Abstract
Oxidation of the pyrazol-1-yldithiocarbamate compounds {[3,5-R2C3HN2CS2]- (R = H, Me} and indazol-1-lydithiocarbamate by iodine produces the sulfur-sulfur coupling compounds {R'C(S)S-S(S)CR'} (R’ = pyrazolyl, 3,5-dimethylpyrazolyl, indazolyl). All compounds were spectroscopically characterised, and, in some cases, structurally characterised. The X-ray structures reveal that these compounds contain a disulfide bridging the pyrazolylthiocarbonyl units. Two of the three disulfide compounds showed very good anticancer activities against HeLa cells at micromolar concentrations, with the most active compound active being 9.6 times more selective in its activity towards tumour cells than normal cells.
References
1.
Cookson J.
, and
Beer P. D.
, Dalton Trans. , 2007 , 1459 .
2.
Spath A.
, and
Tempel K.
, Chem.-Biol. Interact , 1987 , 64 , 151 .
3.
Wickström M.
,
Danielsson K.
,
Rickardson L.
,
Gullbo J.
,
Nygren P.
,
Isaksson A.
,
Larsson R.
, and
Lövborg H.
, Biochem. Pharmacol. , 2007 , 73 , 25 .
4.
Sauna Z.E.
,
Shukla S.
, and
Ambudkar S. V.
, Mol. BioSyst. , 2005 , 1 , 127 .
5.
Yakisich J.S.
,
Siden A.
,
Eneroth P.
, and
Cruz M.
, Biophys. Res. Commun. , 2001 , 289 , 586 .
6.
Shiah S.G.
,
Kao Y. R.
,
Wu F. Y. H.
, and
Wu C. W.
, Mol. Pharmacol. , 2003 , 64 , 1076 .
7.
Lövborg H.
,
Oberg F.
,
Rickardson L.
,
Gullbo J.
,
Nygren P.
, and
Larsson R.
, Int. J. Cancer , 2006 , 118 , 1577 .
8.
Liu G.Y.
,
Frank N.
,
Bartsch H.
, and
Lin J. K.
, Mol. Carcinog. , 1998 , 22 , 235 .
9.
Gen D.
,
Gonzalez R. I.
,
Buckmeier J. A.
,
Kahlon R. S.
,
Tohidian N. B.
, and
Meyskens F. L.
Jr.
, Mol. Cancer Ther. , 2002 , 1 , 197 .
10.
Chen D.
,
Cui Q. C.
,
Yang H.
, and
Dou Q. P.
, Cancer Res. , 2006 , 66 , 10425 .
11.
Hacker M.P.
,
Ershler W. B.
,
Newman R. A.
, and
Gamelli R. L.
, Cancer Res. , 1982 , 42 , 4490 .
12.
Neims A.H.
,
Coffey D. S.
, and
Hellerman L.
, J. Biol. Chem. , 1966 , 241 , 5941 .
13.
Nakagawa H.
,
Tsuta K.
,
Kiuchi K.
,
Senzaki H.
,
Tanaka K.
,
Hioki K.
, and
Tsubura A.
, Carcinogenesis , 2001 , 22 , 891 .
14.
Smart D.K.
,
Ortiz K. L.
,
Mattson D.
,
Bradbury CM
.,
Bisht K. S.
,
Sieck L. K.
,
Brechbiel M. W.
, and
Gius D.
, Cancer Res. , 2004 , 64 , 6716 .
15.
Trofimenko S.
, J. Org. Chem. , 1968 , 33 , 890 .
16.
Mukhopadhyay S.
,
Mukhopadhyay U.
,
Mak T. C. W.
, and
Ray D.
, Inorg. Chem. , 2001 , 40 , 1057 .
17.
El ldrissi A.
,
Tebbji K.
, and
Radi S.
, Molecules , 2001 , 6 , M233 .
18.
Mills A.M.
,
Chalbot M.
,
Bouwman E.
, and
Spek A. L.
, Acta Cryst. Sect. E. , 2003 , E59 , o258 .
19.
El ldrissi A.
,
Tebbji K.
, and
Radi S.
, Molecules , 2001 , 6 , M235 .
20.
Mullica D.F.
,
Trawick M. L.
,
Wu P. W. N.
, and
Sappenfield E. L.
, J. Chem. Crystallogr. , 1998 , 28 , 761 .
21.
Paul C.
, and
Srikrishnan T.
, J. Chem. Crystaallogr. , 2004 , 34 , 211 .
22.
Brar S.S.
,
Grigg C.
,
Wilson K. S.
,
Holder WD.
Jr.
,
Dreau D.
,
Austin C.
,
Foster M.
,
Ghio A. J.
,
Whorton A. R.
,
Stowell G. W.
,
Whittall L. B.
,
Whittle R. R.
,
White D. P.
, and
Kennedy T. P.
, Mol. Cancer Ther. , 2004 , 3 , 1049 .
23.
Mossman T.
, J. Immunol. Meth. , 1983 , 65 , 55 .