Facile Synthesis and Biological Evaluation of Cyclopropyl-Pyrazole Hybrids in [bmim][PF6]- Water Biphasic System as Antifungal Agents

P.C. Burde; A.M. Rahatgaonkar

doi:10.14233/ajomc.2019.AJOMC-P192

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Abstract

3-Cyclopropyl-5-(4-substituted)-1-phenyl-4,5-dihydro-1H-pyrazoles derived from corresponding chalcones were synthesized and evaluated for their biological activities. A convenient synthesis of a library of these compounds in 1-butyl-3-methylimidazolium hexafluorophosphatewater biphasic system at ambient temperature has been accomplished. The ionic liquid, [bmim][PF₆] and water which are immiscible, has been easily recycled and reused after separation of the products without any noticeable diminution in its activity.

Keywords

Cyclopropyl Pyrazole ([bmim][PF6]) Biphasic Antifungal activity

How to Cite

Burde, P., & Rahatgaonkar, A. (2019). Facile Synthesis and Biological Evaluation of Cyclopropyl-Pyrazole Hybrids in [bmim][PF6]- Water Biphasic System as Antifungal Agents. Asian Journal of Organic & Medicinal Chemistry, 4(3), 152–158. https://doi.org/10.14233/ajomc.2019.AJOMC-P192

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References

B.C. Das, D. Bhowmilk, B. Chiranjib and G. Mariappan, Synthesis and Biological Evaluation of Some Pyrazoline Derivatives, J. Pharm. Res., 3, 1345 (2010).
R. Gupta, N. Gupta and A. Jain, Improved Synthesis of Chalcones and Pyrazolines under Ultrasonic Irradiation, Indian J. Chem., 49B, 351 (2010).
A. Solankee, S. Lad, S. Solankee and G. Patel, Chalcones, Pyrazolines and Aminopyrimidines as Antibacterial Agents, Indian J. Chem., 48B, 1442 (2009).
B.C. Revanasiddappa, R.N. Rao, E.V.S. Subrahmanyam and D. Satyanarayana, Synthesis and Biological Evaluation of Some Novel 1,3,5-Trisubstituted Pyrazolines, E-J. Chem., 7, 295 (2010); https://doi.org/10.1155/2010/415723.
A. Voskiene, V. Mickevicius and G. Mikulskiene, Synthesis and Structural Characterization of Products Condensation 4-Carboxy-1-(4-Styryl-carbonylphenyl)-2-Pyrrolidinones with Hydrazines, ARKIVOC, 303 (2007); https://doi.org/10.3998/ark.5550190.0008.f29.
S. Kataade, U. Phalgune, S. Biswas, R. Wakharkar and N. Deshpande, Microwave Studies on Synthesis of Biologically Active Chalcones Derivatives, Indian J. Chem., 47B, 927 (2008).
S.A. Al-Issa and N.A.L. Andis, Solvent Free Synthesis of Chalcones and N-Phenyl-2-Pyrazolines under Microwave Irradiation, J. Saudi Chem. Soc., 9, 687 (2005).
V.K. Mishra, M. Mishra, V. Kashaw and S.K. Kashaw, Synthesis of 1,3,5-Trisubstituted Pyrazolines as Potential Antimalarial and Antimicrobial Agents, Bioorg. Med. Chem., 25, 1949 (2017); https://doi.org/10.1016/j.bmc.2017.02.025.
M.A. Halim, A.B. Keeton, E. Gurpinar, B.D. Gary, S.M. Vogel, M. Engel, G.A. Piazza, F.M.Boeckler, R.W. Hartmann and A.H. Abadi, Trisubsti-tuted and Tetrasubstituted Pyrazolines as a Novel Class of Cell-Growth Inhibitors in Tumor cells with Wild Type p53, Bioorg. Med. Chem., 21, 7343 (2013); https://doi.org/10.1016/j.bmc.2013.09.055.
C. Kharbanda, M.S. Alam, H. Hamid, K. Javed, S. Bano, A. Dhulap, Y. Ali, S. Nazreen and S. Haider, Synthesis and Evaluation of Pyrazolines Bearing Benzothiazole as Anti-Inflammatory Agents, Bioorg. Med. Chem., 22, 5804 (2014); https://doi.org/10.1016/j.bmc.2014.09.028.
H.H. Wang, K.M. Qiu, H.E. Cui, Y.S. Yang, Y. luo, M. Xing, X.-Y. Qiu, L.-F. Bai and H.L. Zhu, Synthesis, Molecular Docking and Evaluation of Thiazolyl-Pyrazoline Derivatives Containing Benzodioxole as Potential Anticancer Agents, Bioorg. Med. Chem., 21, 448 (2013); https://doi.org/10.1016/j.bmc.2012.11.020.
M. Shaharyar, A.A. Siddiqui, M.A. Ali, D. Sriram and P. Yogeeswari, Synthesis and in vitro Antimycobacterial Activity of N1-Nicotinoyl-3-(4¢-hydroxy-3¢-methyl phenyl)-5-[(sub)phenyl]-2-pyrazolines, Bioorg. Med. Chem. Lett., 16, 3947 (2006); https://doi.org/10.1016/j.bmcl.2006.05.024.
R.A. Nugent, M. Murphy, S.T. Schlachter, C.J. Dunn, R.J. Smith, N.D. Staite, L.A. Galinet, S.K. Shields, D.G. Aspar, K.A. Richard and N.A. Rohloff, Pyrazoline Bisphosphonate Esters as Novel Antiinflammatory and Antiarthritic Agents, J. Med. Chem., 36, 134 (1993); https://doi.org/10.1021/jm00053a017.
F. Manna, F. Chimenti, A. Bolasco, M.L. Cenicola, M. D’Amico, C. Parrillo, F. Rossi and E. Marmo, Anti-inflammatory, Analgesic and Antipyretic N-Acetyl-D2-pyrazolines and Dihydrothienocoumarines, Eur. J. Med. Chem., 27, 633 (1992); https://doi.org/10.1016/0223-5234(92)90142-N.
A.A. Bilgin, E. Palaska and R. Sunal, Studies on the Synthesis and Anti-depressant Activity of Some 1-Thiocarbamoyl-3,5-Diphenyl-2-Pyrazolines, Arzneim. Forsch. Drug Res., 43, 1041 (1993).
A.A. Bilgin, E. Palaska, R. Sunal and B. Gumusel, Some 1,3,5-Triphenyl-2-pyrazolines with Antidepressant Activities, Pharmazie, 49, 67 (1994).
A.R. Katrizky, C.W. Rees and E.F.V. Scriven, Comprehensive Hetero-cyclic Chemistry II, Elsevier Science Ltd.: Oxford, vol. 6 (1996).
H.G. Bonacorso, M.R. Oliveira, A.P. Wentz, A.D. Wastowski, A.B. de Oliveira, M. Höerner, N. Zanatta and M.A.P. Martins, Haloacetylated Enol Ethers: 12 [18]. Regiospecific Synthesis and Structural Determination of Stable 5-Hydroxy-1H-Pyrazolines, Tetrahedron, 55, 345 (1999); https://doi.org/10.1016/S0040-4020(98)01057-6.
D.N. Moreira, C.P. Frizzo, K. Longhi, N. Zanatta, H.G. Bonacorso and M.A.P. Martins, An Efficient Synthesis of 1-Cyanoacetyl-5-Halomethyl-4,5-Dihydro-1H-Pyrazoles in Ionic Liquid, Monatsh. Chem., 139, 1049 (2008); https://doi.org/10.1007/s00706-008-0874-8.
R. Ghahremanzadeh, G.I. Shakibaei and A. Bazgir, An Efficient One-Pot Synthesis of 1H-Pyrazolo[1,2-b]phthalazine-5,10-dione Derivatives, Synlett, 1129 (2008); https://doi.org/10.1055/s-2008-1072716.
D. Chaturvedi, Ionic Liquids: A Class of Versatile Green Reaction Media for the Syntheses of Nitrogen Heterocycles, Curr. Org. Synth., 8, 438 (2011); https://doi.org/10.2174/157017911795529092.
A.P. Acharya, R.D. Kamble, S.D. Patil, S.V. Hese and B.S. Dawane, An Efficient and Green Synthesis of Some Novel Benzodiazepine Derivatives and Their Antimicrobial Screening, Der Chem. Sin., 4, 189 (2013).
M.A. Kira, M.O. Abdel-Rahman and K.Z. Gadalla, The Vilsmeier-Haack Reaction-III Cyclization of Hydrazones to Pyrazoles, Tetrahedron Lett., 10, 109 (1969); https://doi.org/10.1016/S0040-4039(01)88217-4.
G.G. Mandawad, S.S. Chobe, O.S. Yemul and B.S. Dawane, An Efficient Green Synthesis of Some Novel Hetero Chalcones as Potent Anti-microbial Agents, J. Pharm. Res., 4, 3360 (2011).
M. Kidwai, R. Venkataramanan and B. Dave, Potassium Carbonate, A Support for the Green Synthesis of Azoles and Diazines, J. Heterocycl. Chem., 39, 1045 (2002); https://doi.org/10.1002/jhet.5570390530.
M. Kidwai, S. Saxena, M.K. Rahman Khan and S.S. Thukral, Aqua Mediated Synthesis of Substituted 2-Amino-4H-Chromenes and in vitro Study as Antibacterial Agents, Bioorg. Med. Chem. Lett., 15, 4295 (2005); https://doi.org/10.1016/j.bmcl.2005.06.041.
M. Kidwai and S. Priya, Rastogi and K. Singhal. Unpublished results.
M. Kidwai, Green Chemistry Trends Toward Sustainability, Pure Appl. Chem., 78, 1983 (2006); https://doi.org/10.1351/pac200678111983.
J.L. Brewbaker and H. Hart, Cyclization of 3-Diazoalkenes to Pyrazoles, J. Am. Chem. Soc., 91, 711 (1969); https://doi.org/10.1021/ja01031a034.
M.P. Doyle and M.J. Yan, Effective and Highly Stereoselective Coupling with Vinyldiazomethanes to form Symmetrical Trienes, J. Org. Chem., 67, 602 (2002); https://doi.org/10.1021/jo016135k.
N. Almirante, A. Cerri, G. Fedrizzi, G. Marazzi and M.A. Santagostino, A General, [1+4] Approach to the Synthesis of 3(5)-Substituted Pyrazoles from Aldehydes, Tetrahedron Lett., 39, 3287 (1998); https://doi.org/10.1016/S0040-4039(98)00472-9.
V.K. Aggarwal, J. de Vicente and R.V. Bonnert, A Novel One-Pot Method for the Preparation of Pyrazoles by 1,3-Dipolar Cycloadditions of Diazo Compounds Generated in situ, J. Org. Chem., 68, 5381 (2003); https://doi.org/10.1021/jo0268409.
R. Grandi, W. Messerotti, U.M. Pagnoni and R. Trave, Decomposition of Conjugated p-Tosylhydrazones in Base. Partition between Solvolysis and Cycloaddition Products, J. Org. Chem., 42, 1352 (1977); https://doi.org/10.1021/jo00428a018.
A. Corradi, C. Leonelli, A. Rizzuti, R. Rosa, P. Veronesi, R. Grandi, S. Baldassari and C. Villa, New “Green” Approaches to the Synthesis of Pyrazole Derivatives, Molecules, 12, 1482 (2007); https://doi.org/10.3390/12071482.
D. Nair, P. Pavashe and I.N.N. Namboothiri, 1,3-Dipolar Cycloaddition of Chalcones and Arylidene-1,3-Dicarbonyls with Diazosulfone for the Regioselective Synthesis of Functionalized Pyrazoles and Pyrazolines, Tetrahedron, 74, 2716 (2018); https://doi.org/10.1016/j.tet.2018.04.030.
K. Lanjewar, A. Rahatgaonkar, M. Chorghade and B. Saraf, Facile Synthesis of Pyrimidine-Isoxazoline Hybrids in a [bmim][PF6]-Water Biphasic System, Synthesis, 2644 (2011); https://doi.org/10.1055/s-0030-1260099.

References

B.C. Das, D. Bhowmilk, B. Chiranjib and G. Mariappan, Synthesis and Biological Evaluation of Some Pyrazoline Derivatives, J. Pharm. Res., 3, 1345 (2010).

R. Gupta, N. Gupta and A. Jain, Improved Synthesis of Chalcones and Pyrazolines under Ultrasonic Irradiation, Indian J. Chem., 49B, 351 (2010).

A. Solankee, S. Lad, S. Solankee and G. Patel, Chalcones, Pyrazolines and Aminopyrimidines as Antibacterial Agents, Indian J. Chem., 48B, 1442 (2009).

B.C. Revanasiddappa, R.N. Rao, E.V.S. Subrahmanyam and D. Satyanarayana, Synthesis and Biological Evaluation of Some Novel 1,3,5-Trisubstituted Pyrazolines, E-J. Chem., 7, 295 (2010); https://doi.org/10.1155/2010/415723.

A. Voskiene, V. Mickevicius and G. Mikulskiene, Synthesis and Structural Characterization of Products Condensation 4-Carboxy-1-(4-Styryl-carbonylphenyl)-2-Pyrrolidinones with Hydrazines, ARKIVOC, 303 (2007); https://doi.org/10.3998/ark.5550190.0008.f29.

S. Kataade, U. Phalgune, S. Biswas, R. Wakharkar and N. Deshpande, Microwave Studies on Synthesis of Biologically Active Chalcones Derivatives, Indian J. Chem., 47B, 927 (2008).

S.A. Al-Issa and N.A.L. Andis, Solvent Free Synthesis of Chalcones and N-Phenyl-2-Pyrazolines under Microwave Irradiation, J. Saudi Chem. Soc., 9, 687 (2005).

V.K. Mishra, M. Mishra, V. Kashaw and S.K. Kashaw, Synthesis of 1,3,5-Trisubstituted Pyrazolines as Potential Antimalarial and Antimicrobial Agents, Bioorg. Med. Chem., 25, 1949 (2017); https://doi.org/10.1016/j.bmc.2017.02.025.

M.A. Halim, A.B. Keeton, E. Gurpinar, B.D. Gary, S.M. Vogel, M. Engel, G.A. Piazza, F.M.Boeckler, R.W. Hartmann and A.H. Abadi, Trisubsti-tuted and Tetrasubstituted Pyrazolines as a Novel Class of Cell-Growth Inhibitors in Tumor cells with Wild Type p53, Bioorg. Med. Chem., 21, 7343 (2013); https://doi.org/10.1016/j.bmc.2013.09.055.

C. Kharbanda, M.S. Alam, H. Hamid, K. Javed, S. Bano, A. Dhulap, Y. Ali, S. Nazreen and S. Haider, Synthesis and Evaluation of Pyrazolines Bearing Benzothiazole as Anti-Inflammatory Agents, Bioorg. Med. Chem., 22, 5804 (2014); https://doi.org/10.1016/j.bmc.2014.09.028.

H.H. Wang, K.M. Qiu, H.E. Cui, Y.S. Yang, Y. luo, M. Xing, X.-Y. Qiu, L.-F. Bai and H.L. Zhu, Synthesis, Molecular Docking and Evaluation of Thiazolyl-Pyrazoline Derivatives Containing Benzodioxole as Potential Anticancer Agents, Bioorg. Med. Chem., 21, 448 (2013); https://doi.org/10.1016/j.bmc.2012.11.020.

M. Shaharyar, A.A. Siddiqui, M.A. Ali, D. Sriram and P. Yogeeswari, Synthesis and in vitro Antimycobacterial Activity of N1-Nicotinoyl-3-(4¢-hydroxy-3¢-methyl phenyl)-5-[(sub)phenyl]-2-pyrazolines, Bioorg. Med. Chem. Lett., 16, 3947 (2006); https://doi.org/10.1016/j.bmcl.2006.05.024.

R.A. Nugent, M. Murphy, S.T. Schlachter, C.J. Dunn, R.J. Smith, N.D. Staite, L.A. Galinet, S.K. Shields, D.G. Aspar, K.A. Richard and N.A. Rohloff, Pyrazoline Bisphosphonate Esters as Novel Antiinflammatory and Antiarthritic Agents, J. Med. Chem., 36, 134 (1993); https://doi.org/10.1021/jm00053a017.

F. Manna, F. Chimenti, A. Bolasco, M.L. Cenicola, M. D’Amico, C. Parrillo, F. Rossi and E. Marmo, Anti-inflammatory, Analgesic and Antipyretic N-Acetyl-D2-pyrazolines and Dihydrothienocoumarines, Eur. J. Med. Chem., 27, 633 (1992); https://doi.org/10.1016/0223-5234(92)90142-N.

A.A. Bilgin, E. Palaska and R. Sunal, Studies on the Synthesis and Anti-depressant Activity of Some 1-Thiocarbamoyl-3,5-Diphenyl-2-Pyrazolines, Arzneim. Forsch. Drug Res., 43, 1041 (1993).

A.A. Bilgin, E. Palaska, R. Sunal and B. Gumusel, Some 1,3,5-Triphenyl-2-pyrazolines with Antidepressant Activities, Pharmazie, 49, 67 (1994).

A.R. Katrizky, C.W. Rees and E.F.V. Scriven, Comprehensive Hetero-cyclic Chemistry II, Elsevier Science Ltd.: Oxford, vol. 6 (1996).

H.G. Bonacorso, M.R. Oliveira, A.P. Wentz, A.D. Wastowski, A.B. de Oliveira, M. Höerner, N. Zanatta and M.A.P. Martins, Haloacetylated Enol Ethers: 12 [18]. Regiospecific Synthesis and Structural Determination of Stable 5-Hydroxy-1H-Pyrazolines, Tetrahedron, 55, 345 (1999); https://doi.org/10.1016/S0040-4020(98)01057-6.

D.N. Moreira, C.P. Frizzo, K. Longhi, N. Zanatta, H.G. Bonacorso and M.A.P. Martins, An Efficient Synthesis of 1-Cyanoacetyl-5-Halomethyl-4,5-Dihydro-1H-Pyrazoles in Ionic Liquid, Monatsh. Chem., 139, 1049 (2008); https://doi.org/10.1007/s00706-008-0874-8.

R. Ghahremanzadeh, G.I. Shakibaei and A. Bazgir, An Efficient One-Pot Synthesis of 1H-Pyrazolo[1,2-b]phthalazine-5,10-dione Derivatives, Synlett, 1129 (2008); https://doi.org/10.1055/s-2008-1072716.

D. Chaturvedi, Ionic Liquids: A Class of Versatile Green Reaction Media for the Syntheses of Nitrogen Heterocycles, Curr. Org. Synth., 8, 438 (2011); https://doi.org/10.2174/157017911795529092.

A.P. Acharya, R.D. Kamble, S.D. Patil, S.V. Hese and B.S. Dawane, An Efficient and Green Synthesis of Some Novel Benzodiazepine Derivatives and Their Antimicrobial Screening, Der Chem. Sin., 4, 189 (2013).

M.A. Kira, M.O. Abdel-Rahman and K.Z. Gadalla, The Vilsmeier-Haack Reaction-III Cyclization of Hydrazones to Pyrazoles, Tetrahedron Lett., 10, 109 (1969); https://doi.org/10.1016/S0040-4039(01)88217-4.

G.G. Mandawad, S.S. Chobe, O.S. Yemul and B.S. Dawane, An Efficient Green Synthesis of Some Novel Hetero Chalcones as Potent Anti-microbial Agents, J. Pharm. Res., 4, 3360 (2011).

M. Kidwai, R. Venkataramanan and B. Dave, Potassium Carbonate, A Support for the Green Synthesis of Azoles and Diazines, J. Heterocycl. Chem., 39, 1045 (2002); https://doi.org/10.1002/jhet.5570390530.

M. Kidwai, S. Saxena, M.K. Rahman Khan and S.S. Thukral, Aqua Mediated Synthesis of Substituted 2-Amino-4H-Chromenes and in vitro Study as Antibacterial Agents, Bioorg. Med. Chem. Lett., 15, 4295 (2005); https://doi.org/10.1016/j.bmcl.2005.06.041.

M. Kidwai and S. Priya, Rastogi and K. Singhal. Unpublished results.

M. Kidwai, Green Chemistry Trends Toward Sustainability, Pure Appl. Chem., 78, 1983 (2006); https://doi.org/10.1351/pac200678111983.

J.L. Brewbaker and H. Hart, Cyclization of 3-Diazoalkenes to Pyrazoles, J. Am. Chem. Soc., 91, 711 (1969); https://doi.org/10.1021/ja01031a034.

M.P. Doyle and M.J. Yan, Effective and Highly Stereoselective Coupling with Vinyldiazomethanes to form Symmetrical Trienes, J. Org. Chem., 67, 602 (2002); https://doi.org/10.1021/jo016135k.

N. Almirante, A. Cerri, G. Fedrizzi, G. Marazzi and M.A. Santagostino, A General, [1+4] Approach to the Synthesis of 3(5)-Substituted Pyrazoles from Aldehydes, Tetrahedron Lett., 39, 3287 (1998); https://doi.org/10.1016/S0040-4039(98)00472-9.

V.K. Aggarwal, J. de Vicente and R.V. Bonnert, A Novel One-Pot Method for the Preparation of Pyrazoles by 1,3-Dipolar Cycloadditions of Diazo Compounds Generated in situ, J. Org. Chem., 68, 5381 (2003); https://doi.org/10.1021/jo0268409.

R. Grandi, W. Messerotti, U.M. Pagnoni and R. Trave, Decomposition of Conjugated p-Tosylhydrazones in Base. Partition between Solvolysis and Cycloaddition Products, J. Org. Chem., 42, 1352 (1977); https://doi.org/10.1021/jo00428a018.

A. Corradi, C. Leonelli, A. Rizzuti, R. Rosa, P. Veronesi, R. Grandi, S. Baldassari and C. Villa, New “Green” Approaches to the Synthesis of Pyrazole Derivatives, Molecules, 12, 1482 (2007); https://doi.org/10.3390/12071482.

D. Nair, P. Pavashe and I.N.N. Namboothiri, 1,3-Dipolar Cycloaddition of Chalcones and Arylidene-1,3-Dicarbonyls with Diazosulfone for the Regioselective Synthesis of Functionalized Pyrazoles and Pyrazolines, Tetrahedron, 74, 2716 (2018); https://doi.org/10.1016/j.tet.2018.04.030.

K. Lanjewar, A. Rahatgaonkar, M. Chorghade and B. Saraf, Facile Synthesis of Pyrimidine-Isoxazoline Hybrids in a [bmim][PF6]-Water Biphasic System, Synthesis, 2644 (2011); https://doi.org/10.1055/s-0030-1260099.

Facile Synthesis and Biological Evaluation of Cyclopropyl-Pyrazole Hybrids in [bmim][PF6]- Water Biphasic System as Antifungal Agents

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