Ultrasound Assisted One Pot Synthesis, Spectral, Antimicrobial and Antioxidant Studies of Novel 4-[1-Oxo-3-(substituted phenyl)-2-propenyl]-3-substituted Phenyl Sydnones

Sachin K. Bhosale; Shreenivas R. Deshpande; Rajendra D. Wagh

doi:10.14233/ajchem.2015.18864

Issue

Vol. 27 No. 8 (2015): Vol 27 Issue 8

Issue Published : April 27, 2015

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

Ultrasound Assisted One Pot Synthesis, Spectral, Antimicrobial and Antioxidant Studies of Novel 4-[1-Oxo-3-(substituted phenyl)-2-propenyl]-3-substituted Phenyl Sydnones

https://doi.org/10.14233/ajchem.2015.18864

Sachin K. Bhosale

Department of Pharmaceutical Chemistry, S.M.B.T. College of Pharmacy, Nandi Hills, Dhamangaon-422 403, India

Shreenivas R. Deshpande

1DepartmeDepartment of Medicinal and Pharmaceutical Chemistry, HSK College of Pharmacy, BVVS Campus, Bagalkote-587 101, India

Rajendra D. Wagh

Department of Pharmaceutical Chemistry, A.R.A. College of Pharmacy, Nagaon, Dhule-424 005, India

Corresponding Author(s) : Sachin K. Bhosale

sachiniper@rediffmail.com

Asian Journal of Chemistry, Vol. 27 No. 8 (2015): Vol 27 Issue 8
Article Published : April 28, 2015

Abstract

4-[1-Oxo-3-(substituted aryl)-2-propenyl]-3-substituted phenyl sydnones (2a-i, 3a-i, 4a-i) are synthesized by ultrasonication method. The synthesis was carried out by reaction of 4-acetyl-3- (substituted phenyl)sydnones (1a-i) with various substituted aryl aldehydes (Ar-CHO). The structures of compounds were established by using NMR, IR, MS and elemental analysis. Compounds were evaluated for antibacterial, antifungal and antioxidant activity. Some of the synthesized compounds have shown good to moderate activity against gram negative bacteria whereas compounds 3c, 4c and 4f have shown marked activity against fungal strains. The compounds 2c, 3c, 4f have shown potent antioxidant activity as compared to reference standards. The compound 4f (IC₅₀ = 3.17 μM) is the most potent with methyl group as substituent showing good antioxidant activity even at very low concentrations. The ultrasonic method of synthesis was found to be simple, reduces reaction time and gives good yield when compared with traditional methods of synthesis.

Keywords

1 2 3-Oxadiazol-5-olate Ultrasonication Chalcones

K. Bhosale, S., R. Deshpande, S., & D. Wagh, R. (2015). Ultrasound Assisted One Pot Synthesis, Spectral, Antimicrobial and Antioxidant Studies of Novel 4-[1-Oxo-3-(substituted phenyl)-2-propenyl]-3-substituted Phenyl Sydnones. Asian Journal of Chemistry, 27(8), 3063–3068. https://doi.org/10.14233/ajchem.2015.18864

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References

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A.D. McNaught and A. Wilkinson, IUPAC Compendium of Chemical Terminology, Blackwell Scientific Publications, vol. 67, p. 1370 (1995).

S.G. Mallur, A.K. Tiwari, R.B. China, R.K. Suresh, A.A. Zehra, B.S. Sastry and R.J. Madhusudana, Indian J. Chem., 46B, 1686 (2007).

M.-H. Shih and F.-Y. Ke, Bioorg. Med. Chem., 12, 4633 (2004); doi:10.1016/j.bmc.2004.06.033.

R.J. Anto, G. Kuttan, R. Kuttan, K. Sathyanarayana and M.N.A. Rao, J. Clin. Biochem. Nutr., 17, 73 (1994); doi:10.3164/jcbn.17.73.

K. Satyanarayana, S.R. Deshpande, B. Subbarao and M.N.A. Rao, Indian J. Pharm. Sci., 66, 679 (2004).

C.S. Dunkley and C.J. Thoman, Bioorg. Med. Chem. Lett., 13, 2899 (2003); doi:10.1016/S0960-894X(03)00487-6.

F.H.C. Stewart, J. Chem. Soc., 701 (1963); doi:10.1039/JR9630000701.

L.B. Kier, D. Dhawan and M.J. Fregly, J. Pharm. Sci., 53, 677 (1964); doi:10.1002/jps.2600530623.

J.R. Kavali and B.V. Badami, IL Farmaco, 55, 406 (2000); doi:10.1016/S0014-827X(00)00061-6.

A.M. Rahiman, B. Kalluraya and J.C. Hegde, Indian J. Heterocycl. Chem., 12, 241 (2003).

S.S. Khadabadi and G.S. Puranik, Indian Drug, 31, 472 (1994).

G.H. Pilli, C. Safak and U. Abbasoglu, Arch. Pharm., 9, 559 (1993); doi:10.1002/ardp.19933260912.

P.S. Shinge, S.G. Mallur and B.V. Badami, J. Indian Chem. Soc., 82, 659 (2005).

B.M. Patil, B.V. Badami and G.S. Puranik, Indian Drugs, 32, 493 (1995).

J.J. Jogul and B.V. Badami, J. Serb. Chem. Soc., 71, 851 (2006); doi:10.2298/JSC0609851J.

K. Satyanarayana and M.N.A. Rao, J. Pharm. Sci., 84, 263 (1995); doi:10.1002/jps.2600840228.

K. Satyanarayana and M.N.A. Rao, Eur. J. Med. Chem., 30, 641 (1995); doi:10.1016/0223-5234(96)88280-8.

B. Kalluraya and M.A. Rahiman, Indian J. Chem., 42B, 1141 (2003).

J.T. Li, X.H. Zhang and Z.P. Lin, Beilstein J. Org. Chem., 3, 13 (2007); doi:10.1186/1860-5397-3-13.

J.T. Li, W.Z. Yang, S.-X. Wang, S.-H. Li and T.-S. Li, Sonochem., 9, 237 (2002); doi:10.1016/S1350-4177(02)00079-2.

T.S. Saleh, N.M. Abd El-Rahman, A.A. Elkateb, N.O. Shaker, N.A. Mahmoud and S.A. Gabal, Ultrason. Sonochem., 19, 491 (2012); doi:10.1016/j.ultsonch.2011.10.008.

M. Dabiri, Z.N. Tisseh, M. Bahramnejad and A. Bazgir, Ultrason. Sonochem., 18, 1153 (2011); doi:10.1016/j.ultsonch.2010.12.004.

M.I. Choudhary, A. Begum, A. Abbaskhan, S.G. Musharraf, A. Ejaz and Atta-ur-Rahman, Chem. Biodivers., 5, 2676 (2008); doi:10.1002/cbdv.200890221.

Issue

Vol. 27 No. 8 (2015): Vol 27 Issue 8

Ultrasound Assisted One Pot Synthesis, Spectral, Antimicrobial and Antioxidant Studies of Novel 4-[1-Oxo-3-(substituted phenyl)-2-propenyl]-3-substituted Phenyl Sydnones

Corresponding Author(s) : Sachin K. Bhosale

Abstract

Keywords

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