Main Article Content
Abstract
The compounds containing thiazole, thiadiazole, oxazole, oxadiazole, imidazole, pyrimidine, pyridine & benzothiazole rings have been found to exhibit broad spectrum of biological activities.
Derivatives of 1, 2, 4-thiadiazole and 1, 2, 4-thiadiazolidines exhibit antibacterial and antifungal activity1. Thiazolyl guanidines2 and various substituted aryl guanidine’s have been found to exhibit antibacterial & antifungal activities3.Keeping all these views in mind attempts were made to synthesized some new 1,3-di methyl Substituted Guanidine.
In the present work 2,4 Dimethyl -3,5-(di Aryl imino)-1,2,4-thiadiazolidines were prepared by nitrous acid oxidation of N-methyl –N Aryl thiourea4 & 2,4 dimethyl-3,5-(diaryl imino)-1,2,4-thiazolidines were converted to corresponding 1,3 di methyl substituted guanidine’s by their acid catalyzed re-arrangment5.(Scheme-1)
Antibacterial & Antifungal activity of the title compounds were evaluated against two bacteria, E.coli & lactobacillus & two fungi, A.Brassicicola & Aspergillus Niger. N=methyl-N`-Aryl thiourea (1-10) were prepared by refluxing a mixture of different 2-Amino Heterocyclic moieties with methyl iso thiocyanate in Ethanol.
A mixture of compound (1-100 and conc. HCl, ethanol was added drop wise & under stirring to a solution of NaNO2 in water afforded 2, 4-dimethyl-3,5-(di Aryl imino)-1,2,4-thiadiazolidine (11-20) afforded 1,3 di methyl substituted guanidine’s (21-30). Structures of the compounds were established by elemental analysis & spectral data.
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References
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- H. Schroeder & J. H. Reinhart: Belg.Pat. 624, 636/1963 (Chem. Abstr. 1963, 59, 11508).
- R.E. Alleno, R.S. Shelton and M.G. Vanampen: J.Am. Chem. Soc., 1954, 1158. G.D. Thorn: Can.J. Chem. 1960, 38, 2349. DOI: https://doi.org/10.1139/v60-318
- P.N. Bhargawa and Shree Prakash, J. Ind. Chem. Soc. 1980 56 (9), 937.
- S. N. Pandey and P.R. Naik: J. Ind. Chem. Soc., Vol.73 July 1996, 363-365.
- D.C. Schroeder: Chem. Rev., 1955, 55, 181. DOI: https://doi.org/10.1021/cr50001a005
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References
G. Brekel hammer and G. Asato, Science 1968; 162, 1146. I. B. Simon and I. Kovlunovskaya, L. Evshina: Chem abstr.19, 60, 54, 24760. C. K. Bradsher, F. C. Brown, E. F. Sinclair & S.T. Webster: J. Am Chem Soc., 1958, 80, 414.
T.Noguchi, A.Kaji, S.Kosak & T. Muraina: Jap. Pat. 17997/1962 (Chem. Abstr. 1963; 59, 11540).
H. Schroeder & J. H. Reinhart: Belg.Pat. 624, 636/1963 (Chem. Abstr. 1963, 59, 11508).
R.E. Alleno, R.S. Shelton and M.G. Vanampen: J.Am. Chem. Soc., 1954, 1158. G.D. Thorn: Can.J. Chem. 1960, 38, 2349. DOI: https://doi.org/10.1139/v60-318
P.N. Bhargawa and Shree Prakash, J. Ind. Chem. Soc. 1980 56 (9), 937.
S. N. Pandey and P.R. Naik: J. Ind. Chem. Soc., Vol.73 July 1996, 363-365.
D.C. Schroeder: Chem. Rev., 1955, 55, 181. DOI: https://doi.org/10.1021/cr50001a005
C. Christopheresen, T. Ottersen, K. Seff and S. Treppendahi: J.Am. Chem.Soc, 1975, 97, 5237. Horning: Collective Volume III, 599. DOI: https://doi.org/10.1021/ja00851a036
R.M. Dodson and L.C. King: J.Am. Chem. Soc., 1945, 2242, 67. DOI: https://doi.org/10.1021/ja01228a059
Y.L.Nene & P.N. Thapliyal: Fungicides in Plant Diseases Control 1982 (Oxford and IBH Publ., New Delhi) P.192.