Synthesis, characterization and derivatization of some novel types of mono- and bis-imidazolidineiminothiones and imidazolidineiminodithiones with antitumor, antiviral, antibacterial and antifungal activities - part I

European Journal of Medicinal Chemistry

Volumn 44, Issue 11, 2009, Pages 4315-4334

  El Sharief, Ahmed M Sh ^a   Moussa, Ziad ^a  

^a TAIBAH UNIVERSITY   (Saudi Arabia)

Author keywords

[No Author keywords available]

Indexed keywords

(3,4 DICHLOROPHENYL)CARBAMOTHIOYL CYANIDE; 1 (4 BROMOPHENYL) 3 (9H FLUOREN 2 YL) 4 IMINO 5 THIOXOIMIDAZOLIDIN 2 ONE; 1 (4 BROMOPHENYL) 3 [4 CHLORO 3 (TRIFLUOROMETHYL)PHENYL] 4 IMINO 5 THIOXOIMIDAZOLIDIN 2 ONE; 1 (4 CHLOROPHENYL) 3 (3,4 DICHLOROPHENYL) 1H IMIDAZO[4,5 B]QUINOXALIN 2(3H) ONE; 1 (4 CHLOROPHENYL) 3 (3,4 DICHLOROPHENYL) 4 THIOXOIMIDAZOLIDIN 2 ONE; 1 (4 CHLOROPHENYL) 3 (3,4 DICHLOROPHENYL) 5 IMINO 4 THIOXOIMIDAZOLIDIN 2 ONE; 1 (4 CHLOROPHENYL) 4 IMINO 3 (NAPHTHALEN 1 YL) 5 THIOXOIMIDAZOLIDIN 2 ONE; 1 (4 ETHOXYPHENYL) 3 (9H FLUOREN 2 YL) 4 IMINO 5 THIOXOIMIDAZOLIDIN 2 ONE; 1 (4 ETHOXYPHENYL) 3 (9H FLUOREN 2 YL) 5 THIOXOIMIDAZOLIDINE 2,4 DIONE; 1 (9H FLUOREN 2 YL) 5 IMINO 3 (4 IODOPHENYL) 4 THIOXOIMIDAZOLIDIN 2 ONE; 1,2 PHENYLENEDIAMINE; 1,3 BIS(4 BROMOPHENYL) 5 IMINOIMIDAZOLIDINE 2,4 DITHIONE; 3 (3,4 DICHLOROPHENYL) 5 IMINO 2 METHYLOXAZOLIDINE 4 THIONE; 3 (4 CHLOROPHENYL) 6 METHYL 1 4 TOLYL 1H IMIDAZO[4,5 B]QUINOXALIN 2(3H) ONE; 3,3' [4,4' METHYLENE BIS(2,6 DIETHYL 4,1 PHENYLENE)]BIS[1 (4 ETHOXYPHENYL) 4 IMINO 5 THIOXOIMIDAZOLIDIN 2 ONE]; 3,3' [4,4' OXYBIS(4,1 PHENYLENE)]BIS[1 (3,4 DICHLOROPHENYL) 4 IMINO 5 THIOXOIMIDAZOLIDIN 2 ONE]; 4 IMINO 1 (4 IODOPHENYL) 5 THIOXO 3 (2,4,5 TRICHLOROPHENYL)IMIDAZOLIDIN 2 ONE; 4 IMINO 3 (4 IODOPHENYL) 5 (4 IODOPHENYLIMINO)THIAZOLIDINE 2 THIONE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; HYDROGEN SULFIDE; IMIDAZOLIDINEIMINODITHIONE DERIVATIVE; IMIDAZOLIDINEIMINOTHIONE DERIVATIVE; QUINOXALINE DERIVATIVE; THIOHYDANTOIN DERIVATIVE; TRIETHYLAMMONIUM(3,4 DICHLOROPHENYL)CARBAMOTHIOYLCYANIDE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; ASPERGILLUS NIGER; CANCER CELL CULTURE; CANDIDA ALBICANS; CONCENTRATION RESPONSE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE;

ANTI-INFECTIVE AGENTS; ANTINEOPLASTIC AGENTS; BACTERIA; CELL LINE, TUMOR; CELL SURVIVAL; DRUG SCREENING ASSAYS, ANTITUMOR; FORMAMIDES; FUNGI; HUMANS; IMIDAZOLES; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; THIONES; VIRUSES;

EID: 70349972338     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.07.019     Document Type: Article

References (54)

1. Reissert A., and Bruggemann K. Berichte 57B (1924) 981-989
2. Water W., and Bode K.D. Leibigs Ann. 131 (1966) 698
3. Kömürcü S.Q.G., Rollas S., Yilmaz N., and Çevikbas A. Drug Metab. Drug Interact 12 (1995) 161-169
4. Tanaka K., Matsuo K., Nakanishi A., Jo M., Shiota H., Yamaguchi M., Yoshino S., and Kawaguchi K. Chem. Pharm. Bull. 32 (1984) 3291-3298
5. El-Sharief A.M.Sh., Al-Amri A., and Al-Raqa S.Y. J. Sulfur Chem 27 (2006) 245-263
6. El-Sharief A.M.Sh., Mahmoud F.F., Taha N.M., and Ahmed E.M. Phosphorus, Sulfur Silicon Relat. Elem. 180 (2005) 573-589
7. Ketcham R., and Schaumann E. J. Org. Chem. 45 (1980) 3748-3750
8. Al-Raqa S.Y., El-Sharief A.M.Sh., Khalil S.M.E., and Al-Amri A.M. Heteroat. Chem. 17 (2006) 634-647
9. El-Sharief A.M.Sh., El-Gaby M.S.A., Atalla A.A., and El-Adasy A.A.A.M. Heteroat. Chem. 16 (2005) 218-225
10. El-Sharief A.M.Sh., Ammar Y.A., Mohamed Y.A., and El-Gaby M.S.A. Heteroat. Chem. 13 (2002) 291-298
11. Ketcham R., Schaumann E., and Niemer T. Synthesis 11 (1980) 869-870
12. El-Gaby M.S.A., Ammar Y.A., El-Sharief A.M.Sh., Zahran M.A., and Khames A.A. Heteroat. Chem. 13 (2002) 611-616
13. Khattak I., Ketcham R., Schaumann E., and Adiwidjaja G. J. Org. Chem. 50 (1985) 3431-3434
14. Huang J., and Graves M.D. Heterocyclic Chem. 24 (1987) 1781-1785
15. El-Sharief A.M.Sh., and Al-Raqa S.Y. Phosphorus, Sulfur Silicon Relat. Elem. 182 (2007) 1557-1580
16. El-Sharief A.M.Sh., Ketcham R., and Schaumann E. Phosphorus, Sulfur Silicon Relat. Elem. 46 (1989) 83-86
17. Mohamed A.M., El-Sharief A.M.Sh., Ammar Y.A., and Aly M.M. Pharmazie 44 (1989) 765-767
18. Mohamed Y.A., Ammar Y.A., El-Sharief A.M.Sh., and Aly M.M. J. Chin. Chem. Soc. 37 (1990) 511-516
19. El-Gaby M.S.A., El-Sharief A.M.Sh., Atalla A.A., and El-Adasy A.A. J. Chin. Chem. Soc. 51 (2004) 327-333
20. El-Sharief A.M.Sh., Ammar Y.A., Mohamed Y.A., and El-Gaby M.S.A. Phosphorus, Sulfur Silicon Relat. Elem 148 (1999) 215-226
21. Ammar Y.A., El-Sharief A.M.Sh., Aly M.M., Mohamed Y.A., and Mohamed Sh.I. Phosphorus, Sulfur Silicon Relat. Elem 166 (2000) 173-185
22. El-Sharief A.M.Sh., Ammar Y.A., Mohamed Y.A., Aly M.M., El-Gaby M.S.A., and Aly A.S. Phosphorus, Sulfur Silicon Relat. Elem 173 (2001) 39-58
23. El-Sharief A.M.Sh., Hussein A.M., El-Gaby M.S.A., Atalla A.A., and Ahmed A.A. Phosphorus, Sulfur Silicon Relat. Elem 170 (2001) 47-63
24. El-Sharief A.M.Sh., Ammar Y.A., El-Gaby M.S.A., Zahran M.A., and Khames A.A. Afinidad 60 (2003) 47-54
25. El-Sharief A.M.Sh., Ammar Y.A., Zahran M.A., and Sabet H.Kh. Phosphorus, Sulfur Silicon Relat. Elem 179 (2004) 267-275
26. El-Sharief A.M.Sh., Ammar Y.A., and El-Gaby M.S.A. Afinidad 61 (2004) 240-255
27. El-Sharief A.M.Sh., El-Gaby M.S.A., Atalla A.A., and El-Adasy B.-B.A.A.M. Afinidad 60 (2003) 475-481
28. El-Sharief A.M.Sh., Atalla A.A., Hussein A.M., El-Gaby M.S.A., and Hassan A.A. Phosphorus, Sulfur Silicon Relat. Elem 160 (2000) 141-158
29. El-Sharief A.M.Sh., Ammar Y.A., Zahran M.A., and Sabet H.Kh. J. Chem. Res., Synop. 3 (2003) 162-167
30. For a general procedure for the preparation of cyanothioformanilides see:. Papadopoulos E.P. J. Org. Chem. 44 (1979) 3858-3861 For the preparation of Ia, see the following references
31. Ref. [1]
32. Hyunil L., and Kyongtae K. Bull. Korean Chem. Soc. 13 (1992) 107-108
33. Ib:. Grabenko A.D., and Pel'kis P.S. Zh. Obshch. Khim. 30 (1960) 1222-1226
34. Ic: commercially available; Also see:. Kumelj B., and Tisler M. Vestn. Slov. Kem. Drus. 5 (1958) 69-73
35. For both Ic and Id; Also see Ref. [5] For Id; Ic-e:. Grabenko A.D., and Pel'kis P.S. Inst. Org. Chem., Kiev, Zh. Obshch. Khim. 31 (1961) 2739-2743
36. If:. Kobayashi-Matsunaga Y., Ishiia T., Hamaguchia T., Osadab H., and Sato M. Lett. Drug Des. Discov. 2 (2005) 224-227
37. Groziak M.P., and Ding H. Acta Chim. Slov. 47 (2000) 1-18
38. In: Goodman S., and Gilman A. (Eds). The Pharmacological Basis of Therapeutics (1996), Macmillan, New York
39. Takayama C., Yamamoto S., Kato T., Hisada Y., and Fujinami A. Ger. Offen (1977) 24
40. Kato T., Yamamoto S., Takayama C., Kameda N., and Fujinami A. Jpn. Kokai Tokkyo Koho (1978) 15
41. Takayama C., Kato T., Yamamoto S., Hisada Y., Kameda N., and Fujinami A. Ger. Offen (1978) 24
42. Hsu C.Y., Knapp D.R., and Halushka P.V. J. Pharmacol. Exp. Ther. 208 (1979) 366-370
43. Miller D.D., Hamada A., Clark M.T., Adejare A., Patil P.N., Shams G., Romstedt K.J., Kim S.U., Intrasuksri U., Mekenzie J.L., and Feller D.R. J. Med. Chem. 33 (1990) 1138-1144
44. Shiba S.A., El-Khamry A.A., Shaban M.E., and Atia K.S. Pharmazie 52 (1997) 189-194
45. Kalwinsch I., Xingya L., Gottstein J., and Huisgen R. J. Am. Chem. Soc. 103 (1981) 7032-7033
46. El-Sharief A.M.S., and Hammad N.E. Indian J. Chem., Sect. B 20B 12 (1981) 1039-1042
47. El-Sharief A.M.S., and Hassanin A.A. Indian J. Chem., Sect. B 21B 12 (1982) 1102-1105
48. 4. NCCLS, National Committee for Clinical Laboratory Standards. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Fourth ed. (1997)
49. NCCLS, National Committee for Clinical Laboratory Standards. Method M27 A2. second ed. vol. 22 (15) (2002), Wayne, Ed.; NCCLS, Pennsylvania 1-29 19
50. NCCLS, National Committee for Clinical Laboratory Standards. Method M-38A. second ed. vol. 22 (16) (2002), Wayne, Ed.; NCCLS, Pennsylvania 1-27
51. Mclimans W.F., Davis E.V., Glover F.L., and Rake G.W. J. Immunol. 79 (1957) 428-433
52. Skehan P., Storeng R., Scudiero D., Monks A., McMahon J., Vistica D., Warren J.T., Bokesch H., Kenny S., and Boyd M.R. J. Natl. Cancer Inst. 82 (1990) 1107-1112
53. Dulbecco R., and Vogt M. J Exp. Med. 99 (1954) 167-182
54. Cooper R.E. In: Kavangeh F.W. (Ed). Analytical Microbiology vol. 1&2 (1972), Academic Press, New York and London