Arylidene Carbazole Carbohydrazides: Synthesis and Characterization
Year 2018,
Volume: 46 Issue: 2, 169 - 175, 03.06.2018
Cevher Gündoğdu Hızlıateş
Abstract
Because of the wide range of pharmacological activities and their distinctive structural features hydrazones
and carbazole alkaloids have attracted considerable attention in medicinal chemistry. In this study, new
carbazole acyl hydrozones (3a-k) which may have high biological activity potential, were synthesized with
condensation reaction between carbazole hydrazide and benzaldehyde derivatives. After determination of the
melting points of all synthesized derivatives, their structures were identified by FT-IR and 1
H-NMR spectroscopic
methods.
References
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- K. Hirata, C. Ito, H. Furukawa, M. Itoigawa, L.M. Cosentino, K.H. Lee, Substituted 7H-pyrido[4,3-c] carbazoles with potent anti-HIV activity, Bioorg. Med. Chem. Lett., 9 (1999) 119-122.
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- S. Sarkar, D. Dutta, S.K. Samanta, K. Bhattacharya, B.C. Pal, J. Li, K. Datta, C. Mandal, Oxidative inhibition of Hsp90 disrupts the super-chaperone complex and attenuates pancreatic adenocarcinoma in vitro and in vivo, Int. J. Cancer, 132 (2013) 695-706.
- C. Ito, M. Itoigawa, K. Nakao, T. Murata, N. Kaneda, H. Furukawa, Apoptosis of HL-60 leukemia cells induced by carbazole alkaloids isolated from Murraya euchrestifolia, J. Nat. Med., 66 (2012) 357-361.
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Year 2018,
Volume: 46 Issue: 2, 169 - 175, 03.06.2018
Cevher Gündoğdu Hızlıateş
References
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- J. Ragavendran, D. Sriram, S. Patel, I. Reddy, N. Bharathwajan, J. Stables, Design and synthesis of anticonvulsants from a combined phthalimide-GABAanilide and hydrazone pharmacophore, Eur. J. Med. Chem., 42 (2007) 146-151.
- N. Ergenç, N.S. Günay, Synthesis and antidepressant evaluation of new 3-phenyl-5-sulfonamid indole derivatives, Eur. J. Med. Chem., 33 (1998) 143-148.
- A.R. Todeschini, A.L. Miranda, C.M. Silva, S.C. Parrini, E.J. Barreiro, Synthesis and evaluation of analgesic, antiinflammatory and antiplatelet properties of new 2- pyridylarylhydrazone derivatives, Eur. J. Med. Chem., 33 (1998) 189-199.
- A.G.M. Fraga, C.R. Rodrigues, A.L.P. Miranda, E.J. Barreiro, C.A.M. Fraga, Synthesis and pharmacological evaluation of novel heterocyclic acylhydrazone derivatives, designed as PAF antagonists, Eur. J. Pharm. Sci., 11 (2000) 285-290.
- Walcourt, M. Loyevsky, D.B. Lovejoy, V.R. Gordeuk, D.R. Richardson, Novel aroylhydrazone and thiosemicarbazone iron chelators with anti-malarial activity against chloroquine-resistant and -sensitive parasites, Int. J. Biochem. Cell Biol., 36 (2004) 401- 407.
- P. Vicini, F. Zani, P. Cozzini, I. Doytchinova, Hydrazones of 1,2-benzisothiazole hydrazides: synthesis, antimicrobial activity and QSAR investigations, Eur. J. Med. Chem., 37 (2002) 553-564.
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- B.K. Kaymakçıoğlu, S. Rollas, Synthesis, characterization and evaluation of antituberculosis activity of some hydrazones, Farmaco, 57 (2002) 595-599.
- D.G. Rando, D.N. Sato, L. Siqueira, A. Malvezzi, C.Q. F. Leite, A.T. Amaral, Potential tuberculostatic agents. Topliss application on benzoic acid [(5-nitro-thiophen2-yl)-methylene]-hydrazide series, Bioorg. Med. Chem., 10 (2002) 557-560.
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- S.A.M. El-Hawash, A.E. Abdel Wahab, M.A. ElDewellawy, Cyanoacetic acid hydrazones of 3- (and 4-) acetylpyridine and some derived ring systems as potential antitumor and anti-HCV agents, Arch. Pharm. Chem. Life Sci., 339 (2006) 14-23.
- J. Pandey, R. Pal, A. Dwivedi, K. Hajela, Synthesis of some new diaryl and triaryl hydrazone derivatives as possible estrogen receptor modulators, Arzneimittelforschung., 52 (2002) 39-44.
- N. Demirbas, S. Karaoglu, A. Demirbas, K. Sancak, Synthesis and antimicrobial activities of some new 1-(5-phenylamino-[1,3,4]thiadiazol-2-yl)methyl-5- oxo-[1,2,4]triazole and 1-(4-phenyl-5- thioxo-[1,2,4] triazol-3-yl)methyl-5-oxo-[1,2,4]triazole derivatives,
Eur. J. Med. Chem., 39 (2004) 793-804.
- N. Terzioğlu, A. Gürsoy, Synthesis and anticancer evaluation of some new hydrazone derivatives of 2,6-dimethylimidazo[2,1-b]-[1,3,4]thiadiazole-5- carbohydrazide, Eur. J. Med. Chem., 38 (2003) 781- 786.
- Gürsoy, N. Karali, Synthesis and primary cytotoxicity evaluation of 3-[[(3-phenyl-4(3H)-quinazolinone-2-yl) mercaptoacetyl]hydrazono]-1H-2-indolinones, Eur. J. Med. Chem., 38 (2003) 633-643.
- M.T.H. Nutan, A.Hasnat, M.A. Rashid, Antibacterial and cytotoxic activities of Murraya koenigii, Fitoterapia, 69 (1998) 173-175.
- M. Fiebig, J.M. Pezzuto, D.D. Soejarto, A.D. Kinghorn, Koenoline, a further cytotoxic carbazole alkaloid from Murraya koenigii, Phytochemistry, 24 (1985) 3041-3043.
- M. Chakrabarty, A.C. Nath, S. Khasnobis, M. Chakrabarty, Y. Konda, Y. Harigaya, K. Komiyama, Carbazole alkaloids from Murraya koenigii, Phytochemistry, 46 (1997) 751-755.
- K. Hirata, C. Ito, H. Furukawa, M. Itoigawa, L.M. Cosentino, K.H. Lee, Substituted 7H-pyrido[4,3-c] carbazoles with potent anti-HIV activity, Bioorg. Med. Chem. Lett., 9 (1999) 119-122.
- B.A. Khan, A. Abraham, S. Leelamma, Antioxidant effects of Curry leaf, Murraya koenigii and mustard seeds, Brassica juncea in rats fed with high fat diet, Indian J. Exp. Biol., 35 (1997) 148-150.
- S. Sarkar, D. Dutta, S.K. Samanta, K. Bhattacharya, B.C. Pal, J. Li, K. Datta, C. Mandal, Oxidative inhibition of Hsp90 disrupts the super-chaperone complex and attenuates pancreatic adenocarcinoma in vitro and in vivo, Int. J. Cancer, 132 (2013) 695-706.
- C. Ito, M. Itoigawa, K. Nakao, T. Murata, N. Kaneda, H. Furukawa, Apoptosis of HL-60 leukemia cells induced by carbazole alkaloids isolated from Murraya euchrestifolia, J. Nat. Med., 66 (2012) 357-361.
- M.K. Roy, V. N. Thalang, G. Trakoontivakorn, K. Nakahara, Mechanism of mahanine-induced apoptosis in human leukemia cells (HL-60), Biochem. Pharm., 67 (2004) 41-51.
- S. Sinha, B.C. Pal, S. Jagadeesh, P.P. Banerhee, A. Bandyopadhaya, S. Bhattacharya, Mahanine inhibits growth and induces apoptosis in prostate cancer cells through the deactivation of akt and activation of caspases, The Prostate, 66 (2006) 1257-1265.
- T. Thongthoom, P. Promsuwan, C. Yenjai, Synthesis and cytotoxic activity of the heptaphylline and 7-methoxyheptaphylline series, Eur. J. Med. Chem, 46 (2011) 3755-3761.
- G. Palla, G. Predieri, P. Domiano, Conformational behaviour and E/Z isomerization of N-acyl and N-aroylhydrazones, Tetrahedron, 42 (1986) 3649- 3654.
- O. Unsal Tan, K. Ozden, A. Rauk, A. Balkan, Synthesis and cyclooxygenase inhibitory activities of some N-acylhydrazone derivatives of isoxazolo[4,5-d] pyridazin-4(5H)-ones, Eur. J. Med. Chem., 45 (2010) 2345-2352.
- V.V. Syakaev, S.N. Podyachev, B.I. Buzykin, S. K. Latypov, W.D. Habicher, A.I. Konovalov, NMR study of conformation and isomerization of aryl- and heteroarylaldehyde 4-tertbutylphenoxyacetylhydrazones, J. Mol. Struct. 788 (2006) 55-62.
- D. Sarıgöl, D. Yüksel, G. Okay, A. Uzgören-Baran, Synthesis and structural studies of acyl hydrazone derivatives having tetrahydrocarbazole moiety, J. Mol. Struct., 1086 (2015) 146–152.
- B.S. Holla, M. Mahalinga, M.S. Karthikeyan, B. Poojary, P.M. Akberali, N.S. Kumari, Synthesis, characterization and antimicrobial activity of some substituted 1,2,3-triazoles, Eur. J. Med. Chem., 40 (2005) 1173-1178.
- K.A. Metwally, L.M. Abdel-Aziz, E.M. Lashine, M.I. Husseiny, R.H. Badawy, Hydrazones of 2-arylquinoline-4-carboxylic acid hydrazides: synthesis and preliminary evaluation as antimicrobial agents, Bioorg. Med. Chem., 14 (2006) 8675-8682.
- V. Judge, B. Nrasimhan, M. Ahuja, D. Sriram, P. Yogeeswari, E.D. Clercq, C. Pannecouque, J. Balzarini, Isonicotinic acid hydrazide derivatives: Synthesis, antimicrobial activity, and QSAR studies, Med. Chem. Res., 21 (2011) 1-20.
- B. Koçyiğit Kaymakçıoğlu, E.E. Oruç Emre, S. Unsalan, S. Rollas, Antituberculosis activity of hydrazones derived from 4-fluorobenzoic acid hydrazide, Med. Chem. Res., 18 (2009) 277-286.