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Synthesis, Characterization of 2-Methylthio-1, 4-Dihydropyrimidines for its Antibacterial Potential


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1 Dr. D. Y. Patil Unitech Society’s, Dr. D. Y. Patil Institute of Pharmaceutical Sciences and Research, Pimpri, Pune-411018, India
     

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Some novel 2-methylthio-1, 4-dihydropyrimidine derivatives (II) have been prepared in good yields by alkylation of 1,2,3,4-tetrahydropyrimidines (I) with methyl iodide in the presence of pyridine. All the synthesized compounds were characterized by, IR and 1H NMR spectra, Mass spectra and by elemental analysis. The title compounds were screened for their antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Proteus vulgaris. Ampicillin was used as a standard drug for evaluating antibacterial activity. Compounds with chlorine (IIe, IIf), nitro (IIi) and 3, 4, 5-trimethoxy groups (IIj) at para position in the aryl moiety were found to have potent activity amongst other compounds. Other compounds shows moderate activity.

Keywords

2-Methylthio-1, 4-Dihydropyrimidine, Biginelli Reaction, Synthesis, Antibacterial Activity.
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  • Mohammad A, Zahra Z. 1, 3-Dibromo-5, 5-dimethylhydantoin as a useful reagent for the efficient synthesis of 3, 4-dihydropyrimidin-2-(1H)-ones under solvent-free conditions. Chemical Papers. 2009; 63: 97–101.
  • Ezzat R, Hadi J. A practical and green approach towards the synthesis of dihydropyrimidinones: Using heteropoly acids as efficient catalysts. Bioorganic & Medicinal Chemistry Letters, 2006; 16: 2463–2466.
  • Kotharkar SA, Nagawade RR, Shinde DB. Chlorosulfonic acid catalyzed the highly efficient solvent_free synthesis of 3, 4-dihydropyrimidin-2(1H)-ones and thiones. Ukrainica Bioorganica Act. 2006; 2: 17—21.
  • Ahmad S, Abbas R. Ionic liquid promoted efficient synthesis of 3, 4-dihydropyrimidin-2-(1H)-ones. Catalysis Letters, April. 2005; Vol. 100: Nos. 3–4.
  • Shinde SV, Jadhav WN, Lande MK, Gadekar LS, Arbad BR, Kondre JM, Karade NN. Scolecite as a Novel Heterogeneous Acid Catalyst for an Efficient Synthesis of 3, 4-Dihydropyrimidin-2(1H)-ones Via Multi-component Biginelli Reaction. Catalysis Letters, 2008; 125: 57–61.
  • Arfan A, Paquin L, Bazureau JP. Acidic Task-Specific Ionic Liquid as Catalyst of Microwave-Assisted Solvent-Free Biginelli Reaction. Russian Journal of Organic Chemistry, 2007; Vol. 43: 1058–1064.
  • Chen-Jiang Liu, Ji-De Wang. Copper (II) Sulfamate: An Efficient Catalyst for the One-Pot Synthesis of 3, 4 Dihydropyrimidine-2(1H)-ones and thiones. Molecules, 2009; 14: 763-770 8. Yang Yu, Di Liu, Chunsheng Liu, Genxiang Luo. One-pot synthesis of 3, 4-dihydropyrimidin-2(1H)-ones using chloroacetic acid as catalyst. Bioorganic & Medicinal Chemistry Letters, 2007; 17: 3508–3510.
  • Fang Dong, Luo Jun, Zhou Xinli, Ye Zhiwen, Liu Zuliang. One-pot green procedure for Biginelli reaction catalyzed by novel task-specific room-temperature ionic liquids. Journal of Molecular Catalysis A: Chem. 2007; 27: 208–211.
  • Chitra S, Devanathan D, Pandiarajan K. Synthesis and in vitro microbiological evaluation of novel 4-aryl-5-isopropoxycarbonyl-6-methyl-3,4-dihydropyrimidinones. European Journal of Medicinal Chemistry. 2009; 1–5.
  • Kappe CO. Biologically active dihydropyrimidones of the Biginelli-type —a literature survey. European Journal of Medicinal Chemistry 2000; 3: 1043–105.
  • Mohammad A, Sadique AJ, Harish K. Synthesis and biological evaluation of some 4-(1H-indol-3-yl)-6-phenyl-1,2,3,4-tetrahydropyrimidin--2-ones/thiones as potent anti-inflammatory agents. Acta Pharmaceutica. 2008; 58: 467–477.
  • Ramesh S and Varsha S, Synthesis, Spectral Characterization and Analgesic Activity of 2-Methylthio-1, 4-Dihydropyrimidines, Iranian journal of pharmaceutical research, 2011; 10(4): 733-739.
  • Inci Selin Zorkun, Selma Sarac, Semra C. elebib, Kevser Erol. Synthesis of 4-aryl-3,4-dihydropyrimidin-2(1H)-thione derivatives as potential calcium channel blockers. Bioorganic & Medicinal Chemistry Letters, 2006; 14: 8582–8589.
  • Rovnyak GC, Atwal KS, Hedberg A, Kimball SD, Moreland S. Gougoutas J.Z. Dihydropyrimidine Calcium Channel Blockers. 4. Basic 3-Substituted-4-aryl-1,4-dihydropyrimidine-5-carboxylic acid Esters. Potent Antihypertensive Agents. Journal of Medicinal Chemistry, 1992; 35: 3254-3263.
  • Ramesh LS, Varsha IS, Ganesh DJ & Jyoti BW, Synthesis, molecular docking, and cardioprotective activity of 2-methylthio-1,4-dihydropyrimidines”, Medicinal Chemistry Research, 2012; 21(8): pp 1825-1832.
  • Ismaili L, Nadaradjane A, Nicod L, Guyon C, Xicluna A. Synthesis and antioxidant activity evaluation of new hexahydropyrimido[5,4-c]quinoline-2,5-diones and 2-thioxohexahydropyrimido[5,4-c]quinoline-5-ones obtained by Biginelli reaction in two steps. European Journal of Medicinal Chemistry, 2008; 43: 1270-1275.
  • Chakraborty P., A text book of microbiology, Second Edition., New central book Agency Ltd.India, 2003; 101-104.
  • Bhole RP. Chikhale RV, Khedekar PB, Bhusari KP, Synthesis and pharmacological investigation of 3-(substituted 1-phenylethanone)-4-(substituted phenyl)-1, 2, 3,4-tetrahydropyrimidine-5-carboxylates, European Journal of Medicinal Chemistry, 2009; 44: 3645–3653
  • Dr. Kokare C. R., Pharmaceutical microbiology experiment and techniques, Second Edition. Career Publications, 2007; 138.
  • Bhole RP, Bonde CG, Zambare YB, Effective potential studies for some new hybrid molecules for their activity against prostate cancer, Ars Pharmaceutica 2018; 59 (3): 133-144

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  • Synthesis, Characterization of 2-Methylthio-1, 4-Dihydropyrimidines for its Antibacterial Potential

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Authors

Varsha I. Sarode
Dr. D. Y. Patil Unitech Society’s, Dr. D. Y. Patil Institute of Pharmaceutical Sciences and Research, Pimpri, Pune-411018, India
Ritesh P. Bhole
Dr. D. Y. Patil Unitech Society’s, Dr. D. Y. Patil Institute of Pharmaceutical Sciences and Research, Pimpri, Pune-411018, India

Abstract


Some novel 2-methylthio-1, 4-dihydropyrimidine derivatives (II) have been prepared in good yields by alkylation of 1,2,3,4-tetrahydropyrimidines (I) with methyl iodide in the presence of pyridine. All the synthesized compounds were characterized by, IR and 1H NMR spectra, Mass spectra and by elemental analysis. The title compounds were screened for their antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Proteus vulgaris. Ampicillin was used as a standard drug for evaluating antibacterial activity. Compounds with chlorine (IIe, IIf), nitro (IIi) and 3, 4, 5-trimethoxy groups (IIj) at para position in the aryl moiety were found to have potent activity amongst other compounds. Other compounds shows moderate activity.

Keywords


2-Methylthio-1, 4-Dihydropyrimidine, Biginelli Reaction, Synthesis, Antibacterial Activity.

References