Green synthesis, characterization, biological evaluation and docking study of some pyrazoline and pyrimidine derivatives

2021 ◽  
Vol 25 (12) ◽  
pp. 88-97
Author(s):  
H.A. Al-Ghulikah ◽  
A.S. El-Azab ◽  
M.S. AL-Saleem ◽  
M.S. AL-Towayan ◽  
S.A. Al-Issa
Keyword(s):  
Ultrasonic Method ◽  
Guanidine Hydrochloride ◽  
Acid Hydrazide ◽  
Docking Study ◽  
Biological Evaluation ◽  
High Yield ◽  
Pyrimidine Derivatives ◽  
New Synthesis ◽  
In Vitro Antibacterial Activity

Green and classical techniques have been utilized for preparing of a variety of aryl - substituted pyrazoline and pyrimidine derivatives (2-8). Reactions of chalcones 1 with semicarbazide and thiosemicarbazide, nicotinic acid hydrazide and amino guanidine hydrochloride afforded the corresponding N-substituted pyrazoline derivatives 2-5. Pyrimidine derivatives 6-8 were achieved via reaction of chalcone derivatives 1 with several reagents namely: guanidine nitrate, thiourea and 6-amino-2-thioxo-2,3- dihydropyrimidin-4(1H)-one under conventional and ultrasonic conditions. Ultrasonic method was found to be an easy work-up procedure and it gave high yield in comparison with conventional method. The structures of new synthesis compounds were characterized by elemental and spectral analyses. Some of newly compounds were tested in vitro antibacterial activity against some gram–positive and gram–negative. The antimicrobial results displayed favorable antimicrobial activity. Molecular docking has been perfomed for compound 5b using MOE 2008.10, The data results obtained are quite promising.

scholarly journals PYRIMIDINE INCORPORATED SCHIFF BASE OF ISONIAZID WITH THEIR SYNTHESIS, CHARACTERIZATION AND IN VITRO BIOLOGICAL EVALUATION

2017 ◽  
Vol 10 (10) ◽  
pp. 209 ◽  
Author(s):  
Hetal I Soni ◽  
Navin B Patel
Keyword(s):  
Pyridine Ring ◽  
Biological Activities ◽  
Condensation Reaction ◽  
Biological Evaluation ◽  
Resonance Spectroscopy ◽  
Antituberculosis Activity ◽  
Aspergillus Clavatus ◽  
Pyrimidine Derivatives ◽  
In Vitro Antibacterial Activity

  Objective: Versatile biological activities of nitrogen containing heterocycles in medicinal chemistry, mainly pyrimidine and pyridine ring based heterocyclic moieties are very important. Pharmaceutical important of pyrimidine and isoniazid moiety prompted us to synthesize isoniazid clubbed pyrimidine derivatives and evaluated for antimicrobial and antituberculosis activity.Method: 2-(2-(3-bromo benzylidene)-1-isonicotinoyl hydrazinyl)-N-(4-(substituted phenyl)-6-(substituted aryl) pyrimidin-2-yl) acetamide 2(A-J) have been synthesized by condensation reaction of 2-chloro-N-[4-(substituted phenyl)-6-(substituted aryl) pyrimidin-2-yl] acetamide and N’-[(E)- (3-bromophenyl) methylidene]pyridine-4-carbohydrazide. All newly synthesized compounds were screened for in vitro antibacterial activity against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Staphylococcus pyogenes, antifungal against Candida albicans, Aspergillus niger, and Aspergillus clavatus, and antituberculosis activity against Mycobacterium tuberculosis H37RV.Results: Majority of the compounds exhibited good antibacterial, antifungal, and antituberculosis activity. All titled compounds were characterized by spectral analyses (infrared spectroscopy, nuclear magnetic resonance spectroscopy, and mass spectroscopy).Conclusion: 2-(2-(3-bromo benzylidene)-1-isonicotinoyl hydrazinyl)-N-(4-(substituted phenyl)-6-(substituted aryl) pyrimidin-2-yl) acetamide 2(A-J) showed good antimicrobial activity and comparatively good antituberculosis activity. Hence, all the compounds of this series considered for future investigation mainly in area of antibacterial, antifungal study.

scholarly journals Novel Pyrimidine Derivatives as Potential Anticancer Agents: Synthesis, Biological Evaluation and Molecular Docking Study

2021 ◽  
Vol 22 (8) ◽  
pp. 3825
Author(s):  
Beata Tylińska ◽  
Benita Wiatrak ◽  
Żaneta Czyżnikowska ◽  
Aneta Cieśla-Niechwiadowicz ◽  
Elżbieta Gębarowska ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Anticancer Agents ◽  
Topoisomerase Ii ◽  
Colon Adenocarcinoma ◽  
Docking Study ◽  
Biological Evaluation ◽  
Dermal Fibroblasts ◽  
Pyrimidine Derivatives ◽  
Molecular Docking Study

In the present paper, new pyrimidine derivatives were designed, synthesized and analyzed in terms of their anticancer properties. The tested compounds were evaluated in vitro for their antitumor activity. The cytotoxic effect on normal human dermal fibroblasts (NHDF) was also determined. According to the results, all the tested compounds exhibited inhibitory activity on the proliferation of all lines of cancer cells (colon adenocarcinoma (LoVo), resistant colon adenocarcinoma (LoVo/DX), breast cancer (MCF-7), lung cancer (A549), cervical cancer (HeLa), human leukemic lymphoblasts (CCRF-CEM) and human monocytic (THP-1)). In particular, their feature stronger influence on the activity of P-glycoprotein of cell cultures resistant to doxorubicin than doxorubicin. Tested compounds have more lipophilic character than doxorubicin, which determines their affinity for the molecular target and passive transport through biological membranes. Moreover, the inhibitory potential against topoisomerase II and DNA intercalating properties of synthesized compounds were analyzed via molecular docking.

Hybrid Design of Isonicotinic Acid Hydrazide Derivatives: Machine Learning Studies, Synthesis and Biological Evaluation of their Antituberculosis Activity

2020 ◽  
Vol 17 (3) ◽  
pp. 365-375
Author(s):  
Vasyl Kovalishyn ◽  
Diana Hodyna ◽  
Vitaliy O. Sinenko ◽  
Volodymyr Blagodatny ◽  
Ivan Semenyuta ◽  
...  
Keyword(s):  
Machine Learning ◽  
Isonicotinic Acid ◽  
Acid Hydrazide ◽  
Predictive Ability ◽  
Antitubercular Activity ◽  
Biological Evaluation ◽  
Starting Point ◽  
Binary Classifiers ◽  
Synthesis And Biological Evaluation

Background: Tuberculosis (TB) is an infection disease caused by Mycobacterium tuberculosis (Mtb) bacteria. One of the main causes of mortality from TB is the problem of Mtb resistance to known drugs. Objective: The goal of this work is to identify potent small molecule anti-TB agents by machine learning, synthesis and biological evaluation. Methods: The On-line Chemical Database and Modeling Environment (OCHEM) was used to build predictive machine learning models. Seven compounds were synthesized and tested in vitro for their antitubercular activity against H37Rv and resistant Mtb strains. Results: A set of predictive models was built with OCHEM based on a set of previously synthesized isoniazid (INH) derivatives containing a thiazole core and tested against Mtb. The predictive ability of the models was tested by a 5-fold cross-validation, and resulted in balanced accuracies (BA) of 61–78% for the binary classifiers. Test set validation showed that the models could be instrumental in predicting anti- TB activity with a reasonable accuracy (with BA = 67–79 %) within the applicability domain. Seven designed compounds were synthesized and demonstrated activity against both the H37Rv and multidrugresistant (MDR) Mtb strains resistant to rifampicin and isoniazid. According to the acute toxicity evaluation in Daphnia magna neonates, six compounds were classified as moderately toxic (LD50 in the range of 10−100 mg/L) and one as practically harmless (LD50 in the range of 100−1000 mg/L). Conclusion: The newly identified compounds may represent a starting point for further development of therapies against Mtb. The developed models are available online at OCHEM http://ochem.eu/article/11 1066 and can be used to virtually screen for potential compounds with anti-TB activity.

Structure-Based Design, Synthesis, Biological Evaluation and Molecular Docking Study of 4-Hydroxy-N'-methylenebenzohydrazide Derivatives Acting as Tyrosinase Inhibitors with Potentiate Anti-Melanogenesis Activities

2020 ◽  
Vol 16 (7) ◽  
pp. 892-902 ◽  
Author(s):  
Aida Iraji ◽  
Mahsima Khoshneviszadeh ◽  
Pegah Bakhshizadeh ◽  
Najmeh Edraki ◽  
Mehdi Khoshneviszadeh
Keyword(s):  
Molecular Docking ◽  
Active Site ◽  
Competitive Inhibition ◽  
Docking Study ◽  
Biological Evaluation ◽  
Primary Response ◽  
Ratio Method ◽  
Molecular Docking Study ◽  
Metal Chelating

Background: Melanogenesis is a process of melanin synthesis, which is a primary response for the pigmentation of human skin. Tyrosinase is a key enzyme, which catalyzes a ratelimiting step of the melanin formation. Natural products have shown potent inhibitors, but some of these possess toxicity. Numerous synthetic inhibitors have been developed in recent years may lead to the potent anti– tyrosinase agents. Objective: A number of 4-hydroxy-N'-methylenebenzohydrazide analogues with related structure to chalcone and tyrosine were constructed with various substituents at the benzyl ring of the molecule and evaluate as a tyrosinase inhibitor. In addition, computational analysis and metal chelating potential have been evaluated. Methods: Design and synthesized compounds were evaluated for activity against mushroom tyrosinase. The metal chelating capacity of the potent compound was examined using the mole ratio method. Molecular docking of the synthesized compounds was carried out into the tyrosine active site. Results: Novel 4-hydroxy-N'-methylenebenzohydrazide derivatives were synthesized. The two compounds 4c and 4g showed an IC50 near the positive control, led to a drastic inhibition of tyrosinase. Confirming in vitro results were performed via the molecular docking analysis demonstrating hydrogen bound interactions of potent compounds with histatidine-Cu+2 residues with in the active site. Kinetic study of compound 4g showed competitive inhibition towards tyrosinase. Metal chelating assay indicates the mole fraction of 1:2 stoichiometry of the 4g-Cu2+ complex. Conclusion: The findings in the present study demonstrate that 4-Hydroxy-N'- methylenebenzohydrazide scaffold could be regarded as a bioactive core inhibitor of tyrosinase and can be used as an inspiration for further studies in this area.

Synthesis and Biological Evaluation of Novel 4-Phenylaminobenzofuro[2,3-d]pyrimidine Derivatives

2020 ◽  
Vol 42 (4) ◽  
pp. 564-564
Author(s):  
Ju liu Ju liu ◽  
Jun Li Jun Li ◽  
Jian tao Shi Jian tao Shi ◽  
Jie Li Jie Li ◽  
Xue chen Hao Xue chen Hao ◽  
...  
Keyword(s):  
Cell Lines ◽  
A549 Cells ◽  
Positive Control ◽  
Biological Evaluation ◽  
Dependent Manner ◽  
Pyrimidine Derivatives ◽  
Concentration Dependent Manner ◽  
Ic50 Value ◽  
Synthesis And Biological Evaluation

A series of novel 4-phenylaminobenzofuro[2,3-d]pyrimidine derivatives had been prepared and assessed for their in vitro antiproliferative activities against three lung cancer cell lines (A549, H460 and H1975). The bioassay results showed most of the designed compounds exhibited potential antiproliferation activities. Among them, compound 8f exhibited remarkable inhibitory activity against A549 and H460 cell lines with IC50 value of 2.54 μM and 2.68 μM, respectively, which was comparable to that of the positive control sorafenib (IC50 = 2.69 μM for A549 and 3.71 μM for H460). AO/EB staining suggests that compound 8f could induce apoptosis in A549 cells. Furthermore, cell cycle analyses show that compound 8f increased G0/G1 A549 cells arrest in a concentration-dependent manner. The preliminary structure-activity relationships (SARs) studies indicated that mono-electron-withdrawing groups (mono-EWGs) on the phenyl ring are positive on the antitumor activity.

Novel tacrine-1,2,3-triazole hybrids: In vitro, in vivo biological evaluation and docking study of cholinesterase inhibitors

2017 ◽  
Vol 125 ◽  
pp. 1200-1212 ◽  
Author(s):  
Zahra Najafi ◽  
Mohammad Mahdavi ◽  
Mina Saeedi ◽  
Elahe Karimpour-Razkenari ◽  
Raymond Asatouri ◽  
...  
Keyword(s):  
Cholinesterase Inhibitors ◽  
Docking Study ◽  
Biological Evaluation

scholarly journals Microwave Mediated Synthesis of Novel 1,3,5-Triazine Derivative and their Biological Evaluation

2021 ◽  
Vol 3 (12) ◽  
pp. 181-185
Author(s):  
Krishn Kumar Barmase ◽  
Deepak Basedia ◽  
Balkrishna Dubey
Keyword(s):  
Antibacterial Activity ◽  
Antibacterial Effect ◽  
Bacterial Species ◽  
Biological Evaluation ◽  
Chloride Ions ◽  
Gram Negative ◽  
Triazine Derivative ◽  
Triazine Derivatives ◽  
In Vitro Antibacterial Activity

1,3,5-Triazine derivative are synthesized by replacement of chloride ions of Cyanuric chloride and 1,3,5-Triazine derivative are showing promising biologically activity such as Antibacterial, Antifungal, Antimalarial, Antivirus, Anticancer that’s why interest of researches on synthesis of 1,3,5-Triazine derivatives always in focused. The present study reported the synthesis of 2,4,6-Trisubstituted 1,3,5-Triazine derivatives by Microwave mediated Method which gave the desired result in less time with higher yield. The structure of 1,3,5-Triazine derivatives have been elucidated by Spectral of IR, NMR and MASS. The derivative of 1,3,5-Triazine are evaluated for their In vitro Antibacterial activity against Gram Positive and Gram Negative Bacterial species and shown good Antibacterial effect.

Synthesis and biological evaluation of 2-(2-methyl-1H-pyrrol-3-yl)-2-oxo-N-(pyridine-3-yl) acetamide derivatives: in vitro α-glucosidase inhibition, and kinetic and molecular docking study

2019 ◽  
Vol 74 (5) ◽  
pp. 1583-1596
Author(s):  
Tadesse Bekele Tafesse ◽  
Ebrahim Saeedian Moghadam ◽  
Mohammed Hussen Bule ◽  
Neda Abadian ◽  
Mohammad Abdollahi ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Docking Study ◽  
Biological Evaluation ◽  
Molecular Docking Study ◽  
Synthesis And Biological Evaluation

scholarly journals SYNTHESIS, BIOLOGICAL EVALUATION, AND DOCKING STUDY OF NOVEL 2-PHENYL-1- BENZOPYRAN-4-ONE DERIVATIVES - AS A POTENT CYCLOOXYGENASE-2 INHIBITOR

2019 ◽  
pp. 304-310
Author(s):  
NATARAJAN KIRUTHIGA ◽  
THANGAVELU PRABHA ◽  
CHELLAPPA SELVINTHANUJA ◽  
KULANDAIVEL SRINIVASAN ◽  
THANGAVEL SIVAKUMAR
Keyword(s):  
Chronic Diseases ◽  
Radical Scavenging ◽  
Data Bank ◽  
Docking Study ◽  
Biological Evaluation ◽  
Cyclooxygenase 2 ◽  
Spectroscopic Techniques ◽  
Cox 2 ◽  
Anti Inflammatory

Objective: The inflammation and oxidative stress were related together in the generation of reactive oxygen species, which is responsible for the enhancement of inflammation associated with various chronic diseases. Methods: The aim of this study is to synthezise and characterizes the flavones (2-phenyl-1-benzopyran-4-one) derivatives and analyzed by their docking hypothetical data as an effective anti-inflammatory mediator against cyclooxygenase-2 (COX-2) enzyme. Further, the evaluation of various in vitro antioxidant and anti-inflammatory studies was carried out. Results: The 10 compounds were synthesized and characterized by ultraviolet, infrared, nuclear magnetic resonance, and mass spectroscopic techniques. The docking data results of these 10 flavones derivatives against COX-2 enzymes (Protein Data Bank ID: 3LN1) showed the binding energy ranging between −5.53 kcal/mol and −7.02 kcal/mol when compared with that of the standard diclofenac (−6.34 kcal/mol). The in vitro studies suggest that the lipophilic character of the side chain donor, along with the hydroxyl substituted flavones found to have significant half maximal inhibitory concentration values. Conclusion: Based on these in silico and in vitro evaluation results, these synthesized compounds could act as a promising inhibitor to target the COX- 2 enzyme. Hence, those compounds were effective in the management of chronic diseases by exhibits free radical scavenging and anti-inflammatory property.

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