Synthesis and anticancer activities of new 3-allylthio-6-(mono or disubstituted)aminopyridazines

Archives of Pharmacal Research

Volumn 33, Issue 2, 2010, Pages 189-196

  Won, Yong Hoon ^a   Park, Myung Sook ^b  

^a Kwang Dong Pharmaceutical Co Ltd   (South Korea)

^b Duksung Women's University   (South Korea)

Author keywords

Allylthiopyridazines; Anticancer activities; MTT assay; Substituted aminopyridazines

Indexed keywords

3 ALLYLTHIO 6 (4 METHYLPIPERAZINYL)AMINOPYRIDAZINE; 3 ALLYLTHIO 6 (4 THIOMORPHOLINYL)AMINOPYRIDAZINE; 3 ALLYLTHIO 6 HOMOPIPERIDINYLAMINOPYRIDAZINE; 3 ALLYLTHIO 6 MORPHOLINYLAMINOPYRIDAZINE; 3 ALLYLTHIO 6 N BUTYLANILINOPYRIDAZINE; 3 ALLYLTHIO 6 N ETHYLANILINOPYRIDAZINE; 3 ALLYLTHIO 6 N METHYLANILINOPYRIDAZINE; 3 ALLYLTHIO 6 N PENTYLANILINOPYRIDAZINE; 3 ALLYLTHIO 6 N PROPYLANILINOPYRIDAZINE; 3 ALLYLTHIO 6 PIPERIDINYLAMINOPYRIDAZINE; 3 AMINOPYRIDAZINE DERIVATIVE; ANTINEOPLASTIC AGENT; FLUOROURACIL; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANCER CHEMOTHERAPY; CANCER INHIBITION; COLON CANCER; CONTROLLED STUDY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HEPATOBLASTOMA; HUMAN; HUMAN CELL; LUNG CANCER; PROSTATE CANCER; UTERINE CERVIX CANCER;

ALLYL COMPOUNDS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MOLECULAR STRUCTURE; PYRIDAZINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77949880837     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-010-0201-x     Document Type: Article

References (25)

1. K. C. Agarwal 1996 Therapeutic actions of garlic constituents Med. Res. Rev. 16 111 124 10.1002/(SICI)1098-1128(199601)16:1<111::AID-MED4>3.0. CO;2-5 1:CAS:528:DyaK28XhtFyls7o%3D 8788216 (Pubitemid 26037077)
2. E. Block S. Ahmad J. L. Catalfamo M. K. Jain R. Apitz-Castro 1986 Antithrombotic organosulfur compounds from garlic: Structural, mechanistic and synthetic studies J. Am. Chem. Soc. 108 7045 7055 10.1021/ja00282a033 1:CAS:528:DyaL2sXjt1Kkug%3D%3D
3. Brunton, L. L., Lazo, J. S., and Parker, K. L., Goodman & Gilman's the pharmacological basis of therapeutics, 11th ed. McGraw-Hill, New York, pp. 1339-1343, (2006).
4. C. J. Cavallito J. S. Buck C. M. Suter 1944 Allicin, the antibacterial principle of Allium sativum. II. determination of the chemical structure J. Am. Chem. Soc. 66 1952 1954 10.1021/ja01239a049 1:CAS:528:DyaH2MXhvFGm
5. J. M. Contreras I. Parrot W. Sippl Y. M. Rival C. G. Wermuth 2001 Design, synthesis, and structure-activity relatioships of series of 3-[2-(1-benzylpiperidin-4-yl)ethylamino] pyridazine derivatives as acetylcholinesterase inhibitors J. Med. Chem. 44 2707 2718 10.1021/jm001088u 1:CAS:528:DC%2BD3MXlt1Okur0%3D 11495583 (Pubitemid 32879713)
6. J. M. Contreras Y. M. Rival S. Chayer J. J. Bourguignon C. G. Wermuth 1999 Aminopyridazines as acetylcholinesterase inhibitors J. Med. Chem. 42 730 741 10.1021/jm981101z 1:CAS:528:DyaK1MXosVyntQ%3D%3D 10052979 (Pubitemid 29110788)
7. M. Y. Jung S. K. Kwon A. Moon 2001 Chemopreventive allylthiopyridazine derivatives induce apoptosis in SKHep-1 hepatocarcinoma cells through a caspase-3-dependent mechanism Eur. J. Cancer 37 2104 2110 10.1016/S0959-8049(01) 00242-8 1:CAS:528:DC%2BD3MXntlOrsro%3D 11597391 (Pubitemid 32938116)
8. Kleemann, A. and Engel, J., Pharmaceutical Substances, 4th ed. Thieme, Stuttgart & New York, pp. 1340-1342, (2001).
9. S. K. Kwon M. S. Lee 2005 Synthesis of 3-allylthio-6- heterocyclylalkylaminopyridazine derivatives and their anti-tumor activities against SK-Hep-1 human liver cancer cells Yakhakhoe Chi 49 505 510 1:CAS:528:DC%2BD28XislaisA%3D%3D
10. S. K. Kwon A. Moon 2005 Synthesis of 3-alkylthio-6-allylthio-pyridazine derivatives and their antihepatocarcinoma activity Arch. Pharm. Res. 28 391 394 10.1007/BF02977666 1:CAS:528:DC%2BD2MXkt1WhtbY%3D 15918510
11. S. K. Kwon 2002 Synthesis of 4,5-substituted 3-alkoxy-6-allylthio- pyridazine derivatives Yakhakhoe Chi 46 155 160 1:CAS:528:DC%2BD38XltlCksLw%3D
12. S. K. Kwon 2002 Synthesis of aryloxyallylthiopyridazine derivatives Yakhakhoe Chi 46 89 92 1:CAS:528:DC%2BD38Xjs1OltLs%3D
13. E. J. Lee I. C. Shin S. K. Kwon H. S. Shin A. Moon 2003 Chemopreventive allylthiopyridazines inhibit invasion, migration and angiogenesis in hepatocarcinoma cells Int. J. Oncol. 23 1645 1650 1:CAS:528:DC%2BD3sXpvFymu78%3D 14612936
14. J. I. Lee H. Park Y. S. Yun S. K. Kwon 2001 An efficient synthesis of 3-alkoxy-6-allylthiopyridazines J. Kor. Chem. Soc. 45 386 390 1:CAS:528:DC%2BD3MXmvFCgsLk%3D
15. M. S. Lee E. S. Kim A. Moon M. S. Park 2009 Synthesis of novel allylthio heterocyclo(or aryl)alkylaminopyridazines and their anticancer activity against SK-Hep-1 Cells Bull. Korean Chem. Soc. 30 83 91 1:CAS:528:DC%2BD1MXislaktbc%3D
16. E. H. Park M. S. Park 2005 Acylation of pyridazinylamines by acyclic anhydrides; synthesis of N-substituted 3-amino-6-chloropyridazines Yakhakhoe Chi 49 56 59 1:CAS:528:DC%2BD2MXisVGntLo%3D
17. E. H. Park M. S. Park 2007 Synthesis of potential anticancer 6-allylthio-3-aminopyridazine derivatives J. Kor. Chem. Soc. 51 244 250 1:CAS:528:DC%2BD2sXosFWiu7Y%3D
18. I. Parrot Y. Rival C. G. Wermuth 1999 Synthesis of substituted 3-amino-6-arylpyridazines via Suzuki reaction Synthesis 7 1163 1168 10.1055/s-1999-3528
19. I. Parrot C. G. Wermuth M. Hibert 1999 Resin-bound thiophenols as SNAR-labile linkers: application to the solid phase synthesis of aminopyridazines Tetrahedron Lett. 40 7975 7978 10.1016/S0040-4039(99)01533-6 1:CAS:528:DyaK1MXntV2rsrc%3D (Pubitemid 29499977)
20. H. S. Shin S. K. Kwon 2003 Synthesis of allylthiopyridazine derivatives and inhibition of aflatoxin B1-induced hepatotoxicity in rats Arch. Pharm. Res. 26 351 357 10.1007/BF02976691 1:CAS:528:DC%2BD3sXkslaiurk%3D 12785730
21. J. H. Song S.G. Kim Z. S. No Y. L. Hyun D. J. Jeon I. Kim 2008 Discovery and synthesis of novel N-cyanopyrazolidine and N-cyanohexahydropyridazine derivatives as cathepsin inhibitors Bull. Korean Chem. Soc. 29 1467 10.1007/s11814-008-0241-9 1:CAS:528:DC%2BD1cXhtFKhtrvM
22. Tisler, M. and Stanovnik, B., Advances in heterocyclic chemistry, Katritzky & Boulton, pp. 1-56, (1984).
23. C. G. Wermuth J. J. Bourguignon G. Schlewer J. P. Gies A. Schoenfelder A. Melikian M. J. Bouchet D. Chantreux J. C. Molimard M. Heaulme J. P. Chambon K. Biziere 1987 Synthesis and structure-activity relationships of a series of aminopyridazine derivatives of γ-aminobutyric acid acting as selective GABA-A antagonists J. Med. Chem. 30 239 249 10.1021/jm00385a003 1:CAS:528:DyaL2sXhtlygtb0%3D 3027337
24. C. G. Wermuth G. Schlewer J. J. Bourguignon G. Maghiros M. J. Bouchet C. Moire J. P. Kan P. Worms K. Biziere 1989 3-Aminopyridazine derivatives with atypical antidepressant, serotonergic, and dopaminergic activities J. Med. Chem. 32 528 537 10.1021/jm00123a004 1:CAS:528:DyaL1MXhtFCktbg%3D 2563772
25. T. Yamasaki R. W. Teel B. H. Lau 1991 Effect of allixin, a phytoalexin produced by garlic, on mutagenesis, DNAbinding and metabolism of aflatoxin B1 Cancer Lett. 59 89 94 10.1016/0304-3835(91)90171-D 1:CAS:528:DyaK3MXlslCht7o%3D 1909211