Synthesis and antitumor studies on novel Co(II), Ni(II) and Cu(II) metal complexes of bis(3-acetylcoumarin)thiocarbohydrazone

M.P. Sathisha, U.N. Shetti, V.K. Revankar, K.S.R. Pai

Research output: Contribution to journalArticle

65 Citations (Scopus)

Abstract

The synthesis, structure, physico-chemical investigation and biological studies of some metal complexes of thiocarbohydrazone ligands are described. The ligand is obtained by condensation of N,N′-thiocarbohydrazide with 3-acetylcoumarin. The metal complexes of Co(II), Ni(II) and Cu(II) with bis(3-acetylcoumarin)thiocarbohydrazone were synthesized and isolated as solid products and characterized by analytical means as well as by spectral techniques such as FT-IR, 1H NMR and EPR and UV spectrometry. The ligand acts as bidentate, through NO or NN, neutral in coordinating the M(II) ions. The bonding sites are the azomethine nitrogen, lactone carbonyl oxygen and respective anion counterparts. The metal complexes exhibit either octahedral or distorted octahedral structures. The complexes are found to be soluble in dimethylformamide and dimethylsulphoxide. Molar conductance values in dimethylsulphoxide indicate the non-electrolytic nature of the complexes. The compounds tested in present study have shown promising cytotoxic activity when screened using the in vitro method and at the same time were shown to have good activity when tested using the Ehrlich Ascites Carcinoma model. Preliminary antimicrobial screening shows the promising results against both bacterial and fungal strains. © 2007 Elsevier Masson SAS. All rights reserved.
Original languageEnglish
Pages (from-to)2338-2346
Number of pages9
JournalEuropean Journal of Medicinal Chemistry
Volume43
Issue number11
DOIs
Publication statusPublished - 2008

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Coordination Complexes
Ligands
Dimethyl Sulfoxide
Dimethylformamide
Lactones
Ascites
Spectrometry
Anions
Paramagnetic resonance
Condensation
Spectrum Analysis
Screening
Nitrogen
Nuclear magnetic resonance
Ions
Oxygen
Carcinoma
3-acetylcoumarin

Cite this

@article{33ac45003091463c979e7731a2d3939a,
title = "Synthesis and antitumor studies on novel Co(II), Ni(II) and Cu(II) metal complexes of bis(3-acetylcoumarin)thiocarbohydrazone",
abstract = "The synthesis, structure, physico-chemical investigation and biological studies of some metal complexes of thiocarbohydrazone ligands are described. The ligand is obtained by condensation of N,N′-thiocarbohydrazide with 3-acetylcoumarin. The metal complexes of Co(II), Ni(II) and Cu(II) with bis(3-acetylcoumarin)thiocarbohydrazone were synthesized and isolated as solid products and characterized by analytical means as well as by spectral techniques such as FT-IR, 1H NMR and EPR and UV spectrometry. The ligand acts as bidentate, through NO or NN, neutral in coordinating the M(II) ions. The bonding sites are the azomethine nitrogen, lactone carbonyl oxygen and respective anion counterparts. The metal complexes exhibit either octahedral or distorted octahedral structures. The complexes are found to be soluble in dimethylformamide and dimethylsulphoxide. Molar conductance values in dimethylsulphoxide indicate the non-electrolytic nature of the complexes. The compounds tested in present study have shown promising cytotoxic activity when screened using the in vitro method and at the same time were shown to have good activity when tested using the Ehrlich Ascites Carcinoma model. Preliminary antimicrobial screening shows the promising results against both bacterial and fungal strains. {\circledC} 2007 Elsevier Masson SAS. All rights reserved.",
author = "M.P. Sathisha and U.N. Shetti and V.K. Revankar and K.S.R. Pai",
note = "Cited By :55 Export Date: 10 November 2017 CODEN: EJMCA Correspondence Address: Revankar, V.K.; Department of Studies in Chemistry, Karnatak University, Pavate Nagar, Dharwad, 580 003 Karnataka, India; email: vkrevankar@rediffmail.com Chemicals/CAS: cobalt, 7440-48-4; nickel, 7440-02-0; Anti-Bacterial Agents; Antineoplastic Agents; Cobalt, 7440-48-4; Copper, 7440-50-8; Hydrazones; Nickel, 7440-02-0; Organometallic Compounds References: Ali, M.A., Livingstone, S.E., (1974) Coord. Chem. Rev., 13, p. 279; Preti, C., Tosi, G., (1976) J. Inorg. Nucl. Chem., 38, p. 1125; Egan, D., O'Kennedy, R., Moran, E., Cox, D., Prosser, E., Thornes, R.D., (1990) Drug Metab. Rev., 22, pp. 503-529; Matsumoto, A., Hanawalt, P.C., (2000) Cancer Res., 60, pp. 3921-3926; Kelly, V.P., Ellis, E.M., Manson, M.M., (2000) Cancer Res., 60, pp. 957-969; Kirkiacharian, S., Thuy, D.T., Sicsic, S., Bakhchinian, R., Kurkjian, R., Tonnaire, T., (2002) Il Farmaco, 57, pp. 703-708; Yu, D., Suzuki, M., Xie, L., Morris-Natschke, S.L., Lee, K.H., (2003) Med. Res. Rev., 23, pp. 322-345; Conley, D., Marshall, E.M., (1987) Proc. Am. Assoc. Cancer Res., 28, p. 63; Thornes, R.D., Daly, L., Lynch, G., (1994) J. Cancer Res. Clin. Oncol., 120, pp. S32-S34; Marshall, M.E., Mohler, J.L., Edmonds, K., (1994) J. Cancer Res. Clin. Oncol., 120, pp. S39-S42; Mohler, J.L., Williams, B.T., Thompson, I.M., Marshall, M.E., (1994) J. Cancer Res. Clin. Oncol., 120, pp. S35-S38; von Angerer, E., Kager, M., Maucher, A., (1994) J. Cancer Res. Clin. Oncol., 120, pp. S14-S16; Lake, B.G., (1999) Food Chem. Toxicol., 37, pp. 423-453; Marshall, M.E., Butler, K., Fried, A., (1991) Mol. Biother., 3, pp. 170-178; Marshall, M.E., Kervin, K., Benefield, C., (1994) J. Cancer Res. Clin. Oncol., 120, pp. S3-S10; Myers, R.B., Parker, M., Grizzle, W.E., (1994) J. Cancer Res. Clin. Oncol., 120, pp. S11-S13; Kawaii, S., Tomono, Y., Ogawa, K., Sugiura, M., Yano, M., Yoshizawa, Y., (2001) Anticancer Res., 21, pp. 917-923; Kolodziej, H., Kayser, O., Woerdenbag, H.J., van Uden, W., Pras, N., (1997) Z. Naturforsch., C: Biosci., 52, pp. 240-244; Stunzi, H., (1982) Aust. J. Chem., 35, p. 1145; Campbell, M.J.M., (1975) Coord. Chem. Rev., 5, p. 279; Padhye, S.B., Kauffman, G.B., (1985) Coord. Chem. Rev., 63, p. 127; Emara, A.A.A., Khalil, S.M.E., Salib, K.A.R., (1995) J. Coord. Chem., 36, p. 289; Cheng, H., Chun-Ying, D., Chen-Jie, F., Yong-Jiang, L., Qing-Jin, M., (2000) J. Chem. Soc., Dalton Trans., p. 1207; Audrieth, L.F., Scott, E.S., Kippur, P.S., (1954) J. Org. Chem., 19, p. 733; Knoevengel, E., (1898) Ber., 31, p. 732; Scott, E.S., Audrieth, L.F., (1954) J. Org. Chem., 19, p. 743; Geary, W.J., (1971) Coord. Chem. Rev., 7, p. 81; Sengupta, S.K., Sahani, S.K., Kapoor, R.N., (1980) Indian J. Chem., 19 A, p. 703; Sengupta, S.K., Sahani, S.K., Kapoor, R.N., (1980) Synth. React. Inorg. Met.-Org. Chem., 10, p. 269; Pandey, O.P., (1987) Polyhedron, 6, p. 1021; Rao, T.R., Sahay, M., Aggarwal, R.C., (1985) Synth. React. Inorg. Met.-Org. Chem., 15, p. 175; Alcock, N.W., Tracy, V.M., Waddington, T.C., (1976) J. Chem. Soc., Dalton Trans., p. 2243; Nakamoto, K., McCarthy, P.J., (1968) Spectroscopy and Structure of Metal Chelate Compounds, , John-Wiley and Sons Inc., New York; Nakamoto, K., (1970) Infrared Spectra of Inorganic and Coordination Compounds, , Wiley-Interscience, New York; Lever, A.B.P., (1968) Inorganic Electronic Spectroscopy, , Elsevier Publishing Company, New York; Underhill, A.E., Billing, D.E., (1966) Nature, 210, p. 834; Drago, R.S., (1965) Physical Methods in Inorganic Chemistry, , Reinhold Publishing Corporation, London; Patel, K.C., Goldberg, D.E., (1972) J. Inorg. Nucl. Chem., 34, p. 637; Syamal, A., Kale, K.S., (1981) Indian J. Chem., 20 A, p. 205; Figgis, B.N., Lewis, J., (1960) Modern Coordination Chemistry, , Lewis J., and Wilkins R.G. (Eds), Interscience, New York; Chandra, S., Pandeya, K.B., Singh, R.P., (1979) Indian J. Chem., 18 A, p. 476; Mayer, B.N., Forrigni, N.R., Mc Laughlin, J.C., (1982) Planta Med., 45, pp. 31-34; Umadevi, P., Emerson, S.F., Sharada, A.C., (1994) Indian J. Exp. Biol., 32, p. 523; Geren, R.I., Greenberg, N.H., Mac Donald, M.M., Schumacher, A.M., Abbot, B.J., (1972) Cancer Chemother. Rep., 3, p. 1; Orberlling, C., Guerin, M., (1954) Adv. Cancer Res., 2, p. 353; M.N. Ghosh, Fundamentals of Experimental Pharmacology, second ed., Indian Pharmacological Society, Scientific Book Agency, Calcutta, 1984, p. 153; Uma Devi, P.R., Solomon, F.E., (1998) Indian J. Exp. Biol., 36, p. 891; Echardt, A.E., Malone, B.N., Goldstein, I., (1982) Cancer Res., 42, p. 2977; D' Amour, F.E., Blood, F.R., Belden, D.A., (1965) Manual for laboratory work in Mammalian Physiology. third ed., , The University of Chicago Press, Chicago pp. 4-6",
year = "2008",
doi = "10.1016/j.ejmech.2007.10.003",
language = "English",
volume = "43",
pages = "2338--2346",
journal = "European Journal of Medicinal Chemistry",
issn = "0223-5234",
publisher = "Elsevier Masson SAS",
number = "11",

}

Synthesis and antitumor studies on novel Co(II), Ni(II) and Cu(II) metal complexes of bis(3-acetylcoumarin)thiocarbohydrazone. / Sathisha, M.P.; Shetti, U.N.; Revankar, V.K.; Pai, K.S.R.

In: European Journal of Medicinal Chemistry, Vol. 43, No. 11, 2008, p. 2338-2346.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis and antitumor studies on novel Co(II), Ni(II) and Cu(II) metal complexes of bis(3-acetylcoumarin)thiocarbohydrazone

AU - Sathisha, M.P.

AU - Shetti, U.N.

AU - Revankar, V.K.

AU - Pai, K.S.R.

N1 - Cited By :55 Export Date: 10 November 2017 CODEN: EJMCA Correspondence Address: Revankar, V.K.; Department of Studies in Chemistry, Karnatak University, Pavate Nagar, Dharwad, 580 003 Karnataka, India; email: vkrevankar@rediffmail.com Chemicals/CAS: cobalt, 7440-48-4; nickel, 7440-02-0; Anti-Bacterial Agents; Antineoplastic Agents; Cobalt, 7440-48-4; Copper, 7440-50-8; Hydrazones; Nickel, 7440-02-0; Organometallic Compounds References: Ali, M.A., Livingstone, S.E., (1974) Coord. Chem. Rev., 13, p. 279; Preti, C., Tosi, G., (1976) J. Inorg. Nucl. Chem., 38, p. 1125; Egan, D., O'Kennedy, R., Moran, E., Cox, D., Prosser, E., Thornes, R.D., (1990) Drug Metab. Rev., 22, pp. 503-529; Matsumoto, A., Hanawalt, P.C., (2000) Cancer Res., 60, pp. 3921-3926; Kelly, V.P., Ellis, E.M., Manson, M.M., (2000) Cancer Res., 60, pp. 957-969; Kirkiacharian, S., Thuy, D.T., Sicsic, S., Bakhchinian, R., Kurkjian, R., Tonnaire, T., (2002) Il Farmaco, 57, pp. 703-708; Yu, D., Suzuki, M., Xie, L., Morris-Natschke, S.L., Lee, K.H., (2003) Med. Res. Rev., 23, pp. 322-345; Conley, D., Marshall, E.M., (1987) Proc. Am. Assoc. Cancer Res., 28, p. 63; Thornes, R.D., Daly, L., Lynch, G., (1994) J. Cancer Res. Clin. Oncol., 120, pp. S32-S34; Marshall, M.E., Mohler, J.L., Edmonds, K., (1994) J. Cancer Res. Clin. Oncol., 120, pp. S39-S42; Mohler, J.L., Williams, B.T., Thompson, I.M., Marshall, M.E., (1994) J. Cancer Res. Clin. Oncol., 120, pp. S35-S38; von Angerer, E., Kager, M., Maucher, A., (1994) J. Cancer Res. Clin. Oncol., 120, pp. S14-S16; Lake, B.G., (1999) Food Chem. Toxicol., 37, pp. 423-453; Marshall, M.E., Butler, K., Fried, A., (1991) Mol. Biother., 3, pp. 170-178; Marshall, M.E., Kervin, K., Benefield, C., (1994) J. Cancer Res. Clin. Oncol., 120, pp. S3-S10; Myers, R.B., Parker, M., Grizzle, W.E., (1994) J. Cancer Res. Clin. Oncol., 120, pp. S11-S13; Kawaii, S., Tomono, Y., Ogawa, K., Sugiura, M., Yano, M., Yoshizawa, Y., (2001) Anticancer Res., 21, pp. 917-923; Kolodziej, H., Kayser, O., Woerdenbag, H.J., van Uden, W., Pras, N., (1997) Z. Naturforsch., C: Biosci., 52, pp. 240-244; Stunzi, H., (1982) Aust. J. Chem., 35, p. 1145; Campbell, M.J.M., (1975) Coord. Chem. Rev., 5, p. 279; Padhye, S.B., Kauffman, G.B., (1985) Coord. Chem. Rev., 63, p. 127; Emara, A.A.A., Khalil, S.M.E., Salib, K.A.R., (1995) J. Coord. Chem., 36, p. 289; Cheng, H., Chun-Ying, D., Chen-Jie, F., Yong-Jiang, L., Qing-Jin, M., (2000) J. Chem. Soc., Dalton Trans., p. 1207; Audrieth, L.F., Scott, E.S., Kippur, P.S., (1954) J. Org. Chem., 19, p. 733; Knoevengel, E., (1898) Ber., 31, p. 732; Scott, E.S., Audrieth, L.F., (1954) J. Org. Chem., 19, p. 743; Geary, W.J., (1971) Coord. Chem. Rev., 7, p. 81; Sengupta, S.K., Sahani, S.K., Kapoor, R.N., (1980) Indian J. Chem., 19 A, p. 703; Sengupta, S.K., Sahani, S.K., Kapoor, R.N., (1980) Synth. React. Inorg. Met.-Org. Chem., 10, p. 269; Pandey, O.P., (1987) Polyhedron, 6, p. 1021; Rao, T.R., Sahay, M., Aggarwal, R.C., (1985) Synth. React. Inorg. Met.-Org. Chem., 15, p. 175; Alcock, N.W., Tracy, V.M., Waddington, T.C., (1976) J. Chem. Soc., Dalton Trans., p. 2243; Nakamoto, K., McCarthy, P.J., (1968) Spectroscopy and Structure of Metal Chelate Compounds, , John-Wiley and Sons Inc., New York; Nakamoto, K., (1970) Infrared Spectra of Inorganic and Coordination Compounds, , Wiley-Interscience, New York; Lever, A.B.P., (1968) Inorganic Electronic Spectroscopy, , Elsevier Publishing Company, New York; Underhill, A.E., Billing, D.E., (1966) Nature, 210, p. 834; Drago, R.S., (1965) Physical Methods in Inorganic Chemistry, , Reinhold Publishing Corporation, London; Patel, K.C., Goldberg, D.E., (1972) J. Inorg. Nucl. Chem., 34, p. 637; Syamal, A., Kale, K.S., (1981) Indian J. Chem., 20 A, p. 205; Figgis, B.N., Lewis, J., (1960) Modern Coordination Chemistry, , Lewis J., and Wilkins R.G. (Eds), Interscience, New York; Chandra, S., Pandeya, K.B., Singh, R.P., (1979) Indian J. Chem., 18 A, p. 476; Mayer, B.N., Forrigni, N.R., Mc Laughlin, J.C., (1982) Planta Med., 45, pp. 31-34; Umadevi, P., Emerson, S.F., Sharada, A.C., (1994) Indian J. Exp. Biol., 32, p. 523; Geren, R.I., Greenberg, N.H., Mac Donald, M.M., Schumacher, A.M., Abbot, B.J., (1972) Cancer Chemother. Rep., 3, p. 1; Orberlling, C., Guerin, M., (1954) Adv. Cancer Res., 2, p. 353; M.N. Ghosh, Fundamentals of Experimental Pharmacology, second ed., Indian Pharmacological Society, Scientific Book Agency, Calcutta, 1984, p. 153; Uma Devi, P.R., Solomon, F.E., (1998) Indian J. Exp. Biol., 36, p. 891; Echardt, A.E., Malone, B.N., Goldstein, I., (1982) Cancer Res., 42, p. 2977; D' Amour, F.E., Blood, F.R., Belden, D.A., (1965) Manual for laboratory work in Mammalian Physiology. third ed., , The University of Chicago Press, Chicago pp. 4-6

PY - 2008

Y1 - 2008

N2 - The synthesis, structure, physico-chemical investigation and biological studies of some metal complexes of thiocarbohydrazone ligands are described. The ligand is obtained by condensation of N,N′-thiocarbohydrazide with 3-acetylcoumarin. The metal complexes of Co(II), Ni(II) and Cu(II) with bis(3-acetylcoumarin)thiocarbohydrazone were synthesized and isolated as solid products and characterized by analytical means as well as by spectral techniques such as FT-IR, 1H NMR and EPR and UV spectrometry. The ligand acts as bidentate, through NO or NN, neutral in coordinating the M(II) ions. The bonding sites are the azomethine nitrogen, lactone carbonyl oxygen and respective anion counterparts. The metal complexes exhibit either octahedral or distorted octahedral structures. The complexes are found to be soluble in dimethylformamide and dimethylsulphoxide. Molar conductance values in dimethylsulphoxide indicate the non-electrolytic nature of the complexes. The compounds tested in present study have shown promising cytotoxic activity when screened using the in vitro method and at the same time were shown to have good activity when tested using the Ehrlich Ascites Carcinoma model. Preliminary antimicrobial screening shows the promising results against both bacterial and fungal strains. © 2007 Elsevier Masson SAS. All rights reserved.

AB - The synthesis, structure, physico-chemical investigation and biological studies of some metal complexes of thiocarbohydrazone ligands are described. The ligand is obtained by condensation of N,N′-thiocarbohydrazide with 3-acetylcoumarin. The metal complexes of Co(II), Ni(II) and Cu(II) with bis(3-acetylcoumarin)thiocarbohydrazone were synthesized and isolated as solid products and characterized by analytical means as well as by spectral techniques such as FT-IR, 1H NMR and EPR and UV spectrometry. The ligand acts as bidentate, through NO or NN, neutral in coordinating the M(II) ions. The bonding sites are the azomethine nitrogen, lactone carbonyl oxygen and respective anion counterparts. The metal complexes exhibit either octahedral or distorted octahedral structures. The complexes are found to be soluble in dimethylformamide and dimethylsulphoxide. Molar conductance values in dimethylsulphoxide indicate the non-electrolytic nature of the complexes. The compounds tested in present study have shown promising cytotoxic activity when screened using the in vitro method and at the same time were shown to have good activity when tested using the Ehrlich Ascites Carcinoma model. Preliminary antimicrobial screening shows the promising results against both bacterial and fungal strains. © 2007 Elsevier Masson SAS. All rights reserved.

U2 - 10.1016/j.ejmech.2007.10.003

DO - 10.1016/j.ejmech.2007.10.003

M3 - Article

VL - 43

SP - 2338

EP - 2346

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

SN - 0223-5234

IS - 11

ER -