Microwave assisted synthesis and in vitro antimicrobial activities of fluorine containing 4-benzofuran-2-yl-6-phenyl-pyrimidin-2-ylamines

Medicinal Chemistry

Volumn 10, Issue 4, 2014, Pages 409-417

  Chundawat, Tejpal Singh ^a   Sharma, Nutan ^a   Bhagat, Sunita ^a  

^a UNIVERSITY OF DELHI   (India)

Author keywords

Antimicrobial; Benzofuran; Claisen Schmidt condensation; Microwave assisted synthesis; Pyrimidine

Indexed keywords

1 BENZOFURAN 2 YL 3 (2 TRIFLUOROMETHYL PHENYL) PROP 2 EN 1 ONE; 1 BENZOFURAN 2 YL 3 (2,4 DIFLUOROPHENYL) PROP 2EN 1 ONE; 1 BENZOFURAN 2 YL 3 (2,5 DIFLUOROPHENYL) PROP 2EN 1 ONE; 1 BENZOFURAN 2 YL 3 (2,6 DIFLUOROPHENYL) PROP 2EN 1 ONE; 1 BENZOFURAN 2 YL 3 (3,4 DIFLUOROPHENYL) PROP 2EN 1 ONE; 1 BENZOFURAN 2 YL 3 (4 FLUOROPHENYL) PROP 2 EN 1 ONE; 1 BENZOFURAN 2 YL 3 (4 TRIFLUOROMETHYL PHENYL)PROP 2 EN 1 ONE; 4 BENZOFURAN 2 YL 6 (2 TRIFLUOROMETHYL PHENYL)PYRIMIDIN 2 YLAMINE; 4 BENZOFURAN 2 YL 6 (2,4 DIFLUOROPHENYL) PYRIMIDIN 2 YLAMINE; 4 BENZOFURAN 2 YL 6 (2,5 DIFLUOROPHENYL) PYRIMIDIN 2 YLAMINE; 4 BENZOFURAN 2 YL 6 (2,6 DIFLUOROPHENYL) PYRIMIDIN 2 YLAMINE; 4 BENZOFURAN 2 YL 6 (3,4 DIFLUOROPHENYL) PYRIMIDIN 2 YLAMINE; 4 BENZOFURAN 2 YL 6 (4 FLUOROPHENYL) PYRIMIDIN 2 YLAMINE; 4 BENZOFURAN 2 YL 6 (4 TRIFLUOROMETHYL PHENYL)PYRIMIDIN 2 YLAMINE; BENZALDEHYDE DERIVATIVE; BENZOFURAN DERIVATIVE; CHALCONE DERIVATIVE; FLUORINE DERIVATIVE; GUANIDINE; PYRIMIDINE; UNCLASSIFIED DRUG; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; BENZAMIDE DERIVATIVE; FLUORINE; PYRIMIDINE DERIVATIVE;

ALKALINITY; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; CHEMICAL REACTION; CLAISEN SCHMIDT CONDENSATION; CONTROLLED STUDY; CYCLOCONDENSATION; DRUG SYNTHESIS; FLUORINATION; IN VITRO STUDY; MICROWAVE RADIATION; NONHUMAN; PRIORITY JOURNAL; BACTERIA; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; FUNGUS; MICROBIAL SENSITIVITY TEST; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; BACTERIA; BENZAMIDES; DOSE-RESPONSE RELATIONSHIP, DRUG; FLUORINE; FUNGI; MICROBIAL SENSITIVITY TESTS; MICROWAVES; MOLECULAR STRUCTURE; PYRIMIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84899794633     PISSN: 15734064     EISSN: 18756638     Source Type: Journal    
DOI: 10.2174/15734064113099990036     Document Type: Article

References (48)

1. Ding, D.; Li, X.; Du, J.; Shen, J. Microwave assisted rapid and straightforward synthesis of 2-aryl-4-quinolones from acylated-2'- aminoacetophenones. Tetrahedron Lett., 2006, 47, 6997-6999.
2. Tan, W.; Zhao, B.X.; Sha, L.; Jiao, P.F.; Wan, M.S.; Su, L.D.; Shin, S. Synthetic Communication., 2006, 36, 1353-1359.
3. Laurence, P.; Andre, L. A tentative rationalization of microwave effects in organic synthesis according to the reaction medium and mechanistic considerations. Tetrahedron, 2001, 57, 9199-9223.
4. Kappe, C.O. Controlled Microwave Heating in Modern Organic Synthesis. Angew. Chem. Int. Ed., 2004, 43, 6250-6284.
5. Lin, S.Y.; Chen, C.L.; Lee, Y.J. Total Synthesis of Ailanthoidol and Precursor XH14 by Stille Coupling. J. Org. Chem., 2003, 68, 2968-2971.
6. Fuganti, C.; Serra, S. A new approach to 2-aryl-7-alkoxybenzofurans: Synthesis of ailanthoidol, a natural neolignan. Tetrahedron Lett., 1998, 39, 5609-5610.
7. Basawaraj, R.; Yadav, B.; Sangapure, S.S. Synthesis of some 1Hpyrazolines bearing benzofuran as biologically active agents. Indian J. Heterocycl. Chem., 2001, 11, 31-34.
8. Rida, S.M.; El-Hawash, S.A.M.; Fahmy, H.T.Y.; Hazzaa, A.A.; El-Meligy, M.M.M. Synthesis of novel benzofuran and related benzimidazole derivatives for evaluation of in vitro anti-HIV-1, anticancer and antimicrobial activities. Arch. Pharm. Res., 2006, 29, 826-833.
9. Ujjinamatada, R.K.; Appala, R.S.; Agasimundin, Y.S. Synthesis and antimicrobial activity of new benzofuranyl-1,3-benzoxazines and 1,3-benzoxazin-2-ones. J. Heterocycl. Chem., 2006, 43, 437-441.
10. Wachi, S.; Takagi, K.; Menichi, G.; Hubert-Habart, M. Research on potential antitumor agents. Methods for preparing hydropyrimidines from coumarins. Bull. Soc. Chim. Fr., 1978, 5-6, 230-233.
11. Singh, D.V.; Mishra, A.R.; Mishra, R.M.; Pandey, A.K.; Singh, C.R.; Dwivedi, A.K. Synthesis and Fungicidal activity of Benzofuran incorporated substituted pyrimidines. Indian J. Heterocycl. Chem., 2005, 14, 319-322.
12. Cho, J.U.; Kim, C.J.; Lee, H.B.; Lim, C.H. Patent Korea KR 2004064795, 2004 (CA: 145, 182279).
13. Druzgala, P.; Milner, P.G. Patent U.S. Patent. Appl. Publ. 2002193428, 2002 (CA: 138, 39179).
14. Dawood, K.M.; Abdel-Gawad, H.; Rageb, E.A.; Ellithey, M.; Mohamed, H.A. Synthesis, anticonvulsant and anti-inflammatory evaluation of somenew benzotriazole and benzofuran-based heterocycles. Bioorg. Med. Chem., 2006, 14, 3672-3680.
15. Nagaraj, A.; Reddy, S.C. Synthesis and Biological Study of Novel Bis-chalcones, Bis-thiazines and Bis-pyrimidines. J. Iran Chem. Soc., 2008, 5, 262-267.
16. Aruna Kumar, D.B.; Prakash, G.K.; Kumaraswamy, M.N.; Nandeshwarappa, D.P.; Sherigara, B.S.; Mahadevan, K.M. Microwave Assisted Facile Synthesis of Amino Pyrimidines Bearing Benzofuran and Investigation of their Antimicrobial activity. Indian J. Chem., 2006, 45B, 1699-1703.
17. Vashi, K.; Naik, H.B. Synthesis and Antibacterial activity of some novel chalcones and Pyrimidine-2-one derivatives. Asian J. Chem., 2005, 17, 240-244
18. Vyas, R.; Choudhary, P.C.; Sharma, H.; Verma, B.L. Microwave-assisted synthesis of 6H-2-amino-4,6-diaryl-1,3-thiazines. Indian J. Heterocycl. Chem., 2008, 17, 237-240
19. Bharucha, P.B.; Naik, H.B. Synthesis and Antibacterial activity of 2-Amino-4-(2'4'-Dichloro-5'-Fluorophen-1'yl)-6-Aryl Pyrimidine Derivatives and Related Compounds. Asian J. Chem., 1999, 11, 1553-1555.
20. Cheng, C.C. Some pyrimidines of biological and medicinal interest. I. Prog. Med. Chem., 1969, 6, 67-134.
21. Abdel-Wahab, B.F.; Abdel-Aziz, H.A.; Ahmed, E.M. Convenient Synthesis and Antimicrobial Activity of New 3-Substituted 5-(Benzofuran-2-yl)-pyrazole Derivatives. Arch. Pharm. Chem. Life Sci., 2008, 341, 734-739.
22. Abdel-Wahab, B.F.; Abdel-Aziz, H.A.; Ahmed, E.M. Synthesis and antimicrobial evaluation of 1-(benzofuran-2-yl)-4-nitro-3-arylbutan-1-ones and 3-(benzofuran-2-yl)-4,5-dihydro-5-aryl-1-[4-(aryl)-1,3-thiazol-2-yl] -1H-pyrazoles. Eur. J. Med. Chem., 2009, 44, 2632-2635.
23. Nimavat, K.S.; Popat, K.H.; Vasoya, S.L.; Joshi, H.S. Synthesis of some new pyrimidine derivatives. Indian J. Heterocycl. Chem., 2003, 12, 217-220.
24. Amir, M.; Javed, S.A. 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 Pharma., 2008, 58, 467-477.
25. Atwal, K.S.; Rovnyak, G.C.; Malley, M.F. Dihydropyrimidine calcium channel blockers. 2. 3-substituted-4-aryl-1,4-dihydro-6-methyl-5- pyrimidinecarboxylic acid esters as potent mimics of dihydropyridines. J. Med. Chem., 1990, 33, 2629-2635
26. Atwal, K.S.; Swanson, B.N.; Moreland, S.; Reilly, B. 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., 1991, 34, 806-811
27. Rovnyak, G.C.; Atwal, K.S.; Malley, M.F. Dihydropyrimidine calcium channel blockers. 4. Basic 3-substituted-4-aryl-1,4-dihydropyrimidine-5- carboxylic acid esters. Potent antihypertensive agents. J Med Chem., 1992, 35 3254-3263
28. Rovnyak, G.C.; Beyer, B; Moreland, S. Calcium Entry Blockers and Activators: Conformational and Structural Determinants of Dihydropyrimidine Calcium Channel Modulators. J. Med. Chem., 1995, 38, 119-129.
29. Joule, J.; Smith, G. Heterocyclic Chemistry. ELBS Low Price Edn, London, 1979.
30. Garg, H.G.; Prakash, C. Potential antidiabetics. 7-N1- (betahydroxybenzylmethyl)-3methyl-4-arylhydrazono-2-pyrazolin-5-ones and N1-(beta-hydroxybenzylmethyl)-3-methyl-4-arylazo-5-methyl-or -phenylpyrazoles. J. Med. Chem., 1971, 14, 175-176.
31. Girardet, J.L.; Gunii, E.; Ester, C.; Cieslak, D.; Pietrzkowki, Z.; Wang, G. Synthesis and cytotoxicity of 4-amino-5-oxopyrido [2,3-d] pyrimidine nucleosides. J. Med. Chem., 2000, 43, 3704-3713.
32. Mostahar, S.; Alam, S.; Islam, A. Cytotoxic and Antimicrobial activities of some synthetic flavones. Indian J. Chem., 2006, 45B, 1478-1486.
33. Mogilaiah, K.; Rao, R.B. Claisen-Schmidt condensation in the solid state. Indian J. Chem., 1999, 38B, 869-871.
34. Zhai, L.; Chen, M.; Blom, J.; Theander, T.G.; Christensen, S.B.; Kharazmi, A. The antileishmanial activity of novel oxygenated chalcones and their mechanism of action. J. Anti Microb. Chemother., 1999, 43, 793-803.
35. Jhala, Y.S.; Dulawat, S.S.; Verma, B.L. Solvent free improved synthesis of some substituted 1,3-diaryl propenones and 3,5-diaryl-6- carbethoxycyclohexanones under microwave irradiation and their antibacterial activity. Indian J. Chem., 2006, 45B, 466-469.
36. Jun, N.; Hong, G.; Jun, K. Synthesis and evaluation of 2′,4′,6′-trihydroxychalcones as a new class of tyrosinase inhibitors. Bioorg. Med. Chem., 2007, 15, 2396-2402.
37. Patel, V.M.; Desai, K.R. Microwave assisted heterocyclization: a rapid and efficient synthesis of 1,5-benzothiazepines. Indian J. Chem., 2004, 43, 199-201.
38. Bharucha, P. B.; Naik, H. B. Synthesis and antibacterial activity of some chalcone and 1,4-oxazipine Derivatives. Asian J. Chem., 2000, 12, 318-320.
39. Naik, V.R.; Naik, H.B. Synthesis and Antibacterial Activity of 2'-hydroxy 3'-bromo-5'ethyl chalcones and 3-(2'-hydroxy-3'bromo-5'-ethylphen-1'-yl)-5- substituted phenyl-2-isoxazoles. Asian J. Chem., 2000, 12, 305-307.
40. Purser, S.; Moore, P.R.; Swallow, S.; Gouverneur, V. Fluorine in medicinal chemistry. Chem. Soc. Rev., 2008, 37, 320-330.
41. Smart, B.E. Fluorine substitution effect (on bioactivity). J. Fluorine Chem., 2001, 109, 3-11.
42. Rowley, M.; Hallett, D.J.; Goodacre, S.; Moyes, C.; Crawforth, J.; Sparey, T.J.; Patel, S.; Marwood, R.; Thomas, S.; Hitzel, L.; O'Connor, D.; Szeto, N.; Castro, J.L.; Hutson, P.H.; Macleod, A.M. 3-(4-Fluoropiperidin-3-yl)- 2-phenylindoles as high affinity, selective, and orally bioavailable h5-HT(2A) receptor antagonists. J. Med. Chem., 2001, 44, 1603-1614.
43. Chakraborty, M.; Baweja, S.; Bhagat, S.; Chundawat, T.S. Microwave Assisted Synthesis of Schiff Bases: A Green Approach. IJCRE, 2012, 10, 1-12.
44. Bhagat, S.; Sharma, N.; Chundawat, T.S. Synthesis of Some Salicylaldehyde-Based Schiff Base in Aquous media. E. J. Chem., Article ID 909217, 2013. http://dx.doi.org/10.1155/2013/909217.
45. Paizs, C.; Tosa, M.; Majdik, C.; Moldovan, P.; Novak, L.; Kolonits, P.; Marcovivi, A.; Irimie, F.D.; Poppe, L. Optically active 1-(benzofuran-2-yl) ethanols and ethane-1,2-diols by enantiotopic selective bioreductions. Tetrahedron Asymmetry, 2003, 14, 1495-1501.
46. Carson, C.F.; Hammer, K.A.; Riley, T.V. Broth microdilution method for determining the susceptibility of Escherichia coli and Staphylococcus aureus to the essential oil of Melaleuca alternifolia (tea tree oil). Microbios, 1995, 82, 181-185.
47. Tarpay, M.M.; Welch, D.F.; Marks, M.I. Antimicrobial susceptibility testing of Streptococcus pneumoniae by micro-broth dilution. Antimicrob. Agents Chemother., 1980, 18, 579-581.
48. Riesselman, M.H.; Hazen, K.C.; Cutler, J.E. Determination of antifungal MICs by a rapid susceptibility assay. J. Clin. Microbiol., 2000, 38, 333-340.