One Pot Three-Component Synthesis of Thiazolidinone Derivatives of 4-Methylthiazole-5-carbaldehyde and its Biological Evaluation

Ramesh M. Borde; Satish B. Jadhav; Mahendra A. Gaikwad; Achut S.Munde

doi:10.14233/ajomc.2018.AJOMC-P145

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Abstract

Thiazolidin-4-one is synthesized by highly efficient three-component reaction system. Three component involved are 2-(4-phenyl substituted)-4-methylthiazole-5-carbaldehyde (1) with p-substituted aniline (2), in presence of p-toluene sulfonic acid (p-TsOH) as an acid catalyst in toluene as an solvent with separation of azeotropic water, followed by cyclo-condensation with mercaptoacetic acid in a single pot. A series of compounds 2-(4-methyl-2-phenylthiazol-5-yl)-3-phenylthiazolidin -4-one (4a-h) were synthesized and structures of these compounds were elucidated by IR, ¹H NMR, GC-MS. Synthesized compounds were screened for antibacterial activity against Gram-negative (E. coli and P. aeruginosa) and Gram-positive (S. aureus and B. subtilis) bacteria, antifungal activity against pathogenic fungal strains and in vitro anti-inflammatory activities. Some of the compounds exhibited promising antibacterial, antifungal and anti-inflammatory activities.

Keywords

p-Substituted aniline p-Toluene sulfonic acid Mercaptoacetic acid Thiazolidinone Antimicrobial activity Anti-inflammatory activities

How to Cite

M. Borde, R., B. Jadhav, S., A. Gaikwad, M., & S.Munde, A. (2018). One Pot Three-Component Synthesis of Thiazolidinone Derivatives of 4-Methylthiazole-5-carbaldehyde and its Biological Evaluation. Asian Journal of Organic & Medicinal Chemistry, 3(4), 159–163. https://doi.org/10.14233/ajomc.2018.AJOMC-P145

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References

K.D. Hargrave, F.K. Hess and J.T. Oliver, N-(4-Substituted-thiazolyl)-oxamic Acid Derivatives, New Series of Potent, Orally Active Antiallergy Agents, J. Med. Chem., 26, 1158 (1983); https://doi.org/10.1021/jm00362a014.
W.C. Patt, H.W. Hamilton, M.D. Taylor, M.J. Ryan, D.G. Taylor Jr., C.J.C. Connolly, A.M. Doherty, S.R. Klutchko and I. Sircar, Structure-Activity Relationships of a Series of 2-Amino-4-thiazole Containing Renin Inhibitors, J. Med. Chem., 35, 2562 (1992); https://doi.org/10.1021/jm00092a006.
B.S. Holla, K.V. Malini, B.S. Rao, B.K. Sarojini and N.S. Kumari, Synthesis of Some New 2,4-Disubstituted Thiazoles as Possible Anti-bacterial and Anti-inflammatory agents, Eur. J. Med. Chem., 38, 313 (2003); https://doi.org/10.1016/S0223-5234(02)01447-2.
J.C. Jaen, L.D. Wise, B.W. Caprathe, H. Tecle, S. Bergmeier, C.C. Humblet, T.G. Heffner, L.T. Meltzer and T.A. Pugsley, 4-(1,2,5,6-Tetrahydro-1-alkyl-3-pyridinyl)-2-thiazolamines: A Novel Class of Compounds with Central Dopamine Agonist Properties, J. Med. Chem., 33, 311 (1990); https://doi.org/10.1021/jm00163a051.
K. Tsuji and H. Ishikawa, Synthesis and Anti-pseudomonal Activity of New 2-isocephems with a Dihydroxypyridone Moiety at C-7, Bioorg. Med. Chem. Lett., 4, 1601 (1994); https://doi.org/10.1016/S0960-894X(01)80574-6.
F.W. Bell, A.S. Cantrell, M. Hoegberg, S.R. Jaskunas, N.G. Johansson, C.L. Jordan, M.D. Kinnick, P. Lind and J.M. Morin, Phenethylthiazol-ethiourea (PETT) Compounds, A New Class of HIV-1 Reverse Transcri-ptase Inhibitors. 1. Synthesis and Basic Structure-Activity Relationship Studies of PETT Analogs, J. Med. Chem., 38, 4929 (1995); https://doi.org/10.1021/jm00025a010.
V. Ergenc, G. Capan, N.S. Gunay, S. Ozkirimli, M. Gungor, S. Ozbey and E. Kendi, Arch. Pharm. (Weinheim), Synthesis and Hypnotic Activity of New 4-Thiazolidinone and 2-Thioxo-4,5-imidazolidinedione Derivatives, 332, 343 (1999); https://doi.org/10.1002/(SICI)1521-4184(199910)332:10<343::AID-ARDP343>3.0.CO;2-0.
J.S. Carter, S. Kramer, J.J. Talley, T. Penning, P. Collins, M.J. Graneto, K. Seibert, C.M. Koboldt, J. Masferrer and B. Zweifel, Synthesis and Activity of Sulfonamide-Substituted 4,5-Diaryl Thiazoles as Selective Cyclooxygenase-2 inhibitors, Bioorg. Med. Chem. Lett., 9, 1171 (1999); https://doi.org/10.1016/S0960-894X(99)00157-2.
A. Badorc, M.F. Bordes, P. De Cointet, P. Savi, A. Bernat, A. Lale, M. Petitou, J.P. Maffrand and J.M. Herbert, New Orally Active Non-Peptide Fibrinogen Receptor (GpIIb-IIIa) Antagonists: Identification of Ethyl 3-[N-[4-[4-[Amino[(ethoxycarbonyl)imino]methyl]phenyl]-1,3-thiazol-2-yl]-N-[1-[(ethoxycarbonyl)methyl]piperid-4-yl]amino]-propionate (SR 121787) as a Potent and Long-Acting Antithrombotic Agent, J. Med. Chem., 40, 3393 (1997); https://doi.org/10.1021/jm970240y.
J. Rudolph, H. Theis, R. Hanke, R. Endermann, L. Johannsen and F.U. Geschke, seco-Cyclothialidines: New Concise Synthesis, Inhibitory Activity toward Bacterial and Human DNA Topoisomerases and Antibacterial Properties, J. Med. Chem., 44, 619 (2001); https://doi.org/10.1021/jm0010623.
A.A. Hassan, Y.R. Ibrahim, E.M. El-Sheref, M. Abdel-Aziz, S. Bräse and M. Nieger, Synthesis and Antibacterial Activity of 4-Aryl-2-(1-substituted ethylidene)thiazoles, Arch. Pharm. (Weinheim), 346, 562 (2013); https://doi.org/10.1002/ardp.201300099.
V.S. Palekar, A.J. Damle and S.R. Shukla, Synthesis and Antibacterial Activity of Some Novel bis-1,2,4-Triazolo[3,4-b]-1,3,4-thiadiazoles and bis-4-Thiazolidinone Derivatives from Terephthalic Dihydrazide, Eur. J. Med. Chem., 44, 5112 (2009); https://doi.org/10.1016/j.ejmech.2009.07.023.
R.P. Pawar, N.M. Andurkar and Y.B. Vibhute, Studies on Synthesis and Antibacterial Activity of Some New Schiff Bases, 4-Thiazolidinones and 2-Azetidinones, J. Indian Chem. Soc., 76, 271 (1999).
V.P. Trivedi, N.K. Undavia and P.B. Trivadi, Synthesis and Biological Activity of Some New 4-Thiazolidinone Derivatives, J. Indian Chem. Soc., 81, 506 (2004).
G. Küçükgüzel, A. Kocatepe, E. De Clercq, F. Sahin and M. Güllüce, Synthesis and Biological Activity of 4-Thiazolidinones, Thiosemi-carbazides Derived from Diflunisal Hydrazide, Eur. J. Med. Chem., 41, 353 (2006); https://doi.org/10.1016/j.ejmech.2005.11.005.
T. Srivastava, A.K. Gaikwad, W. Haq, S. Sinha and S.B. Katti, Synthesis and Biological Evaluation of 4-Thiazolidinone Derivatives as Potential Antimycobacterial Agent, ARKIVOC, 120 (2005); https://doi.org/10.3998/ark.5550190.0006.209.
M.H. Shih and F.Y. Ke, Syntheses and Evaluation of Antioxidant Activity of Sydnonyl Substituted Thiazolidinone and Thiazoline Derivatives, Bioorg. Med. Chem., 12, 4633 (2004); https://doi.org/10.1016/j.bmc.2004.06.033.
M.G. Vigorita, R. Ottana, F. Monforte, R. Maccari, A. Trovato, M.T. Monforte and M.F. Taviano, Synthesis and Antiinflammatory, Analgesic Activity of 3,3¢-(1,2-Ethanediyl)-bis[2-aryl-4-thiazolidinone] Chiral Compounds. Part 10, Bioorg. Med. Chem. Lett., 11, 2791 (2001); https://doi.org/10.1016/S0960-894X(01)00476-0.
G.C. Look, J.R. Schullek, C.P. Holmes, J.P. Chinn, E.M. Gordon and M.A. Gallop, The Identification of Cyclooxygenase-1 Inhibitors from 4-Thiazolidinone Combinatorial Libraries, Bioorg. Med. Chem. Lett., 6, 707 (1996); https://doi.org/10.1016/0960-894X(96)00097-2.
M.L. Barreca, J. Balzarini, A. Chimirri, E.D. Clercq, L.D. Luca, H.D. Höltje, M. Höltje, A.M. Monforte, P. Monforte, C. Pannecouque, A. Rao and M. Zappalà, Design, Synthesis, Structure-Activity Relationships and Molecular Modeling Studies of 2,3-Diaryl-1,3-thiazolidin-4-ones as Potent Anti-HIV Agents, J. Med. Chem., 45, 5410 (2002); https://doi.org/10.1021/jm020977+.
M.V. Diurno, O. Mazzoni, E. Piscopo, A. Calignano, F. Giordano and A. Bolognese, Synthesis and Antihistaminic Activity of Some Thiazolidin-4-ones, J. Med. Chem., 35, 2910 (1992); https://doi.org/10.1021/jm00093a025.
C.P. Holmes, WO 199600148 Patent (1996).
V. Gududuru, V. Nguyen, J.T. Dalton and D.D. Miller, Efficient Microwave Enhanced Synthesis of 4-Thiazolidinones, Synlett, 2357 (2004); https://doi.org/10.1055/s-2004-832811.
I. Ugi, B. Werner and A. Dömling, eds.: O.A. Attanasi and D. Spinelli, Targets in Heterocycles Systems, Chemistry and Properties, Italian Society of Chemistry, Rome, vol. 4, pp. 1-23 (2000).
I. Ugi, Recent Progress in the Chemistry of Multicomponent Reactions, Pure Appl. Chem., 73, 187 (2001); https://doi.org/10.1351/pac200173010187.
A. Dömling, Recent Developments in Isocyanide Based Multicompo-nent Reactions in Applied Chemistry, Chem. Rev., 106, 17 (2006); https://doi.org/10.1021/cr0505728.
E. Ruijter, R. Scheffelaar and R.V.A. Orru, Multicomponent Reaction Design in the Quest for Molecular Complexity and Diversity, Angew. Chem. Int. Ed., 50, 6234 (2011); https://doi.org/10.1002/anie.201006515.
C.O. Kappe, 100 years of the Biginelli Dihydropyrimidine Synthesis, Tetrahedron, 49, 6937 (1993); https://doi.org/10.1016/S0040-4020(01)87971-0.
N. Ma, B. Jiang, G. Zhang, S.J. Tu, W. Wever and G. Li, New Multicomponent Domino Reactions (MDRs) in Water: Highly Chemo-, Regio- and Stereoselective Synthesis of Spiro{[1,3]dioxanopyridine}-4,6-diones and Pyrazolo[3,4-b]pyridines, Green Chem., 12, 1357 (2010); https://doi.org/10.1039/c0gc00073f.
R.M. Borde, S.B. Jadhav, R.R. Dhavse and A.S. Munde, Design, Synthesis and Pharmacological Evaluation of Some Novel bis-Thiazole Derivatives, Asian J. Pharm. Clin. Res., 11, 164 (2018).
R.M. Borde, R.A. Waghmare, S.B. Jadhav and A.S. Munde, One Pot Synthesis of Nitriles from Aldehydes and Hydroxylamine Hydrochloride Using Calcium Chloride in DMF Solvent under Reflux Condition, Heterocycl. Lett., 7, 829 (2017).
R. Cruickshank, J.P. Duguid, B.P. Marion and R.H.A. Swain, Medicinal Microbiology, Churchill Livingstone: London, edn. 12, vol. II, pp. 196-202 (1975).
S.T. Pai and M.W. Platt, Antifungal Effects of Allium sativum (Garlic) Extract Against the Aspergillus Species involved in Otomycosis, Lett. Appl. Microbiol., 20, 14 (1995); https://doi.org/10.1111/j.1472-765X.1995.tb00397.x.
G. Ellias and M.N.A. Rao, Inhibition of Albumin Denaturation and Antiinflammatory Activity of Dehydrozingerone and its Analogs, Indian J. Exp. Biol., 26, 540 (1998).
K. Ishizaka, eds.: M. Samter and H.L. Alexander, Experimental Anaphylaxis, In: Immunological Diseases, Little Brown and Co.: Boston, pp. 131-145 (1965).

References

K.D. Hargrave, F.K. Hess and J.T. Oliver, N-(4-Substituted-thiazolyl)-oxamic Acid Derivatives, New Series of Potent, Orally Active Antiallergy Agents, J. Med. Chem., 26, 1158 (1983); https://doi.org/10.1021/jm00362a014.

W.C. Patt, H.W. Hamilton, M.D. Taylor, M.J. Ryan, D.G. Taylor Jr., C.J.C. Connolly, A.M. Doherty, S.R. Klutchko and I. Sircar, Structure-Activity Relationships of a Series of 2-Amino-4-thiazole Containing Renin Inhibitors, J. Med. Chem., 35, 2562 (1992); https://doi.org/10.1021/jm00092a006.

B.S. Holla, K.V. Malini, B.S. Rao, B.K. Sarojini and N.S. Kumari, Synthesis of Some New 2,4-Disubstituted Thiazoles as Possible Anti-bacterial and Anti-inflammatory agents, Eur. J. Med. Chem., 38, 313 (2003); https://doi.org/10.1016/S0223-5234(02)01447-2.

J.C. Jaen, L.D. Wise, B.W. Caprathe, H. Tecle, S. Bergmeier, C.C. Humblet, T.G. Heffner, L.T. Meltzer and T.A. Pugsley, 4-(1,2,5,6-Tetrahydro-1-alkyl-3-pyridinyl)-2-thiazolamines: A Novel Class of Compounds with Central Dopamine Agonist Properties, J. Med. Chem., 33, 311 (1990); https://doi.org/10.1021/jm00163a051.

K. Tsuji and H. Ishikawa, Synthesis and Anti-pseudomonal Activity of New 2-isocephems with a Dihydroxypyridone Moiety at C-7, Bioorg. Med. Chem. Lett., 4, 1601 (1994); https://doi.org/10.1016/S0960-894X(01)80574-6.

F.W. Bell, A.S. Cantrell, M. Hoegberg, S.R. Jaskunas, N.G. Johansson, C.L. Jordan, M.D. Kinnick, P. Lind and J.M. Morin, Phenethylthiazol-ethiourea (PETT) Compounds, A New Class of HIV-1 Reverse Transcri-ptase Inhibitors. 1. Synthesis and Basic Structure-Activity Relationship Studies of PETT Analogs, J. Med. Chem., 38, 4929 (1995); https://doi.org/10.1021/jm00025a010.

V. Ergenc, G. Capan, N.S. Gunay, S. Ozkirimli, M. Gungor, S. Ozbey and E. Kendi, Arch. Pharm. (Weinheim), Synthesis and Hypnotic Activity of New 4-Thiazolidinone and 2-Thioxo-4,5-imidazolidinedione Derivatives, 332, 343 (1999); https://doi.org/10.1002/(SICI)1521-4184(199910)332:10<343::AID-ARDP343>3.0.CO;2-0.

J.S. Carter, S. Kramer, J.J. Talley, T. Penning, P. Collins, M.J. Graneto, K. Seibert, C.M. Koboldt, J. Masferrer and B. Zweifel, Synthesis and Activity of Sulfonamide-Substituted 4,5-Diaryl Thiazoles as Selective Cyclooxygenase-2 inhibitors, Bioorg. Med. Chem. Lett., 9, 1171 (1999); https://doi.org/10.1016/S0960-894X(99)00157-2.

A. Badorc, M.F. Bordes, P. De Cointet, P. Savi, A. Bernat, A. Lale, M. Petitou, J.P. Maffrand and J.M. Herbert, New Orally Active Non-Peptide Fibrinogen Receptor (GpIIb-IIIa) Antagonists: Identification of Ethyl 3-[N-[4-[4-[Amino[(ethoxycarbonyl)imino]methyl]phenyl]-1,3-thiazol-2-yl]-N-[1-[(ethoxycarbonyl)methyl]piperid-4-yl]amino]-propionate (SR 121787) as a Potent and Long-Acting Antithrombotic Agent, J. Med. Chem., 40, 3393 (1997); https://doi.org/10.1021/jm970240y.

J. Rudolph, H. Theis, R. Hanke, R. Endermann, L. Johannsen and F.U. Geschke, seco-Cyclothialidines: New Concise Synthesis, Inhibitory Activity toward Bacterial and Human DNA Topoisomerases and Antibacterial Properties, J. Med. Chem., 44, 619 (2001); https://doi.org/10.1021/jm0010623.

A.A. Hassan, Y.R. Ibrahim, E.M. El-Sheref, M. Abdel-Aziz, S. Bräse and M. Nieger, Synthesis and Antibacterial Activity of 4-Aryl-2-(1-substituted ethylidene)thiazoles, Arch. Pharm. (Weinheim), 346, 562 (2013); https://doi.org/10.1002/ardp.201300099.

V.S. Palekar, A.J. Damle and S.R. Shukla, Synthesis and Antibacterial Activity of Some Novel bis-1,2,4-Triazolo[3,4-b]-1,3,4-thiadiazoles and bis-4-Thiazolidinone Derivatives from Terephthalic Dihydrazide, Eur. J. Med. Chem., 44, 5112 (2009); https://doi.org/10.1016/j.ejmech.2009.07.023.

R.P. Pawar, N.M. Andurkar and Y.B. Vibhute, Studies on Synthesis and Antibacterial Activity of Some New Schiff Bases, 4-Thiazolidinones and 2-Azetidinones, J. Indian Chem. Soc., 76, 271 (1999).

V.P. Trivedi, N.K. Undavia and P.B. Trivadi, Synthesis and Biological Activity of Some New 4-Thiazolidinone Derivatives, J. Indian Chem. Soc., 81, 506 (2004).

G. Küçükgüzel, A. Kocatepe, E. De Clercq, F. Sahin and M. Güllüce, Synthesis and Biological Activity of 4-Thiazolidinones, Thiosemi-carbazides Derived from Diflunisal Hydrazide, Eur. J. Med. Chem., 41, 353 (2006); https://doi.org/10.1016/j.ejmech.2005.11.005.

T. Srivastava, A.K. Gaikwad, W. Haq, S. Sinha and S.B. Katti, Synthesis and Biological Evaluation of 4-Thiazolidinone Derivatives as Potential Antimycobacterial Agent, ARKIVOC, 120 (2005); https://doi.org/10.3998/ark.5550190.0006.209.

M.H. Shih and F.Y. Ke, Syntheses and Evaluation of Antioxidant Activity of Sydnonyl Substituted Thiazolidinone and Thiazoline Derivatives, Bioorg. Med. Chem., 12, 4633 (2004); https://doi.org/10.1016/j.bmc.2004.06.033.

M.G. Vigorita, R. Ottana, F. Monforte, R. Maccari, A. Trovato, M.T. Monforte and M.F. Taviano, Synthesis and Antiinflammatory, Analgesic Activity of 3,3¢-(1,2-Ethanediyl)-bis[2-aryl-4-thiazolidinone] Chiral Compounds. Part 10, Bioorg. Med. Chem. Lett., 11, 2791 (2001); https://doi.org/10.1016/S0960-894X(01)00476-0.

G.C. Look, J.R. Schullek, C.P. Holmes, J.P. Chinn, E.M. Gordon and M.A. Gallop, The Identification of Cyclooxygenase-1 Inhibitors from 4-Thiazolidinone Combinatorial Libraries, Bioorg. Med. Chem. Lett., 6, 707 (1996); https://doi.org/10.1016/0960-894X(96)00097-2.

M.L. Barreca, J. Balzarini, A. Chimirri, E.D. Clercq, L.D. Luca, H.D. Höltje, M. Höltje, A.M. Monforte, P. Monforte, C. Pannecouque, A. Rao and M. Zappalà, Design, Synthesis, Structure-Activity Relationships and Molecular Modeling Studies of 2,3-Diaryl-1,3-thiazolidin-4-ones as Potent Anti-HIV Agents, J. Med. Chem., 45, 5410 (2002); https://doi.org/10.1021/jm020977+.

M.V. Diurno, O. Mazzoni, E. Piscopo, A. Calignano, F. Giordano and A. Bolognese, Synthesis and Antihistaminic Activity of Some Thiazolidin-4-ones, J. Med. Chem., 35, 2910 (1992); https://doi.org/10.1021/jm00093a025.

C.P. Holmes, WO 199600148 Patent (1996).

V. Gududuru, V. Nguyen, J.T. Dalton and D.D. Miller, Efficient Microwave Enhanced Synthesis of 4-Thiazolidinones, Synlett, 2357 (2004); https://doi.org/10.1055/s-2004-832811.

I. Ugi, B. Werner and A. Dömling, eds.: O.A. Attanasi and D. Spinelli, Targets in Heterocycles Systems, Chemistry and Properties, Italian Society of Chemistry, Rome, vol. 4, pp. 1-23 (2000).

I. Ugi, Recent Progress in the Chemistry of Multicomponent Reactions, Pure Appl. Chem., 73, 187 (2001); https://doi.org/10.1351/pac200173010187.

A. Dömling, Recent Developments in Isocyanide Based Multicompo-nent Reactions in Applied Chemistry, Chem. Rev., 106, 17 (2006); https://doi.org/10.1021/cr0505728.

E. Ruijter, R. Scheffelaar and R.V.A. Orru, Multicomponent Reaction Design in the Quest for Molecular Complexity and Diversity, Angew. Chem. Int. Ed., 50, 6234 (2011); https://doi.org/10.1002/anie.201006515.

C.O. Kappe, 100 years of the Biginelli Dihydropyrimidine Synthesis, Tetrahedron, 49, 6937 (1993); https://doi.org/10.1016/S0040-4020(01)87971-0.

N. Ma, B. Jiang, G. Zhang, S.J. Tu, W. Wever and G. Li, New Multicomponent Domino Reactions (MDRs) in Water: Highly Chemo-, Regio- and Stereoselective Synthesis of Spiro{[1,3]dioxanopyridine}-4,6-diones and Pyrazolo[3,4-b]pyridines, Green Chem., 12, 1357 (2010); https://doi.org/10.1039/c0gc00073f.

R.M. Borde, S.B. Jadhav, R.R. Dhavse and A.S. Munde, Design, Synthesis and Pharmacological Evaluation of Some Novel bis-Thiazole Derivatives, Asian J. Pharm. Clin. Res., 11, 164 (2018).

R.M. Borde, R.A. Waghmare, S.B. Jadhav and A.S. Munde, One Pot Synthesis of Nitriles from Aldehydes and Hydroxylamine Hydrochloride Using Calcium Chloride in DMF Solvent under Reflux Condition, Heterocycl. Lett., 7, 829 (2017).

R. Cruickshank, J.P. Duguid, B.P. Marion and R.H.A. Swain, Medicinal Microbiology, Churchill Livingstone: London, edn. 12, vol. II, pp. 196-202 (1975).

S.T. Pai and M.W. Platt, Antifungal Effects of Allium sativum (Garlic) Extract Against the Aspergillus Species involved in Otomycosis, Lett. Appl. Microbiol., 20, 14 (1995); https://doi.org/10.1111/j.1472-765X.1995.tb00397.x.

G. Ellias and M.N.A. Rao, Inhibition of Albumin Denaturation and Antiinflammatory Activity of Dehydrozingerone and its Analogs, Indian J. Exp. Biol., 26, 540 (1998).

K. Ishizaka, eds.: M. Samter and H.L. Alexander, Experimental Anaphylaxis, In: Immunological Diseases, Little Brown and Co.: Boston, pp. 131-145 (1965).

One Pot Three-Component Synthesis of Thiazolidinone Derivatives of 4-Methylthiazole-5-carbaldehyde and its Biological Evaluation

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