Synthesis of Quinoline‐8‐selenol, Its Complex Compounds with Metals and Their Cytotoxic Activity.

Ashaks, J.; Bankovsky, Yu.; Zaruma, D.; Шестакова, И.; Домрачева, Илона; Нестерова, А. В.; Lukevics, É.

doi:10.1002/chin.200512182

Cited by 3 publications

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“…Di(8-quinolyl)disulfides were synthesized by the following methods: 1 [3], 2 [4], 3 [5], 4 [6], 5 [7], 6 [8], 7 [9], 8 [10], 9 [11], 10,11 [12], 12 [13], 13 [14], 14 [15], 15 [16], 16 [17], 17 [18], 18 [19], 19,20 [20], 21,22 [21], 23 [22], 24 [23], 25 [24], 26 [25], 27 [26], and 28 [27].…”

Section: Methodsmentioning

confidence: 99%

Cytotoxic di(8-quinolyl) disulfides

Lukevics

Шестакова

Домрачева

et al. 2007

Chem Heterocycl Compd

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It has been shown that the nature of the substituent and its position in the quinoline ring markedly affects the antitumor activity and toxicity of di (8-quinolyl) disulfides. The greatest cytotoxicity in the series of methyl derivatives was shown by the 7-, 6-, and 3-isomers towards HT-1080 (human fibrosarcoma) and MG-22A (mouse hepatoma) tumor cells while the 2-methyl derivatives generally have no effect on these cells. High cytotoxicity was also shown (LC 50 <1 µg/ml) by other 7-substituted compounds (Cl, PhO, PhS) but they also appear to be highly toxic towards normal NIH 3Y3 mouse embryonic fibroblasts. A similar trend was observed in the series of 5-substituted compounds (NH 2 , Cl, OMe, NO 2 ) which were highly active towards tumor cells but were toxic to normal cells. The best selectivity was found for the 6-substituted quinolines, the 6-methoxy derivative at low concentration brought about the death of tumor cells but appeared much less toxic towards normal fibroblasts (LC 50 100 µg/ml with a corresponding LD 50 of 874 mg/kg ).We have previously shown that di(8-quinolyl) disulfide 1 has high cytotoxicity (LC 50 0.3-0.4 µg/ml) towards HT-1080 tumor cells (human fibrosarcoma) and MG-22A (mouse hepatoma) [1]. However, while this disulfide is highly active towards tumor cells it is toxic towards normal NIH 3T3 mouse embryonic fibroblasts (LC 50 0.7 µg/ml) [1].With the aim of decreasing the toxicity and increasing the selectivity we have prepared a series of disulfides containing one (2-25) or two (26-28) electron donor or electron acceptor substituents both in the pyridine and in the benzene part of the quinoline ring and we have studied the effect of the nature and position of the substituent on their cytotoxicity (LC 50 ) in two lines of tumor cells (HT-1080 and MG-22A) as well as to normal NIH 3T3 fibroblasts which served as a measure of the toxicity of the compound (alternative method of determining LD 50 see [2]). N S S N R R 1-28 1 R = H, 2 R = 2-Me, 3 R = 3-Me, 4 R = 4-Me, 5 R = 5-Me, 6 R = 6-Me, 7 R = 7-Me, 8 R = 2-Ph, 9 R = 4-Ph, 10 R = 5-Ph, 11 R = 6-Ph, 12 R = 4-Cl, 13 R = 5-Cl, 14 R = 7-Cl, 15 R = 2-MeO, 16 R = 5-MeO, 17 R = 6-MeO, 18 R = 4-PhO, 19 R = 5-PhO, 20 R = 7-PhO, 21 R = 5-PhS, 22 R = 7-PhS, 23 R = 5-SO 3 H, 24 R = 5-NO 2 , 25 R = 5-NH 2 , 26 R = 2,4-Me 2 , 27 R = 2,7-Me 2 , 28 R = 5,7-Cl 2

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Section: Methodsmentioning

confidence: 99%

Cytotoxic di(8-quinolyl) disulfides

Lukevics

Шестакова

Домрачева

et al. 2007

Chem Heterocycl Compd

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“…Palladium Quinoline-8-selenolate (1) was synthesized by the procedure of [18]. X-Ray Structural Analysis.…”

Section: Methodsmentioning

confidence: 99%

Structure of palladium quinoline-8-selenolate Pd(C9H6NSe)2

Silina

Ashaks

Belyakov

et al. 2006

Chem Heterocycl Compd

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The molecular and crystal structure of palladium quinoline-8-selenolate Pd(C 9 H 6 NSe) 2 has been determined by X-ray structural analysis. The structures of the five-membered metallocycles of palladium 8-hydroxy-, 8-mercapto-, and 8-hydroselenoquinolinates of one type are compared.Keywords: 8-mercapto-, 8-hydroseleno-, and 8-hydroxyquinolinates, chelate compounds of palladium, molecular structure.A great number of the complexes of 8-mercaptoquinoline and its derivatives [1] have been synthesized and structurally examined while investigating the metal-sulfur bond in chelate compounds of transition and nontransition elements in the Laboratory of Chelate Compounds of the Institute of Inorganic Chemistry of Riga Technical University. Where possible the results obtained were compared with the structural data of the corresponding 8-hydroxyquinolinates.To clarify the character of the M-Se(S, O) bond and the overall picture of their dynamics in fivemembered isomolecular complexes of one type with ligand atoms of one group (VI), the synthesis and X-ray structural investigations have been continued on chelate compounds of 8-hydroselenoquinoline and its derivatives. Systematic structural investigations on chelate compounds the ligands of which would contain the coordinationally reactive SeH group are not known in the literature. Consequently the main problem was the coordination possibility of selenium(II) as a ligand atom and the experimental determination of the lengths of the M-Se bonds in chelate compounds. Previously we established the molecular and crystal structures of the complexes Pt(C 9 H 6 NSe) 2 , Cd(C 9 H 6 NSe) 2 [2], Zn(C 9 H 6 NSe) 2 [3,4], In(C 9 H 6 NSe) 3 [5], and Sb(C 9 H 6 NSe) 3 [6].In the present work the synthesis and the results of the X-ray structural investigation of palladium(II) quinoline-8-selenolate Pd(C 9 H 6 NSe) 2 (1) are described. Since the crystal structures of palladium 8-mercaptoquinolinate (2) [7] and palladium 8-hydroxyquinolinate (3) [8] are known, a comparison of the structure of the five-membered metallocycles of one type and consideration of the dynamics of the experimentally found Pd-Se, Pd-S, Pd-O, and Pd-N bond lengths is possible.The crystal structure of complex 1 consists of neutral centrosymmetric Pd(C 9 H 6 NSe) 2 molecules (Fig. 1). The palladium atoms are disposed at the centers of symmetry [(000)] of the unit cell. They coordinate in a bidentate manner (Se, N) with two quinoline-8-selenol ligands, the chelate angle Se(1)PdN(1) is 85.6(1)°. Surrounding the central palladium is a trans square (2Se + 2N). The Pd-Se and Pd-N bonds (Table 1) have a covalent character, since their lengths are less than the sum of the covalent radii of the corresponding atoms (r Pd + r Se = 2.537 and r Pd + r N = 2.102 Å [9]. The Se-C(8) bond length = 1.881(4) Å is close to the value of __________________________________________________________________________________________

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“…Bankovsky [1]. At the initiative of Academician Bankovsky, studies were undertaken of chelate compounds of 8-quinolineselenol (SeQu), which is a structural analog of 8-quinolinethiol and 8-quinolinol [2][3][4][5][6][7]. 8-Quinolineselenol, its derivatives, and their complexes hold interest in regard to their possible biological activity.…”

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Synthesis and structure of bismuth 8-quinoline-selenolate Bi(C9H6NSe)3

Silina

Ashaks

Belyakov

et al. 2007

Chem Heterocycl Comp

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Bismuth 8-quinolineselenolate Bi(C 9 H 6 NSe) 3 was synthesized. The molecular and crystal structure of this compound was determined by X-ray diffraction structural analysis. The effect of replacing the ligand atoms Se→S and the role of the unshared electron pair on the formation of the coordination polyhedron of the central bismuth atom in bismuth(III) 8-quinolineselenolate and bismuth(III) 8-quinolinethiolate, which are complexes of a Group V p-element in an incomplete valence state was discussed.Keywords: bismuth chelate compounds, bismuth 8-quinolineselenolate, bismuth 8-quinolinethiolate, unshared electron pair (UEP), X-ray diffraction structural analysis.Multifaceted systematic studies of chelate compounds of transition and nontransition metals with 8-quinolinethiol (SQu), 8-quinolinol (OQu), and its derivatives have been carried out at the Chelate Compounds Laboratory in the Institute of Inorganic Chemistry at the Riga Technical University headed by Academician Yu. Bankovsky [1]. At the initiative of Academician Bankovsky, studies were undertaken of chelate compounds of 8-quinolineselenol (SeQu), which is a structural analog of 8-quinolinethiol and 8-quinolinol [2-7]. 8-Quinolineselenol, its derivatives, and their complexes hold interest in regard to their possible biological activity.In systematic studies, the differences in the physicochemical properties of chelate compounds of transition and nontransition elements and the possible use of these compounds have been repeatedly interpreted using X-ray diffraction structural analysis data, leading to an understanding of the role of the chelate-forming M-O, M-S, M-Se, and M-N chemical bonds. Physicochemical and X-ray diffraction data on the M-O, M-S, and M-Se chemical bond nature in chelate compounds of transition metals and conclusions regarding additional M←S π-bonding (direct donor-acceptor π-bond) have been examined in our previous work [8,9]. _______ * Dedicated to the memory of Academician Yurii Bankovsky, the founder of the chemistry of 8-mercaptoquinoline (December 22, 1927 -January 28, 2003 on the occasion of the eightieth anniversary of his birth. __________________________________________________________________________________________

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Synthesis of Quinoline‐8‐selenol, Its Complex Compounds with Metals and Their Cytotoxic Activity.

Cited by 3 publications

References 1 publication

Cytotoxic di(8-quinolyl) disulfides

Cytotoxic di(8-quinolyl) disulfides

Structure of palladium quinoline-8-selenolate Pd(C9H6NSe)2

Synthesis and structure of bismuth 8-quinoline-selenolate Bi(C9H6NSe)3

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