Novel derivatives of methyl and ethyl 2-(4-oxo-8-aryl-2H-3,4,6,7-tetrahydroimidazo[2,1-c][1,2,4]triazin-3-yl)acetates from biologically active 1-aryl-2-hydrazinoimidazolines: Synthesis, crystal structure and antiproliferative activity

European Journal of Medicinal Chemistry

Volumn 41, Issue 12, 2006, Pages 1373-1384

  Sztanke, Krzysztof ^a   Rzymowska, Jolanta ^a   Niemczyk, Maciej ^a   Dybała, Izabela ^b   Kozioł, Anna E ^b  

^a Department of Biology and Genetics ^*  (Poland)

^b MARIA CURIE SK ODOWSKA UNIVERSITY   (Poland)

Author keywords

Antibacterial activity; Antiproliferative activity; Crystal structure; Hydrazino group; Imidazo 2,1 c 1,2,4 triazines; Imidazolines; In vitro study; MIC

Indexed keywords

1 (2 METHOXYPHENYL) 2 HYDRAZINOIMIDAZOLINE HYDROIODIDE; 1 (2,6 DICHLOROPHENYL) 2 HYDRAZINOIMIDAZOLINE HYDROIODIDE; 1 (3 CHLOROPHENYL) 2 HYDRAZINOIMIDAZOLINE HYDROIODIDE; 1 (3,4 DICHLOROPHENYL) 2 HYDRAZINOIMIDAZOLINE HYDROIODIDE; 1 (4 CHLOROPHENYL) 2 HYDRAZINOIMIDAZOLINE HYDROIODIDE; 1 (4 METHOXYPHENYL) 2 HYDRAZINOIMIDAZOLINE HYDROIODIDE; 1 (4 METHYLPHENYL) 2 HYDRAZINOIMIDAZOLINE HYDROIODIDE; 1 PHENYL 2 HYDRAZINOIMIDAZOLINE HYDROIODIDE; AMPICILLIN; CHLORAMPHENICOL; ETHYL 2 [4 OXO 8 (3 CHLOROPHENYL) 2H 3,4,6,7 TETRAHYDROIMIDAZO[2,1 C][1,2,4]TRIAZIN 3 YL]ACETATE; ETHYL 2 [4 OXO 8 (4 CHLOROPHENYL) 2H 3,4,6,7 TETRAHYDROIMIDAZO[2,1 C][1,2,4]TRIAZIN 3 YL]ACETATE; ETHYL 2 [4 OXO 8 (4 METHOXYPHENYL) 2H 3,4,6,7 TETRAHYDROIMIDAZO[2,1 C][1,2,4]TRIAZIN 3 YL]ACETATE; ETHYL 2 [4 OXO 8 (4 METHYLPHENYL) 2H 3,4,6,7 TETRAHYDROIMIDAZO[2,1 C][1,2,4]TRIAZIN 3 YL]ACETATE; HYDRAZINE; IMIDAZOLINE DERIVATIVE; METHYL 2 (4 OXO 8 PHENYL 2H 3,4,6,7 TETRAHYDROIMIDAZO[2,1 C][1,2,4] TRIAZIN 3 YL)ACETATE; METHYL 2 [4 OXO 8 (2 METHOXYPHENYL) 2H 3,4,6,7 TETRAHYDROIMIDAZO[2,1 C][1,2,4]TRIAZIN 3 YL]ACETATE; METHYL 2 [4 OXO 8 (3 CHLOROPHENYL) 2H 3,4,6,7 TETRAHYDROIMIDAZO[2,1 C][1,2,4]TRIAZIN 3 YL]ACETATE; METHYL 2 [4 OXO 8 (4 CHLOROPHENYL) 2H 3,4,6,7 TETRAHYDROIMIDAZO[2,1 C][1,2,4]TRIAZIN 3 YL]ACETATE; METHYL 2 [4 OXO 8 (4 METHOXYPHENYL) 2H 3,4,6,7 TETRAHYDROIMIDAZO[2,1 C][1,2,4]TRIAZIN 3 YL]ACETATE; METHYL 2 [4 OXO 8 (4 METHYLPHENYL) 2H 3,4,6,7 TETRAHYDROIMIDAZO[2,1 C][1,2,4]TRIAZIN 3 YL]ACETATE;

ADDITION REACTION; ANALYTIC METHOD; ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; BACTERIAL STRAIN; BREAST CARCINOMA; CANCER CELL; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; COLON ADENOCARCINOMA; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; CRYSTAL STRUCTURE; CYCLIZATION; CYTOTOXICITY TEST; DRUG ACTIVITY; DRUG EFFICACY; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; ESCHERICHIA COLI; FUNGAL STRAIN; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; HUMAN; HUMAN CELL; INFRARED RADIATION; KIDNEY CELL; MINIMUM INHIBITORY CONCENTRATION; MOULD; NONHUMAN; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SKIN FIBROBLAST; STAPHYLOCOCCUS AUREUS; UTERUS CANCER; X RAY CRYSTALLOGRAPHY;

CELL LINE, TUMOR; CELL PROLIFERATION; CRYSTALLOGRAPHY, X-RAY; HUMANS; IMIDAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; SPECTROPHOTOMETRY, INFRARED;

EID: 33845346460     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2006.06.013     Document Type: Article

References (36)

1. Kleemann A., and Engel J. Pharmaceutical Substances (1999), Thieme, Stuttgart, New York
2. Negwer M. Organisch-Chemische Arzneimittel und ihre Synonyma (1987), Akademie-Verlag, Berlin
3. Donkor I.O., and Clark A.M. Eur. J. Med. Chem. 34 (1999) 639-643
4. Szymańska E., and Kieć-Kononowicz K. Farmaco 57 (2002) 355-362
5. Matysiak J., Niewiadomy A., Krajewska-Kułak E., and Ma{ogonek}cik-Niewiadomy G. Farmaco 58 (2003) 455-461
6. Erickson J.G. Chem. Heterocycl. Compd. 10 (1956) 44-137
7. Jones R.L., and Kershaw J.R. Rev. Pure Appl. Chem. 21 (1971) 23-48
8. Neunhoeffer H., and Wiley P.F. Chem. Heterocycl. Compd. 33 (1978) 189-574
9. Neunhoeffer H. In: Katrizky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry vol. 3 (1984), Pergamon Press, Oxford 385-456
10. El Ashry E.S.H., Rashed M., Taha E., and Ramadan E. Adv. Heterocycl. Chem. 59 (1994) 39-177
11. Diana P., Barraja P., Lauria A., Montalbano A., Almerico A.M., Dattolo G., and Cirrincione G. Eur. J. Med. Chem. 37 (2002) 267-272
12. Patil S.A., Otter R.S., and Klein R.S. Tetrahedron Lett. 35 (1994) 5339-5342
13. Partridge M.W., and Stevens M.F.G. J. Chem. Soc. (C) (1966) 1127-1131
14. Kurasawa Y., Kanoh M., Kamigaki J., Okiyama M., Takada A., and Okamoto Y. J. Heterocycl. Chem. 25 (1988) 1015-1018
15. de Clercq E. J. Med. Chem. 29 (1986) 1561-1569
16. de Clercq E. Anticancer Res. 6 (1986) 549-556
17. Heidelberg C., and Arafield F.G. Cancer Res. 23 (1963) 1226-1231
18. Baba M., Pauwels R., Herwig P., de Clercq E., Desmyster J., and Vandepulfe M. Biochem. Biophys. Res. Commun. 142 (1987) 128-134
19. Sztanke K., and Tkaczyński T. Acta Pol. Pharm. 54 (1997) 71-74
20. Sztanke K., and Tkaczyński T. Acta Pol. Pharm. 54 (1997) 147-149
21. Sztanke K., and Tkaczyński T. Acta Pol. Pharm. 54 (1997) 223-224
22. Sztanke K., Fidecka S., Ke{ogonek}dzierska E., Karczmarzyk Z., Pihlaja K., and Matosiuk D. Eur. J. Med. Chem. 40 (2005) 127-134
23. Sztanke K., Sidor-Wójtowicz A., Truchlińska J., Pasternak K., and Sztanke M. Ann. UMCS, Sect. D 59 2 (2004) 96-99
24. Tkaczyński T., Janocha R., Szacoń E., and Sztanke K. Acta Pol. Pharm. 52 (1995) 39-41
25. National Committee for Clinical and Laboratory Standards, Method for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved standard fourth ed., NCCLS Document M 100-S7, Villanova, Italy, 1997.
26. Isenberg D.H. Essential Procedure for Clinical Microbiology (1998), American Society for Microbiology, Washington
27. Zgoda J.R., and Porter J.R. Pharm. Biol. 39 (2001) 221-225
28. National Committee for Clinical Laboratory Standards, Disc-Diffusion Eleventh International Supplement, NCCLS Document M 100-S11, Wayne Pa, 2001.
29. Dzierżanowska D. Antybiotykoterapia praktyczna (1994), α-Medica press, Bielsko Biała
30. Ke{ogonek}dzia W.B. Diagnostyka mikrobiologiczna w medycynie (1990), PZWL, Warszawa
31. Sheldrick G.M. SHELXS-97, Program for Crystal Structure Solution (1997), University of Göttingen, Germany
32. Sheldrick G.M. SHELXL-97, Program for the Refinement of Crystal Structures From Diffraction Data (1997), University of Göttingen, Germany
33. Ellwart J., and Dormer P. Cytometry 6 (1985) 513-520
34. Magaud J.P., Sargent I., and Mason D.Y. J. Immunol. Methods 106 (1988) 95-100
35. Muir D., Varon S., and Manthorpe M. Anal. Biochem. 185 (1990) 377-382
36. Huong P.L.T. J. Immunol. Methods 140 (1991) 243-248