Arbeiten über Phosphorsäure‐ und Thiophosphorsäureester mit einem heterocyclischen Substituenten. 3. Mitteilung. Thiadiazol‐Ringschluss und eine dabei auftretende Methylübertragung

Rüfenacht, K.

doi:10.1002/hlca.19720550414

Cited by 18 publications

(6 citation statements)

References 8 publications

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“…All reagents were obtained from commercially available sources and were used as received unless otherwise noted. Diacetyl-2-(4- N -methyl-3-thiosemicarbazone), 1-phenyl-2-propanone-1-(4- N -methyl-3-thiosemicarbazone), hydrazinecarbothioic acid O -ethyl ester, and hydrazinecarbothioic acid O -ethyl ester were prepared using previously reported methods. The glyoxal(bisthiosemicarbazone) (H 2 GTSM) was synthesized using modification of the previously known procedure .…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Characterization, and Biological Activity of Hybrid Thiosemicarbazone–Alkylthiocarbamate Metal Complexes

et al. 2020

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A series of hybrid ligands (H 2 L 1 −H 2 L 3 ) derived from 4-methyl-3-thiosemicarbazide and hydrazinecarbothioic acid O-alkyl esters were synthesized and characterized by NMR. The ligands were chelated with copper (4−6), nickel (7−9), and zinc (10−12) and characterized by spectroscopy, electrochemistry, and single crystal X-ray crystallography. The chelated metals displayed substantial anodic shifts in the Cu II/I reduction potential of ∼160 mV relative to their bis(thiosemicarbazone) analogues. The metal chelates 4−12 were evaluated for potential anticancer activity by MTT assays, and selected results were confirmed by clonogenic and trypan blue assays. The copper derivatives 4 and 6 were found to have potent and cancer-selective antiproliferative effects, with GI 50 values less than 100 nM in A549 lung adenocarcinoma cells compared with at least 20-fold less activity in IMR90 nonmalignant lung fibroblasts. In comparison, the nickel complexes were much less active and had little cancer-selectivity. Varying by ligand, the zinc complexes were less potent or had comparable activity compared to that of the corresponding copper complex. UV−visible spectroscopy indicated that zinc complex 10 was transmetalated in the presence of equimolar copper, whereas nickel complex 7 was not. Copper complexes 4 and 6 were also assessed in the NCI60 screen and were found to have cytotoxic activity against most solid tumor cell lines. In MTT assays, 4 and 6 were substantially more active against A549 cancer cells than Cu(ATSM) and were more cancer-selective (for A549 compared to IMR-90) than Cu(GTSM). Our results suggest that hybrid thiosemicarbazone− alkylthiocarbamate copper complexes have potential for development as new anticancer agents.

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Section: Methodsmentioning

confidence: 99%

Synthesis, Characterization, and Biological Activity of Hybrid Thiosemicarbazone–Alkylthiocarbamate Metal Complexes

et al. 2020

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“…Reactions were conducted open to air and under ambient conditions unless otherwise noted. Xanthates 24 and hydrazinecarbothioc acid O-alkyl esters 25 were synthesized according to literature methods.…”

Section: Methodsmentioning

confidence: 99%

“…xanthates were prepared from the appropriate alcohol and carbon disulfide 24 and subsequently condensed with hydrazine monohydrate to yield the hydrazinecarbothioc acid O-alkyl esters. 25 Condensation of the ester with butanedione (1 -5) or hexanedione (6) yielded the desired ligand in a reaction similar to H 2 ATSM synthesis. 29…”

Section: Cu(etcb) (8)mentioning

confidence: 99%

Syntheses, structures, and electrochemical studies of N,N′-bis(alkylthiocarbamate)butane-2,3-diimine Cu(II) complexes as pendent alkoxy derivatives of Cu(ATSM)

Vishnosky

Mashuta

Buchanan

et al. 2017

Inorganica Chimica Acta

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A series of N 2 S 2-Cu(II) complexes based on N,N′-bis(alkylthiocarbamate)butane-2,3-diimine ligands have been synthesized and characterized by spectroscopic, electrochemical, and single crystal x-ray diffraction methods. This class of ligands contains a conjugated N 2 S 2 chelate framework with a non-coordinating, terminal alkoxy (-OR) group. Ligands and Cu(II) complexes were investigated for R = Me, Et, n Pr, i Pr, and octyl. Additionally, N,N′bis(ethylthiocarbamate)hexane-3,4-diimine and its Cu(II) complex were analyzed. Single crystal x-ray diffraction studies on all six Cu(II) complexes confirm a square planar Cu(II) environment with no significant changes in the core structure as a function of R. Spectroscopic studies are consistent with a similar electronic environment in all complexes. However, electrochemical investigations reveal significant shifts in the Cu (II/I) and Cu (III/II) reduction potentials throughout the series. The complexes are analogues of the well-known bis(thiosemicarbazone) Cu(II) which contain a similar donor core with terminal, non-coordinating amines. Substitution of the terminal amines of bis(thiosemicarbazones) with the alkoxy groups of N,N′bis(alkylthiocarbamate)butane-2,3-diimines allows tuning of redox potentials with minimal changes in the physical and electronic structure.

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“…Solvents ethanol and methanol were grades absolute and 99.8%, respectively. Xanthates, 79 hydrazinecarbothioic acid O-alkyl esters 80 , mono-keto-thiosemicarbazones, 18,81 H2ATSM, H2ATSDM, H2ATSM-F6, 1, 2, and 3 were synthesized according to literature methods. 8,32 was added with stirring, giving a red-brown precipitate.…”

Section: Synthetic Proceduresmentioning

confidence: 99%

“…79 The xanthates were subsequently condensed with hydrazine monohydrate to yield the hydrazinecarbothioc acid O-alkyl esters. 80 Condensation of the ester with butanedione (4 -8) or hexanedione (9) yielded the desired ligand in a reaction similar to H2ATSM synthesis. 14 (Figures A20-A24).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and evaluation of metal complexes with cancer selective anti-proliferative effects and hydrogen evolution catalytic properties.

Vishnosky¹

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Arbeiten über Phosphorsäure‐ und Thiophosphorsäureester mit einem heterocyclischen Substituenten. 3. Mitteilung. Thiadiazol‐Ringschluss und eine dabei auftretende Methylübertragung

Cited by 18 publications

References 8 publications

Synthesis, Characterization, and Biological Activity of Hybrid Thiosemicarbazone–Alkylthiocarbamate Metal Complexes

Synthesis, Characterization, and Biological Activity of Hybrid Thiosemicarbazone–Alkylthiocarbamate Metal Complexes

Syntheses, structures, and electrochemical studies of N,N′-bis(alkylthiocarbamate)butane-2,3-diimine Cu(II) complexes as pendent alkoxy derivatives of Cu(ATSM)

Synthesis, characterization, and evaluation of metal complexes with cancer selective anti-proliferative effects and hydrogen evolution catalytic properties.

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