A step-by-step synthesis of triazole-benzimidazole-chalcone hybrids: Anticancer activity in human cells+

Published on Mar 15, 2020in Journal of Molecular Structure2.463
· DOI :10.1016/J.MOLSTRUC.2019.127487
Amar Djemoui2
Estimated H-index: 2
Abdelkader Naouri2
Estimated H-index: 2
+ 12 AuthorsArtur M. S. Silva46
Estimated H-index: 46
(University of Aveiro)
Abstract Novel series of triazole-benzimidazole-chalcone hybrid compounds have been synthesized via click chemistry, between different azide derivatives and substituted benzimidazole terminal alkynes bearing a chalcone moiety. The starting alkynes are prepared via base-catalysed nitrogen alkylation of pre-synthetized benzimidazole-chalcone substrates. All the intermediates as well as the final products are fully characterized by 1D and 2D NMR and mass spectrometry techniques. HMBC correlations permits the identification of a unique 1,4-disubstitued triazole-benzimidazole-chalcone isomer. Evaluation of the anti-proliferative potential in breast and prostate cancer cell lines showed that the presence of chloro substituents at the chalcone ring of the triazole-benzimidazole-chalcone skeleton enhanced the cytotoxic effects. The benzyl group linked to the 1,2,3-triazole moiety provides more antiproliferative potential.
#1Cheng Ying Hsieh (NTHU: National Tsing Hua University)H-Index: 3
#2Pi Wen Ko (NTHU: National Tsing Hua University)H-Index: 2
Last. Ming Hua HsuH-Index: 3
view all 9 authors...
Numerous reports have shown that conjugated benzimidazole derivatives possess various kinds of biological activities, including anticancer properties. In this report, we designed and synthesized 24 new molecules comprising a benzimidazole ring, arene, and alkyl chain-bearing cyclic moieties. The results showed that the N-substituted benzimidazole derivatives bearing an alkyl chain and a nitrogen-containing 5- or 6-membered ring enhanced the cytotoxic effects on human breast adenocarcinoma (MCF-7...
7 CitationsSource
#1Rachid AmeraouiH-Index: 1
#2Mohamed Hammadi (University of Boumerdes)H-Index: 6
Last. Artur M. S. Silva (University of Aveiro)H-Index: 46
view all 11 authors...
The uncatalyzed reaction of hydrogen peroxide with (E)-3-[3-(2-hydroxyaryl)-3-oxoprop-1-en-1-yl]chromones resulted in a regio­selective epoxidation of the chromone intracyclic C(2)=C(3) double bond to afford unique isomeric (E)-7a-[3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl]-1aH-oxireno[2,3-b]chromen-7(7aH)-ones in high yields. 2D NMR and single-crystal X-ray diffraction were used to elucidate the structures of the chromanone epoxides. Density functional theoretical studies demonstrated a high elec...
1 CitationsSource
#1Mohamed Reda Aouad (Taibah University)H-Index: 13
#2Moataz A. Soliman (Taibah University)H-Index: 1
Last. Yaseen A. Al-Soud (Al al-Bayt University)H-Index: 19
view all 9 authors...
A library of novel regioselective 1,4-di and 1,4,5-trisubstituted-1,2,3-triazole based benzothiazole-piperazine conjugates were designed and synthesized using the click synthesis approach in the presence and absence of the Cu(I) catalyst. Some of these 1,2,3-triazole hybrids possess in their structures different heterocyclic scaffold including 1,2,4-triazole, benzothiazole, isatin and/or benzimidazole. The newly designed 1,2,3-triazole hybrids were assessed for their antiproliferative inhibition...
21 CitationsSource
#1Md. Jawaid Akhtar (Jamia Hamdard)H-Index: 1
#2Ahsan Ahmed Khan (Jamia Hamdard)H-Index: 6
Last. M. Shahar Yar (Jamia Hamdard)H-Index: 15
view all 11 authors...
Abstract A new series of benzimidazole linked pyrazole derivatives were synthesized by cyclocondensation reaction through one-pot multicomponent reaction in absolute ethanol. All the synthesized compounds were tested for their in vitro anticancer activities on five human cancer cell lines including MCF-7, HaCaT, MDA-MB231, A549 and HepG2. EGFR receptor inhibitory activities were carried out for all the compounds. Majority of the compounds showed potent antiproliferative activity against the test...
21 CitationsSource
#1Aicha SaidounH-Index: 2
#2Leila BoukennaH-Index: 2
Last. Artur M. S. SilvaH-Index: 46
view all 9 authors...
A new series of some interesting bispyrazole-thiazole-pyran-2-one heterocyclic hybrids has been efficiently synthesized via a one-pot catalyst-free three-component reaction of α-bromoacetylated pyran-2-one derivatives, thiosemicarbazide, and polysubstituted-1-(1H-pyrazol-4-yl)butane-1,3-diones. This multicomponent procedure has been advantageously applied to prepare a structural diversity of hetero­cyclic hybrids characterized by extensive 1D and 2D NMR spectroscopic studies.
3 CitationsSource
#1Nawel LechaniH-Index: 2
#2Maamar HamdiH-Index: 10
Last. Artur M. S. Silva (University of Aveiro)H-Index: 46
view all 7 authors...
The synthesis of novel heterocyclic [1,2,4]triazolo[3,4-b][1,3,4]thiadiazine hybrids by a bimolecular reaction of 2-(4-amino-5-mercapto-4H-[1,2,4]triazol-3-yl)phenol with an aromatic or heterocyclic α-bromoacetyl derivatives is described. This synthetic procedure starts from an unprotected phenol.
4 CitationsSource
#1Yerrabelly Jayaprakash Rao (Osmania University)H-Index: 2
#2Thummala Sowjanya (Jawaharlal Nehru Technological University, Hyderabad)H-Index: 1
Last. Sudha Sravanti Kotapalli (Indian Institute of Chemical Technology)H-Index: 9
view all 5 authors...
: A series of new flavone/isoxazole fused heterocycles 5a-f and flavone/1,2,3-triazole/benzimidazole hybrid heterocycles compounds 7a-t were synthesized via an intramolecular cyclization and Cu(I)-catalyzed click 1,3-dipolar cycloaddition. The products were evaluated for their antiproliferative activity against human breast cancer cell line (MCF-7) using sulforhodamine B assay (SRB) and antimycobacterial activity using turbidometric assay. The majority of the tested compounds exhibited antiproli...
6 CitationsSource
#1Houria LakhdariH-Index: 3
#2Oualid Talhi (University of Aveiro)H-Index: 9
Last. Artur M. S. Silva (University of Aveiro)H-Index: 46
view all 10 authors...
A one-pot synthesis of a novel series of chromeno-imidazo-pyridinone derivatives from 3-[(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl]chromones and ethane-1,2-diamine at room temperature under catalyst-free conditions has been successfully developed. This approach involves a tandem aza-Michael addition reaction, a chromone-to-chromanone rearrangement, and a heterocyclization sequence, leading to chromeno-imidazo-pyridinone polyheterocycles. The structure and absolute configurations of the new compounds...
1 CitationsSource
#1Róbson Ricardo Teixeira (UFV: Universidade Federal de Viçosa)H-Index: 17
#2Poliana Aparecida Rodrigues Gazolla (UFV: Universidade Federal de Viçosa)H-Index: 2
Last. Wallace Pacienza Lima (UFRJ: Federal University of Rio de Janeiro)H-Index: 5
view all 9 authors...
Abstract In this paper, it is described the synthesis and the evaluation of the leishmanicidal activity of twenty-six eugenol derivatives bearing 1,2,3-triazole functionalities. The evaluation of the compounds on promastigotes of Leishmania amazonensis (WHOM/BR/75/Josefa) showed that eugenol derivatives present leishmanicidal activities with varying degrees of effectiveness. The most active compound, namely 4-(3-(4-allyl-2-methoxyphenoxy)propyl)-1-(4-methylbenzyl)-1 H -1,2,3-triazole ( 7k ) (IC ...
20 CitationsSource
#1Neesha Yadav (DU: University of Delhi)H-Index: 4
#2Drishti Agarwal (DU: University of Delhi)H-Index: 4
Last. Satish Kumar Awasthi (DU: University of Delhi)H-Index: 24
view all 6 authors...
Abstract Twenty two diverse coumarin-triazole derivatives were synthesized by alkylation of 7-hydroxy-4-methyl-coumarin followed by click chemistry at 7-position. These compounds were evaluated for their in vitro antiplasmodial activity against chloroquine sensitive strain of Plasmodium falciparum (3D7). Compound 9 (7-[1-(2, 4-dimethoxy-phenyl)-1H- [1–3] triazol-4-ylmethoxy]-4-methyl-chromen-2-one) was found most active with IC50 value 0.763 ± 0.0124 μg/mL. Further, the structure of compound 20 ...
26 CitationsSource
Cited By3
#1Minghui Zuo (Heilongjiang University)H-Index: 2
#2Weihao Guo (Heilongjiang University)H-Index: 4
Last. Wenyi Chu (Heilongjiang University)H-Index: 10
view all 9 authors...
A Co (II) complex with stable structure was designed and synthesized with quinalic acid and Co (OAc)2.4H2O. The single crystal structure of complex was characterized by X-ray diffraction. A dehydrogenative coupling of aromatic diamines and primary alcohols was developed by using the Co (II) complex as the catalyst to synthesize 2-substituted benzimidazole. A series of 2-substituted benzimidazole were obtained with good to excellent yields under mild reaction conditions. In addition, a compound w...
1 CitationsSource
#1Elizabeth J. Diana (St. Thomas College)H-Index: 1
#2U.S. Kanchana (St. Thomas College)H-Index: 2
Last. Gopinathan Anilkumar (Mahatma Gandhi University)H-Index: 27
view all 4 authors...