Synthesis, Characterization and Evaluation of Anticancer Activity of Some New Schiff Bases of 1, 3, 4-THIADIAZOLE Derivatives (original) (raw)
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2015
Objective: N-benzylidene-5-phenyl-1, 3, 4-thiadiazol-2-amine derivatives: Synthesis and anticancer activity. Methods: In the present study five new derivatives of N-benzylidene-5-phenyl-1, 3, 4-thiadiazol-2-amine (Schiff bases containing 1, 3, 4thiadiazole) were synthesized according to the literature methods and were characterized by FT-IR, 1 Results: The compounds were found to reduce tumor volume, viable cell count and increase the tumor weight (%) inhibition, ascites cells (%) inhibition, non-viable cell count and increase in life span (%ILS). All the compounds exhibited significant (P< 0.01) anticancer activity compared to control and the compound 2d & 4d was found to be most potent. H NMR spectroscopy and C, H, N analysis. Anticancer activity was evaluated in Male Swiss albino mice using Ehrlich’s Ascites carcinoma cells. Compounds were administered at a dose of 25 mg/kg, body weight intraperitoneally. Conclusion: It is concluded that synthesized Schiff bases of 2-amino-5-a...
INTERNATIONAL RESEARCH JOURNAL OF PHARMACY, 2014
Schiff Bases of 5-(2-phenoxypyridin-3-yl)-1, 3, 4-thiadiazol-2-aminederivatives 6(a-h) have been synthesized with different aromatic aldehyde and tested for in vitro anticancer activity; the 1, 3, 4-thiadiazole derivatives were prepared by the reaction ofthiosemicarbazide, phosphorousoxychloride and aromatic acids. The synthesized final Schiff base compounds were purified by column-chromatography and the structures of the titled Schiff bases were elucidated by IR, 1 H NMR and LCMS spectral measurements. Three different cell lines namely Hela, Hep-G2 and MCF7 are used for the present study. The compounds tested were, in most of cases shows cytotoxic effect but, only one compound showed good activity on breast carcinoma cell line having IC50 = 2.28 μg/ mL.
2017
5-(4-aminophenyl )-2-amino -1,3,4-thiadiazole was prepared by reaction of Thiosemicarbazide with 4-amino benzoic acid under reflux condition for 7 hours. The compound which has been synthesized successfully was subjected to addition reaction with 4-(Dimethylamino) benzaldehyde under reflux condition for 6 hours to synthesize Schiff bases. These compounds was characterized by using FTIR) and evaluated for their anticancer activity. The effect of (1, 3, 4-thiadiazole derivative) on the activity of malignant cells was studied by using different types of cell lines [Breast cancer, and human prostate cancer]. And was used the Electron microscope to show that the effect of the derivative on the cancer cells before and after 3 days of the injection time. It was found that the Schiff base of thiadiazole-1,3,4-(Dimethylamino)benzylidineamino]- [4-2-phenyl]amino was effective in reducing the size and density of malignant cells. That of 46.7 while in breast ) 145(DUprostate for growth inhibiti...
2017
5-(4-aminophenyl )-2-amino -1,3,4-thiadiazole was prepared by reaction of Thiosemicarbazide with 4-amino benzoic acid under reflux condition for 7 hours. The compound which has been synthesized successfully was subjected to addition reaction with 4-(Dimethylamino) benzaldehyde under reflux condition for 6 hours to synthesize Schiff bases. These compounds was characterized by using FTIR) and evaluated for their anticancer activity. The effect of (1, 3, 4-thiadiazole derivative) on the activity of malignant cells was studied by using different types of cell lines [Breast cancer, and human prostate cancer]. And was used the Electron microscope to show that the effect of the derivative on the cancer cells before and after 3 days of the injection time. It was found that the Schiff base of thiadiazole-1,3,4-(Dimethylamino)benzylidineamino]- [4-2-phenyl]amino was effective in reducing the size and density of malignant cells. That of 46.7 while in breast ) 145(DUprostate for growth inhibiti...
Promising anti-cancer potency of 4,5,6,7-tetrahydrobenzo[d]thiazole-based Schiff-bases
Journal of Molecular Liquids, 2019
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Chinese Chemical Letters, 2017
A new series of multi-heterocyclic Schiff base was constructed starting from 4 0-(imidazol-1-yl)acetophenone which was converted to its 2-bromoethanone precursor which on cyclic condensation with thiourea yielded final thiazol-2-amine intermediate (3) to be reacted with substituted aldehydes to generate final imidazolylphenylheterocyclic-2-ylmethylenethiazole-2-amines (4a-4i). New Schiff base was investigated for their in vitro cytotoxic efficacies against a panel of three human cancer cell lines namely, MCF7 (human breast cancer), HCT116 (human colon cancer), and DU145 (human prostate cancer) and one normal skin fibroblast (SF). Most of these synthetic derivatives shown important cytotoxic actions against individual carcinoma cell line collections, but weak actions against SF, which is as anticipated. Observations of SAR suggested that the difference in the characteristics of substituents attached to the Schiff base function leads to the interesting variations within pharmacological effects of resultant molecular systems. Structural analysis performed using FT-IR, 1 H NMR, 13 C NMR spectroscopy and CHN analysis for final potent anticancer Schiff base, which warrant further investigations.
Design and Synthesis of Benzothiazole Schiff Bases of Potential Antitumor Activitiy
HETEROCYCLES, 2016
In an attempt to develop a new class of selective antitumor agents, a novel series of benzothiazole derivatives was prepared via the condensation of 5-fluoro-6-(4-methylpiperazin-1-yl)benzo[d]thiazol-2-amine with aromatic aldehydes. The preliminary bioassay reveals that (4-fluorobenzylidene)-[5-fluoro-6-(4-methylpiperazin-1-yl)-benzothiazol-2-yl]-amine show specific anticancer cytotoxicity. Structural modification of heterocyclic compounds may alter the biological properties via introduction of potent moieties. For instance, Schiff bases have been used extensively in drug design and proven to be outstanding moieties with a wide spectrum of biological activities. 1 Moreover, benzothiazole scaffold serve as a useful constituent for many natural products and pharmaceutical candidates which are known to possess a wide spectrum of biological activities. They attracted much attention in recent years due to their wide range of biological activities and they have shown significant antimicrobial, 2 anticancer, 3 anti-AD (Alzheimer's disease), anti-inflammatory, 4 anti-HIV (human immunodeficiency virus), 5 antioxidant, 6 anticonvulsant, 7 antidiabetic, 8 antitubercular, 9 antidepressant, 10 antiviral, 11 and antimalarial 12 activities.
Journal of the Chilean Chemical Society, 2011
The synthesis of some new Schiff bases bearing a 1,3,4-thiadiazole moiety, 3a-l, by reaction of 2-amino-5-mercapto-1,3,4-thiadiazole with aromatic aldehydes under acidic and phase transfer catalyst (PTC) conditions was studied. The structure of all the Schiff bases was characterized using FT-IR and NMR spectroscopy, and elemental analyses. The antibacterial activity of these compounds was investigated against Staphylococcus aureus (RTCC, 1885), and Escherichia coli (ATCC, 35922).
A Schiff base ligand [(E)-4-(((5-ethyl-1,3,4-thiadiazol-2-yl)imino)methyl)benzene-1,2,3-triol] (ETIMB) has been synthesized by condensation of an equimolar mixture of 5-Ethyl-1,3,4-thiadiazole-2-amino (0.01 mole) and 2,3,4-Trihydroxybenzaldehyde (0.01 mole) in absolute ethanol (25 ml). The ligand (ETIMB) was reacted with Ag(I), Ni(II), Cu(II) in ratio 1:1, 2:1, 2:1 respectively. The mixture was refluxed for 24 hrs. The Schiff base and its complexes were characterized by elemental (CHN) analysis, FTIR, electronic spectra,1HNMR spectra and Mass spectra. All complexes were screened for their in vitro anticancer potential using HeLa and PC3 cells. Cu(II) complex showed excellent cytotoxic activity towards HeLa cells.
2022
A series of new usnic acid ketamine compounds [1-8] and their oxime analogues [9-12] were synthesized by reacting (+)-usnic acid with various amines and subsequent treatment with hydroxylamine hydrochloride. They were evaluated on the human glioblastoma-astrocytoma cell line (U87MG) by a MTT assay for cell viability in vitro. The ketamine-derivatives (Schiff bases) show significant cytotoxicity on U87MG cells. A novel N-heterocyclic derivative (1,4-diazepine) showed an interesting tautomeric structure and displayed more activity on cancer cell line than (+)-usnic acid itself.