Meng, L.; Peng, Y.; Xing, Y.; Sun, Q.; Ge, Z.; Li, R. ZnCl2-promoted one-pot three-component synthesis of multisubstituted thiazolo[4,5-b]pyridines and thieno[2,3-b:4,5-b′]dipyridines. Eur. J. Org. Chem., 2014, 2015(3), 631-637.
[http://dx.doi.org/10.1002/ejoc.201403156]]
[36]
Hashem, H.E.; Haneen, D.S.; Saied, K.F.; Youssef, A.S. Synthesis of new annulated pyridazine derivatives and studying their antioxidant and antimicrobial activities. Synth. Commun., 2019, 49(22), 3169-3180.
[http://dx.doi.org/10.1080/00397911.2019.1658786]]
[37]
El-Mariah, F.; Nassar, E.; Hosny, M.; Deeb, A. Pyridazine derivatives and related compounds, Part 28. Pyridazinesulfonamides: Synthesis and antimicrobial activity. Phosphorus Sulfur Silicon Relat. Elem., 2008, 184(1), 92-102.
[http://dx.doi.org/10.1080/10426500802080246]]
[38]
Quintela, J.M.; Veiga, M.C.; Conde, S.; Peinador, C. A general route for the synthesis of pyrimido [4′, 5′: 4, 5] thieno [2, 3-c] pyridazine derivatives. Monatsh. Chem., 1996, 127(6-7), 739-745.
[http://dx.doi.org/10.1007/BF00817265]]
[39]
Deeb, A.; El-Mariah, F.; El-Badry, K.; Abd El-Mawgoud, H.K. Pyridazine and its related compounds, part 39. Synthesis and antimicrobial evaluation of some thienopyridazine based heterocycle. Eur. Chem. Bull., 2014, 3(9), 897-903.
[40]
Thomae, D.; Kirsch, G.; Seck, P. Synthesis of selenophene analogues of the tacrine series: comparison of classical route and microwave irradiation. Synthesis, 2008, (10), 1600-1606.
[41]
Abdillahi, I.; Revelant, G.; Datoussaid, Y.; Kirsch, G. Synthesis of novel 2-thienylimino -1, 3-thiazolidin-4-ones. Synthesis, 2010, (15), 2543-2546.
[42]
Revelant, G.; Hesse, S.; Kirsch, G. Synthesis of novel 2-aminothieno [3, 2-d] thiazoles and selenolo [3, 2-d] thiazoles. Tetrahedron, 2011, 67(48), 9352-9357.
[http://dx.doi.org/10.1016/j.tet.2011.09.134]]
[43]
Datoussaid, Y.; Kirsch, G.; Othmana, A.A.; Abdillahi, I. Synthesis of novel thieno[3,2-b] quinolines and thieno[3,2-d] [1,3] thiazoles. S. Afr. J. Chem., 2012, 65, 223-227.
[44]
Ren, W-Y.; Rao, K.; Kein, R. Convenient synthesis of substituted 3‐aminothiophene‐2‐carbonitriles from α‐acetylenic nitriles and their conversion to thieno[3,2‐d]pyrimidines. J. Heterocycl. Chem., 1986, 23, 1757-1763.
[45]
Bouayad, Z.; Chanet‐Ray, J.; Ducher, S.; Vessière, R. The regioselectivity of the ring opening of 1‐activated or nonactivated 2‐alkoxycarbonyl or 2‐cyanoaziridines by carbanions of the dicarbonyl compounds. J. Heterocycl. Chem., 1991, 28, 1757-1767.
[http://dx.doi.org/10.1002/jhet.5570280719]]
[46]
Hartmann, H.; Liebscher, J. Asimple method for the synthesis of 5-aryl-3-amino-2-alkoxy-carbonylthiophenes. Synthesis, 1984, 1984(3), 275-276.
[http://dx.doi.org/10.1055/s-1984-30808]]
[47]
Hussein, H.A.R.; Abu-Zied, K.M.; Abu-Hashem, A.A. Novel synthesis of fused pyrazolopyrimidines and C-nucleosides of thienopyrimidone with expected anti-microbial activity. Egypt. J. Chem., 2010, 53(4), 527-540.
[http://dx.doi.org/10.21608/ejchem.2010.1247]]
[48]
Liebscher, J.; Neumann, B.; Hartmann, H. Eine einfache synthese von β-Chlorzimtsäu-renitrilen nach einer modifiziertenVilsmeyer-Haack-Arnold-Reaktion. J. Prakt. Chem., 1983, 325, 915-918.
[http://dx.doi.org/10.1002/prac.19833250606]]
[49]
Liebscher, J.; Hartmann, H. 3-Chloro-2-propeniminium-salze (vinyloge Amidchloride) als vorteilhafte synthesebausteine der organischen chemie. Synthesis, 1979, 1979(04), 241.
[http://dx.doi.org/10.1055/s-1979-28636]]
[50]
Migianu, E.; Kirsch, G. Synthesis of new thieno[b]azepinediones from α-methylene ketones. Synthesis, 2002, 1096-1100
[http://dx.doi.org/10.1055/s-2002-31963]]
[51]
Thomae, D.; Kirsch, G.; Seck, P. Synthesis of thiophene analogues of the tacrine series. Synthesis, 2007, (07), 1027-1032.
[52]
Thomae, D.; Kirsch, G.; Seck, P. Synthesis of thiophene analogues of the tacrine series. Proceedings of ECSOC-10 Inter. Electronic Conference on Synthetic Organic Chemistry, 2006, pp. 1-30.
[53]
Song, Y.H.; Jo, B.S. Synthesis of 9‐amino‐5,6,7,8‐tetrahydrothieno [3, 2‐b] quinoline and 9‐amino‐5,6,7,8‐tetrahydrothieno [3, 2‐b] quinolin‐8‐ol derivatives. J. Heterocycl. Chem., 2009, 46(6), 1132-1136.
[http://dx.doi.org/10.1002/jhet.186]]
[54]
Lee, H.M.; Song, Y-H. Synthesis of 10-amino-5, 6, 7, 9-tetrahydro-1-thia-4,9-diazacyclo-hepta[f]inden-8-one derivatives using Schmidt reaction. J. Korean Chem. Soc., 2009, 53(3), 387-390.
[http://dx.doi.org/10.5012/jkcs.2009.53.3.387]]
[55]
Ellman, G.L.; Courtney, K.D.; Andres, V.J.; Feather-Stone, R.M. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol., 1961, 7(2), 88-95.
[http://dx.doi.org/10.1016/0006-2952(61)90145-9] [PMID: 13726518]
[56]
Ninomiya, K.; Saito, K.; Sugano, M.; Tobe, A.; Morinaka, Y.; Bessho, T.; Harada, H. Preparation of 4-acylaminopyridine derivatives for treatment of Alzheimer's disease. European Patent EP427636 A2 1991.
[57]
Qiu, F.; Yang, J.; Shi, D.; Zhang, Q.; Li, J. Synthesis of thieno [2, 3-b] thiophene fused pyrimidine derivatives via sequential conversion of 3, 4-diaminothieno [2, 3-b] thiophene-2, 5-dicarbonitrile with carbonyl compounds. Tetrahedron Lett., 2016, 57(11), 1210-1214.
[http://dx.doi.org/10.1016/j.tetlet.2016.01.040]]
[58]
Moon, S.Y.; Lee, S.H.; Kim, H.R.; Choi, Y.H.; Kim, S.G.; Park, C.H. Preparation of fused heterocylic compounds for organic electroluminescent devices and electronic devices. Korean Patent KR2017057526 A, 2017.
[59]
Loven, L.; Summer Fard, W.T. Some 2-(2-carboxyethyl) amino-1,4-naphthoquinone derivatives. J. Chem. Eng. Data, 1966, 11, 264-264.
[60]
Khalafallah, A.K.; El-Kanzi, N.A.A.; Soleiman, H.A.; Younis, M. The synthesis of new spiro β-lactam and thiazolidinone compounds incorporating quinones and their biological activity. Phosphorus Sulfur Silicon Relat. Elem., 2006, 181(11), 2483-2503.
[http://dx.doi.org/10.1080/10426500600754760]]
[61]
Loo, Y.H.; Skell, P.S.; Thornberry, H.H.; Ehrlich, J.; McGuire, J.M.; Savage, G.M.; Sylvester, J.C. Assay of Streptomycin by the paper-disc plate method. J. Bacteriol., 1945, 50, 701-709.
[http://dx.doi.org/10.1128/JB.50.6.701-709.1945]]
[62]
Abu-Hashem, A.A.; Abu-Zied, K.M.; Zaki, M.E.A.; El-Shehry, M.F.; Awad, H.M.; Khedr, M.A. Design, synthesis, and anticancer potential of the enzyme (PARP-1) inhibitor with computational studies of new triazole, thiazolidinone, -thieno [2, 3-d] pyrimidinones. Lett. Drug Des. Discov., 2020, 17(6), 799-819.
[http://dx.doi.org/10.2174/1570180817666200117114716]]
[63]
Abu-Hashem, A.A.; Al-Hussain, S.A.; Zaki, M.E.A. Synthesis of novel benzodifuranyl; 1, 3, 5-triazines; 1, 3, 5-oxadiazepines; and thiazolopyrimidines derived from visnaginone and khellinone as anti-Inflammatory and analgesic agents. Molecules, 2020, 25(1), 220.
[http://dx.doi.org/10.3390/molecules25010220] [PMID: 31948127]
[64]
Abu-Hashem, A.A.; Fathy, U.; Gouda, M.A. Synthesis of 1, 2, 4-triazolopyridazines, isoxazolofuropyridazines, and tetrazolo-pyridazines as antimicrobial agents. J. Heterocycl. Chem., 2020, 57, 3461-3474.
[65]
Gouda, M.A.; Abu-Hashem, A.A.; Hussein, H.A.R.; Aly, A.S. Recent development in the chemistry of bicyclic 6+5 systems, Part II: chemistry of triazolopyrimidine derivatives. Lett. Org. Chem., 2020, 17(12), 897-925.
[66]
Abu-Hashem, A.A.; Hussein, H.A.R.; Aly, A.S. Synthesis and antimicrobial activity of novel 1, 2, 4-triazolo- pyrimidofuro-quinazolinones from natural furochromones (visnagenone and khellinone). Med. Chem., 2020, 17(7), 707-723.
[67]
Abu-Hashem, A.A.; Zaki, M.E.A. Direct amination and synthesis of fused N-substituted isothiochromene derivatives. J. Heterocycl. Chem., 2019, 56, 886-894.
[http://dx.doi.org/10.1002/jhet.3466]]
[68]
Abu-Hashem, A.A.; Faty, R.A.M. Synthesis, antimicrobial evaluation of some new 1, 3, 4-thiadiazoles and 1, 3, 4-thiadiazines. Curr. Org. Synth., 2018, 15(8), 1161-1170.
[http://dx.doi.org/10.2174/1570179415666180720114547]]
[69]
Abu-Hashem, A.A. Synthesis of new furothiazolo pyrimido quinazolinones from visnagenone or khellinone and antimicrobial activity. Molecules, 2018, 23(11), 2793.
[http://dx.doi.org/10.3390/molecules23112793] [PMID: 30373270]
[70]
Abu-Hashem, A.A.; Gouda, M.A.; Badria, F.A. Design, synthesis and identification of novel substituted isothiochromene analogs as potential antiviral and cytotoxic agents. Med. Chem. Res., 2018, 27, 2297-2311.
[http://dx.doi.org/10.1007/s00044-018-2236-3]]
[71]
Abu-Hashem, A.A. Synthesis and biological activity of pyrimidines, quinolines, thiazines and pyrazoles bearing a common thieno moiety. Acta Pol. Pharm., 2018, 75(1), 59-70.
[72]
Abu-Hashem, A.A.; El-Shazly, M. Synthesis of new isoxazole-, pyridazine-, pyrimidopyrazines and their anti-inflammatory and analgesic activity. Med. Chem., 2018, 14(4), 356-371.
[http://dx.doi.org/10.2174/1573406414666180112110947] [PMID: 29332598]
[73]
Abu-Hashem, A.A.; El-Shazly, M. Synthesis of new quinoxaline, pyrimidine, and pyrazole furochromone derivatives as cytotoxic agents. Monatsh. Chem., 2017, 148, 1853-1863.
[http://dx.doi.org/10.1007/s00706-017-1960-6]]
[74]
Abu-Hashem, A.A.; Gouda, M.A. Synthesis and antimicrobial activity of some novel quinoline, chromene, pyrazole derivatives bearing triazolopyrimidine moiety. J. Heterocycl. Chem., 2017, 54, 850-858.
[http://dx.doi.org/10.1002/jhet.2645]]
[75]
Gouda, M.A.; Abu-Hashem, A.A.; Saad, H.H.; Elattar, K.M. 5-Chloropyrazole-4-carboxaldehydes as synthon in heterocyclic synthesis. Res. Chem. Intermed., 2016, 42(3), 2119-2162.
[http://dx.doi.org/10.1007/s11164-015-2139-6]]
[76]
Abu-Hashem, A.A.; El-Shazly, M. Synthesis, reactions and biological activities of furochromones: a review. Eur. J. Med. Chem., 2015, 90, 633-665.
[http://dx.doi.org/10.1016/j.ejmech.2014.12.001] [PMID: 25499986]
[77]
Abu-Hashem, A.A.; Aly, A.S. Synthesis of new pyrazole, triazole, and thiazolidine-pyrimido [4, 5-b] quinoline derivatives with potential antitumor activity. Arch. Pharm. Res., 2012, 35(3), 437-445.
[http://dx.doi.org/10.1007/s12272-012-0306-5] [PMID: 22477190]
[78]
Abu-Hashem, A.A.; Abu-Zied, K.M.; El-Shehry, M.F. Synthetic utility of bifunctional thiophene derivatives and antimicrobial evaluation of the newly synthesized agents. Monatsh. Chem., 2011, 142, 539-545.
[http://dx.doi.org/10.1007/s00706-011-0456-z]]
[79]
Abu-Hashem, A.A.; El-Shehry, M.F.; Badria, F.A. Design and synthesis of novel thiophenecarbohydrazide, thienopyrazole and thienopyrimidine derivatives as antioxidant and antitumor agents. Acta Pharm., 2010, 60(3), 311-323.
[http://dx.doi.org/10.2478/v10007-010-0027-6] [PMID: 21134865]
[80]
Abu-Hashem, A.A.; Gouda, M.A.; Badria, F.A. Synthesis of some new pyrimido[2′,1′:2,3]thiazolo[4,5-b]quinoxaline derivatives as anti-inflammatory and analgesic agents. Eur. J. Med. Chem., 2010, 45(5), 1976-1981.
[http://dx.doi.org/10.1016/j.ejmech.2010.01.042] [PMID: 20149490]
[81]
Gouda, M.A.; Abu-Hashem, A.A.; Abdelgawad, A.A.M. Recent progress on the chemistry of thieno [3, 2‐b] quinoline derivatives (part III). J. Heterocycl. Chem., 2021, 58, 908-927.
[http://dx.doi.org/10.1002/jhet.4205]

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