scholarly journals DITHIOCARBAMATE SUBSTITUTED PHENOTHIAZINE DERIVATIVES: IN SILICO EXPERIMENTS, SYNTHESIS, AND BIOLOGICAL EVALUATION

2021 ◽  
pp. 25-30
Author(s):  
ANUSHA KOTHA ◽  
MUNI SIREESHA S. ◽  
ASHMA MD ◽  
JYOTHI VEMURI ◽  
SARITHA JYOSTNA T.
Keyword(s):  
Antioxidant Activity ◽  
Anticancer Activity ◽  
Biological Evaluation ◽  
Binding Energies ◽  
Side Chain ◽  
Phenothiazine Derivatives ◽  
Standard Drug ◽  
Antimitotic Activity ◽  
Dpph Method ◽  
Tubulin Protein

Objective: The present study was designed to study the anticancer activity of a series of novel analogs of phenothiazine with dithiocarbamate as a side chain. Methods: A novel series of derivatives containing dithiocarbamate as a side chain at the tenth position of phenothiazine nucleus were synthesized, characterized by spectral analysis, and evaluated for their antimitotic and antioxidant activity using germinated Bengal gram seeds and 2,2-diphenyl-1-picrylhydrazyl (DPPH) method, respectively. A quantitative estimate of drug-likeness was also performed, which calculated the molecular properties and screened the molecules based on drug-likeness rules. Further, molecular docking study was performed for finding the binding affinity with tubulin protein to rationalize their anticancer activity. Results: The results revealed that the antioxidant activity of compounds 3e, 3g, 3i, 3j and standard Ascorbic acid were 10 mmol, 14 mmol, 16 mmol, 16 mmol and 35 mmol, respectively. Further compounds 3e, 3g, 3h and 3i have shown promising antimitotic activity. Compound 3i (-9 K. Cal/mol) showed the highest binding energies towards tubulin protein when compared to standard drug colchicine (-8.6 K. Cal/mol). Among all, compound 3i showed promising antimitotic and antioxidant activity, which correlated with insilico docking studies. Conclusion: Dithiocarbamate substituted phenothiazine derivatives proved to be encouraging leads as tubulin inhibitors.

SYNTHESIS, BIOLOGICAL EVALUATION AND DOCKING STUDIES OF NON HEPATOTOXIC 5-SUBSTITUTED THIAZOLIDINE-2, 4-DIONES AS ANTIDIABETIC, ANTI-HYPERLIPIDEMIC, ANTI-OXIDANT AND CYTOTOXIC AGENTS

INDIAN DRUGS ◽  
2020 ◽  
Vol 57 (09) ◽  
pp. 19-37
Author(s):  
Karuna S. Shukla ◽  
Shailendra Pandey ◽  
A Pooja Chawla
Keyword(s):  
Antioxidant Activity ◽  
Biological Evaluation ◽  
Cytotoxic Agents ◽  
Assay Method ◽  
Diabetic Rat ◽  
Standard Drug ◽  
Docking Score ◽  
Starting Point ◽  
Dpph Method

A series of eleven thiazolidine-2, 4-dione (TZD) derivatives, were synthesized and characterized by FT-IR, 1 H NMR and mass spectral analysis. All the synthesized TZD derivatives were screened for their in vitro and in vivo anti-diabetic and antioxidant, activities and cytotoxicity. In vivo antihyperglycemic effect was assessed by measuring plasma glucose (PG) levels in alloxan-induced type II diabetic rat models. The compound 4h exhibited better blood glucose lowering activity than the standard drug rosiglitazone. The synthesized TZD derivatives were evaluated for hepatotoxicity and pancreatic tissue studies. Antioxidant activity was evaluated by DPPH method and H2 O2 method. Compounds 4a and 4b exhibited potent antioxidant activity. Among the tested compounds for cytotoxicity using MTT assay method, compound 4i exhibited better viability and cytotoxicity activity. Thiazolidinedione derivatives were evaluated for their affinity towards target PPARg, using rosiglitazone as the reference compound molecular docking visualization through FlexX docking program. From selected anti-diabetic targets, the proposed derivatives exhibited better interaction with PPARγ receptor, where rosiglitazone showed docking score of -19.891 kJ/ mol, compound 4h exhibited highest docking score of -31.6068 kJ/mol. The study showed that all the studied compounds were showing higher docking score when compared to control drug rosiglitazone and it could be a remarkable starting point to evaluate structure activity relationships to develop new lead molecules with potential anti-diabetic activities.

Thiazolidine-2, 4-Diones as Non-Hepatotoxic Tri-action Drug Candidates: Design, Synthesis, Characterization, Biological Evaluation and Docking Studies

2020 ◽  
Vol 17 (9) ◽  
pp. 659-679
Author(s):  
Karuna S. Shukla ◽  
Shailendra Pandey ◽  
Pooja A. Chawla
Keyword(s):  
Antioxidant Activity ◽  
Molecular Docking ◽  
Benzoic Acid ◽  
Docking Studies ◽  
Biological Evaluation ◽  
Standard Drug ◽  
Peripheral Tissues ◽  
Docking Score ◽  
Dpph Method

Thiazolidine-2, 4-diones and their derivatives are a well-established chemical class of compounds that express their pharmacological actions through insulin sensitization and enhanced glucose utilization in peripheral tissues. In the current research different approaches have been employed to synthesize thiazolidine-2, 4-dione derivatives and these synthesized compounds were chemically characterized for the establishment of their chemical structures. A series of thiazolidine-2, 4-dione (TZD) derivatives, Scheme 1 (3A-3V) 22 compounds, were synthesized and characterized by FT-IR, 1H NMR and mass spectral analysis. The title compounds were screened for their in vitro and in vivo antidiabetic, antioxidant, and cytotoxicity studies. In vivo antihyperglycemic effect was assessed by measuring plasma glucose (PG) levels in alloxan-induced type II diabetic rat models. The synthesized TZD derivatives were evaluated for hepatotoxicity and pancreatic tissue integrity. Antioxidant activity was evaluated by the DPPH method and H2O2 method. Thiazolidinedione derivatives were subjected to predict free energy of binding towards target PPARγ, using rosiglitazone as the reference compound for molecular docking visualization through the FlexX docking program. Molecular docking studies are also performed for understanding the binding of a ligand to a receptor. The compound 3V 4-(5- (naphthalen-1-ylmethylene)-2, 4-dioxothiazolidin-3-yl) benzoic acid exhibited better blood glucoselowering activity than that of the standard drug rosiglitazone. Compound 3T and 3U exhibited potent antioxidant activity. Among the tested compounds for cytotoxicity using an MTT assay, compound 3H 5-(4-chlorobenzylidene)-2, 4-dioxothiazolidin-3-yl) benzoic acid exhibited better viability and cytotoxicity activity. From selected anti-diabetic targets, the proposed derivatives exhibited better interaction with PPARγ receptor, for example, while rosiglitazone showed a docking score of -19.891 kJ/mol, compound 3V exhibited highest docking score of -31.6617 kJ/mol. Computational molecular docking study demonstrated the selectivity and provided a binding model for the further refinement of this chemotype. Therefore, this series of thiazolidine-2, 4-diones derivatives (3A-3V) have considerable importance for development as a potential antihyperglycemic and hypolipidemic agents.

scholarly journals Microwave-Assisted Synthesis, Molecular Docking Studies and Biological Evaluation of Benzothiazole Containing Novel Indole Derivatives

2021 ◽  
Vol 33 (11) ◽  
pp. 2755-2761
Author(s):  
Shaheen Sultana ◽  
P. Pandian ◽  
B. Rajkamal
Keyword(s):  
Molecular Docking ◽  
Reaction Mechanism ◽  
Anticancer Activity ◽  
Mannich Base ◽  
Docking Studies ◽  
Biological Evaluation ◽  
Indole Derivatives ◽  
Standard Drug ◽  
Molecular Docking Studies ◽  
Microwave Assisted

The synthesis of novel indole derivatives 4a-o using a microwave assisted method via Schiff’s base and Mannich base reaction mechanism was described. Compounds 3a-c were synthesized via reaction of 2-amino benzothiazole with substituted isatin by Schiff base reaction mechanism. Also, indole derivatives 4a-o were synthesized via reaction of compounds 3a-c with substituted benzaldehydes by Mannich base reaction. The biological potentials of the newly synthesized indole derivatives were evaluated for their anthelmintic activity and in vitro anticancer activity by MTT assay. The anticancer activity results suggested that indole derivatives 4c-o have activity against MCF-7 and SKOV3 cells in comparison with doxorubicin as standard drug. Furthermore, the molecular docking studies of these novel derivatives of indole showed good agreement with the biological results when their binding pattern and affinity towards the active site of EGFR was also investigated.

One-pot synthesis and biological evaluation of novel 3-(5-((aryl) methyl) isoxazol-3-yl)-4H-chromen-4-one derivatives as potent antibacterial and anticancer agents

2021 ◽  
Vol 25 (11) ◽  
pp. 80-85
Author(s):  
Rani Janapatla Uma ◽  
Babu H. Ramesh ◽  
M. Prashanthi
Keyword(s):  
Antibacterial Activity ◽  
Anticancer Activity ◽  
Cell Line ◽  
Anticancer Agents ◽  
Biological Evaluation ◽  
Bacterial Strains ◽  
Standard Drug ◽  
Cell Line Hela ◽  
Aryl Methyl ◽  
Mcf 7

In search of better antibacterial and anticancer agents, a series of novel 3-(5-((aryl) methyl) isoxazol-3-yl)-4Hchromen- 4-one derivatives was synthesized (4a-4l) by using 4-oxo-4H-chromene-3-carbaldehyde and alkyne via in situ generated nitrile oxide and evaluated for their antibacterial and anticancer activity in vitro. Antibacterial activity was evaluated against three G+ bacterial strains and anticancer activity against breast cancer cell line (MCF-7) and cervical carcinoma cell line (HeLa). Among all the tested compounds, 4j and 4g exhibited potent antibacterial activity against tested grampositive bacterial strains. 4g, 4i and 4j exhibited potent cytotoxic activity against MCF-7 with IC50 values nearer to the standard drug doxorubicin.

scholarly journals Antioxidant potential study of some synthesized N-heterocycles

2009 ◽  
Vol 35 (2) ◽  
pp. 49-52 ◽  
Author(s):  
Mohammad Mamun Hossain ◽  
Sukanta Kumar Shaha ◽  
Foysal Aziz
Keyword(s):  
Antioxidant Activity ◽  
Ascorbic Acid ◽  
Anticancer Activity ◽  
Heterocyclic Compounds ◽  
Antioxidant Properties ◽  
Biological Properties ◽  
Antioxidant Potential ◽  
Heating Method ◽  
Dpph Method ◽  
First Time

Nitrogen containing heterocyclic compounds such as oxindoles especially isatins and their derivatives have excellent biological properties such as anti-inflammatory, antimicrobial, anticancer activity. In addition, this is first time ever we would like to report the antioxidant properties of the said class of compounds. To determine such an important bioactivity a number of halogenated oxindoles 1-3, their diaza-biphenyl derivatives (4-6), ring extended biphenyl (7) and bis-amide (8) were synthesized by classical heating method. The antioxidant activity of all the synthesized compounds was screened by DPPH method with respect to ascorbic acid. In our present investigation some of the synthesized compounds (1, 2, 3, 5 and 6) were found to be active.Keywords: Antioxidant; Isatin; OxindoleOnline 12 August 2009DOI: 10.3329/bmrcb.v35i2.2564Bangladesh Med Res Counc Bull 2009; 35: 49-52 

scholarly journals Biotinylated xanthohumol: synthesis and in vitro biological evaluation for anticancer therapy

2018 ◽  
Author(s):  
Monika Stompor ◽  
Rafał Podgórski ◽  
Marta Świtalska ◽  
Joanna Wietrzyk
Keyword(s):  
Breast Cancer ◽  
Antioxidant Activity ◽  
Cancer Cells ◽  
Cell Lines ◽  
Biological Evaluation ◽  
Breast Cancer Cell Lines ◽  
Dpph Method ◽  
Ic50 Values ◽  
Mcf 7

Two biotinylated derivatives of the main hop chalcone xanthohumol (1) were prepared by a one-step synthesis via esterification using biotin and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC HCl) and 4-dimethylaminopyridine (DMAP) as coupling reagents. The products were characterized spectroscopically and their antiproliferative activity toward MCF-7, MCF-10A, HepG2, MDA-MB-231, 4T1 and Balb/3T3 cell lines was investigated using the SRB assay. For all three tested compounds the best activity was noted in the case of human (MCF-7) and mice (4T1) breast cancer cell lines (IC50 values < 9 μM). Both biotinylated derivatives showed higher anticancer activity than xanthohumol (1) towards all types of tested breast cancer cells. Double biotinylated xanthohumol (3) proved to be the most active in inhibiting cell growth, with IC50 values equal to 5.35 ± 1.5 μM for 4T1 and 8.03 ± 0.53 µM for MCF-7 cell lines. Compound 3 was also more active than 1 and 2 against liver cancer cells HepG2 (IC50 = 17.37 ± 5.1 μM), while the IC50 values for 1 and 2 were equal to 21.5 ± 2.7 and 22.1 ± 3.9 µM, respectively. 4‑O‑biotinylxanthohumol (2) was the second most active growth inhibitor, particularly with respect to MCF-7 (IC50 = 6.19 ± 1.7 μM) and 4T1 (IC50 = 6.64 ± 0.4 μM) cell lines. The antioxidant activity was evaluated using the 1.1-diphenyl-2-picrylhydrazyl radical (DPPH) method. All tested compounds (1-3) have antioxidant activity between 2.73 and 3.38 mM. It was reported for the first time that new prenylated chalcones containing the biotin moiety effectively inhibited proliferation of cancer cells in vitro.

SYNTHESIS AND BIOLOGICAL EVALUATION OF 1-SUBSTITUTED-2-THIENYL- 5-(4-CHLOROPHENYL) PYRAZOLINE DERIVATIVES AS ANTIPROLIFERATIVE AGENTS

INDIAN DRUGS ◽  
2019 ◽  
Vol 56 (06) ◽  
pp. 24-30
Author(s):  
Amandeep Kaur ◽  
◽  
Baljeet Kaur ◽  
Monika Gupta
Keyword(s):  
Growth Inhibition ◽  
Anticancer Activity ◽  
Heterocyclic Ring ◽  
Biological Evaluation ◽  
Inhibitory Effects ◽  
Standard Drug ◽  
Growth Inhibitory ◽  
Control Growth ◽  
In Series ◽  
Synthesis And Biological Evaluation

Cancer is not a single disease, but a large group of diseases characterized by uncontrolled, rapid and pathological proliferation of abnormally transformed cells. Pyrazoline is a five-membered heterocyclic ring having two adjacent nitrogen atoms within the ring. It has only one endocyclic double bond and is basic in nature. The present study involves synthesis of 1-substituted-2-thienyl-5-(4-chlorophenyl) pyrazoline derivatives. The synthesized compounds were subjected to anticancer screening against SK-OV-3 cells line to determine the growth inhibitory effects of the compounds. Amongst all the derivatives in series (6a-j), the pyrazoline derivatives exhibited potent anticancer activity. All synthesized compounds possessed good to moderate anticancer activity. Compounds 6b and 6c at concentration 80 μg/mL possessed % control growth inhibition comparable to standard drug andriamycin. The order for the % control growth inhibition of SK-OV-3 was found to be 6h> 6j> 6f> 6i> 6e> 6g> 6d> 6a. All the compounds inhibited 50 % of the cell growth at the conc.

Synthesis, biological evaluation and molecular docking studies against EGFR tyrosine kinase of 3,5-bis(substituted benzylidene)-1-ethylpiperidin-4-one analogues

2020 ◽  
Vol 17 ◽  
Author(s):  
Mohamed Jawed Ahsan ◽  
Deepak Saini ◽  
Piush Sharma ◽  
Surender Singh Jadav ◽  
Mohammad Afroz Bakht ◽  
...  
Keyword(s):  
Breast Cancer ◽  
Antioxidant Activity ◽  
Ascorbic Acid ◽  
Tyrosine Kinase ◽  
Anticancer Activity ◽  
Cancer Cell Line ◽  
Docking Studies ◽  
Molecular Target ◽  
Standard Drug ◽  
Mcf 7

Background:: Cancer is one of the leading causes of death. The aim of present studies is to synthesize and investigate the anticancer and antioxidant activities of some 3,5-bis(substituted benzylidene)-1-ethylpiperidin-4-one analogues (4a-g). The 3,5-bis(substituted benzylidene)-1-ethylpiperidin-4-one analogues (4a-g) was prepared from the precursor, piperidin-4-one hydrochloride (1). The initial step involved the synthesis of intermediates, 3,5-bis(substituted benzylidene)piperidin-4-one analogues (3a-g) followed by their ethylation with C2H5I in acetone and K2CO3 to obtain the title compounds (4a-g). The Fourier transform infrared (FTIR), nuclear magnetic resonance (1H & 13C NMR), mass spectrometry and microanalysis were used to characterized the title compounds (4a-g). All the compounds were further evaluated for their anticancer activity by SRB assay and NCI US protocol, while the antioxidant activity was evaluated by DPPH free radical assay. All the title com-pounds (4a-g) were subjected to molecular docking studies against EGRF tyrosine kinase, a potential target for anticancer agents, to study the possible mode of interaction of our compounds with the molecular target. The compound, 4g showed significant anticancer activity with GI50 of 28.2 μM against MCF-7 (Breast cancer cell line). The antioxidant activity of compound, 4g (IC50 = 14.98±0.91 μM) was found to be comparable to the standard drug ascorbic acid. The binding modes of compounds, 4a-g against the molecular target EGFR tyrosine kinase were also studied. The structure activity relationship (SAR) was also studied. The compound, 4g showed significant anticancer activity with GI50 of 28.2 μM against MCF-7 (Breast cancer cell line). The antioxidant activity of the compound, 4g was found to be comparable to the standard drug ascorbic acid, while its anticancer activity was found to be less than that of the standard drug adriamycin.

scholarly journals Evaluation of in vitro Antioxidant and Cytotoxic Effect of Methanol Extract from aerial parts of Myristica beddomei King ssp. ustulata W.J. de Wilde

2020 ◽  
pp. 115-121
Author(s):  
Neethu Joy ◽  
Mahesh Mohan
Keyword(s):  
Antioxidant Activity ◽  
Anticancer Activity ◽  
Cytotoxic Effect ◽  
Total Phenolic ◽  
Ovarian Cancer Cells ◽  
Cytotoxicity Test ◽  
Antioxidant Power ◽  
Ic50 Value ◽  
Dpph Method

Plants are traditionally used for pharmacological activities because of its ability to produce bioactive compounds. Myristica beddomei King ssp. ustulata W.J. de Wilde is an ethnomedicinal plant and it is seen in South Western Ghats of Kerala, India. The present study assessed the phenolic content, flavonoid concentration, in vitro antioxidant and cytotoxic effect of different parts of Myristica beddomei King. The total phenolic contents in the extracts ranged from 96.29 (pericarp) to 314.47 (bark) mg g-1 gallic acid equivalent. The concentration of flavonoids in different plant part extracts ranged from 1.81   to 2.76 mg g-1 equivalent to quercetin. All the parts exhibited potential antioxidant activity with an IC50 value of 2.87 to 9.67 μg ml-1 when compared to the standard ascorbic acid with an IC50 value of 2 μg ml-1 in 1,1-diphenyl-2- picryl-hidrasil (DPPH) method. Bark showed highest activity in terms of DPPH radical scavenging (IC50 value of 2.87 µg ml-1), phosphomolybdenum test (2261.33 ± 1.65 mg g-1 trolox equivalent) and ferric ion reducing antioxidant power (FRAP) (113.1 ± 0.28 µmol Fe2+ µg-1) while pericarp showed low antioxidant activity. The in vitro screening results revealed that the seeds exhibited promising anticancer activity compared to PA1 (Ovarian Cancer) cells (50 % inhibition) were observed at a concentration 100.68 µg ml-1.  In cytotoxicity test L929 (Fibroblast) cell line compared to the other parts pericarp, mace and seed needed higher concentration (>240 µg ml-1) for LC50 value. It is a promising plant for further development of antioxidant agent as it got high content of phenolic compounds and potential antioxidant and anticancer activity.

Synthesis, Biological Evaluation and Molecular Docking Studies of Novel Di-hydropyridine Analogs as Potent Antioxidants

2019 ◽  
Vol 19 (29) ◽  
pp. 2676-2686 ◽  
Author(s):  
Saddala Madhu Sudhana ◽  
Pradeepkiran Jangampalli Adi
Keyword(s):  
Molecular Docking ◽  
In Silico ◽  
Docking Studies ◽  
Biological Evaluation ◽  
Binding Energies ◽  
Molecular Docking Studies ◽  
Metal Chelating ◽  
In Silico Admet ◽  
Dpph Method

Aims: The aim of this study is to synthesize, characterize and biological evaluation of 3-ethyl 5- methyl2-(2-aminoethoxy)-4-(2-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylate derivatives. Background: An efficient synthesis of two series of novel carbamate and sulfonamide derivatives of amlodipine, 3-ethyl 5-methyl 2-(2-aminoethoxy)-4-(2-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (amlodipine) 1 were chemical synthesized process. Materials & Methods: In this process, various chloroformates 2(a-e) and sulfonyl chlorides 4(a-e) on reaction with 1 in the presence of N,N–dimethylpiperazine as a base in THF at 50-550 oC, the corresponding title compounds 3(a-e) and 5(a-e) in high yields. Furthermore, the compounds 3(a-e) and 5(a-e) were evaluated for antioxidant activity (DPPH method), metal chelating activity, hemolytic activity, antioxidant assay (ABTS method), cytotoxicity, molecular docking and in silico ADMET properties. Result: Results revealed that 5a, 5e, 3d, 3a and 5c exhibited high antioxidant, metal chelating activities, but 5a, 5e and 3d exhibited low activity. The molecular docking studies and ADMET of suggested ligands showed the best binding energies and non-toxic properties. Conclusion: The present in silico and in vitro evaluations suggested that these dihydropyridine derivatives act as potent antioxidants and chelating agents which may be useful in treating metals induced oxidative stress associated diseases.

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