Synthesis of novel 1,4-disubstituted-1,2,3-triazole semi synthetic analogues of forskolin by click reaction

Reddy, M. Jaipal; Kumar, Krishan; Sreenivas, P.; Krupadanam, G. L. David; Reddy, K. Janardhan

doi:10.1016/j.tetlet.2011.08.154

Cited by 13 publications

(2 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Many triazole-based derivatives are available as medicines; however, they also have a wide range of important applications in the agrochemical, dendrimer, supramolecular, electrochemical, corrosion retardant, optical brightener, metal chelator, and material fields . Their important biological activities include anticancer, antitumor, anti-HSV-1, antimalarial, antitubercular, antileishmanial, antifungal, antibacterial, antimicrobial, antidiabetic, antihypertensive, anti-inflammatory, anti-Alzheimer, antiepileptic, and anticonvulsant …”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1,4-Biphenyl-triazole Derivatives as Possible 17β-HSD1 Inhibitors: An in Silico Study

et al. 2020

View full text Add to dashboard Cite

Triazoles occupy an important position in medicinal chemistry because of their various biological activities. The structural features of 1,2,3triazoles enable them to act as a bioisostere of different functional groups such as amide, ester, carboxylic acid, and heterocycle, being capable of forming hydrogen bonds and π−π interactions or coordinate metal ions with biological targets. In this work, the synthesis of 1,2,3-triazole derivatives via copper(I)-catalyzed azide−alkyne cycloaddition (CuAAC) is reported. Overexpression of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) is often found in breast cancer cells. Molecular similarity and docking analysis were used to evaluate the potential inhibitory activity of 1,2,3-triazoles synthesized over 17β-HSD1 for the treatment of mammary tumors. Our in silico analysis shows that compounds 4c, 4d, 4f, 4g, and 4j are good molecular scaffold candidates as 17β-HSD1 inhibitors.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis of 1,4-Biphenyl-triazole Derivatives as Possible 17β-HSD1 Inhibitors: An in Silico Study

et al. 2020

View full text Add to dashboard Cite

show abstract

“…This problem has challenged researchers to develop new antimicrobial agents that will be more potent, more selective and less toxic for combating drug-resistant pathogens. Thus, nitrogen-containing heterocycles, in particular 1,2,3-triazoles [2], have attracted a great deal of interest from medicinal chemists in the design of potential drug candidates owing to their high biocompatibility and various pharmacological actions such as antibacterial [3], antiviral [4], antifungal [5], antimalarial [6], anti-HIV [7], antiallergic [8], antitubercular [9], CNS depressant [10], analgesic [11], anticonvulsant [12], antihypertensive [13] and antiproliferative activities [14].…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, ADME prediction and pharmacological evaluation of novel benzimidazole-1,2,3-triazole-sulfonamide hybrids as antimicrobial and antiproliferative agents

Al-blewi

Almehmadi

Aouad

et al. 2018

Chemistry Central Journal

View full text Add to dashboard Cite

BackgroundNitrogen heterocyclic rings and sulfonamides have attracted attention of several researchers.ResultsA series of regioselective imidazole-based mono- and bis-1,4-disubstituted-1,2,3-triazole-sulfonamide conjugates 4a–f and 6a–f were designed and synthesized. The first step in the synthesis was a regioselective propargylation in the presence of the appropriate basic catalyst (Et3N and/or K2CO3) to afford the corresponding mono-2 and bis-propargylated imidazoles 5. Second, the ligation of the terminal C≡C bond of mono-2 and/or bis alkynes 5 to the azide building blocks of sulfa drugs 3a–f using optimized conditions for a Huisgen copper (I)-catalysed 1,3-dipolar cycloaddition reaction yielded targeted 1,2,3-triazole hybrids 4a–f and 6a–f. The newly synthesized compounds were screened for their in vitro antimicrobial and antiproliferative activities. Among the synthesized compounds, compound 6a emerged as the most potent antimicrobial agent with MIC values ranging between 32 and 64 µg/mL. All synthesized molecules were evaluated against three aggressive human cancer cell lines, PC-3, HepG2, and HEK293, and revealed sufficient antiproliferative activities with IC50 values in the micromolar range (55–106 μM). Furthermore, we conducted a receptor-based electrostatic analysis of their electronic, steric and hydrophobic properties, and the results were in good agreement with the experimental results. In silico ADMET prediction studies also supported the experimental biological results and indicated that all compounds are nonmutagenic and noncarcinogenic.ConclusionIn summary, we have successfully synthesized novel targeted benzimidazole-1,2,3-triazole-sulfonamide hybrids through 1,3-dipolar cycloaddition reactions between the mono- or bis-alkynes based on imidazole and the appropriate sulfonamide azide under the optimized Cu(I) click conditions. The structures of newly synthesized sulfonamide hybrids were confirmed by means of spectroscopic analysis. All newly synthesized compounds were evaluated for their antimicrobial and antiproliferative activities. Our results showed that the benzimidazole-1,2,3-triazole-sulfonamide hybrids inhibited microbial and fungal strains within MIC values from 32 to 64 μg/mL. The antiproliferative evaluation of the synthesized compounds showed sufficient antiproliferative activities with IC50 values in the micromolar range (55–106 μM). In conclusion, compound 6a has remarkable antimicrobial activity. Pharmacophore elucidation of the compounds was performed based on in silico ADMET evaluation of the tested compounds. Screening results of drug-likeness rules showed that all compounds follow the accepted rules, meet the criteria of drug-likeness and follow Lipinski’s rule of five. In addition, the toxicity results showed that all compounds are nonmutagenic and noncarcinogenic.

show abstract

Synthesis of novel forskolin isoxazole derivatives with potent anti-cancer activity against breast cancer cell lines

Banala

Voora

Rao

et al. 2017

Bioorganic & Medicinal Chemistry Letters

View full text Add to dashboard Cite

Synthesis of novel 1,4-disubstituted-1,2,3-triazole semi synthetic analogues of forskolin by click reaction

Cited by 13 publications

References 19 publications

Synthesis of 1,4-Biphenyl-triazole Derivatives as Possible 17β-HSD1 Inhibitors: An in Silico Study

Synthesis of 1,4-Biphenyl-triazole Derivatives as Possible 17β-HSD1 Inhibitors: An in Silico Study

Design, synthesis, ADME prediction and pharmacological evaluation of novel benzimidazole-1,2,3-triazole-sulfonamide hybrids as antimicrobial and antiproliferative agents

Synthesis of novel forskolin isoxazole derivatives with potent anti-cancer activity against breast cancer cell lines

Contact Info

Product

Resources

About