Novel 5-(2-hydroxyphenyl)-3-substituted-2,3-dihydro-1,3,4-oxadiazole-2-thione derivatives: Promising anticancer agents (original) (raw)
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International Journal of Scientific Research in Science and Technology, 2020
A new Series of novel N-Substituted 1,3,4-Oxadiazole derivatives (3a-3f) were synthesized by the reacting 3,5-dinitrobenzoic acid and subsequent treatment with thiourea by microwave assisted synthesis as green chemistry. Confirmation of the chemical structure of the synthesized compounds was substantiated by TLC, IR, 1HNMR, and MS spectroscopy. Synthesized compounds were screened for anticancer activity on MCF7 cell line. All synthesized compounds exhibit significant biological activity and certainly hold a greater promise for discovering potent biologically active molecules. Further the compounds 3b, 3c and 3e has been moderate tested for its anticancer activity and out of these all, compound 3c showed most notable anticancer activity against breast cancer cell line. Molecules under study were analysed for ADME properties using SwissADME servers. ADME profiles were evaluated and most of the molecules were found to be suitable for further studies. In silico ADMET analysis is proved to be a good tool in drug discovery.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 2017
A series of new 1,3,4-oxadiazole-2(3H)-thione analogues (3a to 3o) have been designed, synthesized and evaluated for their anticancer activity. Four different cancerous cell lines viz. HeLa (cervical), U-87 (glioblastoma), Panc (pancreatic) and MCF-7 (breast) were used to assess the potency of the synthesized compounds as anticancer agents. Among them 3i and 3j showed promising cytotoxicity against HeLa cell line. Further, 3i and 3j successfully inhibited cell cycle progression and displayed cell death in HeLa cells via apoptosis as visualized by Annexin V APC and DNA fragmentation assay. 3i and 3j induced caspase-3 activation, PARP cleavage, increase in expression of proapoptotic protein Bax and decrease in the expression of antiapoptotic protein Bcl-2. Also, 3i and 3j induced overexpression of p21 and decreased expression of cyclin B1 indicating the arrest of cells in G2-M phase of the cell cycle. Therefore, new lead compounds are being suggested having anticancer activity through...
IOSR Journal of Pharmacy and Biological Sciences, 2014
In the present work a series of novel derivatives of 1,3,4-oxadiazoles containing 5-phenyl thiophene moiety has been synthesized by convergent synthetic method and studied their anticancer properties. The synthesized compounds were characterized by spectral (1 H-NMR, 13 C NMR, MS and elemental) analyses. Three cell lines were used for thecytotoxic evaluation namely, HepG2, Caco-2 and PANC-1. The synthetic chemistry involved conversion of various substituted aromatic acids into ethyl ester 2a-e. The ethyl ester was converted into corresponding carbohydrazide 3a-e. Carbohydrazides3a-e were reacted with 5-phenyl thiophene-2carboxaldehyde(5) in presence of acetic acid as catalyst and obtained novel Schiff base compounds6a-e. The Schiff base derivatives were cyclized using chloramine-T as promoter and obtained novel derivatives of 1,3,4oxadiazole 7a-e.Among the synthesised compounds, the cytotoxicity of the compound 7b i.e. 2-(4'fluorobiphenyl-3-yl)-5-(5-phenylthiophen-2-yl)-1,3,4-oxadiazole against Caco-2 cell line with IC 50 of 5.3µM. The compound 7e i.e.2-(4-methoxyphenyl)-5-(5-phenylthiophen-2-yl)-1,3,4-oxadiazoleshowed moderate cytotoxicity against HepG2 with IC 50 of 28.4µM. Rest of the compounds showed less cytotoxicity against all the three cell lines.
International Journal of Pharmaceutical Sciences and Drug Research, 2018
Neoplasia is a type of abnormal and excessive growth of tissue. The growth of a neoplasia is uncoordinated with that of the normal surrounding tissue, and it persists growing abnormally, even if the original trigger is removed. This abnormal growth usually forms a mass. The main objective of the present research work was the synthesis, characterization and evaluation of in vivo antitumour activity of some novel 2, 5-disubstituted 1, 3, 4-oxadiazole derivatives. The in vivo antitumour activity of synthesized compounds was evaluated by HT 29 cell line induced malignant ascites on mouse model. The apoptosis of HT 29 cells was evaluated by using Gimsa and H33342 stain and the apoptosis ratios were analysed by FCM using AnnexinV-FITC/PI staining. The present experimental data displayed that the mortality was less in all groups except in tumour control group and all the synthesized compounds AB1-AB8 (100 mg/kg) significantly increased the PILS. While 5-FU increased the life span of 97.72%...
Synthesis and Anticancer Evaluation of New 1,3,4-Oxadiazole Derivatives
Pharmaceuticals
In order to develop novel chemotherapeutic agents with potent anticancer activities, a series of new 2,5-diaryl/heteroaryl-1,3,4-oxadiazoles were designed and synthesized. The structures of the new compounds were established using elemental analyses, IR and NMR spectral data. The compounds were evaluated for their anticancer potential on two standardized human cell lines, HT-29 (colon adenocarcinoma) and MDA-MB-231 (breast adenocarcinoma). Cytotoxicity was measured by MTS assay, while cell cycle arrest and apoptosis assays were conducted using a flow cytometer, the results showing that the cell line MDA-MB-231 is more sensitive to the compounds’ action. The results of the predictive studies using the PASS application and the structural similarity analysis indicated STAT3 and miR-21 as the most probable pharmacological targets for the new compounds. The promising effect of compound 3e, 2-[2-(phenylsulfanylmethyl)phenyl]-5-(4-pyridyl)-1,3,4-oxadiazole, especially on the MDA-MB-231 cel...
ChemInform, 2012
The synthetic strategies and characterization of some novel 1,3,4-oxadiazole derivatives carrying different pharmacophores and heterocyclic rings that are relevant to potential antitumor and cytotoxic activities are described. The antitumor activities of the newly synthesized compounds were evaluated according to the protocol of the National Cancer Institute (NCI) in-vitro disease-oriented human cells screening panel assay. The results revealed that five compounds, namely 2, 7a, 11a, 12b, and 17; displayed promising in-vitro antitumor activity in the 4-cell lines assay. Incorporating a thiazole ring to 1,3,4oxadiazole skeleton resulted in better antitumor activities than those displayed by the pyrazole and thiophene ring systems. Transformation of 1,3,4-oxadiazole 2 to N-(6-amino-7H-pyrazolo[5,1-c][1,2,4] triazol-3-yl)benzamide (15) diminished the antitumor activity.
Evaluation of anticancer activity of some 1,3,4-oxadiazole derivatives
Carboxymethyl derivatives of various para substituted/unsubstituted oxadiazole-2-thione have been evaluated for their potential anticancer activity. Male Swiss albino mice have been used as test animal. The anti-cancer activity has been evaluated by comparing the ability of the test compound (25 mg/kg) to inhibit the tumor weight as well as tumor cell count with that of the control. The results suggest that all the studied compounds show significant reduction in both tumor weight and tumor cell count with respect to that of the control. Compound 3 is found to the most potent. The standard compound used is Mitomycin C (1mg/kg).
Synthesis and antitumor evaluation of some new 1,3,4-oxadiazole-based heterocycles
European Journal of Medicinal Chemistry, 2012
The synthetic strategies and characterization of some novel 1,3,4-oxadiazole derivatives carrying different pharmacophores and heterocyclic rings that are relevant to potential antitumor and cytotoxic activities are described. The antitumor activities of the newly synthesized compounds were evaluated according to the protocol of the National Cancer Institute (NCI) in-vitro disease-oriented human cells screening panel assay. The results revealed that five compounds, namely 2, 7a, 11a, 12b, and 17; displayed promising in-vitro antitumor activity in the 4-cell lines assay. Incorporating a thiazole ring to 1,3,4oxadiazole skeleton resulted in better antitumor activities than those displayed by the pyrazole and thiophene ring systems. Transformation of 1,3,4-oxadiazole 2 to N-(6-amino-7H-pyrazolo[5,1-c][1,2,4] triazol-3-yl)benzamide (15) diminished the antitumor activity.
Synthesis and anticancer activities of novel 3,5-disubstituted-1,2,4-oxadiazoles
Bioorganic & Medicinal Chemistry Letters, 2009
a b s t r a c t A series of 3,5-disubstituted-1,2,4-oxadiazoles were synthesized and evaluated for their in vitro anti-proliferative activities against various cancer cell lines. Formation of 1,2,4-oxadiazole ring was accomplished by the reaction of amidoxime with carboxylic acids. The in vitro cytotoxic effects of 3,5-disubstituted-1,2,4-oxadiazoles have been demonstrated across a wide array of tumor cell types and a few compounds exhibited specificity towards pancreatic (3f, 3h, 3j, and 3k) and prostate (3n) cancer cells. Among the prepared 3,5-disubstituted-1,2,4-oxadiazoles, compound 3n is the most selective (>450-fold) and compound 3p is the most cytotoxic (10 nM) against prostate cancer cell lines.