Synthesis, biological evaluation, and molecular modeling studies of novel heterocyclic compounds as anti-proliferative agents

Chaudhary, Anurag; Sharma, Pooja; Bhardwaj, Gautam; Jain, Vaibhav; Bharatam, Prasad V.; Shrivastav, Birendra; Roy, Rajarshi

doi:10.1007/s00044-013-0556-x

Cited by 12 publications

(12 citation statements)

References 42 publications

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“…There are many reports on the modification of ring A, ring B, and/or the ethylene bridge structure connecting the rings . Literature review revealed that alteration of 3,4,5‐trimethoxy phenyl (TMP) group (which sits in the pocket of β‐tubulin) mainly led to decrease of cytotoxic activity of combretastatin derivatives . Furthermore, this unique ring (TMP) has been found in the structure of a wide range of compounds exhibiting cytotoxic, antimicrobial, and anti‐inflammatory (via reduction of TNF‐α and IL‐6 production or inhibition of COX‐1 and COX‐2) activity .…”

Section: Introductionmentioning

confidence: 99%

Novel Aldimine‐Type Schiff Bases of 4‐Amino‐5‐[(3,4,5‐trimethoxyphenyl)methyl]‐1,2,4‐triazole‐3‐thione/thiol: Docking Study, Synthesis, Biological Evaluation, and Anti‐Tubulin Activity

Ameri

Khodarahmi

Hassanzadeh

et al. 2016

Archiv der Pharmazie

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The present study was planned to design some novel aldimine-type Schiff bases bearing 3,4,5-trimethoxyphenyl and 1,2,4-triazole-3-thione/thiol as potential tubulin polymerization inhibitors. The obtained results of the molecular docking study using the tubulin complex (PDB code: 1SA0) showed that compounds H-25 and H-26 were well fitted in the colchicine binding site of tubulin with binding energies of -8.68 and -8.40 kcal/mol, respectively, in comparison to the main ligand (-8.20 kcal/mol). In parallel, molecular simulations were also performed on five other 3,4,5-trimethoxyphenyl-containing ligand targets including hsp90, VEGFR2, and human and microbial (Staphylococcus aureus and Candida albicans) dihydrofolate reductase, among which H-17, H-45, H-27, H-02, and H-19 were the most suitable compounds, respectively. Evaluation of the cytotoxic effect of the most efficient compounds of the docking steps (H-25) revealed IC50 values of 12.48 ± 1.10, 4.25 ± 0.22, 3.33 ± 0.31, and 9.71 ± 0.75 µM against the HT1080, HT29, MCF-7, and A549 cell lines, respectively, compared to doxorubicin (12.69 ± 1.23, 6.12 ± 0.47, 3.51 ± 0.32, and 6.40 ± 0.31 µM, respectively). The in vitro tubulin polymerization investigation launched compounds H-25 and H-26 as potent antitubulin agents due to their IC50 values of 0.17 ± 0.01 and 10.93 ± 0.43 µM, respectively.

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Section: Introductionmentioning

confidence: 99%

Novel Aldimine‐Type Schiff Bases of 4‐Amino‐5‐[(3,4,5‐trimethoxyphenyl)methyl]‐1,2,4‐triazole‐3‐thione/thiol: Docking Study, Synthesis, Biological Evaluation, and Anti‐Tubulin Activity

Ameri

Khodarahmi

Hassanzadeh

et al. 2016

Archiv der Pharmazie

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“…Tubulin-binding agents are potent mitotic poisons [ 73 , 74 ]. To perform our molecular docking study a three dimensional X-ray crystal structure of tubulin complex with colchicine ( PDB ID: 1SA0 ) and a stathmin-like domain was used [ 75 ]. The docking study was carried out using the Surflex-Dock module of the Sybyl 2.1.1 package following the standard procedure.…”

Section: Resultsmentioning

confidence: 99%

Ionic Liquid-Catalyzed Green Protocol for Multi-Component Synthesis of Dihydropyrano[2,3-c]pyrazoles as Potential Anticancer Scaffolds

Nimbalkar¹,

Seijas

Vázquez-Tato

et al. 2017

Molecules

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A series of 6-amino-4-substituted-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles 5a–j were synthesized via one-pot, four-component condensation reactions of aryl aldehydes 1a–j, propanedinitrile (2), hydrazine hydrate (3) and ethyl acetoacetate (4) under solvent-free conditions. We report herein the use of the Brønsted acid ionic liquid (BAIL) triethylammonium hydrogen sulphate [Et3NH][HSO4] as catalyst for this multi-component synthesis. Compared with the available reaction methodology, this new method has consistent advantages, including excellent yields, a short reaction time, mild reaction conditions and catalyst reusability. Selected synthesized derivatives were evaluated for in vitro anticancer activity against four human cancer cell lines viz. melanoma cancer cell line (SK-MEL-2), breast cancer cell line(MDA-MB-231), leukemia cancer cell line (K-562) and cervical cancer cell line (HeLa). Compounds 5b, 5d, 5g, 5h and 5j exhibited promising anticancer activity against all selected human cancer cell lines, except HeLa. Molecular docking studies also confirmed 5b and 5d as good lead molecules. An in silico ADMET study of the synthesized anticancer agents indicated good oral drug-like behavior and non-toxic nature.

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“…To perform molecular docking, the three‐dimensional crystal structure of the VEGFR2 kinase domain in complex with PF‐00337210( N , 2‐dimethyl‐6‐(7‐[2‐morpholinoethoxy] quinolin‐4‐yloxy) benzofuran‐3carboxamide) (PDB ID: 2XIR Resolution 1.50 Å) was used . A docking study was carried out using Surflex‐Dock module of Sybyl 2.1.1 package following standard procedure.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and evaluation of pyrazole‐incorporated monocarbonyl curcumin analogues as antiproliferative and antioxidant agents

Nagargoje

Akolkar

Siddiqui

et al. 2019

J Chinese Chemical Soc

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A series of pyrazole‐incorporated monocarbonyl analogues of curcumin were synthesized via Clasien–Schimidt‐type condensation and subsequently screened for in vitro antiproliferative and antioxidant activity. The analogues 4c, 5d, 5e, 5g, 6e, and 6f showed potential activity against the MDA‐MB‐231 cell line. The synthesized analogues were also screened for their antioxidant activity. Compounds 5a, 5e, 6d, and 6f exhibit comparable radical scavenging activity with respect to the standard drug ascorbic acid. Furthermore, a molecular docking study has been conducted for 5d and 5g and suggests that these compounds have a potential to become lead molecules in drug discovery and process.

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Synthesis, biological evaluation, and molecular modeling studies of novel heterocyclic compounds as anti-proliferative agents

Cited by 12 publications

References 42 publications

Novel Aldimine‐Type Schiff Bases of 4‐Amino‐5‐[(3,4,5‐trimethoxyphenyl)methyl]‐1,2,4‐triazole‐3‐thione/thiol: Docking Study, Synthesis, Biological Evaluation, and Anti‐Tubulin Activity

Novel Aldimine‐Type Schiff Bases of 4‐Amino‐5‐[(3,4,5‐trimethoxyphenyl)methyl]‐1,2,4‐triazole‐3‐thione/thiol: Docking Study, Synthesis, Biological Evaluation, and Anti‐Tubulin Activity

Ionic Liquid-Catalyzed Green Protocol for Multi-Component Synthesis of Dihydropyrano[2,3-c]pyrazoles as Potential Anticancer Scaffolds

Synthesis and evaluation of pyrazole‐incorporated monocarbonyl curcumin analogues as antiproliferative and antioxidant agents

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