Design, synthesis, antifungal activity and 3D-QSAR study of novel pyrazole carboxamide and niacinamide derivatives containing benzimidazole moiety

2019 ◽  
Vol 43 (7) ◽  
pp. 3000-3010 ◽  
Author(s):  
Wei-Jie Si ◽  
Xiao-Bin Wang ◽  
Min Chen ◽  
Meng-Qi Wang ◽  
Ai-Min Lu ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Predictive Ability ◽  
3D Qsar ◽  
Qsar Model ◽  
Qsar Study ◽  
Design Synthesis ◽  
Effective Inhibition

The synthesized pyrazole carboxamide and niacinamide derivatives containing a benzimidazole moiety showed effective inhibition of the fungus B. cinereal growth. The 3D-QSAR model was built and revealed fine predictive ability.

Novel pyrrolidine-2,4-dione derivatives containing pharmacophores of both hydrazine and diphenyl ether as potential antifungal agents: design, synthesis, biological evaluation, and 3D-QSAR study

2020 ◽  
Vol 44 (46) ◽  
pp. 20071-20082
Author(s):  
Hao-Ran Hu ◽  
An Wang ◽  
Ling-Ling Qiu ◽  
Xiao-Bin Wang ◽  
Min Chen ◽  
...  
Keyword(s):  
Electron Microscopy ◽  
Scanning Electron Microscopy ◽  
Antifungal Activity ◽  
Antifungal Agents ◽  
Diphenyl Ether ◽  
3D Qsar ◽  
Biological Evaluation ◽  
Qsar Study ◽  
Design Synthesis ◽  
Scanning Electron

Novel pyrrolidine-2,4-dione derivatives were designed based on natural products. Some synthesized compounds showed excellent antifungal activity. Scanning electron microscopy was used to observe mycelium morphology. 3D-QSAR was also studied.

A new, fully validated and interpreted quantitative structure-activity relationship model of p-aminosalicylic acid derivatives as neuraminidase inhibitors

2013 ◽  
Vol 67 (5) ◽  
Author(s):  
Ana Hartmman ◽  
Daniela Jornada ◽  
Eduardo Melo
Keyword(s):  
Predictive Ability ◽  
3D Qsar ◽  
Qsar Model ◽  
Quantitative Structure Activity Relationship ◽  
Neuraminidase Inhibitors ◽  
Aminosalicylic Acid ◽  
Randomization Tests ◽  
Qsar Study ◽  
Relationship Model ◽  
Mechanism Of Interaction

AbstractA multivariate QSAR study with a set of 34 p-aminosalicylic acid derivatives, described as neuraminidase inhibitors of the H1N1 viruses, is presented in this work. The variable selection was performed with the Ordered Predictors Selection (OPS) algorithm and the model was built with the Partial Least Squares (PLS) regression method. Leave-N-out cross-validation and y-randomization tests showed that the model was robust and free from chance correlation. The external predictive ability was superior to the 3D-QSAR model previously published. Moreover, it was possible to perform a mechanistic interpretation, where the descriptors referred directly to the mechanism of interaction with the neuraminidase.

scholarly journals Synthesis, Antifungal Activity, and 3D-QSAR Study of Novel Nopol-Derived 1,3,4-Thiadiazole-Thiourea Compounds

Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1708
Author(s):  
Ming Chen ◽  
Wen-Gui Duan ◽  
Gui-Shan Lin ◽  
Zhong-Tian Fan ◽  
Xiu Wang
Keyword(s):  
Antifungal Activity ◽  
Alternaria Solani ◽  
3D Qsar ◽  
Qsar Model ◽  
Gibberella Zeae ◽  
Cercospora Arachidicola ◽  
Qsar Study ◽  
Structure Activity ◽  
Better Than

A series of novel nopol derivatives bearing the 1,3,4-thiadiazole-thiourea moiety were designed and synthesized by multi-step reactions in search of potent natural product-based antifungal agents. Their structures were confirmed by FT-IR, NMR, ESI-MS, and elemental analysis. Antifungal activity of the target compounds was preliminarily evaluated by in vitro methods against Fusarium oxysporum f. sp. cucumerinum, Cercospora arachidicola, Physalospora piricola, Alternaria solani, Gibberella zeae, Rhizoeotnia solani, Bipolaris maydis, and Colleterichum orbicalare at 50 µg/mL. All the target compounds exhibited better antifungal activity against P. piricola, C. arachidicola, and A. solani. Compound 6j (R = m, p-Cl Ph) showed the best broad-spectrum antifungal activity against all the tested fungi. Compounds 6c (R = m-Me Ph), 6q (R = i-Pr), and 6i (R = p-Cl Ph) had inhibition rates of 86.1%, 86.1%, and 80.2%, respectively, against P. piricola, much better than that of the positive control chlorothalonil. Moreover, compounds 6h (R = m-Cl Ph) and 6n (R = o-CF3 Ph) held inhibition rates of 80.6% and 79.0% against C. arachidicola and G. zeae, respectively, much better than that of the commercial fungicide chlorothalonil. In order to design more effective antifungal compounds against A. solani, analysis of the three-dimensional quantitative structure–activity relationship (3D-QSAR) was carried out using the CoMFA method, and a reasonable and effective 3D-QSAR model (r2 = 0.992, q2 = 0.753) has been established. Furthermore, some intriguing structure–activity relationships were found and are discussed by theoretical calculation.

2D/3D-QSAR STUDY ON ANALOGUES OF 2-METHOXYESTRADIOL WITH ANTICANCER ACTIVITY

2008 ◽  
Vol 07 (02) ◽  
pp. 287-301 ◽  
Author(s):  
SI YAN LIAO ◽  
LI QIAN ◽  
JIN CAN CHEN ◽  
YONG SHEN ◽  
KANG CHENG ZHENG
Keyword(s):  
Anticancer Activity ◽  
Molecular Design ◽  
Predictive Ability ◽  
Decisive Role ◽  
3D Qsar ◽  
Qsar Model ◽  
Field Analysis ◽  
Qsar Study ◽  
Comfa Model ◽  
2D Qsar

Two-dimensional (2D) and three-dimensional (3D) quantitative structure–activity relationships (QSARs) of 23 analogs of 2-Methoxyestradiol with anticancer activity (expressed as p GI50) against MCF-7 human breast cancer cells have been studied by using a combined method of the DFT, MM2 and statistics for 2D, as well as the comparative molecular field analysis (CoMFA) for 3D. The established 2D-QSAR model in training set shows not only significant statistical quality, but also predictive ability, with the square of adjusted correlation coefficient [Formula: see text] and the square of the cross-validation coefficient (q2= 0.779). The same model was further applied to predict p GI50values of the four compounds in the test set, and the resulting [Formula: see text] being as high as 0.827, further confirms that this 2D-QSAR model has high predictive ability for this kind of compound. The 3D-QSAR model also shows good correlative and predictive capabilities in terms of R2(0.927) and q2(0.786) obtained from CoMFA model. The results that 2D- and 3D-QSAR analyses accord with each other, suggest that the electrostatic interaction plays a decisive role in determining the anticancer activity of the studied compounds, and that increasing the negative charge of substituent R2and the positive charge of substituents linking to C17as well as decreasing the size of substituent R1are advantageous to improving the cytotoxicity. Such results can offer some useful theoretical references for directing the molecular design and understanding the action mechanism of this kind of compound with anticancer activity.

scholarly journals Synthesis of Bioactive Compounds from 3-Carene (II): Synthesis, Antifungal Activity and 3D-QSAR Study of (Z)- and (E)-3-Caren-5-One Oxime Sulfonates

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 477 ◽  
Author(s):  
Guo-Qiang Kang ◽  
Wen-Gui Duan ◽  
Gui-Shan Lin ◽  
You-Pei Yu ◽  
Xiao-Yu Wang ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Three Dimensional ◽  
Alternaria Solani ◽  
3D Qsar ◽  
Qsar Model ◽  
Quantitative Structure Activity Relationship ◽  
Cercospora Arachidicola ◽  
Qsar Study ◽  
In Vitro Antifungal Activity

A series of novel (Z)- and (E)-3-caren-5-one oxime sulfonates were designed and synthesized in search of potent antifungal agents. The structures of the intermediates and target compounds were confirmed by UV-Vis, FTIR, NMR, and ESI-MS. The in vitro antifungal activity of the target compounds was preliminarily evaluated against Cercospora arachidicola, Physalospora piricola, Alternaria solani, Rhizoeotnia solani, Bipolaris maydis and Colleterichum orbicalare at 50 µg/mL. The bioassay results indicated that the target compounds exhibited the best antifungal activity against P. piricola, in which compounds 4b, 4f, 4m, 4e, 4j, 4l, 4y, 4d, and 4p had excellent inhibition rates of 100%, 100%, 100%, 92.9%, 92.9%, 92.9%, 92.9%, 85.7%, and 85.7%, respectively, showing much better antifungal activity than that of the commercial fungicide chlorothanil. Both the compounds 4y and 4x displayed outstanding antifungal activity of 100% against B. myadis, and the former also displayed outstanding antifungal activity of 100% against R. solani. In order to design more effective antifungal compounds against P. piricola, the analysis of three-dimensional quantitative structure-activity relationship (3D-QSAR) was carried out using the CoMFA method, and a reasonable and effective 3D-QSAR model (r2 = 0.990, q2 = 0.569) has been established.

THE EXPLORATION OF CYP17A1 LIGAND SPACE BY THE QSAR MODEL

2021 ◽  
Author(s):  
Natalia Boboriko ◽  
◽  
He Liying ◽  
Yaraslau Dzichenka
Keyword(s):  
Hydrophobic Effect ◽  
Predictive Ability ◽  
Distance Matrix ◽  
Qsar Model ◽  
Aromatic Rings ◽  
Qsar Study ◽  
Test Set ◽  
Highly Active ◽  
High Efficient ◽  
F Measure

Cytochrome P450 17A1 (CYP17A1) is a critically important enzyme in humans that catalyzes the formation of all endogenous androgens. This enzyme is often considered a molecular target for the development of novel high efficient drugs against prostate cancer. In the present work, the random forest algorithm was used to conduct a QSAR study on 370 CYP17A1 ligands with different structures that were collected from the literature and databases, and a QSAR model was created based on the five important descriptors screened out – 2D adjacency and distance matrix descriptors, 2D atom counts and bond counts and 3D surface area, volume and shape descriptors. The model was verified by the test set (accuracy, specificity, sensitivity, F-measure, MCC, and AUC were calculated). It was revealed that the hydrophobic properties of the vdW surface of the ligand have a significant contribution to the activity prediction. The hydrophobic effect of the molecules may be aroused by the presence of the hydrophobic groups or aromatic rings in the molecules. The created QSAR model shows that the molecules with more aromatic rings have better activity. The accuracy of the model on the test set was 84%, precision – 81%, sensitivity – 93%, specificity – 72%, F-measure – 0.87, MCC – 0.67, AUC – 0.88. The model has good robustness and predictive ability and can be used to screen and discover new highly active CYP17A1 inhibitors.

scholarly journals Design, synthesis, and biological evaluation of new 6,N2-diaryl-1,3,5-triazine-2,4-diamines as anticancer agents selectively targeting triple negative breast cancer cells

RSC Advances ◽  
2020 ◽  
Vol 10 (43) ◽  
pp. 25517-25528
Author(s):  
Ahmad Junaid ◽  
Felicia Phei Lin Lim ◽  
Edward R. T. Tiekink ◽  
Anton V. Dolzhenko
Keyword(s):  
Breast Cancer ◽  
Triple Negative Breast Cancer ◽  
Anticancer Agents ◽  
Breast Cancer Cells ◽  
Triple Negative ◽  
3D Qsar ◽  
Qsar Model ◽  
Biological Evaluation ◽  
Design Synthesis ◽  
Synthesis And Biological Evaluation

New highly potent and selective 6,N2-diaryl-1,3,5-triazine-2,4-diamines were designed and prepared using the 3D-QSAR model developed earlier.

2-Methyl-4/5-nitroimidazole derivatives potentiated against sexually transmitted Trichomonas : Design, synthesis, biology and 3D-QSAR study

2016 ◽  
Vol 124 ◽  
pp. 820-839 ◽  
Author(s):  
Dhanaraju Mandalapu ◽  
Bhavana Kushwaha ◽  
Sonal Gupta ◽  
Nidhi Singh ◽  
Mahendra Shukla ◽  
...  
Keyword(s):  
3D Qsar ◽  
Qsar Study ◽  
Design Synthesis ◽  
Sexually Transmitted

Structure Activity Design, Synthesis and Biological Activity of Newer Imidazole-Triazine Clubbed Derivative as Antimicrobial and Antitubercular Agents

2021 ◽  
Vol 18 ◽  
Author(s):  
Jaydeep A. Patel ◽  
Navin B. Patel ◽  
Pratik K. Maisuriya ◽  
Monika R. Tiwari ◽  
Amit C. Purohit
Keyword(s):  
Thermodynamic Properties ◽  
Pharmacological Activity ◽  
Predictive Ability ◽  
Antitubercular Activity ◽  
Qsar Model ◽  
Total Surface Area ◽  
Lead Target ◽  
Antitubercular Agents ◽  
Qsar Study ◽  
2D Qsar

Background: Imidazole and triazine derivatives act as antimicrobial and antitubercular agents. 2D-QSAR determination estimates the pharmacological activity on the basis of thermodynamic properties of the structure. Objective: The structural arrangements and thermodynamic properties of the imidazole derivatives are necessary for the enhancement of pharmacological activity. So imidazole-triazine clubbed derivatives were designed on the bases of molecular modeling 2D-QSAR study of antitubercular activity. Methods: PLSR method was applied for 2D-QSAR determination of the (Z)-5-ethylidene-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-2-phenyl-3,5-dihydro-4H-imidazol-4-one (B1-B10). The designed compounds were synthesized and spectrally evicted by IR, 1H NMR, 13C NMR, Mass spectra data as well as biologically screened opposite different antitubercular and antimicrobial species. Result: Compounds B4, B6, B7 were founds potent against different antimicrobial species. Compound B3 was more effective against M. tuberculosis H37Rv. Statistically significant QSAR model generated by PLSR methods shows external r2=0.9775 and internal q2=0.2798 predictive ability. Whereas, the model incorporates with three parameters PolarSurfaceAreaExcluding P and S, MomInertiaY and SsCH3count with their corresponding values for each molecule. Conclusion: 2D-QSAR study advised antitubercular activity directly proportional to total surface area of the polar atoms having molecules and moment of inertia on Y-axis. Whereas, inversely proportional to methyl group joined with single bond. The present study afforded favorable results which were further used to generate lead target molecules.

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