New Benzylidene‐Triazole Tethered Coumarin Molecular Hybrids: Synthesis, SAR, Molecular Modelling Simulations Targeting Tubulin α/β Dimer and its Antimicrobial Evaluation
Abstract: A series of new 7‐{3‐[3‐(Benzylidene‐amino)‐[1,2,4]triazole‐1‐yl]‐propoxy}‐4‐methyl‐chromen‐2‐one molecular hybrids 7 (a–k) were synthesized using molecular hybridization approach. The synthesized new benzylidene‐triazole tethered coumarin molecular hybrids were characterized by spectroscopic studies and elemental analysis. The coumarin molecular hybrids have been explored for their antifungal efficacy in terms of tubulin inhibitors using molecular modelling studies against tubulin alphabeta hetero dimer protein. The results clearly demonstrated strong binding affinity of coumarin molecular hybrids with indole substituted and 2,4‐dihydroxy substituted as antagonists with respective binding scores of −10.5 and −10.7 kcal/mol towards tubulin alphabeta hetero dimer protein which was higher in comparison to standards griseofulvin (−8.2 kcal/mol) and fluconazole (−8.1 kcal/mol). In addition, broth dilution method was used to conduct in‐vitro antifungal studies against three fungal strains namely Candida albicans, Aspergillus niger and Aspergillus fumigatus. The results obtained clearly illustrate the antifungal activity of indole and 2,4‐dihydroxy substituted compounds which are consistent with docking simulations. Out of all the synthesized molecular hybrids, indole and 2,4‐dihydroxy substituted compounds depict outstanding antifungal activity with Minimum Inhibitory Concentration (MIC) value of 31.25 μg/ml and 62.5 μg/ml towards C.albicans and with MIC value of 31.25 for both these molecules towards A.niger in each case which is quite higher than griseofulvin and fluconazole respectively. Present work clearly demonstrates the potential efficacy of synthesized indole and 2,4‐dihydroxy substituted coumarin molecular hybrids to be considered as lead compounds for the development of new agents against resistant strains for the treatment of fungal infection.
- Standort
-
Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
-
Online-Ressource
- Sprache
-
Englisch
- Erschienen in
-
New Benzylidene‐Triazole Tethered Coumarin Molecular Hybrids: Synthesis, SAR, Molecular Modelling Simulations Targeting Tubulin α/β Dimer and its Antimicrobial Evaluation ; volume:9 ; number:30 ; year:2024 ; extent:15
ChemistrySelect ; 9, Heft 30 (2024) (gesamt 15)
- Urheber
-
Manda, Raja Rameshu
Nadh, Ratnakaram Venkata
Angajala, Gangadhara
Viveka, Tella Lakshmi
Aruna, Valmiki
- DOI
-
10.1002/slct.202401240
- URN
-
urn:nbn:de:101:1-2408071411369.718077380472
- Rechteinformation
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
-
14.08.2025, 10:51 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Manda, Raja Rameshu
- Nadh, Ratnakaram Venkata
- Angajala, Gangadhara
- Viveka, Tella Lakshmi
- Aruna, Valmiki
Ähnliche Objekte (12)
Exploring Novel Coumarin‐Tethered Bis‐Triazoles: Apoptosis Induction in Human Pancreatic Cancer Cells, Antimicrobial Effects, and Molecular Modelling Investigations
Coumarin‐Tethered‐1,2,3‐Triazoles: Synthesis, Characterization, Antimicrobial Evaluation, and DFT Studies
Molecular mechanisms of triazole-mediated toxicity in human hepatocarcinoma cell lines
Tubulin is a molecular target of the Wnt-activating chemical probe
Click Chemistry Approach to Isoindole-1,3-dione Tethered 1,2,3-Triazole Derivatives
Polymer Optical Waveguide Sensor Based on Fe-Amino-Triazole Complex Molecular Switches
Developing multitarget coumarin based anti-breast cancer agents: synthesis and molecular modeling study
STEREO- AND REGIOSELECTIVE PHOTOCYCLOADDITION OF COUMARIN AND THYMINE DERIVATIVES USING MOLECULAR RECOGNITION CATALYST
Cu‐Catalyzed Synthesis of Coumarin‐1,2,3‐Triazole Hybrids connected with Quinoline or Pyridine Framework **
Selective fluorescence sensor for Cu 2+ with a novel triazole Schiff-base derivative with coumarin units
Anticancer evaluation and molecular docking of new pyridopyrazolo-triazine and pyridopyrazolo-triazole derivatives
Atomistic molecular dynamics simulations of tubulin heterodimers explain the motion of a microtubule
Exploring Novel Coumarin‐Tethered Bis‐Triazoles: Apoptosis Induction in Human Pancreatic Cancer Cells, Antimicrobial Effects, and Molecular Modelling Investigations
Coumarin‐Tethered‐1,2,3‐Triazoles: Synthesis, Characterization, Antimicrobial Evaluation, and DFT Studies
Molecular mechanisms of triazole-mediated toxicity in human hepatocarcinoma cell lines
Tubulin is a molecular target of the Wnt-activating chemical probe
Click Chemistry Approach to Isoindole-1,3-dione Tethered 1,2,3-Triazole Derivatives
Polymer Optical Waveguide Sensor Based on Fe-Amino-Triazole Complex Molecular Switches
Developing multitarget coumarin based anti-breast cancer agents: synthesis and molecular modeling study
STEREO- AND REGIOSELECTIVE PHOTOCYCLOADDITION OF COUMARIN AND THYMINE DERIVATIVES USING MOLECULAR RECOGNITION CATALYST
Cu‐Catalyzed Synthesis of Coumarin‐1,2,3‐Triazole Hybrids connected with Quinoline or Pyridine Framework **
Selective fluorescence sensor for Cu 2+ with a novel triazole Schiff-base derivative with coumarin units
Anticancer evaluation and molecular docking of new pyridopyrazolo-triazine and pyridopyrazolo-triazole derivatives
Atomistic molecular dynamics simulations of tubulin heterodimers explain the motion of a microtubule
Exploring Novel Coumarin‐Tethered Bis‐Triazoles: Apoptosis Induction in Human Pancreatic Cancer Cells, Antimicrobial Effects, and Molecular Modelling Investigations
Coumarin‐Tethered‐1,2,3‐Triazoles: Synthesis, Characterization, Antimicrobial Evaluation, and DFT Studies
Molecular mechanisms of triazole-mediated toxicity in human hepatocarcinoma cell lines
Tubulin is a molecular target of the Wnt-activating chemical probe
Click Chemistry Approach to Isoindole-1,3-dione Tethered 1,2,3-Triazole Derivatives
Polymer Optical Waveguide Sensor Based on Fe-Amino-Triazole Complex Molecular Switches
Developing multitarget coumarin based anti-breast cancer agents: synthesis and molecular modeling study
STEREO- AND REGIOSELECTIVE PHOTOCYCLOADDITION OF COUMARIN AND THYMINE DERIVATIVES USING MOLECULAR RECOGNITION CATALYST
Cu‐Catalyzed Synthesis of Coumarin‐1,2,3‐Triazole Hybrids connected with Quinoline or Pyridine Framework **
Selective fluorescence sensor for Cu 2+ with a novel triazole Schiff-base derivative with coumarin units
Anticancer evaluation and molecular docking of new pyridopyrazolo-triazine and pyridopyrazolo-triazole derivatives