Synthesis and evaluation of pyrazole‐incorporated monocarbonyl curcumin analogues as antiproliferative and antioxidant agents

Nagargoje, Amol A.; Akolkar, Satish V.; Siddiqui, Madiha M.; Bagade, Aditi V.; Kodam, Kisan M.; Sangshetti, Jaiprakash N.; Damale, Manoj G.; Shingate, Bapurao B.

doi:10.1002/jccs.201800405

Cited by 15 publications

(7 citation statements)

References 51 publications

(22 reference statements)

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“…Curcumin derivatives/analogs/hybrids are important lead molecules in medicinal chemistry research. [31][32][33][34][35][36][37][38][39][40][41] Use of curcumin as one of the reactant/substrate in various two components and multicomponent reactions (MCRs) generates new curcumin-based heterocycles of enhanced therapeutic potential. Curcumin-pyrazole/ isoxazole, [40] curcumin-3,4-dihydropyrimidones (DHPM)/thions, [38] curcumin-benzothiazole, [42] curcumin-based pyrano [3,2-d]pyrimidine, [43] and so forth are some of the curcumin-derived heterocycles of biological interest.…”

Section: Introductionmentioning

confidence: 99%

Curcumin‐based bioactive heterocycles derived via multicomponent reactions

Nagargoje

Shaikh

Shingate

2023

Archiv der Pharmazie

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Curcumin is an important phytochemical, found in the Asian countries, especially in the Indian subcontinent. The use of this "privileged natural product" in the diversityoriented synthesis of curcumin-based heterocycles via multicomponent reactions (MCRs) is the subject of interest for many medicinal chemists across the globe. This review particularly focuses on the reactions involving curcuminoids as one of the reactants in the MCRs of curcuminoid to synthesize curcumin-based heterocycles.Also, the various pharmacological activities of curcumin-based heterocycles generated via the MCR approach are discussed. The research work published in the last 10 years is in the focus of this review article.

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Section: Introductionmentioning

confidence: 99%

Curcumin‐based bioactive heterocycles derived via multicomponent reactions

Nagargoje

Shaikh

Shingate

2023

Archiv der Pharmazie

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“…These chemical biological activities have also been linked to their ability to scavenge reactive oxygen and nitrogen species, as well as the suppression of neutrophil oxidative burst [31]. Antimicrobial [32,33], antifungal [34], anti-angiogenic [35], antiviral [36], anticancer [37,38], anti-ischemic [39], antiproliferative, antioxidant [40], and cytotoxic [41] actions of these heterocyclic ring systems lead to other applications. In light of these findings, the current research project aims to synthesise chemically a set of new thiophene scaffolds containing the antipyrine moiety and investigate their antioxidant and antibacterial properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of some new antipyrine-thiophene hybrids and their evaluations as antioxidant and antibacterial agents

Saleh¹,

Saeed²,

Ghani³

et al. 2022

Bull. Chem. Soc. Eth.

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ABSTRACT. A novel series of antipyrinyl thienyl ketones 4a-c, 7a-c, 10a-c, and 13a-b was chemically synthesized through the cyclocondensation of 4-chloroacetylantipyrine with various 2-substituted-thioacetanilide scaffolds, including 3-arylazo-4-mercapto-4-phenylamino-buten-2-ones, ethyl 2-arylazo-3-mercapto-3-phenylamino-acrylate, 2-cyano-3-mercapto-3-(phenylamino)-N-arylacrylamide, 4-mercapto-4-(phenylamino)but-3-en-2-one, and/or ethyl-3-mercapto-3-(phenylamino)acrylate. Indeed, the reaction of 4-chloroacetylantipyrine with 4-hydroxybenzaldehyde followed by refluxing with 2-cyanoacetohydrazide yielded 2-cyano-N'-(4-(2-(antipyrin-4-yl)-2-oxoethoxy)benzylidene)-acetohydrazide 17 as a building compound, which was used consequentially to synthesize a set of new antipyrinyl thienyl hybrids 19a-d. The chemical structures of newly synthesised compounds were unambiguously confirmed using extensive elemental and spectral data analyses. The newly synthesized compounds were screened for their antioxidant and antimicrobial activities. Compared to the test reference (Ascorbic acid, 88.0%), the antipyrinyl thienyl ketones 13a and 13b substituted with methyl and/or hydroxyl groups at the thiophene ring system displayed excellent antioxidant properties, 87.8% and 87.2%, respectively. Additionally, antipyrinyl thienyl ketones 13a and 13b showed high antibacterial activities, and their relative activity index (which ranges from 68% to 91.7%) was close to that of a reference compound, Ampicillin. KEY WORDS: 4-Chloroacetylantipyrine, Thioacetanilide, Antipyrinyl thienyl ketones, Antioxidant, Antimicrobial Bull. Chem. Soc. Ethiop. 2023, 37(1), 123-140. a DOI:https://dx.doi.org/10.4314/bcse.v37i1.11

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“…Some heterocyclic compounds such as hydro pyrazole (pyrazoline) analogues have been also reported to have various potencies of pharmacological activities such antidiabetic [5,6], anti-dengue virus [7], anti-inflammatory [8], anticancer [9][10][11], and also antioxidant activity [12,13]. In addition, some pyrazole-incorporated monocarbonyl curcumin analogues have been also reported to exhibit potential antiproliferative and antioxidant activities [14]. In this work, we report the synthesis of a new pyrazolo-pyridine analogue through intermolecular cyclization of a monoketone curcumin analogue with phenyl hydrazine.…”

Section: Introductionmentioning

confidence: 99%

(E)-5-Benzyl-7-(3,4-dimethoxybenzylidene)-3-(3,4-dimethoxyphenyl)-2-phenyl-3,3a,4,5,6,7-hexahydro-2H-pyrazolo[4,3c] Pyridine

Mora

Zamri

Teruna

et al. 2021

Molbank

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A new pyrazolo-pyridine analogue (title compound) was synthesized in two steps. The first stage was synthesis of monoketone curcumin analogue through Claisen–Schmidt reaction. The second stage was synthesis of the title compound through intermolecular cyclization under reflux condition. The structure of the title compound has been confirmed by spectroscopic analysis including UV, FT-IR, HRMS, 1D NMR (1H-NMR, 13C-NMR, 1D-TOCSY), and 2D NMR (COSY, HSQC, HMBC). Based on the DPPH assay, the compound has moderate antioxidant activity, with an IC50 value of 194.06 ± 7.88 µg/mL (0.337 mM).

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Synthesis and evaluation of pyrazole‐incorporated monocarbonyl curcumin analogues as antiproliferative and antioxidant agents

Cited by 15 publications

References 51 publications

Curcumin‐based bioactive heterocycles derived via multicomponent reactions

Curcumin‐based bioactive heterocycles derived via multicomponent reactions

Synthesis of some new antipyrine-thiophene hybrids and their evaluations as antioxidant and antibacterial agents

(E)-5-Benzyl-7-(3,4-dimethoxybenzylidene)-3-(3,4-dimethoxyphenyl)-2-phenyl-3,3a,4,5,6,7-hexahydro-2H-pyrazolo[4,3c] Pyridine

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