Synthesis of triazole-functionalized tetrahydroindazolones by 1,3-dipolar cycloadditions between azides and alkynes

Strakova, I. A.; Turks, Māris; Strakovs, A.

doi:10.1016/j.tetlet.2009.04.009

Cited by 15 publications

(6 citation statements)

References 27 publications

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“…Condensation of 2‐acyl dimedone with hydrazines is a general method used for the preparation of tetrahydroindazolones 12–14. In the present investigation, the starting compound, ethyl 2‐(3,6,6‐trimethyl‐4‐oxo‐4,5,6,7‐tetrahydroindazol‐1‐yl)acetate 3 was prepared by reaction of 2‐acetyl‐dimedone 2 with ethyl hydrazinoacetate (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Trimethyl‐4‐oxo‐4,5,6,7‐tetrahydroindazole‐1‐acetic Acid: A New Lead Compound with Selective COX‐2 Inhibitory Activity

Abdel‐Rahman

Özadalı

2012

Archiv der Pharmazie

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A novel series of 3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydroindazole-1-acetic acid derivatives was designed and synthesized by a new one-step pathway. Structure elucidation of the synthesized compounds was confirmed by various spectral and elemental analyses. The prepared compounds were evaluated for their ability to inhibit cyclooxygenase-2 (COX-2) and cyclooxygenase-1 (COX-1) enzymes in vitro. Among the synthesized compounds, the 2-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydroindazol-1-yl)acetic acid 4 emerged as the most potent COX-2 inhibitor (IC(50) value: 150 nM) with the highest selectivity index (COX-1/COX-2 inhibition ratio: 570.6). Docking studies of compound 4 in the active site of COX-2 recognized its potential binding mode to the enzyme. Based on the preliminary results, compound 4 was considered as a lead compound for further optimization.

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Section: Resultsmentioning

confidence: 99%

Trimethyl‐4‐oxo‐4,5,6,7‐tetrahydroindazole‐1‐acetic Acid: A New Lead Compound with Selective COX‐2 Inhibitory Activity

Abdel‐Rahman

Özadalı

2012

Archiv der Pharmazie

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“…Additionally, tetrahydroindazolones substituted with 2-aminobenzamides have been studied as fluorescent probes (Jia et al, 2012). Other studies on side-chain modifications include the synthesis of polyfluoroalkyl-substituted analogs (Khlebnikova et al, 2012), triazole-functionalized tetrahydroindazolones (Strakova et al, 2009) and their conjugation with biologically active natural products such as lupane triterpenoids (Khlebnicova et al, 2017). Among other synthetic approaches, the Ritter reaction provides a fast entry into structural modifications and is applicable to obtain a combinatorial library of compounds (Turks et al, 2012).…”

Section: Chemical Contextmentioning

confidence: 99%

“…The synthesis of the title compounds is depicted in the reaction scheme below. The 7-aminotetrahydroindazolone derivative 4 was prepared by an analogy of the procedure published by Strakova et al (2011) from the known precursor 3 (Strakova et al, 2009). In our attempts to synthesize metal complexes with ligand 4, we obtained the hydrochloride salt 1 in its anhydrous form.…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%

Crystal structure of 3,6,6-trimethyl-4-oxo-1-(pyridin-2-yl)-4,5,6,7-tetrahydro-1H-indazol-7-aminium chloride and its monohydrate

2017

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The title compounds, C15H19N4O+·Cl−and C15H19N4O+·Cl−·H2O, obtained in attempts to synthesize metal complexes using tetrahydroindazole as a ligand, were characterized by NMR, IR and X-ray diffraction techniques. The partially saturated ring in the tetrahydroindazole core adopts a sofa conformation. An intramolecular N—H...N hydrogen bond formed by the protonated amino group and the N atom of the pyridyl substituent is found in the first structure. In the hydrochloride, the organic moieties are linked by two N—H...Cl−hydrogen bonds, forming aC(4) graph-set. In the hydrate crystal, a Cl−anion and a water molecule assemble the moieties into infinite bands showing hydrogen-bond patterns with graph setsC(6),R64(12) andR42(8). Organic moieties form π–π stacked supramolecular structures running along thebaxis in both structures.

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“…Because of their utility and numerous activities such as antitumoral 11 , antifungal 12 , antiproliferative 13 , antioxidant and anti-inflammatory 14 , several syntheses of 1,2,3-triazoles have been reported. One of the synthetic methods to assemble 1,2,3-triazoles is the Huisgen 1,3-dipolar cycloaddition of azides and alkynes 15 . This cycloaddition reaction usually affords mixtures of 1,4 and 1,5-disubstituted 1,2,3-triazoles.…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of antimicrobial, anticoagulant, and anticholinesterase hybrid molecules from 4-methylumbelliferone

Zayane

Rahmouni

Daami‐Remadi

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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We designed and synthesized new series of diverse triazoles, isoxazoles, isoxazolines, and aziridines linked 4-methylumbelliferone 1 using intermolecular 1,3-dipolar cycloaddition reactions. Structures of these compounds were established on the basis of 1 H NMR, 13 C NMR, and ESI-HRMS. All prepared compounds were evaluated for their antimicrobial, anticoagulant, and anticholinesterase activities. Interestingly, among the tested molecules, some of the analogs displayed better activities than the parent 4-methylumbelliferone 1 such as 6a and 6d for their antifungal properties. Moreover, compounds 4, 5, 6, and 7 showed the importance of the added fragments to 4-methylumbelliferone 1 via the linker methylene to have good activity.

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Synthesis of triazole-functionalized tetrahydroindazolones by 1,3-dipolar cycloadditions between azides and alkynes

Cited by 15 publications

References 27 publications

Trimethyl‐4‐oxo‐4,5,6,7‐tetrahydroindazole‐1‐acetic Acid: A New Lead Compound with Selective COX‐2 Inhibitory Activity

Trimethyl‐4‐oxo‐4,5,6,7‐tetrahydroindazole‐1‐acetic Acid: A New Lead Compound with Selective COX‐2 Inhibitory Activity

Crystal structure of 3,6,6-trimethyl-4-oxo-1-(pyridin-2-yl)-4,5,6,7-tetrahydro-1H-indazol-7-aminium chloride and its monohydrate

Design and synthesis of antimicrobial, anticoagulant, and anticholinesterase hybrid molecules from 4-methylumbelliferone

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