Efficient synthesis and antimicrobial evaluation of some Mannich bases from 2-arylidine-1-thia-4-azaspiro[4.5]decan-3-ones

Chemistry Central Journal

Essam M Hussein¹  Ghada S Masaret²  Khalid S Khairou² 

[1] Department of Chemistry, Faculty of Science, Assiut University, Assiut 71516, Egypt

[2] Department of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah, Saudi Arabia

关键词: Mannich bases;    Antimicrobial activity;    Sodium dodecylbenzene sulfonate;    1-thia-4-azaspiro[4.5]decan-3-one;    Spiro;   

Others  :  1213781
DOI  :  10.1186/s13065-015-0101-8

 received in 2014-12-18, accepted in 2015-04-29,  发布年份 2015

【 摘 要 】

Background

Thiazolidinone, has been employed in the preparation of different important drugs required for treatment of inflammations, bacterial infections, and hypertension. Mannich bases have been shown to exhibit diverse biological activities, such as antibacterial, and antifungal activities. Spiroheterocycles including thiazolidine moiety have antimicrobial activity.

Results

In this study, a novel, rapid, and efficient protocol is developed for the synthesis of various 2-arylidine-1-thia-4-azaspiro[4.5]decan-3-ones using sodium dodecylbenzene sulfonate (DBSNa) as an inexpensive and readily available reagent in acetic acid at room temperature. High yields, easy work-up, and short reaction times are advantages of this procedure. The synthesized arylidines were undergone Mannich reaction with formaldehyde and secondary amines in absolute ethanol at room temperature to afford the corresponding N-Mannich bases. All prepared Mannich bases were evaluated for their antimicrobial activity.

Conclusions

Good activity was noted for Mannich bases from 2-arylidine-1-thia-4-azaspiro[4.5]decan-3-ones, with some members recorded higher antimicrobial activity.

【 授权许可】

   
2015 Hussein et al.; licensee Springer.

【 参考文献 】

• [1]Jain AK, Vaidya A, Ravichandran V, Kashaw SK, Agrawal RK. Recent developments and biological activities of thiazolidinone derivatives: A review. Bioorg Med Chem. 2012; 20:3378-95.
• [2]Lewis JR. Miscellaneous alkaloids: Amaryllidaceae, Sceletium, muscarine, imidazole, oxazole, peptide and other miscellaneous alkaloids. Nat Prod Rep. 1999; 16:389-416.
• [3]Clemence F, Marter OL, Delevalle F, Benzoni J, Jouanen A, Jouquey S et al.. 4-Hydroxy-3-quinolinecarboxamides with antiarthritic and analgesic activities. J Med Chem. 1988; 31:1453-62.
• [4]Tsuji K, Ishikawa H. Synthesis and Anti-pseudomonal Activity of New 2-Isocephems with a Dihydroxypyridone Moiety at C-7. Biorg Med Chem Lett. 1944; 4:1601-6.
• [5]Patt WC, Hamilton HW, Taylor MD, Ryan MJ, Taylor DG, Connolly CJC et al.. Structure-activity relationships of a series of 2-amino-4-thiazole-containing renin inhibitors. J Med Chem. 1992; 35:2562-72.
• [6]Metzger JV. Comprehensive Heterocyclic Chemistry. Pergamon Press, New York; 1984.
• [7]Sridhar SK, Saravanan M, Ramesh A. Synthesis and Antibacterial Screening of Hydrazones, Schiff and Mannich Bases of Isatin Derivatives. Eur J Med Chem. 2001; 36:615-25.
• [8]Pandeya SN, Sriram D. Synthesis and Screening for Antibacterial Activity of Schiff’s and Mannich Bases of Isatin and its Derivatives. Acta Pharm Turc. 1998; 40:33-8.
• [9]Pandeya SN, Yogeeswari P, Sriram D, Nath G. Synthesis, Antibacterial and Antifungal Activities of N-Mannich Bases of 3-[N2-pyrimethaminylimino]isatin. Indian J Pharm Sci. 2002; 64:209-12.
• [10]Chhajed SS, Padwal MS. Antimicrobial Evaluation of Some Novel Schiff and Mannich Bases of Isatin and its Derivatives with Quinolin. Int J ChemTech Res. 2010; 2:209-13.
• [11]Hamley P, McInally T, Tinker A: PCT Int. Appl. WO 98 46, 611, (Cl. CO7D491 10), 1998, 22 Oct. 1998, SE Appl. 97/1, 396, 15 Apr. 1997; 32 PP.; Chem. Abstr. 1998, 129, 316237 f.
• [12]Trani A, Dallanoce C, Panzone G, Ripamonti F, Goldstein BP, Ciabatti R. Semisynthetic derivatives of purpuromycin as potential topical agents for vaginal infections. J Med Chem. 1997; 40:967-71.
• [13]Jain SC, Sinha J, Bhagat S, Errington W, Olsen CE. A Facile Synthesis of Novel Spiro-[Indole-pyrazolinyl-thiazolidine]-2,4′-dione. Synth Commun. 2003; 33:563-77.
• [14]Hussein EM. One-pot, Three-component, Green synthesis of Some Indeno[2′,3′:5,6] pyrido[2,1-b]benzothiazoles and Indeno[2′,3′-e]thiazolo[3,2-a]pyridines. Heterocycl Lett. 2012; 2:19-26.
• [15]Hussein EM. Enviro-economic, Ultrasound-assisted One-pot, Three-component Synthesis of Pyrido[2,3-d]pyrimidines in Aqueous Medium. Z Naturforsch. 2012; 67b:231-7.
• [16]Hussein EM, El-Khawaga AM. Simple and Clean Procedure for Three-component Syntheses of Spiro{pyrido[2,1-b]benzothiazole-3,3′-indolines} and Spiro{thiazolo[3,2-a]pyridine-7,3′-indolines} in Aqueous Medium. J Heterocycl Chem. 2012; 49:1296-301.
• [17]Hussein EM. Ultrasound-promoted Efficient Domino Reaction for One-pot synthesis of Spiro-5-cyanopyrimidines: A Rapid Procedure. Monatsh Chem. 2013; 144:1691-7.
• [18]Hussein EM. Ammonium Chloride-Catalyzed Four-Component Sonochemical Synthesis of Novel Hexahydroquinolines Bearing a Sulfonamide Moiety. Russian J Org Chem. 2015; 1:54-64.
• [19]Hussein EM, Abdel-Monem MI. Regioselective Synthesis and Anti-inflammatory Activity of Novel Dispiro[pyrazolidine-4,3′-pyrrolidine-2′,3″-indoline]-2″,3,5-triones. ARKIVOC. 2011; 10:85-98.
• [20]Hussein EM, Abdel-Monem MI. Regioselective Synthesis of Dispiro[indane-2,3′-pyrrolidine-2′,3″-indoline]-1,2″,3-triones and Evaluation of Their Anti-inflammatory Activities. Int Res J Pharm Pharmacol. 2012; 2:45-51.
• [21]Abdel-Mohsen SA, Hussein EM. A Green Synthetic Approach to the Synthesis of Schiff Bases from 4-Amino-2-thioxo-1,3-diazaspiro[5.5]undec-4-ene-5-carbonitrile as Potential Anti-inflammatory. Agents Russian j Bioorg Chem. 2014; 40:343-9.
• [22]Crossley NS. Carl Djerassi. Studies in Organic Sulphur Compounds. Part XVII. The Synthesis of Previously Inaccessible Acylated Enamines by Desulphurisation of Thiazolidines. J. Chem. Soc, Kielczewski MA; 1965.
• [23]Vogel HG. Drug discovery and evaluation, pharmacological assay. 2nd ed. Springer, New York; 2002.