New Access to Pyrano[2,3-c]pyrazole-3-carboxylates via Domino Four-Component Reaction and Their Antimicrobial Activity

https://doi.org/10.22146/ijc.39566

Muhammad Siddiq Maarop(1), Fatin Nur Ain Abdul Rashid(2), Mohd Fazli Mohammat(3*), Zurina Shaameri(4), Saiful Azmi Johari(5), Mazurah Mohamed Isa(6), Anis Low Muhammad Low(7)

(1) Department of Chemistry, Faculty of Applied Sciences, Universiti Teknologi MARA, UiTM Shah Alam, 40450 Shah Alam, Selangor, Malaysia
(2) Department of Chemistry, Faculty of Applied Sciences, Universiti Teknologi MARA, UiTM Shah Alam, 40450 Shah Alam, Selangor, Malaysia
(3) Organic Chemistry Laboratory, Institute of Science, Universiti Teknologi MARA, Kampus Puncak Alam, 42300 Bandar Puncak Alam, Selangor, Malaysia
(4) Organic Chemistry Laboratory, Institute of Science, Universiti Teknologi MARA, Kampus Puncak Alam, 42300 Bandar Puncak Alam, Selangor, Malaysia
(5) Antimicrobial Laboratory, Anti-Infective Branch, Bioactivity Programme, Natural Products Division, Forest Research Institute Malaysia (FRIM), 52109 Kepong, Selangor, Malaysia
(6) Antimicrobial Laboratory, Anti-Infective Branch, Bioactivity Programme, Natural Products Division, Forest Research Institute Malaysia (FRIM), 52109 Kepong, Selangor, Malaysia
(7) Atta-ur-Rahman Institute (AURINS), Universiti Teknologi MARA, Kampus Puncak Alam, 42300 Bandar Puncak Alam, Selangor, Malaysia
(*) Corresponding Author

Abstract


A library of some novel classes of pyrano[2,3-c]pyrazole-3-carboxylates was synthesized by employing uncatalyzed domino four-component reaction using diethyloxaloacetate, hydrazine hydrate, aldehydes and malononitrile in refluxing of ethanol-acetic acid solvent systems. Series of domino reactions involving of pyrazolone formation, Michael addition, and Thorpe-Ziegler cyclization reaction managed to produce the cyclized products from moderate to excellent yield. This protocol provides a reliable, general and salient procedure for the title compound using a one-pot approach. Preliminary biological screening unveiled limited potentials of this class of compounds for antimicrobial lead compound due to its limited solubility properties.


Keywords


four-component reactions; pyrano[2,3-c]pyrazole-3-carboxylate; diethyloxaloacetate

Full Text:

Full Text PDF


References

[1] Mistry, P.T., Kamdar, N.R., Haveliwala, D.D., and Patel, S.K., 2012, Synthesis, characterization, and in-vitro biological studies of some novel pyran fused pyrimidone derivatives, J. Heterocycl. Chem., 49 (2), 349–357.

[2] Kuo, S.C., Huang, L.J., and Nakamura, H., 1984, Studies on heterocyclic compounds. 6. Synthesis and analgesic and antiinflammatory activities of 3,4-dimethylpyrano[2,3-c]pyrazol-6-one derivatives, J. Med. Chem., 27 (4), 539–544.

[3] Ahluwalia, V.K., Dahiya, A., and Garg, V., 1997, Reaction of 5-amino-4-formyl-3-methyl(or phenyl)-1-phenyl-1H-pyrazoles with active methylene compounds: Synthesis of fused heterocyclic rings, Indian J. Chem., Sect B, 36 (1), 88–90.

[4] Wang, J.L., Liu, D., Zheng, Z.J., Shan, S., Han, X., Srinivasula, S.M., Croce, C.M., Alnemri, E.S., and Huang, Z., 2009, Structure-based discovery of an organic compound that binds Bcl-2-protien and induces apoptosis of tumor cell, Proc. Natl. Acad. Sci. U.S.A., 97 (13), 7124–7129.

[5] Mandha, S.R., Siliveri, S., Alla, M., Bommena, V.R., Bommineni, M.R., and Balasubramanian, S., 2012, Eco-friendly synthesis and biological evaluation of substituted pyrano[2,3-c]pyrazoles, Bioorg. Med. Chem. Lett., 22 (16), 5272–5278.

[6] Foloppe, N., Fisher, L.M., Howes, R., Potter, A., Robertson, A.G.S., and Surgenor, A.E., 2006, Identification of chemically diverse Chk1 inhibitors by receptor-based virtual screening, Bioorg. Med. Chem., 14 (14), 4792–4802.

[7] Ramiz, M.M.M., Hafiz, I.S.A., Rahim, M.A.M.A., and Gaber, H.M., 2012, Pyrazolones as building blocks in heterocyclic synthesis: Synthesis of new pyrazolopyran, pyrazolopyridazine and pyrazole derivatives of expected antifungicidal activity, J. Chin. Chem. Soc., 59 (1), 72–80.

[8] Kiyani, H., Samimi, H.A., Ghorbani, F., and Esmaieli, S., 2013, One-pot, four-component synthesis of pyrano[2,3-c]pyrazolescatalyzed by sodium benzoate in aqueous medium, Curr. Chem. Lett., 2 (4), 197–206.

[9] Otto, S., and Engberts, J.B.F.N., 2000, Diels Alder reactions in water, Pure Appl. Chem., 72 (7), 1365–1372.

[10] Shestopalov, A.M., Emeliyanova, Y.M., Shestopalov, A.A., Rodinovskaya, L.A., Niazimbetova, Z.I., and Evans, D.H., 2003, Cross-condensation of derivatives of cyanoacetic acid and carbonyl compounds. Part 1: Single-stage synthesis of 1′-substituted 6-amino-spiro-4-(piperidine-4′)-2H,4H-pyrano[2,3-c]pyrazole-5-carbonitriles, Tetrahedron, 59 (38), 7491–7496.

[11] Zonouz, A.M., Eskandari, I., and Khavasi, H.R., 2012, A green and convenient approach for the synthesis of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates via a one-pot, multi-component reaction in water, Tetrahedron Lett., 53 (41), 5519–5522.

[12] Weber, L., 2002, Multi-component reactions and evolutionary chemistry, Drug Discovery Today, 7 (2), 143–147.

[13] Gein, V.L., Zamaraeva, T.M., and Kozulina, I.V., 2014, New synthesis of ethyl 6-amino-4-aryl-5-cyano-1,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates, Russ. J. Org. Chem., 50 (5), 691–693.

[14] Kumler, W.D., Kun, E., and Shoolery, J.N., 1962, The enolization of oxaloacetic acid, diethyl oxaloacetate, and diethyl fluorooxaloacetate as determined by NMR analyses, J. Org. Chem., 27 (4), 1165–1167.

[15] Mohammat, M.F., Shaameri, Z., and Hamzah, A.S., 2009, Synthesis of 2,3-dioxo-5-(substituted)arylpyrroles and their 2-oxo-5-aryl-3-hydrazone pyrrolidine derivatives, Molecules, 14 (1), 250–256.

[16] Mohammat, M.F., Najim, N., Mansor, N.S., Sarman, S., Shaameri, Z., Zain, M.M., and Hamzah, A.S., 2011, Synthesis and bioactivity of some 2-oxo-5-aryl-3-hydrazone and 2-oxo-5-aryl-4-hydrazone pyrrolidine derivatives, Arkivoc, 2011 (9), 429−438.

[17] Johari, S.A., Mohtar, M., Syed Mohammad, S.A., Mohammat, M.F., Sahdan, R., Mohamed, A., and Mohamad Ridhwan, M.J., 2017, In vitro evaluations and in vivo toxicity and efficacy studies of MFM501 against MRSA, Biomed Res. Int., 2017, 8032865.

[18] Johari, S.A., Mohtar. M., Syed Mohammad. S.A., Sahdan. R., Shaameri. Z., Hamzah, A.S., and Mohammat, M.F., 2016, In vitro inhibitory and cytotoxic activity of MFM 501, a novel codonopsinine derivative, against methicillin-resistant Staphylococcus aureus clinical Isolates, Biomed Res. Int., 2015, 823829.

[19] Khalil, T., Manouchehr, M., Nosrat, O.M., and Elahe, K., 2009, Ruthenium-catalyzed cross aldol reaction with aldehydes and ketones, Arkivoc, 2009 (2) 68–75.



DOI: https://doi.org/10.22146/ijc.39566

Article Metrics

Abstract views : 157 | views : 127


Copyright (c) 2019 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 


Indonesian Journal of Chemisty (ISSN 1411-9420 / 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.