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Arylidene Carbazole Carbohydrazides: Synthesis and Characterization

Year 2018, Volume: 46 Issue: 2, 169 - 175, 03.06.2018

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

  • J.R. Dimmock, S.C. Vashishtha, J.P. Stables, Anticonvulsant properties of various acetylhydrazones, oxamoylhydrazones and semicarbazones derived from aromatic and unsaturated carbonyl compounds, Eur. J. Med. Chem., 35 (2000) 241-248.
  • 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.
  • J. Jayabharathi, A. Thangamani, M. Padmavathy, B. Krishnakumar, Synthesis and microbial evaluation of novel N(1)-Arilidene-N(2)-t(3)-methyl-r(2), c(6)-diarylpiperidin-4-one azine derivatives, Med. Chem. Res., 15 (2007) 431-442.
  • MT. Cocco, C. Congiu, V. Onnis, MC. Pusceddu, ML. Schivo, A. Logu, Synthesis and antimycobacterial activity of some isonicotinoylhydrazones, Eur. J. Med. Chem., 34 (1999) 1071-1076.
  • S.G. Küçükgüzel, S. Rollas, I. Küçükgüzel, M. Kiraz, Synthesis and antimycobacterial activity of some coupling products from 4-aminobenzoic acid hydrazones, Eur. J. Med. Chem., 34 (1999) 1093-1100.
  • 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.
  • S.G. Küçükgüzel, A. Mazi, F. Sahin, S. Oztürk, J. Stables, Synthesis and biological activities of diflunisal hydrazide-hydrazones, Eur. J. Med. Chem., 38 (2003) 1005-1013.
  • B.N. Swamy, T.K. Suma, G.V. Rao, G.C. Reddy, Synthesis of isonicotinoylhydrazones from anacardic acid and their in vitro activity against Mycobacterium smegmatis, Eur. J. Med. Chem., 42 (2007) 420-424.
  • H. Zhang, J. Drewe, B. Tseng, S. Kasibhatla, S.X. Cai, Discovery and SAR of indole-2-carboxylic acid benzylidenehydrazides as a new series of potent apoptosis inducers using a cellbased HTS assay, Bioorg. Med. Chem., 12 (2004) 3649-3655.
  • 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.
Year 2018, Volume: 46 Issue: 2, 169 - 175, 03.06.2018

Abstract

References

  • J.R. Dimmock, S.C. Vashishtha, J.P. Stables, Anticonvulsant properties of various acetylhydrazones, oxamoylhydrazones and semicarbazones derived from aromatic and unsaturated carbonyl compounds, Eur. J. Med. Chem., 35 (2000) 241-248.
  • 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.
  • J. Jayabharathi, A. Thangamani, M. Padmavathy, B. Krishnakumar, Synthesis and microbial evaluation of novel N(1)-Arilidene-N(2)-t(3)-methyl-r(2), c(6)-diarylpiperidin-4-one azine derivatives, Med. Chem. Res., 15 (2007) 431-442.
  • MT. Cocco, C. Congiu, V. Onnis, MC. Pusceddu, ML. Schivo, A. Logu, Synthesis and antimycobacterial activity of some isonicotinoylhydrazones, Eur. J. Med. Chem., 34 (1999) 1071-1076.
  • S.G. Küçükgüzel, S. Rollas, I. Küçükgüzel, M. Kiraz, Synthesis and antimycobacterial activity of some coupling products from 4-aminobenzoic acid hydrazones, Eur. J. Med. Chem., 34 (1999) 1093-1100.
  • 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.
  • S.G. Küçükgüzel, A. Mazi, F. Sahin, S. Oztürk, J. Stables, Synthesis and biological activities of diflunisal hydrazide-hydrazones, Eur. J. Med. Chem., 38 (2003) 1005-1013.
  • B.N. Swamy, T.K. Suma, G.V. Rao, G.C. Reddy, Synthesis of isonicotinoylhydrazones from anacardic acid and their in vitro activity against Mycobacterium smegmatis, Eur. J. Med. Chem., 42 (2007) 420-424.
  • H. Zhang, J. Drewe, B. Tseng, S. Kasibhatla, S.X. Cai, Discovery and SAR of indole-2-carboxylic acid benzylidenehydrazides as a new series of potent apoptosis inducers using a cellbased HTS assay, Bioorg. Med. Chem., 12 (2004) 3649-3655.
  • 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.
There are 38 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Cevher Gündoğdu Hızlıateş This is me

Publication Date June 3, 2018
Acceptance Date February 27, 2018
Published in Issue Year 2018 Volume: 46 Issue: 2

Cite

APA Hızlıateş, C. G. (2018). Arylidene Carbazole Carbohydrazides: Synthesis and Characterization. Hacettepe Journal of Biology and Chemistry, 46(2), 169-175.
AMA Hızlıateş CG. Arylidene Carbazole Carbohydrazides: Synthesis and Characterization. HJBC. June 2018;46(2):169-175.
Chicago Hızlıateş, Cevher Gündoğdu. “Arylidene Carbazole Carbohydrazides: Synthesis and Characterization”. Hacettepe Journal of Biology and Chemistry 46, no. 2 (June 2018): 169-75.
EndNote Hızlıateş CG (June 1, 2018) Arylidene Carbazole Carbohydrazides: Synthesis and Characterization. Hacettepe Journal of Biology and Chemistry 46 2 169–175.
IEEE C. G. Hızlıateş, “Arylidene Carbazole Carbohydrazides: Synthesis and Characterization”, HJBC, vol. 46, no. 2, pp. 169–175, 2018.
ISNAD Hızlıateş, Cevher Gündoğdu. “Arylidene Carbazole Carbohydrazides: Synthesis and Characterization”. Hacettepe Journal of Biology and Chemistry 46/2 (June 2018), 169-175.
JAMA Hızlıateş CG. Arylidene Carbazole Carbohydrazides: Synthesis and Characterization. HJBC. 2018;46:169–175.
MLA Hızlıateş, Cevher Gündoğdu. “Arylidene Carbazole Carbohydrazides: Synthesis and Characterization”. Hacettepe Journal of Biology and Chemistry, vol. 46, no. 2, 2018, pp. 169-75.
Vancouver Hızlıateş CG. Arylidene Carbazole Carbohydrazides: Synthesis and Characterization. HJBC. 2018;46(2):169-75.

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