1,4-Cyclohexanedione bisthiosemicarbazone as an analytical reagent for spectrophotometric estimation of copper

Ceba, M.Román; Nevado, J. J. Berzas; García, Josefa M.

doi:10.1016/0026-265x(82)90027-3

Cited by 4 publications

(3 citation statements)

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“…Chemistry 1,4-Cyclohexanedione-bis-thiosemicarbazone 3 was reported once in the literature in 1982 as an analytical reagent for spectrophotometric estimation of copper, but no more applications of this substrate in organic synthesis were published so far (Ceba et al, 1982). Thus, when 1,4-cyclohexanedione-bis-thiosemicarbazone 3 was treated with a number of hydrazonoyl chlorides 4a-g in ethanol at refluxing temperature using triethylamine as a base, a single product was isolated, in each case, as detected by TLC analysis.…”

Section: Resultsmentioning

confidence: 99%

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Novel Bis-Thiazole Derivatives: Synthesis and Potential Cytotoxic Activity Through Apoptosis With Molecular Docking Approaches

et al. 2021

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A series of bis-thiazoles 5a–g were synthesized from bis-thiosemicarbazone 3 with hydrazonoyl chlorides 4a–g. Reaction of 3 with two equivalents of α-halocarbonyl compounds 6–8, 10, and 12a–d afforded the corresponding bis-thiazolidines 9, 11, and 13a–d, respectively. Condensation of bis-thiazolidin-4-one 9 with different aromatic aldehydes furnished bis-thiazolidin-4-ones 14a–d. Compounds 5a–g, 9, and 13a,c,d were screened in vitro for their cytotoxic activities in a panel of cancer cell lines. Compounds 5a–c, 5f–g, and 9 exhibited remarkable cytotoxic activities, especially compound 5c with potent IC50 value 0.6 nM (against cervical cancer, Hela cell line) and compound 5f with high IC50 value 6 nM (against ovarian cancer, KF-28 cell line). Compound 5f–induced appreciated apoptotic cell death was measured as 82.76% associated with cell cycle arrest at the G1 phase. The apoptotic pathways activated in KF-28 cells treated with 5a, 5b, and 5f were further investigated. The upregulation of some pro-apoptotic genes, bax and puma, and the downregulation of some anti-apoptotic genes including the Bcl-2 gene were observed, indicating activation of the mitochondrial-dependent apoptosis. Together with the molecular docking studies of compounds 5a and 5b, our data revealed potential Pim-1 kinase inhibition through their high binding affinities indicated by inhibition of phosphorylated C-myc as a downstream target for Pim-1 kinase. Our study introduces a set of bis-thiazoles with potent anti-cancer activities, in vitro.

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Section: Resultsmentioning

confidence: 99%

“…mp. 213-214°C (Ceba et al, 1982)]; IR (KBr) υ 3,255, 3,201, 3,185 (NH, NH 2 ), 1,597 (C N) cm −1 ; 1 H NMR (DMSO-d 6 ) δ 2.42-2.50 (m, 4H, cyclohexane-H's), 2.54-2.74 (m, 4H, cyclohexane-H's), 7.59 (br. s, 2H, NH 2 ), 8.05 (br.…”

Section: Synthesis Of 14-cyclohexane-bis-thiosemicarbazone (3)mentioning

confidence: 99%

Novel Bis-Thiazole Derivatives: Synthesis and Potential Cytotoxic Activity Through Apoptosis With Molecular Docking Approaches

et al. 2021

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“…The survey of literature reveals the use of Acetophenone thiosemicarbazone 3 , Cyclohexanone thiosemicarbazone 4 , Cyclohexane-1,4-dione bisthiosemicarbazone 5 , Phenanthrenequinone monothiosemicarbazone 6 , 3,5-Dibromo salicyladehyde-4-phenyl thiosemicarbazone 7 , Thiophenaldehyde-4-phenyl-3-thiosemicarbazone 8 , Thiophene-2-carbaxaldehyde thiosemicarbazone 9 , Quinoline-2-aldehyde thiosemicarbazone 10 , β-iononethiosemicarbazone 11 , as extractive spectrophotometric reagents for copper. However, these methods have some limitations, such as, low sensitivity 3-6 , longer extraction period 7,8 , slow color reaction 5,9 , use of either masking or synergic extractant 10 and a large number of interferences 3,11 . The proposed method is free from these drawbacks.…”

Section: Introductionmentioning

confidence: 99%