Thionylchloride catalyzed aldol condensation: Synthesis, spectral correlation and antibacterial activities of some 3,5-dichloro-2-hydroxyphenyl chalcones

• Autorzy: Arulkumaran R. , Vijayakumar S. , Sundararajan R. , Sakthinathan S. P. , Kamalakkannan D. , Suresh R. , Ranganathan K. , Vanangamudi G. , Thirunarayanan G.
• Języki publikacji: EN

Abstrakty

EN

A series of substituted styryl 3,5-dichloro-2-hydroxyphenyl ketones [1-(3, 5-dichloro-2-hydroxy)- 3-phenylprop-2-en-1-one] were synthesized using thionyl chloride assisted Crossed Aldol reaction. The yields of chalcones were more than 80%. The synthesized chalcones were characterized by analytical and spectroscopic data. From the spectroscopic data the group frequencies were correlated with Hammett substituent constants, F and R parameters. From the results of statistical analysis the effect of substituents were discussed. The antibacterial activities of these chalcones have been evaluated using Bauer-Kirby method.

Słowa kluczowe

EN

thionyl chloride; styryl 3,5-dichloro-2-hydroxyphenyl ketones; IR and NMR spectra; Hammett correlation; substituent effects; antimicrobial activities

PL

chlorek tionylu; widma IR i NMR; korelacja Hammeta; aktywność antybakteryjna; wpływ podstawników; styrylo 3,5-dichloro-2-hydroksy fenylo ketony

• Wydawca: Przedsiębiorstwo Wydawnictw Naukowych "DARWIN"
• Czasopismo: International Letters of Chemistry, Physics and Astronomy
• Rocznik: 2012
• Tom: Vol. 4
• Strony: 17--38
• Opis fizyczny: Bibliogr. 28 poz., rys., tab.

Twórcy

autor

Arulkumaran R.

autor

Vijayakumar S.

autor

Sundararajan R.

autor

Sakthinathan S. P.

autor

Kamalakkannan D.

autor

Suresh R.

autor

Ranganathan K.

autor

Vanangamudi G.

autor

Thirunarayanan G.

• PG & Research Department of Chemistry, Government Arts College, C-Mutlur, Chidambaram-608102, India.,

Bibliografia

• [1] (a) Thirunarayanan G, Vanangamudi G, Subramanian M, Umadevi U, Sakthinathan S P and Sundararajan R, Elixir Org.Chem, 39 (2011) 4643 – 4653 (b) Ranganathan R, Arulkumaran R, Kamalakkannan D, Vanangamudi G and Thirunarayanan G, IUP J. Chem, 4(2) (2011) 60 - 70
• [2] (a) Yankep E, Fomumand Z T, Dangne E. Phytochem, 46 (1997) 591 -593 (b) Sritularak K and Likhitwayawuid, Phytochem, 67 (2006) 812 - 817
• [3] Thirunarayanan G and Vanangamudi G E-J. Chem, 4 (1) (2007) 90-97
• [4] Ranganathan K, Arulkumaran R, Kamalakkannan D, Sundararajan R, Sakthinathan S P, Vijayakumar S, Suresh R, Vanangamudi G, Thirumurthy K, Mayavel P and Thirunrayanan G, Int.J. Pharm. Med. and Bio. SC, 1(1) (2012) 62 – 85
• [5] Venkat Reddy G, Maitraie G, Narsaiah D, Rambahu B, Rao R, Synth. Commun, 31(18), (2001) 2881 - 2884
• [6] Mulliken R S, J. Chem. Phys, 7 (1939) 121-131
• [7] Deiva C M, Pappano N B and Debattisata N B, Rev.Microbiol., 29(4) (1998) 307 - 310
• [8] Sivakumar M, Phrabusreeneivasan S, Kumarand V, Doble M, Bioorg. Med. Chem. Lett, 17(10) (2000) 3169 - 3172
• [9] Lahtchev K L, Batovska D I, St Parushev P, Ubiyvock V M and Sibirny A A, Eur. J. Med. Chem, 43(1) (2008) 2220 - 2228
• [10] Weber M W, Hunsaker L A, Abcouwer S F, Decker L M and Vander D L Jagat, Bioorg. Med. Chem, 13 (2005) 3811 - 3820
• [11] Parmer V S, Bishit K S, Jain R, Singh S, Sharma S K, Gupta S, Malhotra S, Tyagi O D, Vardhan A, Pati H N, Berghe D V and Vlietinek A J, Indian J. Chem, 35B (1996) 220 - 224
• [12] Dominguez J N, Leon C and Rodrigues J, IL Farmaco., 60(4) (2005), 307 - 311
• [13] Arulkumaran R, Sundararajan R, Vanangamudi G, Subramanian M, Ravi K, Sathiyendidran V, Srinivasan S and Thirunarayanan G, IUP J. Chem, 3(1) (2010) 82 - 98
• [14] Lin Y M, Zhon Y, Flavin M T, Zhon L M, Ne W and Chen F C, Bioorg. Med. Chem, 10(8) (2002) 2795 - 2802
• [15] (a) Liu X and Go M L, Bioorg. Med. Chem, 14 (2006), 153 – 163 (b). Delmulle L, Bellahcene A, Dhooge W, Comhaire F, Roelens F, Huvaere K. Heyerick A, Castronovo V and Keukeleire D D, Phytomed., 13 (2006) 732 - 734
• [16] Nielsen S F, Chen M, Theander T G, Kharazmi A and Christensen S B .Bioorg. Med. Chem. Lett, 5 (1995) 449 - 452
• [17] Hsieh H K, Tsao L T and Wang J P, J. Pham. Pharmacol, 52 (2000) 163 – 171
• [18] Vaiana G S, Banderia M A and Matos F, J. Phytomed., 10 (2003) 189 - 195
• [19] (a). Thirunarayanan G, J. Indian Chem. Soc, 84 (2008) 447 – 451 (b). Thirunarayanan G, Surya S, Srinivasan S, Vanangamudi G and Sathyendiran V, Spectrochim Acta., 75A (2010) 152 - 156
• [20] Dasharathi D, Netaji R, Basheer M A and Vibhute Y B Ultra Sci, 17(1) (2005) 89 -92
• [21] Thirunarayanan G, Mayavel P, Thirumurthy K, Spectrochim Acta, 91A (2012)18-22
• [22] Swain C G, Lupton E C Jr., Am. Chem. Soc. 90 (1968) 4328 - 4337
• [23] Hays W P, Timmons C J, Spectrochim. Acta, 24(A), (1968) 323- 334
• [24] Perjessy A, Hrnciar P, Coll. Czech. Chem. Commun, 35 (1970) 1120 –1128.
• [25] Silver N L, Boykin D W, Jr., J. Org. Chem. 35 (1970) 759 – 764
• [26] Lautrber P C, J. Am. Chem. Soc, 83 (1961) 1846-1852.
• [27] Solcaniova E, Toma S, Fiedlerova A, Org. Mag. Resonance, 14(3) (1980) 181-185.
• [28] Bauer A W, Kirby W M, Sherris J C, Truck M, Am. J. Clin. Pathol. 45 (1996) 493-498.