Main Article Content
Abstract
In this article, acid hydrazide 2, a functional group, was synthesized by the reaction of (4-chloro-12-methyl-16,17-dihydro-15-thia-6,11-diaza-cyclopenta[a]phenanthren-7-ylsulfanyl)acetic acid ethyl ester (1) with hydrazine yield (4-chloro-12-methyl-16,17-dihydro-15-thia-6,11-diazacyclopenta[a]phenanthren-7-ylsulfanyl)acetic acid hydrazide (2) is discussed. The reactive acid hydrazide compound 2 was utilized for the synthesis of amides 3, Schiff’s bases 4 and thiazolidine 5 derivatives. The structures of target compounds were confirmed by elemental analysis and spectral data. The antimicrobial activity of new compounds were studied against Streptococcus sp., Bacillus megaterium, Staphylococcus aureus, Escherichia coli, Bacillus cereus, Bacillus subtilis, Proteus valgaris and Pseudomonas aeroginosa by the agar well diffusion method. Compounds 4b, 5a, 5b and 5c showed good antimicrobial activity.
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References
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References
A.K. Jain, A. Vaidya, V. Ravichandran, S.K. Kashaw and R.K. Agrawal, Recent Developments and Biological Activities of Thiazolidinone Derivatives: A Review, Bioorg. Med. Chem., 20, 3378 (2012); https://doi.org/10.1016/j.bmc.2012.03.069
M.J. Nanjan, M. Mohammed, B.R. Prashantha Kumar and M.J.N. Chandrasekar, Thiazolidinediones as Antidiabetic Agents: A Critical Review, Bioorg. Chem., 77, 548 (2018); https://doi.org/10.1016/j.bioorg.2018.02.009
A. Ahmadi, M. Khalili, S. Samavat, E. Shahbazi and B. Nahri-Niknafs, Synthesis and Evaluation of the Hypoglycemic and Hypolipidemic Activity of Novel Arylidene Thiazolidinedione Analogson a Type 2 Diabetes Model, Pharm. Chem. J., 50, 165 (2016); https://doi.org/10.1007/s11094-016-1416-z
N. Thangavel, M. Al-Bratty, S.A. Javed, W. Ahsan and H.A. Alhazmi, Targeting Peroxisome Proliferator-Activated Receptors Using Thiazo-lidinediones: Strategy for Design of Novel Antidiabetic Drugs, Int. J. Med. Chem., 2017, 1069718 (2017); https://doi.org/10.1155/2017/1069718
S.K. Shrivastava, A. Batham, S.K. Sinha, T.K. Parida, D. Garabadu and P.K. Choubey, Design, Synthesis and Evaluation of Novel Thiazo-lidinedione Derivatives as Anti-Hyperglycemic and Anti-Hyperlipidemic Agents, Med. Chem. Res., 25, 2258 (2016); https://doi.org/10.1007/s00044-016-1675-y
A.S. Chavan, A.S. Kharat, M.R. Bhosle and R.A. Mane, Baker’s Yeast Catalyzed One-Pot Synthesis of Bioactive 2-[Benzylidene(or Pyrazol-4-yl-methylene)hydrazono]-1,3-thiazolidin-4-one-5-yl-acetic Acids, Heterocycl. Commun., 24, 103 (2018); https://doi.org/10.1515/hc-2017-0130
P.K. Sharma, N. Chandak, P. Kumar, C. Sharma and K.R. Aneja, Synthesis and Biological Evaluation of Some 4-Functionalized Pyrazoles as Antimicrobial Agents, Eur. J. Med. Chem., 46, 1425 (2011); https://doi.org/10.1016/j.ejmech.2011.01.060
A.R. Deshmukh, S.T. Dhumal, L.U. Nawale, V.M. Khedkar, D. Sarkar and R.A. Mane, Dicationic Liquid Mediated Synthesis of Tetrazolo-quinolinyl Methoxy Phenyl 4-thiazolidinones and their Antibacterial and Antitubercular Evaluation, Synth. Commun., 49, 587 (2019); https://doi.org/10.1080/00397911.2018.1564928
G. Capan, N. Ulusoy, N. Ergenc and M. Kiraz, New 6-Phenylimidazo-[2,1-b]thiazole Derivatives: Synthesis and Antifungal Activity, Monatsh. Chem., 130, 1399 (1999); https://doi.org/10.1007/PL00010200
A. Ceriello, Thiazolidinediones as Anti-inflammatory and Anti-atherogenic Agents, New 6-Phenylimidazo[2,1-b]thiazole Derivatives: Synthesis and Antifungal Activity, Diabetes Metab. Res. Rev., 24, 14 (2008); https://doi.org/10.1002/dmrr.790
C. Dwivedi, T.K. Gupta and S.S. Parmar, Substituted Thiazolidones as Anticonvulsants, J. Med. Chem., 15, 553 (1972); https://doi.org/10.1021/jm00275a031
H.N. Hafez and A.R. El-Gazzar, Synthesis and Antitumor Activity of Substituted Triazolo[4,3-a]pyrimidin-6-sulfonamide with an Incorpo-rated Thiazolidinone Moiety, Bioorg. Med. Chem. Lett., 19, 4143 (2009); https://doi.org/10.1016/j.bmcl.2009.05.126
L. Barreca, A. Chimirri, L. De Luca, A.-M. Monforte, P. Monforte, A. Rao, M. Zappalà, J. Balzarini, E. De Clercq, C. Pannecouque and M. Witvrouw, Bioorg. Med. Chem. Lett., 11, 1793 (2001); https://doi.org/10.1016/S0960-894X(01)00304-3
C.J. Andres, J.J. Bronson, S.V. D’Andrea, M.S. Deshpande, P.J. Falk, K.A. Grant-Young, W.E. Harte, H.-T. Ho, P.F. Misco, J.G. Robertson, D. Stock, Y. Sun and A.W. Walsh, Bioorg. Med. Chem. Lett., 10, 715 (2000); https://doi.org/10.1016/S0960-894X(00)00073-1
L. Popiolek, I. Piatkowska-Chmiel, M. Gawronska-Grzywacz, A. Biernasiuk, M. Izdebska, M. Herbet, M. Sysa, A. Malm, J. Dudka and M. Wujec, New Hydrazide-Hydrazones and 1,3-Thiazolidin-4-ones with 3-Hydroxy-2-naphthoic Moiety: Synthesis, in vitro and in vivo Studies, Biomed. Pharmacother., 103, 1337 (2018); https://doi.org/10.1016/j.biopha.2018.04.163
C. Saiz, C. Pizzo, E. Manta, P. Wipf and S.G. Mahler, Microwave-Assisted Tandem Reactions for the Synthesis of 2-Hydrazolyl-4-thiazolidinones, Tetrahedron Lett., 50, 901 (2009); https://doi.org/10.1016/j.tetlet.2008.12.020
R.B. Toche, B.P. Pagar, R.R. Zoman, G.B. Shinde and M.N. Jachak, Synthesis of Novel Benzo[h][1,6]naphthyridine Derivatives from 4-Aminoquinoline and Cyclic b-Ketoester, Tetrahedron, 66, 5204 (2010); https://doi.org/10.1016/j.tet.2010.04.085
R.B. Toche, B.K. Ghotekar, M.A. Kazi and M.N. Jachak, Synthesis of Benzohetero[3,2-a]pyrimidines using Cyclic b-Keto Lactone as a Building Block, Monatsh. Chem., 140, 235 (2009); https://doi.org/10.1007/s00706-008-0062-x
R.B. Toche, B.K. Ghotekar, D.B. Kendre, M.A. Kazi and M.N. Jachak, An Efficient Synthesis of Pyrazolo[3,4-b ]pyrrolo[2,3-d ]pyridines from 5-Aminopyrazoles and Cyclic b-Keto ester, J. Heterocycl. Chem., 45, 1711 (2008); https://doi.org/10.1002/jhet.5570450624
R.B. Toche, B.K. Ghotekar, M.A. Kazi, S.P. Patil and M.N. Jachak, New Approach for the Synthesis of Pyrido[l,2-a]pyrimidines, Schol. Res. Exch., 2008, 434329 (2008); https://doi.org/10.3814/2008/434329
B.K. Ghotekar, M.A. Kazi, M.N. Jachak and R.B. Toche, Effect of Substituents on Absorption and Fluorescence Properties of Pyrazolo-[3,4-b]pyrrolo[2,3-d]pyridines, Can. J. Chem., 86, 1070 (2008); https://doi.org/10.1139/v08-155
R.B. Toche, B.K. Ghotekar, M.A. Kazi, D.B. Kendre and M.N. Jachak, Synthesis of Fused Pyrimidines from Amines and Cyclic b-Formylesters, Tetrahedron, 63, 8157 (2007); https://doi.org/10.1016/j.tet.2007.05.123
R.V. Rote, D.P. Shelar, S.R. Patil, S.S. Shinde, R.B. Toche and M.N. Jachak, Effect of Donor-Acceptor Chromophores on Photophysical Properties of Newly Synthesized Pyrazolo-Pyrrolo-Pyrimidines (PPP), J. Fluoresc., 21, 453 (2011); https://doi.org/10.1007/s10895-010-0704-3