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2000
Volume 21, Issue 3
  • ISSN: 1573-4080
  • E-ISSN: 1875-6662

Abstract

Introduction

Indole, a bicyclic heterocyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring, is a versatile structural motif in medicinal chemistry. Its unique structure allows it to interact with various biological targets, making it a valuable scaffold in drug design. Moreover, indole derivatives have been widely explored for their pharmacological activities, including antibacterial, antipsychotic, anticholinergic, anti-inflammatory, anticancer, antiviral, and antifungal properties.

Methods

A novel series of 3-(2-(1H-indol-2-yl)phenyl)-2-(substituted phenyl)-3,4-dihydroimidazo [4,5-b]indoles (4a–4j) was synthesized condensation of 2-(o-aminophenyl)indole with aromatic aldehydes in ethanol. Structures were confirmed using FT-IR and 1H-NMR spectroscopy. The compounds were evaluated for antibacterial and antifungal activities, supported by molecular docking studies targeting Lanosterol 14-α demethylase and DNA Gyrase B.

Results

Five compounds (4g, 4j, 4i, 4c, and 4b) showed significant antibacterial action against gram-positive and gram-negative and antifungal activity against and Molecular docking studies, performed in comparison with the standard drugs chloramphenicol and ketoconazole, revealed how the synthesized ligands bind within the active pockets. The results showed that compound 4b exhibits significant antibacterial activity, while compound 4c demonstrates good antifungal activity.

Discussion

This study successfully synthesized a novel series of indole-based dihydroimidazo[4,5-b]indoles (4a–4j) with confirmed structures FT-IR and 1H-NMR. Compounds 4b and 4c exhibited significant antibacterial and antifungal activities, respectively. Molecular docking revealed strong binding affinities with DNA Gyrase B and Lanosterol 14-α demethylase, supporting the observed bioactivity. These findings suggest promising potential for further antimicrobial drug development.

Conclusion

This study highlights the unique structures and potent antimicrobial activities of the synthesized compounds, showing their strong potential as novel antibacterial and antifungal agents with valuable therapeutic applications.

© 2025 Bentham Science Publishers
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References

  1. ListC Ho-Chi-MinhSARANI PahariaVCPI VaranasiU And-BazarD Geographical indications2020Available from: https://ipvietnam.gov.vn/web/english/geographical-indications
  2. AmbrosiM. CameronN.R. DavisB.G. Lectins: Tools for the molecular understanding of the glycocode.Org. Biomol. Chem.2005391593160810.1039/b414350g 15858635
     [Google Scholar]
  3. TooneE.J. Structure and energetics of protein-carbohydrate complexes.Curr. Opin. Struct. Biol.19944571972810.1016/S0959‑440X(94)90170‑8
     [Google Scholar]
  4. GiffordR. Continuous glucose monitoring: 40 years, what we’ve learned and what’s next.ChemPhysChem201314102032204410.1002/cphc.201300172 23649735
     [Google Scholar]
  5. SunX. JamesT.D. Glucose sensing in supramolecular chemistry.Chem. Rev.2015115158001803710.1021/cr500562m 25974371
     [Google Scholar]
  6. WuQ. WangL. YuH. WangJ. ChenZ. Organization of glucose-responsive systems and their properties.Chem. Rev.2011111127855787510.1021/cr200027j 21902252
     [Google Scholar]
  7. BakhN.A. CortinasA.B. WeissM.A. Glucose-responsive insulin by molecular and physical design.Nat. Chem.201791093794410.1038/nchem.2857 28937662
     [Google Scholar]
  8. LaineR.A.A. Calculation of all possible oligosaccharide isomers both branched and linear yields 1.05×10(12) structures for a reducing hexasaccharide – the isomer‐barrier to development of single‐method saccharide sequencing or synthesis systems.Glycobiology1994475976710.1093/glycob/4.6.759 7734838
     [Google Scholar]
  9. SolísD. BovinN.V. DavisA.P. A guide into glycosciences: How chemistry, biochemistry and biology cooperate to crack the sugar code.Biochim. Biophys. Acta, Gen. Subj.20151850118623510.1016/j.bbagen.2014.03.016 24685397
     [Google Scholar]
  10. DavisA.P. WarehamR.S. Carbohydrate recognition through noncovalent interactions: A challenge for biomimetic and supramolecular chemistry.Angew. Chem. Int. Ed.199938202978299610.1002/(SICI)1521‑3773(19991018)38:20<2978:AID‑ANIE2978>3.0.CO;2‑P 10540404
     [Google Scholar]
  11. WuX. LiZ. ChenX.X. FosseyJ.S. JamesT.D. JiangY.B. Selective sensing of saccharides using simple boronic acids and their aggregates.Chem. Soc. Rev.201342208032804810.1039/c3cs60148j 23860576
     [Google Scholar]
  12. JamesT.D. PhillipsM.D. ShinkaiS. Boronic Acids in Saccharide Recognition.CambridgeRSC200610.1039/9781847557612
     [Google Scholar]
  13. MarvinJ.S. HellingaH.W. Engineering biosensors by introducing fluorescent allosteric signal transducers: Construction of a novel glucose sensor.J. Am. Chem. Soc.1998120171110.1021/ja972993f
     [Google Scholar]
  14. BromfieldS.M. BarnardA. PosoccoP. FermegliaM. PriclS. SmithD.K. Mallard blue: A high-affinity selective heparin sensor that operates in highly competitive media.J. Am. Chem. Soc.201313582911291410.1021/ja311734d 23406254
     [Google Scholar]
  15. BromfieldS.M. PosoccoP. ChanC.W. Nanoscale self-assembled multivalent (SAMul) heparin binders in highly competitive, biologically relevant, aqueous media.Chem. Sci. (Camb.)2014541484149210.1039/c4sc00298a
     [Google Scholar]
  16. CarterT.S. MooibroekT.J. StewartP.F.N. CrumpM.P. GalanM.C. DavisA.P. Platform synthetic lectins for divalent carbohydrate recognition in water.Angew. Chem. Int. Ed.201655329311931510.1002/anie.201603082 27312071
     [Google Scholar]
  17. KrálV. RusinO. CharvátováJ. AnzenbacherP.Jr FoglJ. Porphyrin phosphonates: Novel anionic receptors for saccharide recognition.Tetrahedron Lett.20004151101471015110.1016/S0040‑4039(00)01805‑0
     [Google Scholar]
  18. RenneyC.M. FukuharaG. InoueY. DavisA.P. Binding or aggregation? Hazards of interpretation in studies of molecular recognition by porphyrins in water.Chem. Commun. (Camb.)201551469551955410.1039/C5CC02768C 25970199
     [Google Scholar]
  19. AsensioJ.L. ArdáA. CañadaF.J. Jiménez-BarberoJ. Carbohydrate: Aromatic interactions.Acc. Chem. Res.201346494695410.1021/ar300024d 22704792
     [Google Scholar]
  20. HudsonK.L. BartlettG.J. DiehlR.C. Carbohydrate‐aromatic interactions in proteins.J. Am. Chem. Soc.201513748151521516010.1021/jacs.5b08424 26561965
     [Google Scholar]
  21. LemieuxR.U. How water provides the impetus for molecular recognition in aqueous solution.Acc. Chem. Res.199629837338010.1021/ar9600087
     [Google Scholar]
  22. BillingJ. GrundbergH. NilssonU.J. Amphiphilic anthracene‐ amino acid conjugates as simple carbohydrate receptors in water.Supramol. Chem.200214436737210.1080/10610270290029281
     [Google Scholar]
  23. BhatM.A. Al-OmarM.A. RaishM. Indole derivatives as cyclooxygenase inhibitors: Synthesis, biological evaluation and docking studies.Molecules2018236125010.3390/molecules23061250 29882911
     [Google Scholar]
  24. ShaikhM.A. DebebeT. Synthesis and evaluation of antimicrobial activities of novel N-substituted indole derivatives.J. Chem.202020201910.1155/2020/4358453
     [Google Scholar]
  25. SharmaG.S. Conventional and microwave assisted synthesis of some novel 2-(Substituted phenyl)-4,5-diphenyl-1-(thiazol-2-yl)-1H-imidazoles of Biological interest.Asian J. Chem.20243692019202410.14233/ajchem.2024.32044
     [Google Scholar]
  26. BellavitaR. CasertanoM. GrassoN. Microwave-assisted synthesis of 2-Methyl-1H-indole-3-carboxylate derivatives via Pd-Catalyzed Heterocyclization.Symmetry202214343510.3390/sym14030435
     [Google Scholar]
  27. KumarA. AgrawalA. ChauhanD. SainiP. Structural analysis, antifungal activity and molecular docking study of a compound isolated from Streptomyces species.Antiinfect. Agents202119222022910.2174/2211352518999201022191232
     [Google Scholar]
  28. YadavM. HareenS.K. DinkarR. KumarV. SharmaS. In-vivo and in-silico molecular modeling studies of newly synthesized pyrazoles for their anti-inflammatory and analgesic properties.J Comput Biophys202423510.1142/S273741652450008X
     [Google Scholar]
  29. BhandariA. KumarN. AgarwalA. BhatnagarP. SharmaS. Synthesis and in-vitro and in-silico investigation of pyrazole derivatives as antibacterial, Antifungal Agents.Curr. Organocatal.20241110.2174/0122133372312616240826111851
     [Google Scholar]
  30. SaritaK. KumarN. AgrawalA. MaliS.N. SharmaS. In vitro and in silico evaluation of 2-(1H-Benzo[d]imidazol-2-yl)-3-(4-(piperazin-1-yl)phenyl)propanenitrile as epidermal growth factor receptor tyrosine kinase inhibitors.Russ. J. Bioorganic Chem.20245041563157210.1134/S1068162024040174
     [Google Scholar]
  31. AyazM AlamA Zainab Biooriented synthesis of Ibuprofen-Clubbed novel Bis -Schiff base derivatives as potential hits for malignant glioma: In vitro anticancer activity and in silico approach.ACS Omega2023851492284924310.1021/acsomega.3c07216 38173864
     [Google Scholar]
  32. ZainabK. KhanF. AlamA. Synthesis, anticancer, α-glucosidase inhibition, molecular docking and dynamics studies of hydrazone-Schiff bases bearing polyhydroquinoline scaffold: In vitro and in silico approaches.J. Mol. Struct.2025132113969910.1016/j.molstruc.2024.139699
     [Google Scholar]
  33. AlamA. KhanF. RehmanN.U. Flurbiprofen clubbed schiff’s base derivatives as potent anticancer agents: In vitro and in silico approach towards breast cancer.J. Mol. Struct.20251321113974310.1016/j.molstruc.2024.139743
     [Google Scholar]
/content/journals/cei/10.2174/0115734080356793250326054638
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Microwave-assisted Synthesis and In Vitro and In Silico Studies of Novel Indole Derivatives as Antibacterial and Antifungal Agents
Curr. Enzym. Inhib. 21, 196 (2025); https://doi.org/10.2174/0115734080356793250326054638
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  • Article Type:     Research Article
Keyword(s): antibacterial activity; antifungal activity; antimicrobial activity; imidazole; Indole; microwave-assisted synthesis

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