ChemInform Abstract: Synthesis and Biological Screening of Some Novel Thiazolyl Chromones and Pyrazoles.

Karale, B. K.; Takate, S. J.; Salve, S P; Zaware, Bhaskar H.; Jadhav, Santosh S.

doi:10.1002/chin.201546162

Cited by 2 publications

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“…This selective and fast procedure, involving an excess of hydrazine hydrate in refluxing ethanol, was applied to a wide variety of 2-substituted chromones 97 to afford several 3(5)-(2-hydroxyaryl)-5(3)-substituted pyrazoles 98 . The substitution at carbon C-2 of the chromone unit can include polyfluoroalkyl [ 62 , 63 ], 1-isopropyl-1 H -indazol-3-yl [ 64 ], 4-(allyloxy)-3-methoxyphenyl-1-yl [ 65 ], 4-chloro-3,4-difluorophenyl-1-yl [ 66 ], 1-aryl-3-(benzofuran-2-yl/naphthalen-3-yl/phenyl/pyridin-3/4-yl, thiophen-2-yl/3-bromothiophen-2-yl)pyrazol-4-yl [ 18 , 19 , 20 , 21 , 67 , 68 , 69 , 70 ], 1-methyl-3-propyl-4-substituted pyrazol-5-yl [ 8 ], 2-(3-methylthiophen-2-yl)-1,3-thiazol-5-yl [ 71 ] substituents (step (i), Scheme 31 ). Using a 5-methyl-3-phenylisoxazol-4-yl group as C-2 substituent, the reaction occurs in the presence of glacial acetic acid to afford 3(5)-(2-hydroxyaryl)-5(3)-(5-methyl-3-phenylisoxazol-4-yl)-1 H -pyrazoles, in good yields (59–83%) (step (ii), Scheme 31 ) [ 72 ].…”

Section: Chromones As Starting Materials In the Synthesis Of 3(5)-mentioning

confidence: 99%

“…Replacing ethanol by another alcohol as solvent, a series of 2-(5-aryl-1,2,3-triazol-4-yl)chromones in methanol (step (iii), ( Scheme 31 ) or 2-[2-(quinoxalin-2-one-3-yl)methylidene-chromones in n -butanol (step (iv), Scheme 31 ) undergo condensation with hydrazine hydrate to furnish 5(3)-(5-aryl-1,2,3-triazol-4-yl)-3(5)-(2-hydroxyaryl)-1 H -pyrazoles [ 73 ] or 3(5)-(2-hydroxy-aryl)-5(3)-[2-(quinoxalin-2-one-3-yl)methylidene]-1 H -pyrazoles [ 74 ], respectively. Biological evaluation of a wide range of 3(5)-(2-hydroxyaryl)pyrazoles 96 were performed, mainly as antimicrobial and antioxidant agents [ 8 , 18 , 19 , 20 , 21 , 64 , 65 , 66 , 67 , 70 , 71 , 72 ].…”

Section: Chromones As Starting Materials In the Synthesis Of 3(5)-mentioning

confidence: 99%

“… Synthesis of 3(5)-(2-hydroxyaryl)-5(3)-substituted pyrazoles 98 from the reaction of 2-substituted chromones 97 with an excess of hydrazine hydrate, using different reaction conditions [ 8 , 18 , 19 , 20 , 21 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 74 ]. To simplify the schemes, in all the reactions that can include both 3- and 5-(2-hydroxyaryl)pyrazoles, only the 3-isomer will be represented.…”

Section: Figure and Schemesmentioning

confidence: 99%

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Synthesis of Chromone-Related Pyrazole Compounds

Santos

Silva

2017

Molecules

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Chromones, six-membered oxygen heterocycles, and pyrazoles, five-membered two-adjacent-nitrogen-containing heterocycles, represent two important classes of biologically active compounds. Certain derivatives of these scaffolds play an important role in medicinal chemistry and have been extensively used as versatile building blocks in organic synthesis. In this context, we will discuss the most relevant advances on the chemistry that involves both chromone and pyrazole rings. The methods reviewed include the synthesis of chromone-pyrazole dyads, synthesis of chromone-pyrazole-fused compounds, and chromones as starting materials in the synthesis of 3(5)-(2-hydroxyaryl)pyrazoles, among others. This review will cover the literature on the chromone and pyrazole dual chemistry and their outcomes in the 21st century.

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Section: Chromones As Starting Materials In the Synthesis Of 3(5)-mentioning

confidence: 99%

Section: Chromones As Starting Materials In the Synthesis Of 3(5)-mentioning

confidence: 99%

Section: Figure and Schemesmentioning

confidence: 99%

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Synthesis of Chromone-Related Pyrazole Compounds

Santos

Silva

2017

Molecules

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“…A number of reports available on hybrid scaffolds based on thiazole linked with chromone scaffold with some biological potentials 22 – 25 . Nevertheless, there is no report available on this hybrid class for their α -amylase inhibitory activity.…”

Section: Introductionmentioning

confidence: 99%

New Hybrid Hydrazinyl Thiazole Substituted Chromones: As Potential α-Amylase Inhibitors and Radical (DPPH & ABTS) Scavengers

Salar

Khan

Chigurupati

et al. 2017

Sci Rep

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Current research is based on the identification of novel inhibitors of α-amylase enzyme. For that purpose, new hybrid molecules of hydrazinyl thiazole substituted chromones 5–27 were synthesized by multi-step reaction and fully characterized by various spectroscopic techniques such as EI-MS, HREI-MS, 1H-NMR and 13C-NMR. Stereochemistry of the iminic bond was confirmed by NOESY analysis of a representative molecule. All compounds 5–27 along with their intervening intermediates 1–4, were screened for in vitro α-amylase inhibitory, DPPH and ABTS radical scavenging activities. All compounds showed good inhibition potential in the range of IC50 = 2.186–3.405 µM as compared to standard acarbose having IC50 value of 1.9 ± 0.07 µM. It is worth mentioning that compounds were also demonstrated good DPPH (IC50 = 0.09–2.233 µM) and ABTS (IC50 = 0.584–3.738 µM) radical scavenging activities as compared to standard ascorbic acid having IC50 = 0.33 ± 0.18 µM for DPPH and IC50 = 0.53 ± 0.3 µM for ABTS radical scavenging activities. In addition to that cytotoxicity of the compounds were checked on NIH-3T3 mouse fibroblast cell line and found to be non-toxic. In silico studies were performed to rationalize the binding mode of compounds (ligands) with the active site of α-amylase enzyme.

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ChemInform Abstract: Synthesis and Biological Screening of Some Novel Thiazolyl Chromones and Pyrazoles.

Cited by 2 publications

References 0 publications

Synthesis of Chromone-Related Pyrazole Compounds

Synthesis of Chromone-Related Pyrazole Compounds

New Hybrid Hydrazinyl Thiazole Substituted Chromones: As Potential α-Amylase Inhibitors and Radical (DPPH & ABTS) Scavengers

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