DNA-directed alkylating agents: Synthesis, antitumor activity and DNA affinity of bis-N,N′-trisubstituted 1,2,4-triazolo-piperazines

Farmaco

Volumn 59, Issue 1, 2004, Pages 41-46

  Al Soud, Yaseen A ^a   Al Masoudi, Najim A ^b  

^a AL AL BAYT UNIVERSITY   (Jordan)

^b UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1 (1,5 DIETHYL 1H[1,2,4]TRIAZOL 3 YLMETHYL) 4 METHYLPIPERAZINE; 1 (1,5 DIMETHYL 1H[1,2,4]TRIAZOL 3 YLMETHYL)4 METHYLPIPERAZINE; 1 CYANOMETHYL 4 METHYLPIPERAZINE; 1,4 BIS(1 ETHYL 5 METHYL 1H[1,2,4]TRIAZOL 3 YLMETHYL)PIPERAZINE; 1,4 BIS(1 ISOPROPYL 5 METHYL 1H[1,2,4]TRIAZOL 3 YLMETHYL)PIPERAZINE; 1,4 BIS(1,5 DIETHYL 1H[1,2,4]TRIAZOL 3 METHYL)PIPERAZINE; 2 (4 METHYLPIPERAZIN 1 YLMETHYL) 6,7,8,9 TETRAHYDRO 5H[1,2,4]TRIAZOLO[1,5 A]AZEPINE; 2,2' (PIPERAZIN 1,4 YLMETHYL)BIS(6,7,8,9 TETRAHYDRO 5H[1,2,4]TRIAZOLO[1,4 A]AZEPINE); ALKYLATING AGENT; ANTINEOPLASTIC AGENT; DNA; NITRILE; PIPERAZINE DERIVATIVE; PIPERAZINO 1,4 BIS(ETHANENITRILE); UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; CYCLOADDITION; DRUG ACTIVITY; DRUG DNA BINDING; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL;

EID: 1642497648     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.farmac.2003.08.006     Document Type: Article

References (48)

1. Vacca J.P., Dorsey B.D., Schleif W.A., Levin R.B., McDaniel S.L., Darke P.L., et al. An orally bioavailable human-immunodeficiency-virus type-1 protease inhibitor. Proc. Natl. Acad. Sci. USA. 91:1994;4096-4100.
2. B.D. Dorsey, R.B. Levin, S.L.McDaniel, J.P. Vacca, J.P. Guare, P.L. Darke, et al., L-735,524: the design of a potent and orally bioavailable HIV protease inhibitor, J. Med. Chem. 37 (1994) 3443-3451; D.L. Romero, R.A. Morge, M.J. Genin, C. Biles, M. Busso, L. Resnick, et al., Bis(heteroaryl)piperazine (DHAP) RT inhibitors: structure-activity relationship of novel indole analogues and the indentification of monomethanesulfonate (U-901525), J. Med. Chem. 36 (1993) 1505-1508.
3. Romero D.L., Morge R.A., Biles C., Berriospena T.N., May P.D., Palmer J.R., et al. Discovery, synthesis, and bioactivity of bis(Heteroaryl) piperazines. A novel class of nonnucleosides HIV-1 reverse-transcriptase inhibitors. J. Med. Chem. 37:1994;999-1014.
4. Romero D.L., Busso M., Tan C.K., Reuser F., Palmer J.R., Poppe S.M., et al. Nonnucleosides reverse transcriptase inhibitors that potently and specifically block human immunodeficiency virus type-1 replication. Proc. Natl. Acad. Sci. USA. 88:1991;8806-8810.
5. Mao C., Vig R., Venkatachalam T.K., Tuel-Ahlgren L., Sudbeck E.A., Uckun F.M. Structure-based design of N-[2-(1-piperidinylethyl)]-N′-[2-(5- bromopyridyl)]-thiourea and N-[2-(1-piperazinylethyl)]-N''-[2-(5-bromopyridyl)]- thiourea as potent non-nucleoside inhibitors of HIV-1 reverse transcriptase. Bioorg. Med. Chem. 6:1998;1789-1797.
6. Tuker J.A., Allwine D.A., Grega K.C., Barbachyn M.R., Klock J.L., Adamski J.L., et al. Piperazinyl oxazolidinone antibacterial agents containing a pyridine, diazene, or triazene heteroaromatic ring. J. Med. Chem. 41:1998;3727-3735.
7. Malinka W. Synthesis of some pyrrolo[3,4-d]pyridazinones and their preliminary anticancer, antimycobacterial and CNS screening. Pharmazie. 56:2002;384-389.
8. Malinka W., Sieklucka-Dziuba M., Rajtar G., Zgodzinski W., Kleinrok Z. Synthesis and preliminary screening of derivatives of 2-(4-arylpiperazin-1- ylalkyl)-3-oxoisothiazolo[5,4-b]pyridines as CNS and antimycobacterial agents. Pharmazie. 55:2000;416-425.
9. Winkelmann E., Raether W. Protozoacidal 1-methyl-5-nitro-2-(1- piperazinylmethyl)-imidazoles (Farbwerke Hoechst A.-G). Ger. Offen. J. 1974;. 2,308,826 (Cl.Ci 07c), p 23 08 826.8-44, 10 pp.
10. Da Settimo A., Ferrarini P.L., Mori C., Primofiore G. Synthesis of pyrido[1,2-a]pyrimidin-4-ones. Potential antihypertensive agents. Farmaco. 41:1986;926-933.
11. Archibald J.L., Freed M.E. 1,4-Bis(2-indol-3-ylethyl)piperazines. J. Med. Chem. 17:1974;745-747.
12. Beyerle R., Stachel A., Nitz R.E., Resag K., Schraven B., Ritter H. Piperazinocoumarine coronary dilators, (Cassella Farbwerke Mainkur A.-G.) 1,135,907 (Cl C 07d) 1968. Ger. Appl. 1966;21.
13. Chem. Abstr. 71:1969;49978e.
14. Tanaka A., Sakai H., Motoyama Y., Ishikawa T., Takasugi H. Antiplatelet agents based on cycloxygenase inhibition without ulcergenosis. Evaluation and synthesis of 4,5-bis(4-methoxyphenyl)-2-substituted-thiazoles. J. Med. Chem. 37:1994;1189-1199.
15. Mahajan D.K., Samuels L.T. Inhibtion of 17,20(17-hydroxyprogesterone)- lyase by progesterone. Steriods. 25:1975;217-227.
16. Santen R.J., van den Bosshe H., Symoens J. Site of action of low dose ketoconazole on androgen biosynthesis in men. J. Clin. Endocrind. Metab. 57:1983;732-736.
17. Hammar W.J., Conway A.C. Pharmaceutical 8-(4-methyl-1- piperazinylcarbonyl)-dibenzol[3,4:6,7]bicyclo[3,2.1]octa-3,6-diene. Ger. Offen. J. 1974;11. (Riker Laboratories, Inc.) 2,410,982 (Cl. C 07d).
18. Chem. Abstr. 82:1975;4308x.
19. Bruno A.M., Asis S.E., Gaozza C.H. Bis-naphthylureas and related compounds: synthesis, chemical properties, DNA affinity and antineoplastic activity. Pharmazie. 56:2001;361-365.
20. Renhowe P.A. Growth factor kinases in cancer. Doherty A.M. Annual Reports in Medicinal Chemistry. vol. 35:2001;109-118 Academic Press.
21. Tiwari S.S., Pandey M.P. Search for new antihelmintica, Part I Synthesis of piperazine derivatives. Indian J. Chem. 188:1979;379-381.
22. 1-adrenergic affinity. J. Med. Chem. 34:1991;2633-2638.
23. 1A receptor ligands. Bioorg. Med. Chem. Lett. 8:1998;2457-2462.
24. 3 receptors. Bioorg. Med. Chem. Lett. 8:1998;3567-3570.
25. 4 receptor: synthesis, ligand binding studies and comparison of molecular electrostatic potential maps. Bioorg. Med. Chem. Lett. 9:1999;97-102.
26. 4 receptor with high affinity for the antipsychotic clozapine. Nature. 350:1991;610-614.
27. 3 antagonists. Arch. Pharm. Pharm. Med. Chem. 332:1999;389-398.
28. Tsukuda T., Shiratori Y., Watanabe M., Ontsuka H., Hattori K., Shirai M., et al. Modeling, synthesis and biological activity of novel antifungal agents (1). Bioorg. Med. Chem. Lett. 8:1998;1819-1824.
29. Al-Soud Y.A., Wirschum W., Hassan N.A., Maier G.M., Jochims J.C. Reaction of 1-(chloroalkyl)-1-aza-2-azoniaallene salts with alkenes: preparation of cyclic azo, (azoalkyl)azonium, and formazanium compounds. Synthesis. 1998;721-728. and references cited therein.
30. Benzig E. Über Neue, a,a'-disubstitutierte azoalkane. Leibigs Ann. Chem. 631:1960;1-9.
31. Benzig E. Mechanismus der Zersetzung von aa'-Dichlo-Azoalkanen in Wässerigem Aceton. Leibgis Ann. Chem. 631:1960;10-21.
32. Al-Masoudi N.A., Hassan N.A., Al-Soud Y.A., Schmidt P., Gaafer A.E.-D.M., Weng M., et al. Synthesis of C- and N-nucleosides from 1-aza-2-azoniaellene and 1,3-diaza-2-azoniaallene salts. J. Chem. Soc. Perkin Trans. 1:1998;947-953.
33. Al-Soud Y.A., Al-Masoudi W.A., El-Halawa R.A., Al-Masoudi N.A. Synthesis and antiviral activity of some 1,2,4-triazole C-nucleosides from 1-(chloroalkyl)-1-aza-2-azo-niaallene salts. Nucleos. Nucleot. 18:1999;1985-1994.
34. Al-Masoudi N.A., Al-Soud Y.A., Geyer A. Synthesis and spectroscopic analysis of some acyclic C-nucleosides and the homo-C-analogues from 1-(chloroalkyl)-1-aza-2-azoniaallene salts. Tetrahedron. 15:1999;751-758.
35. Al-Soud Y.A., Al-Masoudi N.A. Synthesis and antiviral activity of some 1-(1,5-dialkyl-1H-1,2,4-triazole-3-yl)thymines. Arch. Pharm. Pharm. Med. Chem. 332:1999;143-144.
36. Al-Soud Y.A., Al-Masoudi N.A. Synthesis and antitumor activity of some new phthalimide analogues. Pharmazie. 56:2001;372-375.
37. Al-Masoudi N.A., Al-Soud Y.A., Lagoja I. Synthesis and reactions of 1,5- and 1,3-dialkyl derivatives of (D-manno-pentitol-1-yl)-1H-1,2,4-triazole nucleosides derived from 1-(chloroalkyl)-1-aza-2-azoniaallene salts. Carbohydr. Res. 318:1999;67-72.
38. Al-Soud Y.A., Al-Masoudi N.A. Synthesis of 1-[4-(1,5-disubstituted-1H-1, 2,4-triazol-3-yl)benzyl]-1H-indols and 5,6-dihaloquinolones as potential antitumor agents. Org. Prep. Proc. Int. (OPPI). 49:2002;658-664.
39. Al-Soud Y.A., Al-Masoudi N.A., El-R A., Ferawanah S. New potential antitumor agents: 1,2,4-triazoles bearing benzotriazol, acetoxyhydrazides, 5-mercapto-1,2,4-triazole and sugar hydrazone analogues. Bioorg. Med. Chem. 11:2003;1701-1708.
40. Al-Soud Y.A., Al-Masoudi N.A. Synthesis of 3'-1,2,4-triazolo- and 3'-1,3,4-thiadiazol-iminothymidines. Heteroatom Chem. 14:2003;298-303.
41. Adelson D.E., Pollard C.B. Derivatives of piperazine, Part IV Reactions with derivatives of monochloroacetic acid. J. Am. Chem. Soc. 57:1935;1280-1281.
42. Luten D.B. The preparation of aminonitriles and their quarternary ammonium derivatives. J. Org. Chem. 3:1937;588-597.
43. Wang Q., Jochims J.C., St. Köhlbrandt L., Dahlenburg M., Al-Talib A., Hamed, et al. 1,2,4-triazolium salts from the reaction of 1-aza-2-azoniaallene salts with nitriles. Synthesis. 1992;710-718.
44. Wang Q., Al-Talib M., Jochims J.C. On the reaction of 1-aza-2-azoniaallene salts with acetylenes. Chem. Ber. 127:1994;541-547.
45. Willker W., Leibfritz D., Kerssebaum W., Bermel W. Gradient selection in inverse heteronuclear correlation spectroscopy. Mag. Reson. Chem. 31:1993;287-297.
46. Monks A., Scudiero D., Skehan P., Shoemaker R., Paull K., Vistica D., et al. Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J. Natl. Cancer Inst. 83:1991;757-766.
47. Seshadri R., Isreal M., Pegg W.J. Adriamycin analogues. Preparation and biological evaluation of some novel 14-thiaadriamycins. J. Med. Chem. 26:1983;11-15.
48. 2. J. Med. Chem. 39:1996;4554-4562.