Exploration of Antifungal Potential of Carbohydrate‐Tethered Triazoles as CYP450 Inhibitors

Nainwal, Lalit Mohan; Azad, Chandra S.; Deswal, Deepa; Narula, Anudeep Kumar

doi:10.1002/slct.201802112

Cited by 6 publications

(3 citation statements)

References 37 publications

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“…All the synthesized compounds were evaluated for their in vitro antifungal activity against Aspergillus fumigates 3007 and C. albicans 3018. For A. fumigatus 3007 the growth inhibiting effect was quantitatively determined by the ratio of diameter of the growth zone in the plate with the synthesized compounds to those with the plate without the compounds (control) (Deswal et al, 2020; Nainwal et al, 2018). The plates were monitored for 96 h. While analyzing the antifungal effect, it was observed that all the compounds inhibited the fungal growth but with variable degree (Figure 6).…”

Section: Resultsmentioning

confidence: 99%

Exploration of novel TOSMIC tethered imidazo[1,2‐a]pyridine compounds for the development of potential antifungal drug candidate

Shukla

Deswal

Pandit

et al. 2021

Drug Development Research

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New candidates of imidazo [1, 2-a] pyridine were designed by combining 2-amino pyridine, TOSMIC isocyanide and various assorted aldehydes were synthesized to explore their antioxidant and antifungal potential. The design of these derivatives was based on utilizing the antifungal potential of azoles and TOSMIC moiety. These derivatives were synthesized by adopting multi-component reaction methodology, as it serves as a rapid and e cient tool to target structurally diverse heterocyclic compounds in quantitative yield. The resulting imidazo [1, 2-a] pyridine derivatives were structurally veri ed by 1 HNMR and 13 CNMR. The compounds were analyzed for their antioxidant and uorescent properties and it was observed that compound 15 depicted good uorescence and antioxidant potential. Additionally, the compounds were evaluated for their antifungal potential against both Aspergillus fumigatus 3007 & Candida albicans 3018 and it was observed that all the compounds had moderate to signi cant antifungal effect. Confocal images depicted the porous nature of compound treated fungal cell membranes leading to fungal growth inhibition. Molecular docking was performed to establish the interaction with the target enzyme (Lanosterol 14 alpha demethylase) which also corroborated with the in vitro results. In silico tools were employed to determine drug-likeliness of the compounds along with determination of ADME properties.

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Section: Resultsmentioning

confidence: 99%

Exploration of novel TOSMIC tethered imidazo[1,2‐a]pyridine compounds for the development of potential antifungal drug candidate

Shukla

Deswal

Pandit

et al. 2021

Drug Development Research

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“…A and B were used as reference compounds because they are natural ligands in the crystalline state of 5fl4 and 4iwz. The Ligprep module of the molecular modelling platform of the Schro ¨dinger Suite (Schro ¨dinger, 2022) was then used to prepare the imported structures by assigning bond lengths, bond angles, generating possible ionization states at pH 7 using Epik and finally to optimize using the OPLS4 force field (Nainwal et al, 2018).…”

Section: Docking Studiesmentioning

confidence: 99%

N-Cycloamino substituent effects on the packing architecture of ortho-sulfanilamide molecular crystals and their in silico carbonic anhydrase II and IX inhibitory activities

et al. 2022

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In the search for new `sulfa drugs' with therapeutic properties, o-nitrosulfonamides and N-cycloamino-o-sulfanilamides were synthesized and characterized using techniques including 1H NMR, 13C NMR and FT–IR spectroscopy, and single-crystal X-ray diffraction (SC-XRD). The calculated density functional theory (DFT)-optimized geometry of the molecules showed similar conformations to those obtained by SC-XRD. Molecular docking of N-piperidinyl-o-sulfanilamide and N-indolinyl-o-sulfanilamide supports the notion that o-sulfanilamides are able to bind to human carbonic anhydrase II and IX inhibitors (hCA II and IX; PDB entries 4iwz and 5fl4). Hirshfeld surface analyses and DFT studies of three o-nitrosulfonamides {1-[(2-nitrophenyl)sulfonyl]pyrrolidine, C10H12N2O4S, 1, 1-[(2-nitrophenyl)sulfonyl]piperidine, C11H14N2O4S, 2, and 1-[(2-nitrophenyl)sulfonyl]-2,3-dihydro-1H-indole, C14H12N2O4S, 3} and three N-cycloamino-o-sulfanilamides [2-(pyrrolidine-1-sulfonyl)aniline, C10H14N2O2S, 4, 2-(piperidine-1-sulfonyl)aniline, C11H16N2O2S, 5, and 2-(2,3-dihydro-1H-indole-1-sulfonyl)aniline, C14H14N2O2S, 6] suggested that forces such as hydrogen bonding and π–π interactions hold molecules together and further showed that charge transfer could promote bioactivity and the ability to form biological interactions at the piperidinyl and phenyl moieties.

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“…All the synthesized compounds were evaluated for their in vitro antifungal activity against Aspergillus fumigates 3007 and Candida albicans 3018. For A.fumigatus 3007 the growth inhibiting effect was quantitatively determined by the ratio of diameter of the growth zone in the plate with the synthesized compounds to those with the plate without the compounds (control) (27,28).…”

Section: Fluorescence Studymentioning

confidence: 99%

Exploration of Novel TOSMIC Tethered Imidazo[1,2-a]pyridine Compounds for the Development of Potential Antifungal Drug Candidate.

Shukla

Deswal

Pandit³

et al. 2021

Preprint

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New candidates of imidazo [1, 2-a] pyridine were designed by combining 2-amino pyridine, TOSMIC isocyanide and various assorted aldehydes were synthesized to explore their antioxidant and antifungal potential. The design of these derivatives was based on utilizing the antifungal potential of azoles and TOSMIC moiety. These derivatives were synthesized by adopting multi-component reaction methodology, as it serves as a rapid and efficient tool to target structurally diverse heterocyclic compounds in quantitative yield. The resulting imidazo [1, 2-a] pyridine derivatives were structurally verified by 1HNMR and 13CNMR. The compounds were analyzed for their antioxidant and fluorescent properties and it was observed that compound 15 depicted good fluorescence and antioxidant potential. Additionally, the compounds were evaluated for their antifungal potential against both Aspergillus fumigatus 3007 & Candida albicans 3018 and it was observed that all the compounds had moderate to significant antifungal effect. Confocal images depicted the porous nature of compound treated fungal cell membranes leading to fungal growth inhibition. Molecular docking was performed to establish the interaction with the target enzyme (Lanosterol 14 alpha demethylase) which also corroborated with the in vitro results. In silico tools were employed to determine drug-likeliness of the compounds along with determination of ADME properties.

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Exploration of Antifungal Potential of Carbohydrate‐Tethered Triazoles as CYP450 Inhibitors

Cited by 6 publications

References 37 publications

Exploration of novel TOSMIC tethered imidazo[1,2‐a]pyridine compounds for the development of potential antifungal drug candidate

Exploration of novel TOSMIC tethered imidazo[1,2‐a]pyridine compounds for the development of potential antifungal drug candidate

N-Cycloamino substituent effects on the packing architecture of ortho-sulfanilamide molecular crystals and their in silico carbonic anhydrase II and IX inhibitory activities

Exploration of Novel TOSMIC Tethered Imidazo[1,2-a]pyridine Compounds for the Development of Potential Antifungal Drug Candidate.

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