Synthesis of New Thiazolidinones and Thiazoles in Indole Series

Sofiane      Khanoussi; Abdelmadjid      Benmohammed; Omar      Khoumeri; Mokhtaria      Kadiri; Ayada      Djafri; Thierry      Terme; Patrice      Vanelle

Abstract

Recent findings confirm that thiosemicarbazones and thiazoles offer a wide range of biological properties. We report here the synthesis of two series of highly functionalized thiazole-derived compounds from the reactions of various indole-derived thiosemicarbazones with diethyl acetylenedicarboxylate and 4-bromophenacyl bromide. As a result, a series of new derivatives of thiosemicarbazone, thiazolidinone, and thiazole bearing an indole moiety was synthesized and developed in good yields.

Keywords: Thiosemicarbazone, thiazolidinone, thiazole, indole, condensation, cyclization.

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[1]
Locock, K.E.S.; Michl, T.D.; Stevens, N.; Hayball, J.D.; Vasilev, K.; Postma, A. ACS Macro Lett.,  2014, 3, 319-323.
 [http://dx.doi.org/10.1021/mz5001527] [PMID: 35590739]

[2]
Samosorn, S.; Bremner, J.B.; Ball, A.; Lewis, K. Bioorg. Med. Chem.,  2006, 14(3), 857-865.
 [http://dx.doi.org/10.1016/j.bmc.2005.09.019] [PMID: 16203150]

[3]
Wan, Y.; Li, Y.; Yan, C.; Yan, M.; Tang, Z. Eur. J. Med. Chem.,  2019, 183111691.
 [http://dx.doi.org/10.1016/j.ejmech.2019.111691] [PMID: 31536895]

[4]
Zhou, D.; Zhou, P.; Evrard, D.A.; Meagher, K.; Webb, M.; Harrison, B.L.; Huryn, D.M.; Golembieski, J.; Hornby, G.A.; Schechter, L.E.; Smith, D.L.; Andree, T.H.; Mewshaw, R.E. Bioorg. Med. Chem.,  2008, 16(14), 6707-6723.
 [http://dx.doi.org/10.1016/j.bmc.2008.05.075] [PMID: 18571421]

[5]
Long, S.Y.; Li, C.L.; Hu, J.; Zhao, Q.J. Fitoterapia,  2018, 129, 145-149.
 [http://dx.doi.org/10.1016/j.fitote.2018.06.017] [PMID: 29935259]

[6]
Zhang, M.Z.; Chen, Q.; Yang, G.F. Eur. J. Med. Chem.,  2015, 89, 421-441.
 [http://dx.doi.org/10.1016/j.ejmech.2014.10.065] [PMID: 25462257]

[7]
Radwan, M.A.A.; Ragab, E.A.; Sabry, N.M.; El-Shenawy, S.M. Bioorg. Med. Chem.,  2007, 15(11), 3832-3841.
 [http://dx.doi.org/10.1016/j.bmc.2007.03.024] [PMID: 17395469]

[8]
Yang, T.; Moreira, W.; Nyantakyi, S.A.; Chen, H.; Aziz, D.; Go, M.L.; Dick, T. J. Med. Chem.,  2017, 60(7), 2745-2763.
 [http://dx.doi.org/10.1021/acs.jmedchem.6b01530] [PMID: 28290692]

[9]
de Souza, M.V.N. J. Sulfur Chem.,  2005, 26(4-5), 429-449.
 [http://dx.doi.org/10.1080/17415990500322792]

[10]
Haribabu, J.; Subhashree, G.R.; Saranya, S.; Gomathi, K.; Karvembu, R.; Gayathri, D. J. Mol. Struct.,  2016, 1110, 185-195.
 [http://dx.doi.org/10.1016/j.molstruc.2016.01.044]

[11]
Bal, T.R.; Anand, B.; Yogeeswari, P.; Sriram, D. Bioorg. Med. Chem. Lett.,  2005, 15(20), 4451-4455.
 [http://dx.doi.org/10.1016/j.bmcl.2005.07.046] [PMID: 16115762]

[12]
Finkielsztein, L.M.; Castro, E.F.; Fabián, L.E.; Moltrasio, G.Y.; Campos, R.H.; Cavallaro, L.V.; Moglioni, A.G. Eur. J. Med. Chem.,  2008, 43(8), 1767-1773.
 [http://dx.doi.org/10.1016/j.ejmech.2007.10.023] [PMID: 18063227]

[13]
Kulandaivelu, U.; Padmini, V.G.; Suneetha, K.; Shireesha, B.; Vidyasagar, J.V.; Rao, T.R.; K N, J.; Basu, A.; Jayaprakash, V. Arch. Pharm. (Weinheim),  2011, 344(2), 84-90.
 [http://dx.doi.org/10.1002/ardp.201000201] [PMID: 21290424]

[14]
Pham, V.H.; Phan, T.P.D.; Phan, D.C.; Vu, B.D. Molecules,  2020, 25(2), 324.
 [http://dx.doi.org/10.3390/molecules25020324]

[15]
Gouvea, F.A.; Vasconcellos, G.A.; Berwaldt, A.C.P.S.; Neto, G.; Fischer, R.P.; Sakata, W.P.; Almeida, W.P.; Cunico, W. Eur. J. Med. Chem.,  2016, 118, 259-265.
 [http://dx.doi.org/10.1016/j.ejmech.2016.04.028] [PMID: 27131068]

[16]
Monte, C.D.; Carradori, S.; Bizzarri, B.; Bolasco, A.; Caprara, F.; Mollica, A.; Rivanera, D.; Mari, E.; Zicari, A.; Akdemir, A. Eur. J. Med. Chem.,  2016, 107, 82-96.
 [http://dx.doi.org/10.1016/j.ejmech.2015.10.048] [PMID: 26562544]

[17]
Ottanà, R.; Maccari, R.; Giglio, M.; Del Corso, A.; Cappiello, M.; Mura, U.; Cosconati, S.; Marinelli, L.; Novellino, E.; Sartini, S.; La Motta, C.; Da Settimo, F. Eur. J. Med. Chem.,  2011, 46(7), 2797-2806.
 [http://dx.doi.org/10.1016/j.ejmech.2011.03.068] [PMID: 21531055]

[18]
Önen-Bayram, F.E.; Buran, K.; Durmaz, I.; Berk, B.; Cetin-Atalay, R. MedChemComm,  2015, 6(1), 90-93.
 [http://dx.doi.org/10.1039/C4MD00306C]

[19]
Aly, A.A.; Ishak, E.A.; El Malah, T.; Brown, A.B.; Elayat, W.M. J. Heterocycl. Chem.,  2015, 52, 1758-1764.
 [http://dx.doi.org/10.1002/jhet.2248]

[20]
Dondoni, A. Phosphorus and Sulfur and the Related Elements,  1985, 24(1-2), 1-38.
 [http://dx.doi.org/10.1080/03086648508073395]

[21]
ZelIsko, N.I.; Demchuk, I.L.; Λesyk, R.B. Ukr. Biochem. J.,  2016, 2, 105-112.

[22]
Yurttas, L.; Özkay, Y.; Gençer, K.; Acar, U. J. Chem.,  2015, 464379, 7.

[23]
da Silva, E.B.; Oliveira e Silva, D.A.; Oliveira, A.R.; da Silva Mendes, C.H.; dos Santos, T.A.R.; da Silva, A.C.; de Castro, M.C.A.; Ferreira, R.S.; Moreira, D.R.M.; Cardoso, M.V.O.; de Simone, C.A.; Pereira, V.R.A.; Leite, A.C.L. Eur. J. Med. Chem.,  2017, 130, 39-50.
 [http://dx.doi.org/10.1016/j.ejmech.2017.02.026] [PMID: 28242550]

[24]
Altıntop, M.; Özdemir, A.; Turan-Zitouni, G.; Ilgın, S.; Atlı, Ö.; Demirci, F.; Kaplancıklı, Z. Molecules,  2014, 19(9), 14809-14820.
 [http://dx.doi.org/10.3390/molecules190914809] [PMID: 25232704]

[25]
Sahu, S.; Ghosh, S.K.; Gahtori, P.; Pratap Singh, U.; Bhattacharyya, D.R.; Bhat, H.R. Pharmacol. Rep.,  2019, 71(5), 762-767.
 [http://dx.doi.org/10.1016/j.pharep.2019.04.006] [PMID: 31351317]

[26]
Ghabbour, H.A.; Kadi, A.A.; ElTahir, K.E.H.; Angawi, R.F.; El-Subbagh, H.I. Med. Chem. Res.,  2015, 24(8), 3194-3211.
 [http://dx.doi.org/10.1007/s00044-015-1371-3]

[27]
Meleddu, R.; Distinto, S.; Corona, A.; Tramontano, E.; Bianco, G.; Melis, C.; Cottiglia, F.; Maccioni, E. J. Enzyme Inhib. Med. Chem.,  2017, 32(1), 130-136.
 [http://dx.doi.org/10.1080/14756366.2016.1238366] [PMID: 27766892]

[28]
Łączkowski, K.Z.; Konklewska, N.; Biernasiuk, A.; Malm, A.; Sałat, K.; Furgała, A.; Dzitko, K.; Bekier, A.; BaranowskaŁączkowska, A.; Paneth, A. Med. Chem. Res.,  2018, 27(9), 2125-2140.
 [http://dx.doi.org/10.1007/s00044-018-2221-x] [PMID: 30220831]

[29]
Benmohammed, A.; Khoumeri, O.; Djafri, A.; Terme, T.; Vanelle, P. Molecules,  2014, 19(3), 3068-3083.
 [http://dx.doi.org/10.3390/molecules19033068] [PMID: 24619352]

[30]
Benmohammed, A.; Rekiba, N.; Sehanine, Y.; Louail, A.A.; Khoumeri, O.; Kadiri, M.; Djafri, A.; Terme, T.; Vanelle, P. Monatsh. Chem.,  2021, 152(8), 977-986.
 [http://dx.doi.org/10.1007/s00706-021-02823-6]

[31]
Rekiba, N.; Benmohammed, A.; Khanoussi, S.; Djafri, A.; Thibonnet, J. Molbank,  2021, 2021(4), M1284.
 [http://dx.doi.org/10.3390/M1284]

[32]
Ma, J.; Bao, G.; Wang, L.; Li, W.; Xu, B.; Du, B.; Lv, J.; Zhai, X.; Gong, P. Eur. J. Med. Chem.,  2015, 96, 173-186.
 [http://dx.doi.org/10.1016/j.ejmech.2015.04.018] [PMID: 25874341]

[33]
Haribabu, J.; Sabapathi, G.; Tamizh, M.M.; Balachandran, C.; Bhuvanesh, N.S.P.; Venuvanalingam, P.; Karvembu, R. Organometallics,  2018, 37(8), 1242-1257.
 [http://dx.doi.org/10.1021/acs.organomet.8b00004]

[34]
Bharti, N.; Sharma, S.S.; Naqvi, F.; Azam, A. Bioorg. Med. Chem.,  2003, 11, 2923-2929.
 [http://dx.doi.org/10.1016/S0968-0896(03)00213-X] [PMID: 12788362]

[35]
Serda, M.; Małecki, J.G.; Mrozek-Wilczkiewicz, A.; Musioł, R.; Polański, J. J. Mol. Struct.,  2013, 1037, 63-72.
 [http://dx.doi.org/10.1016/j.molstruc.2012.11.050]

[36]
Ferreira Alves, J.E.; Ferreira de Oliveira, J.; Couto de Lima Souza, T.R.; Olimpio de Moura, R.; Bezerra de Carvalho, L., Junior; do Carmo Alves de Lima, M.; Vitalino de Almeida, S.M. Int. J. Biol. Macromol.,  2021, 170, 622-635.
 [http://dx.doi.org/10.1016/j.ijbiomac.2020.12.153] [PMID: 33359805]

[37]
Obydennov, K.L.; Khamidullina, L.A.; Galushchinskiy, A.N.; Shatunova, S.A.; Kosterina, M.F.; Kalinina, T.A.; Fan, Z.; Glukhareva, T.V.; Morzherin, Y.Y. J. Agric. Food Chem.,  2018, 66(24), 6239-6245.
 [http://dx.doi.org/10.1021/acs.jafc.8b02151] [PMID: 29807429]

[38]
Hsiu Shih, M.; Ke, Y. Bioorg. Med. Chem.,  2004, 12, 4633-4643.

[39]
Makam, P.; Kankanala, R.; Prakash, A.; Kannan, T. Eur. J. Med. Chem.,  2013, 69, 564-576.
 [http://dx.doi.org/10.1016/j.ejmech.2013.08.054] [PMID: 24095750]

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DOI https://dx.doi.org/10.2174/1570178619666220827152700	Print ISSN 1570-1786
Publisher Name Bentham Science Publisher	Online ISSN 1875-6255

Letters in Organic Chemistry

Synthesis of New Thiazolidinones and Thiazoles in Indole Series

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