A triclinic polymorph of 1,3-thiazolidine-2-thione (2-mercaptothiazoline)

Corrêa, Rodrigo S.; Santana, Sarita A.; Salloum, Rogério; Silva, Rosalice M.

doi:10.1107/s0108270106002484

Cited by 12 publications

(13 citation statements)

References 17 publications

(12 reference statements)

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“…For complex 3 the singlet is observed at 33.3 ppm, a chemical shift in low field is shifted when compared to cis-[RuCl 2 (PPh 3 ) 2 (bipy)], where a singlet is presented at 21.5 ppm [52]. These values are typical of PPh 3 trans to PPh 3 as observed for a series of ruthenium compounds [53,54]. The 1 H NMR spectrum of metal-free tzdtH in CDCl 3 displayed a broad singlet corresponding to the proton of the N-H group around 7.30 ppm and a pair of triplets in the range 3.50-4.00 ppm corresponding to the methylenic protons.…”

Section: Nmr Spectroscopymentioning

confidence: 67%

“…Crystal data collections and structure refinement parameters are summarized in Table 1S. The crystallographic analysis of metal-free tzdtH described in the literature shows that C1-S1 is a double bond, while C1-N1 single-bond [54]. When tzdtH is coordinated to Ru, the length of these bonds significantly changes in which the C1-S1 is longer whereas C1-N1 is shorter in all the complexes.…”

Section: X-ray Crystal Structuresmentioning

confidence: 99%

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Ruthenium(II) complexes of 1,3-thiazolidine-2-thione: Cytotoxicity against tumor cells and anti-Trypanosoma cruzi activity enhanced upon combination with benznidazole

Corrêa

Silva

Graminha

et al. 2016

Journal of Inorganic Biochemistry

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Three new mixed and mononuclear Ru(II) complexes containing 1,3-thiazolidine-2-thione (tzdtH) were synthesized and characterized by spectroscopic analysis, molar conductivity, cyclic voltammetry, high-resolution electrospray ionization mass spectra and X-ray diffraction. The complexes presented unique stereochemistry and the proposed formulae are: [Ru(tzdt)(bipy)(dppb)]PF6 (1), cis-[Ru(tzdt)2(PPh3)2] (2) and trans-[Ru(tzdt)(PPh3)2(bipy)]PF6 (3), where dppb=1,4-bis(diphenylphosphino)butane and bipy=2,2'-bipyridine. These complexes demonstrated strong cytotoxicity against cancer cell lines when compared to cisplatin. Specifically, complex 2 was the most potent cytotoxic agent against MCF-7 breast cells, while complexes 1 and 3 were more active in DU-145 prostate cells. Binding of complexes to ctDNA was determined by UV-vis titration and viscosity measurements and revealed binding constant (Kb) values in range of 1.0-4.9×10(3)M(-1), which are characteristic of compounds possessing weak affinity to ctDNA. In addition, these complexes presented antiparasitic activity against Trypanosoma cruzi. Specifically, complex 3 demonstrated strong potency, moderate selectivity index and acted in synergism with the approved antiparasitic drug, benznidazole. Additionally, complex 3 caused parasite cell death through a necrotic process. In conclusion, we demonstrated that Ru(II) complexes have powerful pharmacological activity, while the metal-free tzdtH does not provoke the same outcome.

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Section: Nmr Spectroscopymentioning

confidence: 67%

Section: X-ray Crystal Structuresmentioning

confidence: 99%

Ruthenium(II) complexes of 1,3-thiazolidine-2-thione: Cytotoxicity against tumor cells and anti-Trypanosoma cruzi activity enhanced upon combination with benznidazole

Corrêa

Silva

Graminha

et al. 2016

Journal of Inorganic Biochemistry

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“…However, very little information of the structure is available from the brief structural description. Furthermore, polymorphic forms of thiazolidine-2-thione derivatives have been reported in the literature [e.g., 40]. Thus as our sample of (1: R ¼ Bu t ) had been obtained by a different and milder route than that used for the preparation of the sample studied in the previous structure determination, we decided to carry out a full characterization, including X-ray diffraction.…”

Section: X-ray Crystallographic Resultsmentioning

confidence: 99%

Cyclization of N-alkyldithiocarbamates in alkaline media, a counter example of well-known chemistry – an experimental and theoretical study

Lima

Menezes

Santos

et al. 2012

Journal of Coordination Chemistry

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In strong alkaline media, the reaction of 2-(tert-butylamino)ethanol (3: R ¼ Bu t ) with CS 2 at 0 C produced a cyclic dithiocarbamate, 3-tert-butylthiazolidine-2-thione (1: R ¼ Bu t ), rather than alkaline metal or ammonium salts of [S 2 CN(Bu t )CH 2 CH 2 OH] À . This is in contrast to isolation of stable alkaline metal or ammonium salts of [S 2 CN(R)CH 2 CH 2 OH] À (R ¼ Me, Et, Pr, or CH 2 CH 2 OH) obtained in analogous reactions. The use of Ni(OAc) 2 , both as a source of Ni(II) and a weaker base, in a one-pot reaction with (3: R¼ Bu t ) and CS 2 , successfully gave the first reported metal complex of [S 2 CN(Bu t )CH 2 CH 2 OH] À , namely [Ni{S 2 CN(Bu t )CH 2 CH 2 OH} 2 ] (2: R ¼ Bu t ). Compounds 1 and 2 have been fully characterized by infrared and NMR spectroscopies, and by X-ray crystallography. DFT calculations on the cyclization and stabilities of [S 2 CN(R)CH 2 CH 2 OH] À (R ¼ Pr and Bu t ) have been carried out.

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“…The five membered heterocycle possesses a distorted half chair conformation along the C12–C13 bond, based on the torsion angle concept. 17 Compared to the C=S bond in the free ligand (1.671–1.680 Å 20 ) no significant coordination-induced lengthening can be observed. Thus, the C11–S bond (1.683(4) Å) in complex 21a exhibits double bond character.…”

Section: Resultsmentioning

confidence: 98%

“…The data were acquired with 512 k data points and zero filled to 2048 k by averaging 64 scans. fac -[(PtMe 3 I) 4 ] 14,25 and fac -[PtMe 3 I(bpy)] 20 were prepared according to literature methods. All other materials were purchased from commercial sources.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, characterization and reactivity of carbohydrate platinum(iv) complexes with thioglycoside ligands

et al. 2010

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Reactions of fac-[PtMe3(4,4′-R2bpy)(Me2CO)][BF4] (R = H, 1a; tBu, 1b) and fac-[PtMe3-(OAc-κ2O,O′)(Me2CO)] (2), respectively, with thioglycosides containing thioethyl (ch-SEt) and thioimidate (ch-STaz, Taz = thiazoline-2-yl) anomeric groups led to the formation of the carbohydrate platinum(IV) complexes fac-[PtMe3(4,4′-R2bpy)(ch*)][BF4] (ch* = ch-SEt, 8–14; ch-STaz, 15–23) and fac-[PtMe3(OAc-κ2O,O′)(ch*)] (ch* = ch-SEt, 24–28; ch-STaz = 29–35), respectively. NMR (1H, 13C, 195Pt) spectroscopic investigations and a single-crystal X-ray diffraction analysis of 19 (ch-STaz = 2-thiazolinyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-d-galactopyranose) revealed the S coordination of the ch-SEt glycosides and the N coordination of the ch-STaz glycosides. Furthermore, X-ray structure analyses of the two decomposition products fac-[PtMe3(bpy)(STazH-κS)][BF4] (21a) and 1,6-anhydro-2,3,4-tri-O-benzoyl-β-d-glucopyranose (23a), where a cleavage of the anomeric C–S bond had occurred in both cases, gave rise to the assumption that this decomposition was mediated due to coordination of the thioglycosides to the high electrophilic platinum(IV) atom, in non-strictly dried solutions. Reactions of fac-[PtMe3(Me2CO)3][BF4] (3) with ch-SEt as well as with ch-SPT and ch-Sbpy thioglycosides (PT = 4-(pyridine-2-yl)-thiazole-2-yl; bpy = 2,2′-bipyridine-6-yl), having N,S and N,N heteroaryl anomeric groups, respectively, led to the formation of platinum(IV) complexes of the type fac-[PtMe3(ch*)][BF4] (ch* = ch-SEt, 36–40, ch-SPT 42–44, ch-Sbpy 45, 46). The thioglycosides were found to be coordinated in a tridentate κS,κ2O,O′, κS,κN,κO and κS,κ2N,N′ coordination mode, respectively. Analogous reactions with ch-STaz ligands succeeded for 2-thiazolinyl 2,3,4-tri-O-benzyl-6-O-(2,2′-bipyridine-6-yl)-1-thio-β-d-glucopyranoside (5h) resulting in fac-[PtMe3(ch-STaz)][BF4] (41, ch-STaz = 5h), having a κ3N,N′,N″ coordinated thioglycoside ligand.

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A triclinic polymorph of 1,3-thiazolidine-2-thione (2-mercaptothiazoline)

Cited by 12 publications

References 17 publications

Ruthenium(II) complexes of 1,3-thiazolidine-2-thione: Cytotoxicity against tumor cells and anti-Trypanosoma cruzi activity enhanced upon combination with benznidazole

Ruthenium(II) complexes of 1,3-thiazolidine-2-thione: Cytotoxicity against tumor cells and anti-Trypanosoma cruzi activity enhanced upon combination with benznidazole

Cyclization of N-alkyldithiocarbamates in alkaline media, a counter example of well-known chemistry – an experimental and theoretical study

Synthesis, characterization and reactivity of carbohydrate platinum(iv) complexes with thioglycoside ligands

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