How to cite this paper
Borse, B., Borude, V & Shukla, S. (2012). Synthesis of novel dihydropyrimidin-2(1h)-ones derivatives using lipase and their antimicrobial activity.Current Chemistry Letters, 1(2), 59-68.
Refrences
1. Atwal, K. S., Swanson, B. N., Unger, S. E., Floyd, D. M., Moreland, S., Hedberg, A., and O’Reilly, B. C. (1991) Dihydropyrimidine calcium channel blockers. 3. 3-Carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidinecarboxylic acid esters as orally effective antihypertensive agents. J. Med. Chem., 34, 806-811
2. Atwal, K. S., and Moreland, S. (1991) Dihydropyrimidine calcium channel blockers 51: bicyclic dihydropyrimidines as potent mimics of dihydropyridines. Biorg. Med. Chem. Lett., 1, 291-294.
3. Kappe, C. O. (2000) Biologically active dihydropyrimidones of the Biginelli-type-a literature survey. Eur. J. Med. Chem., 35, 1043-1052.
4. Stefani, H. A., Oliveira, C. B., Almeida, R. B., Pereira, C. M. P., Braga, R. C., Cella, R., Borges, V. C., Savegnago, L., and Nogueira, C. W. (2006) Dihydropyrimidin-(2H)-ones obtained by ultrasound irradiation: a new class of potential antioxidant. Eur. J. Med. Chem., 41, 513-518.
5. Barrow, J. C., Nantermet, P. G., Selnick, H. G., Glass, K. L., Rittle, K. E., Gilbert, K. F., Steele, T. G., Homnick, C. F., Freidinger, R. M., Ransom, R. W., Kling, P., Reiss, D., Broten, T. P., Schorn, T. W., Chang, R. S. L., O’Malley, S. S., Olah, T. V., Ellis, J. D., Barrish, A., Kassahun, K., Leppert, P., Nagarathnam, D., and Forray, C. (2000) In vitro and in vivo evaluation of dihydropyrimidinone c-5 amides as potent and selective ?1a receptor antagonists for the treatment of benign prostatic hyperplasia. J. Med. Chem., 43, 2703-2718.
6. Mayer, T. U., Kapoor, T. M., Haggarty, S. J., King, R. W., Schreiber, S. L., and Mitchison, T. (1999) Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen. J. Science., 286, 971-974.
7. Tamaddon, F., Razmi, Z., and Jafari, A. (2010) Synthesis of 3,4-dihydropyrimidin-2(1H)-ones and 1,4-dihydropyridines using ammonium carbonate in water. Tetrahedron Lett., 51, 1187-1189.
8. Debache, A., Amimour, M., Belfaitah, A., Rhouati, S., and Carboni, B. (2008) A one-pot Biginelli synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones catalyzed by triphenylphosphine as Lewis base. Tetrahedron Lett., 49, 6119-6121.
9. Chen, X., and Peng, Y. (2008) Chloroferrate(III) ionic liquid: efficient and recyclable catalyst for solvent-free synthesis of 3,4-dihydropyrimidin-2(1 H )-ones. Catal. Lett., 122, 310-313.
10. Yuan, X. L., Zhang, S. J., and Lu, X. M. (2007) Hydroxyl ammonium ionic liquids: synthesis, properties, and solubility of SO2. J. Chem. Eng. Data., 52, 596-599.
11. Hajipour, A. R., and Rafiee, F. (2009) Basic ionic liquids. A short review. J. Iran. Chem. Soc. 6, 647-678.
12. Park, S., and Kazlauskas, R. J. (2003) Biocatalysis in ionic liquids – advantages beyond green technology. Curr. Opin. Biotechnol., 14, 432-437.
13. Davis, B. G., and Boyer, V. (2001) Biocatalysis and enzymes in organic synthesis. Nat. Prod. Rep., 18, 618-640.
14. Rantwijk, F. V., Lau, R. M., and Sheldon, R. A. (2003) Biocatalytic transformations in ionic liquids. Trends Biotechnol., 21, 131-138.
15. Peng, J., and Deng, Y. (2001) Ionic liquids catalyzed Biginelli reaction under solvent-free conditions. Tetrahedron Lett., 42, 5917-5919.
16. Abbott, A. P., Capper, G., Davies, D. L., Munro, H., Rasheed, R., and Tambyrajah, V. (2001) Preparation of novel, moisture-stable, Lewis-acidic ionic liquids containing quaternary ammonium salts with functional side chains. Chem. Commun., 2010-2011.
17. Phadtare, S. B., and Shankling, G. S. (2010) Halogenation reactions in biodegradable solvent: Efficient bromination of substituted 1-aminoanthra-9,10-quinone in deep eutectic solvent (choline chloride : urea). Green Chem., 12, 458-462.
18. Schmid, A., Dordick, J. S., Hauer, B., Kiener, A., Wubbolts, M., and Witholt, B. (2001) Industrial biocatalysis today and tomorrow. Nature, 409, 258-268.
19. Aleu, J., Bustillo, A. J., Hernandez-Galan, R., and Collado, I. G. (2006) Biocatalysis applied to the synthesis of agrochemicals. Curr. Org. Chem., 10, 2037-2054.
20. Klibanov, A. M. (1986) Enzymes that work in organic solvents. Chemtech, 16, 354-359.
21. Fang, J. M., and Wong, C. H. (1994) Enzymes in organic synthesis: Alteration of reversible reactions to irreversible processes. Synlett, 6, 393-402.
22. Sonawane, Y. A., Phadtare, S. B., Borse, B. N., Jagtap, A. R., and Shankerling, G. S. (2010) Synthesis of diphenylamine-based novel fluorescent styryl colorants by knoevenagel condensation using a conventional method, biocatalyst, and deep eutectic solvent. Organic letters, 12, 1456-1459.
23. He, T., Li, C., Feng, X. W., Wang, N., and Yu, X. Q. (2009) Lipase-catalysed direct Mannich reaction in water: utilization of biocatalytic promiscuity for C–C bond formation in a “one-pot” synthesis. Green Chem., 11, 777-779.
24. Li, C. J. (1993) Organic reactions in aqueous media with a focus on carbon-carbon bond formation. Chem. Rev., 93, 2023-2035.
25. Borse, B. N., Shukla, S. R., and Sonawane, Y. A. (2012) Simple, efficient, and green method for synthesis of trisubstituted electrophilic alkenes using lipase as a biocatalyst. Syn. Commun., 42, 412-423.
26. Dondoni, A., and Massi, A. (2001) Parallel synthesis of dihydropyrimidinones using Yb(III)-resin and polymer-supported scavengers under solvent-free conditions. A green chemistry approach to the Biginelli reaction. Tetrahedron Lett., 42, 7975-7978.
27. Kappe, C. O. (1997) A reexamination of the mechanism of the Biginelli dihydropyrimidine synthesis. Support for an N-Acyliminium ion intermediate1. J. Org. Chem., 62, 7201-7204.
28. Schmink, J. R., Kormos, C. M., Devine, W. G., and Leadbeater, N. E. (2010) Exploring the scope for scale-up of organic chemistry using a large batch microwave reactor. Org. Process Res. Dev., 14, 205-214.
29. Mirza?Aghayan, M., Bolourtchian, M., and Hosseini, M. (2004) Microwave-assisted efficient synthesis of dihydropyrimidines in solvent-free condition. Synth. Commun. 34, 3335-3341.
30. Ding, D., Zhao, C. G. (2010) Primary amine catalyzed Biginelli reaction for the enantioselective synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Eur. J. Org. Chem., 3802-3805.
31. National Committee for Clinical Laboratory Standards. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved standard M7-A4. National Committee for Clinical Laboratory Standards, Wayne, PA, 2000.
32. Koeth, L. M., King, A., Knight, H., May, J., Miller, L. A., Phillips, I., and Poupard, J. A. (2000) Comparison of cation-adjusted Mueller-Hinton with Iso-Sensitest broth for the NCCLS broth microdilution method. J. Antimicrob. Chemother., 46, 369-376.
33. Sarkar, S. D., Nahar, L., Kumarasamy, Y. (2007) Microtitre plate-based antibacterial assay incorporating resazurin as an indicator of cell growth, and its application in the in vitro antibacterial screening of phytochemicals. Methods. 42, 321-324.
2. Atwal, K. S., and Moreland, S. (1991) Dihydropyrimidine calcium channel blockers 51: bicyclic dihydropyrimidines as potent mimics of dihydropyridines. Biorg. Med. Chem. Lett., 1, 291-294.
3. Kappe, C. O. (2000) Biologically active dihydropyrimidones of the Biginelli-type-a literature survey. Eur. J. Med. Chem., 35, 1043-1052.
4. Stefani, H. A., Oliveira, C. B., Almeida, R. B., Pereira, C. M. P., Braga, R. C., Cella, R., Borges, V. C., Savegnago, L., and Nogueira, C. W. (2006) Dihydropyrimidin-(2H)-ones obtained by ultrasound irradiation: a new class of potential antioxidant. Eur. J. Med. Chem., 41, 513-518.
5. Barrow, J. C., Nantermet, P. G., Selnick, H. G., Glass, K. L., Rittle, K. E., Gilbert, K. F., Steele, T. G., Homnick, C. F., Freidinger, R. M., Ransom, R. W., Kling, P., Reiss, D., Broten, T. P., Schorn, T. W., Chang, R. S. L., O’Malley, S. S., Olah, T. V., Ellis, J. D., Barrish, A., Kassahun, K., Leppert, P., Nagarathnam, D., and Forray, C. (2000) In vitro and in vivo evaluation of dihydropyrimidinone c-5 amides as potent and selective ?1a receptor antagonists for the treatment of benign prostatic hyperplasia. J. Med. Chem., 43, 2703-2718.
6. Mayer, T. U., Kapoor, T. M., Haggarty, S. J., King, R. W., Schreiber, S. L., and Mitchison, T. (1999) Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen. J. Science., 286, 971-974.
7. Tamaddon, F., Razmi, Z., and Jafari, A. (2010) Synthesis of 3,4-dihydropyrimidin-2(1H)-ones and 1,4-dihydropyridines using ammonium carbonate in water. Tetrahedron Lett., 51, 1187-1189.
8. Debache, A., Amimour, M., Belfaitah, A., Rhouati, S., and Carboni, B. (2008) A one-pot Biginelli synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones catalyzed by triphenylphosphine as Lewis base. Tetrahedron Lett., 49, 6119-6121.
9. Chen, X., and Peng, Y. (2008) Chloroferrate(III) ionic liquid: efficient and recyclable catalyst for solvent-free synthesis of 3,4-dihydropyrimidin-2(1 H )-ones. Catal. Lett., 122, 310-313.
10. Yuan, X. L., Zhang, S. J., and Lu, X. M. (2007) Hydroxyl ammonium ionic liquids: synthesis, properties, and solubility of SO2. J. Chem. Eng. Data., 52, 596-599.
11. Hajipour, A. R., and Rafiee, F. (2009) Basic ionic liquids. A short review. J. Iran. Chem. Soc. 6, 647-678.
12. Park, S., and Kazlauskas, R. J. (2003) Biocatalysis in ionic liquids – advantages beyond green technology. Curr. Opin. Biotechnol., 14, 432-437.
13. Davis, B. G., and Boyer, V. (2001) Biocatalysis and enzymes in organic synthesis. Nat. Prod. Rep., 18, 618-640.
14. Rantwijk, F. V., Lau, R. M., and Sheldon, R. A. (2003) Biocatalytic transformations in ionic liquids. Trends Biotechnol., 21, 131-138.
15. Peng, J., and Deng, Y. (2001) Ionic liquids catalyzed Biginelli reaction under solvent-free conditions. Tetrahedron Lett., 42, 5917-5919.
16. Abbott, A. P., Capper, G., Davies, D. L., Munro, H., Rasheed, R., and Tambyrajah, V. (2001) Preparation of novel, moisture-stable, Lewis-acidic ionic liquids containing quaternary ammonium salts with functional side chains. Chem. Commun., 2010-2011.
17. Phadtare, S. B., and Shankling, G. S. (2010) Halogenation reactions in biodegradable solvent: Efficient bromination of substituted 1-aminoanthra-9,10-quinone in deep eutectic solvent (choline chloride : urea). Green Chem., 12, 458-462.
18. Schmid, A., Dordick, J. S., Hauer, B., Kiener, A., Wubbolts, M., and Witholt, B. (2001) Industrial biocatalysis today and tomorrow. Nature, 409, 258-268.
19. Aleu, J., Bustillo, A. J., Hernandez-Galan, R., and Collado, I. G. (2006) Biocatalysis applied to the synthesis of agrochemicals. Curr. Org. Chem., 10, 2037-2054.
20. Klibanov, A. M. (1986) Enzymes that work in organic solvents. Chemtech, 16, 354-359.
21. Fang, J. M., and Wong, C. H. (1994) Enzymes in organic synthesis: Alteration of reversible reactions to irreversible processes. Synlett, 6, 393-402.
22. Sonawane, Y. A., Phadtare, S. B., Borse, B. N., Jagtap, A. R., and Shankerling, G. S. (2010) Synthesis of diphenylamine-based novel fluorescent styryl colorants by knoevenagel condensation using a conventional method, biocatalyst, and deep eutectic solvent. Organic letters, 12, 1456-1459.
23. He, T., Li, C., Feng, X. W., Wang, N., and Yu, X. Q. (2009) Lipase-catalysed direct Mannich reaction in water: utilization of biocatalytic promiscuity for C–C bond formation in a “one-pot” synthesis. Green Chem., 11, 777-779.
24. Li, C. J. (1993) Organic reactions in aqueous media with a focus on carbon-carbon bond formation. Chem. Rev., 93, 2023-2035.
25. Borse, B. N., Shukla, S. R., and Sonawane, Y. A. (2012) Simple, efficient, and green method for synthesis of trisubstituted electrophilic alkenes using lipase as a biocatalyst. Syn. Commun., 42, 412-423.
26. Dondoni, A., and Massi, A. (2001) Parallel synthesis of dihydropyrimidinones using Yb(III)-resin and polymer-supported scavengers under solvent-free conditions. A green chemistry approach to the Biginelli reaction. Tetrahedron Lett., 42, 7975-7978.
27. Kappe, C. O. (1997) A reexamination of the mechanism of the Biginelli dihydropyrimidine synthesis. Support for an N-Acyliminium ion intermediate1. J. Org. Chem., 62, 7201-7204.
28. Schmink, J. R., Kormos, C. M., Devine, W. G., and Leadbeater, N. E. (2010) Exploring the scope for scale-up of organic chemistry using a large batch microwave reactor. Org. Process Res. Dev., 14, 205-214.
29. Mirza?Aghayan, M., Bolourtchian, M., and Hosseini, M. (2004) Microwave-assisted efficient synthesis of dihydropyrimidines in solvent-free condition. Synth. Commun. 34, 3335-3341.
30. Ding, D., Zhao, C. G. (2010) Primary amine catalyzed Biginelli reaction for the enantioselective synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Eur. J. Org. Chem., 3802-3805.
31. National Committee for Clinical Laboratory Standards. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved standard M7-A4. National Committee for Clinical Laboratory Standards, Wayne, PA, 2000.
32. Koeth, L. M., King, A., Knight, H., May, J., Miller, L. A., Phillips, I., and Poupard, J. A. (2000) Comparison of cation-adjusted Mueller-Hinton with Iso-Sensitest broth for the NCCLS broth microdilution method. J. Antimicrob. Chemother., 46, 369-376.
33. Sarkar, S. D., Nahar, L., Kumarasamy, Y. (2007) Microtitre plate-based antibacterial assay incorporating resazurin as an indicator of cell growth, and its application in the in vitro antibacterial screening of phytochemicals. Methods. 42, 321-324.