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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Review Article

A Multifaceted Scaffold for Building Bioactive Compounds: Phenothiazine

Author(s): Prabhat Kumar Upadhyay*, Shilpi Pathak, Raghav Mishra, Rajesh Kumar and Ankit Jain

Volume 20, Issue 7, 2023

Published on: 13 January, 2023

Page: [618 - 631] Pages: 14

DOI: 10.2174/1570178620666221202100529

Price: $65

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Abstract

In the growing field of heterocyclic compounds, phenothiazine and the associated nucleus are among the most significant potential scaffolds with excellent pharmacological activities. The knowledge of chemistry, synthetic routes, and various physicochemical parameters of these compounds draws particular attention to create a chemical library. Related compounds synthesized by various routes have diverse pharmacological functions. The exhaustive search of phenothiazine literature helps the medicinal chemists who develop the molecules for designing new drugs. A broad view of the synthetic routes has been outlined in this study. This paper includes the chemistry, physiochemical properties, and various biological activities of phenothiazine and related compounds.

Keywords: Phenothiazine, synthesis, chemical library, biological activity, therapeutic, heterocyclic moieties.

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[1]
Agrawal, N. Curr. Chem. Lett., 2021, 9(1), 119-138.
[http://dx.doi.org/10.5267/j.ccl.2020.11.002]
[2]
Agrawal, N.; Mishra, P. Comput. Biol. Chem., 2019, 79, 63-72.
[http://dx.doi.org/10.1016/j.compbiolchem.2019.01.012] [PMID: 30731360]
[3]
Mishra, I.; Sachan, N. ECS Trans., 2022, 107(1), 17745-17768.
[http://dx.doi.org/10.1149/10701.17745ecst]
[4]
Isha; Sachan, N. J. Pharm. Res. Int., 2021, 33(53A), 24-32.
[5]
Sarmiento, G.P.; Vitale, R.G.; Afeltra, J.; Moltrasio, G.Y.; Moglioni, A.G. Synthesis and antifungal activity of some substituted phenothiazines and related compounds. Eur. J. Med. Chem., 2011, 46, 101-105.
[6]
Luo, J.S.; Wan, Z.Q.; Jia, C.Y. Chin. Chem. Lett., 2016, 27(8), 1304-1318.
[http://dx.doi.org/10.1016/j.cclet.2016.07.002]
[7]
Abu-Abdoun, I.I.; Ledwith, A. Eur. Polym. J., 1997, 33(10-12), 1671-1677.
[http://dx.doi.org/10.1016/S0014-3057(97)00044-X]
[8]
Albery, W.J.; Foulds, A.W.; Hall, K.J.; Hillman, A.R.; Egdell, R.G.; Orchard, A.F. Nature, 1979, 282(5741), 793-797.
[http://dx.doi.org/10.1038/282793a0]
[9]
Gooley, C.M.; Keyzer, H.; Setchell, F. Nature, 1969, 223(5201), 80-81.
[http://dx.doi.org/10.1038/223080a0] [PMID: 5792438]
[10]
Yamamura, T.; Suzuki, K.; Yamaguchi, T.; Nishiyama, T. Bull. Chem. Soc. Jpn., 1997, 70(2), 413-419.
[http://dx.doi.org/10.1246/bcsj.70.413]
[11]
Jiang, Y.T.; Zhang, Q. Dyestuffs and Coloration., 2010, 03, 35-41.
[12]
Foye, O.W. Principles of Medicinal Chemistry, 3rd ed; Lippincott Williams & Wilkins Publishers: Philadelphia, 1999, p. 196.
[13]
Mosnaim, A.D.; Ranade, V.V.; Wolf, M.E.; Puente, J.; Antonieta Valenzuela, M. Am. J. Ther., 2006, 13(3), 261-273.
[http://dx.doi.org/10.1097/01.mjt.0000212897.20458.63] [PMID: 16772768]
[14]
El-Said, M.K. Pharmazie, 1981, 36, 678.
[15]
Tilak, S.R.; Tyagi, R.; Goel, B.; Saxena, K.K. Indian Drugs, 1998, 35, 221.
[16]
Domínguez, J.N.; López, S.; Charris, J.; Iarruso, L.; Lobo, G.; Semenov, A.; Olson, J.E.; Rosenthal, P.J. J. Med. Chem., 1997, 40(17), 2726-2732.
[http://dx.doi.org/10.1021/jm970266p] [PMID: 9276017]
[17]
Lin, G.; Midha, K.K.; Hawes, E.M. J. Heterocycl. Chem., 1991, 28(2), 215-219.
[http://dx.doi.org/10.1002/jhet.5570280202]
[18]
Raval, J.P.; Desai, K.R. ARKIVOC, 2005, 2005(13), 21-28.
[http://dx.doi.org/10.3998/ark.5550190.0006.d03]
[19]
Viveros, M.; Amaral, L. Int. J. Antimicrob. Agents, 2001, 17, 225.
[20]
Amaral, L.; Kristiansen, J.E. Int. J. Antimicrob. Agents, 2000, 14(3), 173-176.
[http://dx.doi.org/10.1016/S0924-8579(99)00153-3] [PMID: 10773484]
[21]
Motohashi, N.; Kawase, M.; Saito, S.; Sakagami, H. Curr. Drug Targets, 2000, 1(3), 237-246.
[http://dx.doi.org/10.2174/1389450003349191] [PMID: 11465073]
[22]
Motohashi, N.; Kawase, M.; Saito, S.; Kurihara, T.; Satoh, K.; Nakashima, H.; Premanathan, M.; Arakaki, R.; Sakagami, H.; Molnár, J. Int. J. Antimicrob. Agents, 2000, 14(3), 203-207.
[http://dx.doi.org/10.1016/S0924-8579(99)00156-9] [PMID: 10773488]
[23]
Lednicer, D.; Mitscher, L.A. The Organic chemistry of Drug Synthesis; John Wiley & Sons: New York, 1980, Vol. 1, pp. 372-392.
[24]
Hu, W.; Zhang, S. J. Org. Chem., 2015, 80(12), 6128-6132.
[http://dx.doi.org/10.1021/acs.joc.5b00568] [PMID: 26028127]
[25]
Wu, S.; Hu, W.Y.; Zhang, S.L. RSC Advances, 2016, 6(29), 24257-24260.
[http://dx.doi.org/10.1039/C6RA01295G]
[26]
Zheng, Z.N.; Jun, Y. Petrochem. Engineering., 2018, 15, 622-626.
[27]
Lu, C. China, 106117305, 2016, 11-16.
[28]
Liao, Y.; Liu, X.; Liu, C.; Zhou, G.; Wang, W.; Mai, X.; Zhong, H.; Tu, G.; Huang, H.; Wang, B. Asian J. Chem., 2013, 25(15), 8587-8592.
[http://dx.doi.org/10.14233/ajchem.2013.14853]
[29]
Dixit, Y.; Dixit, R.; Gautam, N.; Gautam, D.C.E-J. Chem, 2008, 5(s1), 1063-1068.
[http://dx.doi.org/10.1155/2008/809419]
[30]
Rajasekaran, A.; Devi, K.S. Med. Chem. Res., 2013, 22(6), 2578-2588.
[http://dx.doi.org/10.1007/s00044-012-0255-z]
[31]
Gautam, N.; Guleria, A.; Sharma, M.; Gupta, S.; Goyal, A.; Gautam, D.C. Curr. Bioact. Compd., 2014, 10(3), 189-195.
[http://dx.doi.org/10.2174/1573407210666140728174315]
[32]
Saranya, A.V.; Ravi, S. Res. Chem. Intermed., 2014, 40(8), 3085-3093.
[http://dx.doi.org/10.1007/s11164-013-1153-9]
[33]
Adekola, E.O.; Ezema, B.E.; Ayogu, J.I.; Ugwu, D.I.; Ezema, C.G.; Nwasi, A.P.; Ike, C.O. Orient. J. Chem., 2014, 30(4), 1493-1500.
[http://dx.doi.org/10.13005/ojc/300406]
[34]
Venkatesan, K.; Satyanarayana, V.S.V.; Mohanapriya, K.; Khora, S.S.; Sivakumar, A. Res. Chem. Intermed., 2015, 41(2), 595-607.
[http://dx.doi.org/10.1007/s11164-013-1213-1]
[35]
Bansode, T.N.; Shelke, J.V.; Dongre, V.G. Eur. J. Med. Chem., 2009, 44(12), 5094-5098.
[http://dx.doi.org/10.1016/j.ejmech.2009.07.006] [PMID: 19651462]
[36]
Bansode, T.N.; Rangari, R.P. Shimpi, P.A. Pharm. Chem. J., 2014, 48(7), 430-433.
[http://dx.doi.org/10.1007/s11094-014-1125-4]
[37]
Swarnkar, P.K.; Kriplani, P.; Gupta, G.N.; Ojha, K.G.E-J. Chem, 2007, 4(1), 14-20.
[http://dx.doi.org/10.1155/2007/402673]
[38]
Upadhyay, K.E-J. Chem, 2009, 6(s1), S254-S258.
[http://dx.doi.org/10.1155/2009/901646]
[39]
Satyanarayana, B.; Muralikrishna, P.; Kumar, D.R.; Ramachandran, D. J. Chem. Pharm. Res., 2013, 5, 262-266.
[40]
Arulmurugan, S.; Kavitha, H.P.; Venkatraman, B.R. Orbital: Electron. J. Chem., 2010, 2, 271-276.
[41]
Vanangamudi, G.; Ranganathan, K.; Thirunarayanan, G. World. J. Chem., 2012, 7, 22-33.
[42]
Siddiqui, A.B.; Trivedi, A.R.; Kataria, V.B.; Shah, V.H. Bioorg. Med. Chem. Lett., 2014, 24(6), 1493-1495.
[http://dx.doi.org/10.1016/j.bmcl.2014.02.012] [PMID: 24582983]
[43]
He, C.X.; Meng, H.; Zhang, X.; Cui, H.Q.; Yin, D.L. Chin. Chem. Lett., 2015, 26(8), 951-954.
[http://dx.doi.org/10.1016/j.cclet.2015.03.027]
[44]
Dunn, E.A.; Roxburgh, M.; Larsen, L.; Smith, R.A.J.; McLellan, A.D.; Heikal, A.; Murphy, M.P.; Cook, G.M. Bioorg. Med. Chem., 2014, 22(19), 5320-5328.
[http://dx.doi.org/10.1016/j.bmc.2014.07.050] [PMID: 25150092]
[45]
Bate, A.B.; Kalin, J.H.; Fooksman, E.M.; Amorose, E.L.; Price, C.M.; Williams, H.M.; Rodig, M.J.; Mitchell, M.O.; Cho, S.H.; Wang, Y.; Franzblau, S.G. Bioorg. Med. Chem. Lett., 2007, 17(5), 1346-1348.
[http://dx.doi.org/10.1016/j.bmcl.2006.11.091] [PMID: 17188865]
[46]
Madrid, P.B.; Polgar, W.E.; Toll, L.; Tanga, M.J. Bioorg. Med. Chem. Lett., 2007, 17(11), 3014-3017.
[http://dx.doi.org/10.1016/j.bmcl.2007.03.064] [PMID: 17407813]
[47]
Sharma, R.; Samadhiya, P.; Srivastava, S.; Srivastava, S. J. Serb. Chem. Soc., 2012, 77(1), 17-26.
[http://dx.doi.org/10.2298/JSC100924152S]
[48]
Ritu, S.; Pushkal, S.; Srivastava, S.D.; Srivastava, S.K. Org. Commun., 2011, 4(2), 42.
[49]
Sadanandam, Y.S.; Shetty, M.M.; Rao, A.B.; Rambabu, Y. Eur. J. Med. Chem., 2009, 44(1), 197-202.
[http://dx.doi.org/10.1016/j.ejmech.2008.02.028] [PMID: 18400337]
[50]
Al Zahrani, N.A.; El-Shishtawy, R.M.; Elaasser, M.M.; Asiri, A.M. Molecules, 2020, 25(19), 4566.
[http://dx.doi.org/10.3390/molecules25194566] [PMID: 33036301]
[51]
Belei, D.; Dumea, C.; Samson, A.; Farce, A.; Dubois, J.; Bîcu, E.; Ghinet, A. Bioorg. Med. Chem. Lett., 2012, 22(14), 4517-4522.
[http://dx.doi.org/10.1016/j.bmcl.2012.06.007] [PMID: 22738631]
[52]
Silva, G.A.; Costa, L.M.M.; Brito, F.C.F.; Miranda, A.L.P.; Barreiro, E.J.; Fraga, C.A.M. Bioorg. Med. Chem., 2004, 12(12), 3149-3158.
[http://dx.doi.org/10.1016/j.bmc.2004.04.009] [PMID: 15158783]
[53]
Kumar, D.; Agarwal, R.C.; Bhati, S.K.; Kumar, A. Orient. J. Chem., 2010, 26, 497.
[54]
Sharma, S.; Srivastava, V.K.; Kumar, A. Pharmazie, 2005, 60(1), 18-22.
[PMID: 15700774]
[55]
Kalkanidis, M.; Klonis, N.; Tilley, L.; Deady, L.W. Biochem. Pharmacol., 2002, 63(5), 833-842.
[http://dx.doi.org/10.1016/S0006-2952(01)00840-1] [PMID: 11911834]
[56]
Kubota, K.; Kurebayashi, H.; Miyachi, H.; Tobe, M.; Onishi, M.; Isobe, Y. Bioorg. Med. Chem. Lett., 2009, 19(10), 2766-2771.
[http://dx.doi.org/10.1016/j.bmcl.2009.03.124] [PMID: 19362477]
[57]
Bisi, A.; Meli, M.; Gobbi, S.; Rampa, A.; Tolomeo, M.; Dusonchet, L. Bioorg. Med. Chem., 2008, 16(13), 6474-6482.
[http://dx.doi.org/10.1016/j.bmc.2008.05.040] [PMID: 18522868]
[58]
Venkatesan, K.; Satyanarayana, V.S.V.; Sivakumar, A.; Ramamurthy, C.; Thirunavukkarusu, C. J Heterocyclic Chem, 2020, 1-7.
[http://dx.doi.org/10.1002/jhet.3980]
[59]
Mucsi, I.; Molnár, J.; Motohashi, N. Int. J. Antimicrob. Agents, 2001, 18(1), 67-72.
[http://dx.doi.org/10.1016/S0924-8579(01)00323-5] [PMID: 11463529]
[60]
Gautam, V.; Sharma, M.; Samarth, R.; Gautam, N.; Kumar, A.; Sharma, I.K.; Gautam, D.C. Phosphorus Sulfur Silicon Relat Elem, 2007, 182(6), 1381-1392. Analele Universităţii din Bucureşti – Chimie (serienouă), 2009, 18,, 85-94.

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