Design, synthesis and in vitro biological evaluation of short-chain C12-sphinganine and its 1,2,3-triazole analogs as potential antimicrobial and anti-biofilm agents

Reddy, T. Vijai Kumar; Jyotsna, Adigopula; Devi, B.L.A. Prabhavathi; Prasad, R. B. N.; Poornachandra, Y.; Kumar, C. Ganesh

doi:10.1016/j.ejmech.2016.04.020

Cited by 23 publications

(8 citation statements)

References 54 publications

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“…Accordingly, the azido alcohol 5 was coupled with different terminal alkynes, namely phenyl acetylene (a), 3-ethynylphenol (b), 2-ethynyl-6-methoxynaphthalene (c), propyn-2-yn-1-ol (d), and oct-1-yn (e) in the presence of copper sulfate pentahydrate (CuSO 4 Á5H 2 O) and sodium ascorbate in 1:1 (v/v) mixture of tert-butyl alcohol:water (t-BuOH:H 2 O) as solvent at ambient temperature to afford the desired 1,4-regioselective isomannide monoundecenoate-based 1,2,3-triazoles 6a-e with good isolated yields (82-88%). [51,60] Chemical structures of all the synthesized 1,2,3-triazole analogs 6a-e were fully analyzed by different spectroscopic data. Triazole ring formation has been confirmed by the following spectral analysis.…”

Section: Resultsmentioning

confidence: 99%

“…Considering the myriad potential biological significance of 1,2,3-triazoles and isomannide, and as an extension of our studies [48][49][50][51][52] to develop new potential bioactive molecules, we herein describe the design, synthesis and biological evaluation of a novel isomannide monoundecenoate-based 1,2,3-triazole analogs. The isomannide monoundecenoate with a lipophilic spacer having 1,2,3-triazole functionality in a single molecular framework might exert in potentiality against bacterial and fungal strains, especially drug-resistant microorganism.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Isomannide monoundecenoate‐based 1,2,3‐triazoles: Design, synthesis, and in vitro bioactive evaluation

Tangadanchu

Gundabathini

Bethala

et al. 2020

Journal of Heterocyclic Chem

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A new series of isomannide monoundecenoate-based 1,2,3-triazole analogs 6a-e were designed by employing click chemistry in good yields. in vitro bioactive assay manifested that the several target compounds exhibited promising antibacterial and antifungal activities. Notably, compounds having phenyl substituted triazole 6a, and hydroxy phenyl substituted triazole 6b possessed highly selective promising inhibition towards Gram-positive bacterial strains namely Bacillus subtilis and Staphylococcus aureus with MIC value of 3.9 μg/ mL. Further, these potential hybrids (6a and 6b) also exhibited highly impressive antifungal activity against the tested panel of Candida strains with MIC value of 3.9 μg/mL. Based on our in vitro preliminary antimicrobial study, these two compounds 6a and 6b have been identified as potential antimicrobial lead compounds. Moreover, all prepared derivatives were also evaluated for their in vitro cytotoxic activities against A549, MCF7, DU145 and HeLa cancer cell lines. The results indicated that only the hydroxy phenyl substituted triazole analog 6b displayed good cytotoxic activity towards all tested human cancer cell lines without any significant effects on normal cell line (HUVEC).

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Isomannide monoundecenoate‐based 1,2,3‐triazoles: Design, synthesis, and in vitro bioactive evaluation

Tangadanchu

Gundabathini

Bethala

et al. 2020

Journal of Heterocyclic Chem

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“…Compound 34 increased the levels of reactive oxygen species in Candida albicans . Structure‐activity relationship revealed that present hydroxy group at phenyl ring next to the 1,2,3‐triazole ring was most suitable for the activity whereas unsubstituted phenyl ring resulted decrease in potency of the compound [62] . Similarly, Lejcher et al .…”

Section: 23‐triazole Derivatives With Antifungal Activity Against As ...mentioning

confidence: 86%

“…Structure-activity relationship revealed that present hydroxy group at phenyl ring next to the 1,2,3-triazole ring was most suitable for the activity whereas unsubstituted phenyl ring resulted decrease in potency of the compound. [62] Similarly, Lejcher et al designed and synthesised a series of 1,3,4-trisubstituted-1,2,3-triazolium salts. The synthesized compounds were evaluated for their antifungal activity against Candida albicans.…”

Section: 23-triazole Derivatives Containing Alkyl Chainsmentioning

confidence: 99%

1,2,3‐Triazole Derivatives as an Emerging Scaffold for Antifungal Drug Development against Candida albicans: A Comprehensive Review

Singh

Sharma

et al. 2023

Chemistry & Biodiversity

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Candida infections are most prominent among fungal infections majorly target immunocompromised and hospitalized patients and cause significant morbidity and mortality. Candida albicans is the notorious and most prevalent among all pathogenic Candida strains. Its emerging resistance toward available antifungal agents making it hard to tackle and emerging as global healthcare emergency. Simultaneously, 1,2,3-triazole nucleus is a privileged scaffold that is gaining importance in antifungal drug development due to being a prominent bioactive linker and isostere of triazole based antifungal class core 1,2,4-triazole. Numerous reports have been updated in scientific literature in last few decades related to utilization of 1,2,3-triazole nucleus in antifungal drug development against Candida albicans. Present review will shed light on various preclinical studies focused on development of 1,2,3-triazole derivatives targeting Candida albicans along with brief highlight on clinical trials and newly approved drugs. Structure-activity relationship has been precisely discussed for each architect along with future perspective that will help medicinal chemists in design and development of potent antifungal agents for tackling infections derived from Candida albicans.

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“…1,2,3-Triazoles have received attention in medicinal chemistry and organic chemistry due to their excellent biological activities and easy synthesis via click reactions. 1,2 In recent years, 1,2,3-triazoles have gained special attention as antiproliferative agents because several biologically active compounds contain that group such as the spirooxindole-derived morpholine-fused-1,2,3-triazole 1, 3 and the 1,2,3-triazole linked chalcone 2 (Fig. 1).…”

mentioning

confidence: 99%

Synthesis of Novel Antiproliferative 1,2,3-triazole Hybrids Using the Molecular Hybridisation Approach

Song

Zhao

et al. 2016

Journal of Chemical Research

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A series of nine novel 1,2,3-triazole-chalcone derivatives were designed using the molecular hybridisation approach and synthesised by click chemistry. Most of the synthesised compounds exhibited moderate to good antiproliferative activity against oesophagus, gastric and neuroendocrine cancer cell lines, but a compound containing a p-bromo group in the A ring and a [(4,5-dihydrothiazol-2-yl)thio]methyl group attached at the 4-position of a p-[3-(1,2,3-triazol-1-yl)propyloxy] group in the B ring showed the highest activity with an IC50 value of 8.16 μM against neuroendocrine cancer cells. The structure activity relationships of all nine compounds were discussed.

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Design, synthesis and in vitro biological evaluation of short-chain C12-sphinganine and its 1,2,3-triazole analogs as potential antimicrobial and anti-biofilm agents

Cited by 23 publications

References 54 publications

Isomannide monoundecenoate‐based 1,2,3‐triazoles: Design, synthesis, and in vitro bioactive evaluation

Isomannide monoundecenoate‐based 1,2,3‐triazoles: Design, synthesis, and in vitro bioactive evaluation

1,2,3‐Triazole Derivatives as an Emerging Scaffold for Antifungal Drug Development against Candida albicans: A Comprehensive Review

Synthesis of Novel Antiproliferative 1,2,3-triazole Hybrids Using the Molecular Hybridisation Approach

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