Non-classical antifolates. Part 2: Synthesis, biological evaluation, and molecular modeling study of some new 2,6-substituted-quinazolin-4-ones

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 8, 2010, Pages 2849-2863

  Al Omary, Fatmah A M ^a   Abou zeid, Laila A ^b   Nagi, Mahmoud N ^a   Habib, El Sayed E ^c   Abdel Aziz, Alaa A M ^a   El Azab, Adel S ^a   Abdel Hamide, Sami G ^a   Al Omar, Mohamed A ^a   Al Obaid, Abdulrahman M ^a   El Subbagh, Hussein I ^a  

^a KING SAUD UNIVERSITY   (Saudi Arabia)

^b Mansoura University 35516   (Egypt)

^c MANSOURA UNIVERSITY   (Egypt)

Author keywords

Antimicrobial activity; Antitumor screening; DHFR inhibition; Molecular modeling study; Quinazolin 4 ones; Synthesis

Indexed keywords

2 ALLYLTHIO 3 BENZYL 6 DIALLYLAMINOQUINAZOLIN 4(3H) ONE; 2 ALLYLTHIO 3 BENZYL 6 DICINNAMYLAMINOQUINAZOLIN 4(3H) ONE; 3 BENZYL 2 CINNAMYLTHIO 6 METHYLQUINAZOLIN 4(3H) ONE; 3 BENZYL 2 MERCAPTO 6 METHYLQUINAZOLIN 4(3H) ONE; 3 BENZYL 2 MERCAPTO 6 NITROQUINAZOLIN 4(3H) ONE; 3 BENZYL 6 CINNAMYLAMINO 2 METHYLTHIOQUINAZOLIN 4(3H) ONE; 3 BENZYL 6 DICINNAMYLAMINO 2 METHYLTHIOQUINAZOLIN 4(3H) ONE; 6 ALLYLAMINO 2 ALLYLTHIO 3 BENZYLQUINAZOLIN 4(3H) ONE; 6 ALLYLAMINO 3 BENZYL 2 METHYLTHIOQUINAZOLIN 4(3H) ONE; 6 ALLYLMETHYLAMINO 3 BENZYL 2 METHYLTHIOQUINAZOLIN 4(3H) ONE; 6 AMINO 3 BENZYLQUINAZOLIN 4(3H) ONE; ANTIINFECTIVE AGENT; BENZYL DERIVATIVE; CLOTRIMAZOLE; DIHYDROFOLATE REDUCTASE; ENZYME INHIBITOR; FLUOROURACIL; FOLIC ACID ANTAGONIST; GENTAMICIN; METHOTREXATE; N (2 ALLYLTHIO 3 BENZYL 4 OXO 3,4 DIHYDROQUINAZOLIN 6 YL)CINNAMAMIDE; N (3 BENZYL 2 CINNAMYLTHIO 4 OXO 3,4 DIHYDROQUINAZOLIN 6 YL)ACRYLAMIDE; N (3 BENZYL 2 CINNAMYLTHIO 4 OXO 3,4 DIHYDROQUINAZOLIN 6 YL)CINNAMAMIDE; N (3 BENZYL 2 METHYLTHIO 4 OXO 3,4 DIHYDROQUINAZOLIN 6 YL)CINNAMAMIDE; QUINAZOLINONE DERIVATIVE; SULFACETAMIDE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CONTROLLED STUDY; DRUG DESIGN; DRUG MECHANISM; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION; ESCHERICHIA COLI; HUMAN; HUMAN CELL; IC 50; MICROCOCCUS LUTEUS; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR MODEL; NONHUMAN; PHARMACOPHORE; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION;

ANTI-INFECTIVE AGENTS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; FOLIC ACID ANTAGONISTS; HUMANS; HYDROPHOBICITY; MOLECULAR DYNAMICS SIMULATION; QUINAZOLINONES; STATIC ELECTRICITY; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAHYDROFOLATE DEHYDROGENASE;

EID: 77950520478     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.03.019     Document Type: Article

References (58)

1. Masur H. J. Infect. Dis. 161 (1990) 858
2. Berman E.M., and Werbel L.M. J. Med. Chem. 34 (1991) 479
3. Borst P., and Quellette M. Annu. Rev. Microbiol. 49 (1995) 427
4. Green E., and Demos C.H. In: Sirotnak F.M., Burchall J.J., Ensminger W.B., and Montgomery J.A. (Eds). Folate Antagonists as Therapeutic Agents 2 (1984), Academic Press, Orlando 191-249
5. Mullarkey M.F., Blumenstein B.A., Andrade W.P., Bailey G.A., Olason I., and Weizel C.E. N. Eng. J. Med. 318 (1988) 603
6. Elslager E.F., Johnson J.L., and Werbel L.M. J. Med. Chem. 26 (1983) 1753
7. Grivsky E.M., Lee S., Sigel C.W., Duch D.S., and Nichol C.A. J. Med. Chem. 23 (1980) 327
8. Bavetsias V., Jackman A.L., Marriott J.H., Kimbell R., Gibson W., Boyle F.T., and Bisset G.M. J. Med. Chem. 40 (1997) 1495
9. Bavetsias V., Marriott J.H., Melin C., Kimbell R., Matusiak Z.S., Boyle F.T., and Jackman A.L. J. Med. Chem. 43 (2000) 1910
10. Werbel L.M., and Degnan M.J. J. Med. Chem. 30 (1987) 2151
11. Sheng-Li C., Yu-Ping F., Yu-Yang J., Shi-Ying L., Guo-Yu D., and Run-tao L. Bioorg. Med. Chem. Lett. 15 (2005) 1915
12. Wyss P.C., Gerber P., Hartman P.G., Hubschwerlen C., Locher H., Marty H., and Stahl M. J. Med. Chem. 46 (2003) 2304
13. El-Subbagh H.I., El-Sherbeny M.A., Nasr M.N., Goda F.E., and Badria F.A. Boll. Chim. Farm. 134 (1995) 80
14. El-Subbagh H.I., Abadi A.H., and Al-Khamees H.A. Arch. Pharm. Pharm. Med. Chem. 330 (1997) 277
15. El-Obaid A.M., El-Shafie F.S., Al-Mutairi M.S., and El-Subbagh H.I. Sci. Pharm. 67 (1999) 129
16. El-Subbagh H.I., Abadi A.H., El-Khawad I.E., and Rashood K.A. Arch. Pharm. Pharm. Med. Chem. 332 (1999) 19
17. Al-Obaid A.M., El-Subbagh H.I., Khodair A.I., and El-mazar M.M. Anti-Cancer Drugs 7 (1996) 873
18. El-Subbagh H.I., Abu-Zaid S.M., Mahran M.A., Badria F.A., and Al-Obaid A.M. J. Med. Chem. 43 (2000) 2915
19. Al-Madi S.H., Al-Obaid A.M., and El-Subbagh H.I. Anti-Cancer Drugs 12 (2001) 835
20. Abdel Hamid S.G., El-Obaid H.A., Al-Rashood K.A., Khalil A.A., and El-Subbagh H.I. Sci. Pharm. 69 (2001) 351
21. Khalil A.A., Abdel Hamide S.G., Al-Obaid A.M., and El-Subbagh H.I. Arch. Pharm. Pharm. Med. Chem. 336 (2003) 95
22. El-Subbagh H.I., and Al-Obaid A.M. Eur. J. Med. Chem. 31 (1996) 1017
23. El-Subbagh H.I., El-Naggar W.A., and Badria F.A. Med. Chem. Res. 3 (1994) 503
24. Abdel Hamid S.G., El-Obaid H.A., Al-Majed A.A., El-Kashef H.A., and El-Subbagh H.I. Med. Chem. Res. 10 (2001) 378
25. Al-Omar M.A., Abdel Hamide S.G., Al-Khamees H.A., and El-Subbagh H.I. Saudi Pharm. J. 12 (2004) 63
26. Al-Rashood S.T., Aboldahab I.A., Abouzeid L.A., Abdel-Aziz A.A.-M., Nagi M.N., Abdul-hamide S.G., Youssef K.M., Al-Obaid A.M., and El-Subbagh H.I. Bioorg. Med. Chem. 14 (2006) 8608
27. Foye W.O., Lemke T.L., and Williams D.A. Principles of Medicinal Chemistry. 4th ed. (2005), Williams and Wilkins, Media, PA
28. Nordberg M.G., Kolmodin K., Aqvist J., Queener S.F., and Hallberg A. J. Med. Chem. 44 (2001) 2391
29. Joshi A.V., Bhusare S., Baidossi M., Qafisheh N., and Sasson Y. Tetrahedron Lett. 46 (2005) 3583
30. Ranu B.C., Dey S.S., and Hajra A. ARKIVOC 7 (2002) 76
31. Ranu B.C., Dey S.S., and Hajra A. Tetrahedron 59 (2003) 2417
32. Ranu B.C., Dey S.S., and Sampak S. ARKIVOC 3 (2005) 44
33. Grag S.K., Kumar R., and Chakraborti A.K. Tetrahedron Lett. 46 (2005) 1721
34. Chu C.-M., Gao S., Sastry M.N.V., and Yao C.-F. Tetrahedron Lett. 46 (2005) 4971
35. Pignatello R., Sapmpinato G., Sorrenti V., Vicari L., Di-Giacomo C., Vanella A., and Puglisi G. Pharm. Pharmacol. Commun. 5 (1999) 299
36. National Committee for Clinical Laboratory Standards (NCCLS) Approved standard document M-7A, Villanova, PA, 1985.
37. Murray P.R., Baron E.J., Pfaller M.A., Tenover F.C., and Yolken R.H. In: Wood G.L., and Washington J.A. (Eds). Manual of Clinical Microbiology (1995), Am. Soc. Microbiol., Washington, DC
38. Grever M.R., Schepartz S.A., and Chabner B.A. Semin. Oncol. 19 (1992) 622
39. Monks A., Scudiero D., and Skehan P. J. Natl. Cancer. Inst. 83 (1991) 757
40. Boyd M.R., and Paull K.D. Drug Rev. Res. 34 (1995) 91
41. Skehan P., Storeng R., Scudiero D., Monks A., McMahon J., Vistica D., Warren J.R., Bokesch H., Kenney S., and Boyd M.R. J. Natl. Cancer Inst. 82 (1990) 1107
42. López-Rodríguez M.L., Murcia M., Benhamú B., Viso A., Campillo M., and Pardo L. Bioorg. Med. Chem. Lett. 11 (2001) 2807
43. PowerFit, Microsimulation, Mahwah, NJ, USA, 1996.
44. Gokhale V.M., and Kulkarni V.M. J. Comput. Aided Mol. Des. 14 (2000) 495
45. Klon A.E., Heroux A., Ross L.J., Pathak V., Johnson C.A., Piper J.R., and Borhani D.W. J. Mol. Biol. 320 (2002) 677
46. Al-Obaid A.M., Abdel-Hamide S.G., El-Kashef H.A., Abdel-Aziz A.A.M., Al-Khamees H.A., and El-Subbagh H.I. Eur. J. Med. Chem. 44 (2009) 2379
47. Labute P., Williams C., Feher M., Sourial E., and Schmidt J.M. J. Med. Chem. 44 (2001) 1483
48. Kearsley S. Tetrahedron Comput. Methodol. 3 (1990) 615
49. Gerhard W., Thomas S., Fabian B., and Thierry L. Drug Discovery Today 13 (2008) 23
50. MOE 2007.9 of Chemical Computing Group. Inc.
51. Halgren T.A.J. J. Comput. Chem. 17 (1996) 490
52. HyperChem: Molecular Modeling System, Hypercube, Inc., Release 6.03, Florida, USA, 1997.
53. Profeta S., and Allinger N.L. J. Am. Chem. Soc. 107 (1985) 1907
54. Allinger N.L. J. Am. Chem. Soc. 99 (1977) 8127
55. Lipton M., and Still W.C. J. Comput. Chem. 9 (1988) 345
56. Dewar M.J.S., Zoebisch E.G., Healy E.F., and Stewart J.J.P. J. Am. Chem. Soc. 107 (1985) 3902
57. Orozco M., and Luque F.J. J. Comput. Chem. 11 (1990) 909
58. DSV pro 2005 by Accelrys Software Inc.