Synthesis, and antitumor activity of some N1-(Coumarin-7-yl) amidrazones and related congeners

Molecules

Volumn 16, Issue 5, 2011, Pages 4305-4317

  Mustafa, Mohammad S ^a   El Abadelah, Mustafa M ^a   Zihlif, Malek A ^a   Naffa, Randa G ^a   Mubarak, Mohammad S ^a  

^a UNIVERSITY OF JORDAN   (Jordan)

Author keywords

1 piperazinyl amidrazones; 7 aminocoumarins; Antitumor activity; N (coumarin 7 yl)hydrazonoyl chloride; Nitrileimine

Indexed keywords

ANTINEOPLASTIC AGENT; COUMARIN DERIVATIVE;

ARTICLE; CELL STRAIN HL 60; CELL STRAIN K 562; CELL SURVIVAL; DRUG EFFECT; HUMAN; IC 50; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; COUMARINS; HL-60 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; K562 CELLS;

EID: 79957607303     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16054305     Document Type: Article

References (39)

1. Abdel-Jalil, R.J.; El Momani, E.Q.; Hamad, M.; Voelter, W.; Mubarak, M.S.; Smith, B.H.; Peters, D.G. Synthesis, antitumor activity, and electrochemical behavior of some piperazinyl amidrazones. Monatsh. Chem. 2010, 141, 251-258, and references cited therein.
2. Tollefson, G.D.; Lancaster, S.P.; Montague-Clouse, J. The association of buspirone and its metabolite 1-pyrimidinylpiperazine in the remission of comorbid anxiety with depressive features and alcohol dependency. Psychopharmacol. Bull. 1991, 27, 163-170.
3. Rotzinger, S.; Fang, J.; Baker, G.B. Trazodone is metabolized to m-chlorophenyl-piperazine by CYP3A4 from human sources. Drug Metab. Dispos. 1998, 26, 572-575. (Pubitemid 28498363)
4. Oh, Y.S.; Yun, M.; Hwang, S.Y.; Hong, S.; Shin, Y.; Lee, K.; Yoon, K.H.; Yoo, Y.J.; Kim, D.S.; Lee, S.H.; et al. Discovery of LB30057, a benzamidrazone-based selective oral thrombin inhibitor. Bioorg. Med. Chem. Lett. 1998, 8, 631-634. (Pubitemid 28122365)
5. Lee, K.; Hwang, S.Y.; Hong, S.; Hong, C.Y.; Lee, C.-S.; Shin, Y.; Kim, S.; Yun, M.; Yoo, Y.J.; Kang, M.; et al. Structural modification of an orally active thrombin inhibitor, LB30057: replacement of the D-pocket-binding naphthyl moiety. Bioorg. Med. Chem. 1998, 6, 869-876. (Pubitemid 28287288)
6. Lee, K.; Jung, W.-H.; Park, C.W.; Park, H.D.; Lee, S.H.; Kwon, O.H. Noncovalent tripeptidic thrombin inhibitors incorporating amidrazone, amine and amidine functions at P1. Bioorg. Med. Chem. Lett. 2002, 12, 1017-1022. (Pubitemid 34242792)
7. Clemens, F.; Drutkowski, G.; Wiese, M.; Frohberg, P. The inactivation of lipoxygenase-1 from soybeans by amidrazones. Biochim. Biophys. Acta 2001, 1549, 88-98. (Pubitemid 32879351)
8. Murray, R.D.H.; Mendenz, J.; Bouwn, S.A. The Natural Coumarins; Wiley & Sons: New York, NY, USA, 1982.
9. Schonberg, A.; Latif, N. Furochromones and coumarins. XI. The molluscicidal activity of bergapten, isopimpinellin, and xanthotoxin. J. Am. Chem. Soc. 1954, 76, 6208.
10. Mitra, A.K.; Misra, S.K.; Patra, A. New synthesis of 3-alkyl coumarins. Synth. Commun. 1980, 10, 915-919.
11. Sardari, S.; Mori, Y.; Horita, K.; Micetich, R.G.; Nishibe, S.; Daneshtalab, M. Synthesis and antifungal activity of coumarins and angular furanocoumarins. Bioorg. Med. Chem. 1999, 7, 1933-1940. (Pubitemid 29457691)
12. Khan, M.S.Y.; Sharma, P. Synthesis of new á-pyronoflavones and related products. Part II. Indian J. Chem. 1993, 32, 817-821.
13. Xie, L.; Takeuchi, Y.; Cosentino, L.M.; MacPhail, A.T.; Lee, H.K. Anti-AIDS agents. 42. Synthesis and anti-HIV activity of disubstituted (3'R,4'R)-3',4'-di-O-(S)-camphanoyl-(+)-ciskhellactone analogues. J. Med. Chem. 2001, 44, 664-671. (Pubitemid 32171663)
14. Singer, L.A.; Kong, N.P. Vinyl radicals. Stereoselectivity in hydrogen atom transfer to equilibrated isomeric vinyl radicals. J. Am. Chem. Soc. 1966, 88, 5213-5219.
15. O'Kennedy, R.; Thornes, R.D. Coumarins: Biology, Application and Mode of Action; Wiley & Sons: Chichester, UK, 1997.
16. Zahradnik, M. The Production and Application of Florescent Brightening Agents; Wiley & Sons: New York, NY, USA, 1992.
17. Brzozowski, Z.; Saczewski, F.; Slawinski, J.; Bednarski, P.; Grunert, R.; Gdaniec, M. Synthesis, structural characterization, and in vitro antitumor activity of novel N-(6-chloro-1,1-dioxo-1,4,2- benzodithiazin-3-yl) arylsulfonamides. Bioorg. Med. Chem. 2007, 15, 2560-2572. (Pubitemid 46367713)
18. Burbuliene, M.M.; Maldutyte, E.; Vainilavicius, P. Synthesis of S- and O-alkanoic acid derivatives of 6-phenyl-2-sulfanyl-4(3H)-pyrimidinone. Chemija. 2005, 16, 39-42.
19. Kontogiorgis, C.; Hadjipavlou-Litina, D. Biological evaluation of several coumarin derivatives designed as possible anti-inflammatory/antioxidant agents. J. Enz. Inhib. Med. Chem. 2003, 18, 63-69. (Pubitemid 36221716)
20. Satyanarayana, V.S.V.; Sreevani, P.; Sivakumar, A.; Vijayakumar, V. Synthesis and antimicrobial activity of new Schiff bases containing coumarin moiety and their spectral characterization. ARKIVOC 2008, 17, 221-233.
21. Al-Zghoul, K.H.A.; Salih, K.S.M.; Ayoub, M.T.; Mubarak, M.S. A convenient procedure for the synthesis of substituted 4-methylaminocoumarins. Heterocycles 2005, 65, 2937-2947.
22. Al-Soud, Y.A.; Al-Sa'doni, H.H.; Amajaour, H.A.S.; Salih, K.S.M.; Mubarak, M.S.; Al-Masoudi, N.A.; Jaber, I.H. Synthesis, characterization and anti-HIV and antitumor activities of new coumarin derivatives. Z. Naturforsch. 2008, 63b, 83-89.
23. Salih, K.S.M.; Ayoub, M.T.; Saadeh, H.A.; Al-Masoudi, N.A.; Mubarak, M.S. Synthesis, characterization, and biological activities of new benzofuran derivatives. Hetrocycles 2007, 71, 1577-1587.
24. Al-Rifai, A.A.; Ayoub, M.T.; Shakya, A.K.; Abu Safieh, K.A.; Mubarak, M.S. Synthesis, characterization, and antimicrobial activity of some new coumarin derivatives. Med. Chem. Res. 2011, 20, (in press).
25. Phillips, R.R. The Japp-Klingemann Reaction. Org. React. 1959, 10, 143-178.
26. Yao, H.-C.; Resnick, P. Azo-hydrazone conversion. I. The Japp-Klingemann reaction. J. Am. Chem. Soc. 1962, 84, 3514-3517.
27. Barrett, G.C.; El-Abadelah, M.M.; Hargreaves, M.K. Cleavage of 2-acetyl-2- phenylazopropionanilide and related compounds by boron trifluoride. New Japp-Klingemann reactions. J. Chem. Soc. (C) 1970, 1986-1989.
28. Pozdnev, V.F. An improved method of synthesis of 7-amino-4- methylcoumarin. Khim. Geterotsikl. Soed. 1990, 3, 312-314.
29. Ronad, P.; Dharbamalla, S.; Hunshal, R.; Maddi, V. Synthesis of novel substituted 7-(benzylideneamino)-4-methyl-2H-chromen-2-one derivatives as anti-inflammatory and analgesic agents. Arch. Pharm. 2008, 341, 696-700.
30. Butler, R.N.; Scott, F.L. Versatile reactive intermediates: Hydrazidic halides. Chem. Ind. (London) 1970, 1216-1221.
31. Ulrich, H. The Chemistry of Imidoyl Halides; Plenum Press: New York, NY, USA, 1968; Chapter 7, pp. 174-192.
32. Hegarty, A.F.; Aylward, J.B.; Scott, F.L. Synthesis and rearrangement of hydrazidic azides. J. Chem. Soc. (C) 1967, 2587-2593.
33. Dalla Corce, P.; Del Buttero, P.; Licandro, E.; Maiorana, S. Synthesis of (arylazomethylene)triphenylphosphoranes from arylhydrazonoyl chlorides (via nitrilimines in situ) and triphenylphosphine. Synthesis 1979, 299-300.
34. Heubach, G. Synthesis of new 2,5-dihydro-1,2,3,5-thiatriazole 1-oxides and 3,4-dihydro-2H- 1,2,4,3-triazaphosphole 3-oxides. Liebigs. Ann. Chem. 1980, 1980, 1376-1383.
35. Hassaneen, H.M.; Mousa, H.A.H.; Abed, N.M. Chemistry of C-heteroarylhydrazidoyl halides. Synthesis and reactions of N-(p-nitrophenyl)-C- (2-thienyl)formohydrazidoyl halides. Heterocycles 1988, 27, 695-706.
36. Benincori, T.; Sannicoló, F. New access to 2-(arylazo)-, 2-(arylhydrazo)-, and 2-aminoindoles, - benzofurans, and -thianaphthenes. J. Org. Chem. 1988, 53, 1309-1312. (Pubitemid 18095825)
37. Galishev, V.A.; Chistokletov, V.N.; Petrov, A.A. 1,3-Dipolar addition to unsaturated compounds. XXXIV. Reactions of diphenylmethyleneaminodiphenylphosphine with nitrilimines. Zh. Obshch. Khim. 1975, 45, 1695-1697.
38. Shawali, A.S.; Párkányi, C. Hydrazidoyl halides in the synthesis of heterocycles. J. Heterocycl. Chem. 1980, 17, 833-854.
39. Al-Soud, Y.A.; Al-Sa'doni, H.; Amajaour, H.A.S.; Al-Masoudi, N.A. Nitroimidazoles. Part 3. Synthesis and anti-HIV activity of new N-alkyl-4-nitroimidazoles bearing benzothiazole and benzoxazole backbones. Z. Naturforsch. 2007, 62, 523-528.