Login Register Cart 0
Generic placeholder image

Current Bioactive Compounds

Editor-in-Chief

ISSN (Print): 1573-4072
ISSN (Online): 1875-6646

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Biopolymer Catalysed Synthesis of 6-methyl-4-phenylcarbamoyl-1, 2, 3, 4- Tetrahydropyrimidine-2-ones and Evaluation of their Anti-bacterial and Anti-tubercular Activities

Author(s): Vasant Chabukswar*, Digamber Pawar, Kalpana Handore, Suresh Shisodia, Balasaheb Diwate, Pravin Adhav, Swati Jagdale, Anuruddha Chabukswar, Vishwas Gaikwad and Sabrina Dallavalle

Volume 15, Issue 4, 2019

Page: [408 - 414] Pages: 7

DOI: 10.2174/1573407214666180503114844

Price: $65

Abstract

Background: An efficient one-pot biocatalysed ultrasound assisted synthesis of dihydropyrimidinones/ thiones has been developed under solvent free conditions.

Materials and Methods: The use of biodegradable, non toxic, agar-powder as a catalyst provide advantages like high yield, simple operation, mild reaction condition with short reaction time. 1,2,3,4- tetrahydropyrimidine-2-ones/thiones formed were characterized by mass and 1H NMR spectroscopy.

Results: The dihydropyrimidinones substituted with electron donating groups like fluorine, hydroxy along with thienyl groups exhibited good antibacterial activity. The compounds exhibited favorable binding interactions with mycobacterium target protein H37Rv.

Conclusion: 4-methoxy substituted dihydropyrimidinones derivative showed significant antituberculosis activity.

Keywords: Biocatalysed synthesis, solvent free, green chemistry, antibacterial activity, anti tubercular activity, carambine.

Graphical Abstract

[1]
Salehi, H.; Guo, Q. A facile and efficient one‐pot synthesis of dihydropyrimidinones catalyzed by magnesium bromide under solvent‐‐free conditions. Synth. Commun., 2004, 34(1), 171-179.
[2]
Nair, A.C.; Jayatilleke, P.; Wang, X.; Miertus, S.; Welsh, W.J. Computational studies on tetrahydropyrimidine-2-one HIV-1 protease inhibitors: Improving three-dimensional quantitative structure-activity relationship comparative molecular field analysis models by inclusion of calculated inhibitor- and receptor-based properties. J. Med. Chem., 2002, 45(4), 973-983.
[3]
Ashok, M.; Holla, B.S.; Kumari, N.S. Convenient one pot synthesis of some novel derivatives of thiazolo[2,3-b]dihydropyrimidinone possessing 4-methylthiophenyl moiety and evaluation of their antibacterial and antifungal activities. Eur. J. Med. Chem., 2007, 42(3), 380-385.
[4]
Bahekar, S.S.; Shinde, D.B. Synthesis and anti-inflammatory activity of some [4,6-(4-substituted aryl)-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acetic acid derivatives. Bioorg. Med. Chem. Lett., 2004, 14(7), 1733-1736.
[5]
Debache, A.; Boumoud, B.; Amimour, M.; Belfaitah, A.; Rhouati, S.; Carboni, B. Phenylboronic acid as a mild and efficient catalyst for biginelli reaction. Tetrahedron Lett., 2006, 47(32), 5697-5699.
[6]
Patil, A.D.; Kumar, N.V.; Kokke, W.C.; Bean, M.F.; Freyer, A.J.; Brosse, C.D.; Mai, S.; Truneh, A.; Carte, B. Novel alkaloids from the sponge batzella sp.: Inhibitors of HIV gp120-human CD4 binding. J. Org. Chem., 1955, 60(5), 1182-1188.
[7]
Kappe, C.O. Biologically active dihydropyrimidones of the Biginelli-type--a literature survey. Eur. J. Med. Chem., 2000, 35(12), 1043-1052.
[8]
Handore, K.; Walunj, D.; Chhattise, P. A novel route towards the ultrasound assisted synthesis of polyindole-TiO2 nanocomposite and evaluation of antibacterial activity. Polym. Plast. Technol. Eng., 2017, 56(12), 1259-1266.
[9]
Udwadia, Z.F.; Amale, R.A.; Ajbani, K.K.; Rodrigues, C. Totally drug-resistant tuberculosis in India. Clin. Infect. Dis., 2012, 54(4), 579-581.
[10]
Debjit, B. Chiranjib; Chandira R. M.; Jayakar, B.; Kumar, K. P. S. Recent trends of drug used treatment of tuberculosis. J. Chem. Pharm. Res., 2009, 1(1), 113-133.
[11]
(a)Upadhayaya, R.S.; Vandavasi, J.K.; Kardile, R.A.; Lahore, S.V.; Dixit, S.S.; Deokar, H.S.; Shinde, P.D.; Sarmah, M.P.; Chattopadhyaya, J. Novel quinoline and naphthalene derivatives as potent antimycobacterial agents. Eur. J. Med. Chem., 2010, 45(5), 1854-1867.
(b)Chabukswar, A.; Kuchekar, B.; Lokhande, P.; Trambakye, M.; Pagare, B.; Kadam, V.; Jagdale, S.; Chabukswar, V. Design, synthesis and evaluation of antibacterial activity of novel indazole derivatives. Curr. Bioact. Compd., 2013, 9(4), 263-269.
[12]
Murthy, J.M. Tuberculous meningitis: The challenges. Neurol. India, 2010, 58(5), 716-722.
[13]
Kappe, C.O.; Falsone, S.F. Polyphosphate ester-mediated synthesis of dihydropyrimidines. improved conditions for the biginelli reaction. Synlett, 1998, 7, 718-720.
[14]
Nasr-Esfahani, M.; Hoseini, S.J.; Mohammadi, F. Fe3O4 nanoparticles as an efficient and magnetically recoverable catalyst for the synthesis of 3,4-dihydropyrimidin-2(1h)-ones under solvent-free conditions. Chin. J. Catal., 2011, 32(9), 1484-1489.
[15]
Jain, S.L.; Joseph, J.K.; Sain, B. Ionic liquid promoted an improved synthesis of 3,4-dihydropyrimidinones using [bmim]BF4 immobilized Cu (II) acetylacetonate as recyclable catalytic system. Catal. Lett., 2007, 115(1-2), 52-55.
[16]
Chen, X.; Peng, Y. Chloroferrate(III) ionic liquid: Efficient and recyclable catalyst for solvent-free synthesis of 3,4-dihydropyrimidin-2(1h)-ones. Catal. Lett., 2008, 122(3), 310-313.
[17]
Nakamura, H.; Matsui, Y. Silica gel nanotubes obtained by the solgel method. J. Am. Chem. Soc., 1995, 117(9), 2651-2652.
[18]
Pozarentzi, M.; Stephanatou, J.S.; Tsoleridis, C.A. An efficient method for the synthesis of 1,5-benzodiazepine derivatives under microwave irradiation without solvent. Tetrahedron Lett., 2002, 43(9), 1755-1758.
[19]
Garbe, T.R.; Kobayashi, M.; Shimizu, N.; Takesue, N.; Ozawa, M.; Yukawa, H. Indolyl carboxylic acids by condensation of indoles with α-keto acids. J. Nat. Prod., 2000, 63(5), 596-598.
[20]
Lal, J.; Gupta, S.K.; Agarwal, D.D. Chitosan: An efficient biodegradable and recyclable green catalyst for one-pot synthesis of 3,4-dihydropyrimidinones of curcumin in aqueous media. Catal. Commun., 2012, 27, 38-43.
[21]
DeCastro, C.; Primo, J.; Corma, A. Heteropolyacids and large-pore zeolites as catalysts in acylation reactions using α,β-unsaturated organic acids as acylating agents. J. Mol. Catal. Chem., 1998, 134(1-3), 215-222.
[22]
Budarin, V.; Clark, J.H.; Deswarte, F.E.I.; Hardy, J.J.E.; Hunt, A.J.; Kerton, F.M. Delicious not siliceous: expanded carbohydrates as renewable separation media for column chromatography. Chem. Commun. (Camb.), 2005, 23(23), 2903-2905.
[23]
Selby, H.H. Agar since 1943.American Chemical Society; Hydrocolloids, N.P., Ed.; Washington, D. C., 1954, Vol. 11, pp. 16-19.
[24]
Hemchandra, K.C.; Afsar, A.S.; Yogesh, D.M. Design and synthesis of novel oxadiazole and diphenyl ether hydrazone derivatives of coumarin as potential antibacterial agents. Curr. Bioact. Compd., 2017, 13(4), 318-325.
[25]
Guillemont, J.; Lieby-Muller, F.; Lounis, N.; Balemans, W.; Koul, A.; Andries, K. New anti-tuberculosis drugs in clinical development: An overview. Curr. Bioact. Compd., 2009, 5(2), 137-154.

Rights & Permissions Print Cite
Article Metrics
47
1
© 2024 Bentham Science Publishers | Privacy Policy