Microwave assisted synthesis of naphthopyrans catalysed by silica supported fluoroboric acid as a new class of non purine xanthine oxidase inhibitors

Sahil Sharma; Kirti Sharma; Ritu Ojha; Dinesh Kumar; Gagandip Singh; Kunal Nepali; P. M.S. Bedi

doi:10.1016/j.bmcl.2013.12.031

Microwave assisted synthesis of naphthopyrans catalysed by silica supported fluoroboric acid as a new class of non purine xanthine oxidase inhibitors

Sahil Sharma, Kirti Sharma, Ritu Ojha, Dinesh Kumar, Gagandip Singh, Kunal Nepali, P. M.S. Bedi

Research output: Contribution to journal › Article › peer-review

50 Citations (Scopus)

Abstract

A series of naphthopyrans was synthesized employing silica supported fluoroboric acid under solvent free conditions in a microwave reactor. The catalytic influence of HBF₄-SiO₂ was investigated in detail to optimize the reaction conditions. The synthesised compounds were evaluated for in vitro xanthine oxidase inhibitory activity for the first time. Structure-activity relationship analyses have also been presented. Among the synthesised compounds, NP-17, NP-19, NP-20, NP-23, NP-24, NP-25 and NP-26 were the active inhibitors with an IC₅₀ ranging from 4 to 17 μM. Compound NP-19 with a thiophenyl ring at position 1 emerged as the most potent xanthine oxidase inhibitor (IC₅₀ = 4 μM) in comparison to allopurinol (IC₅₀ = 11.10 μM) and febuxostat (IC₅₀ = 0.025 μM). The basis of significant inhibition of xanthine oxidase by NP-19 was rationalized by its molecular docking at MTE binding site of xanthine oxidase.

Original language	English
Pages (from-to)	495-500
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	24
Issue number	2
DOIs	https://doi.org/10.1016/j.bmcl.2013.12.031
Publication status	Published - Jan 15 2014
Externally published	Yes

Keywords

Fluoroboric acid
Microwave
Naphthopyrans
Silica
Xanthine oxidase

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2013.12.031

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title = "Microwave assisted synthesis of naphthopyrans catalysed by silica supported fluoroboric acid as a new class of non purine xanthine oxidase inhibitors",

abstract = "A series of naphthopyrans was synthesized employing silica supported fluoroboric acid under solvent free conditions in a microwave reactor. The catalytic influence of HBF4-SiO2 was investigated in detail to optimize the reaction conditions. The synthesised compounds were evaluated for in vitro xanthine oxidase inhibitory activity for the first time. Structure-activity relationship analyses have also been presented. Among the synthesised compounds, NP-17, NP-19, NP-20, NP-23, NP-24, NP-25 and NP-26 were the active inhibitors with an IC50 ranging from 4 to 17 μM. Compound NP-19 with a thiophenyl ring at position 1 emerged as the most potent xanthine oxidase inhibitor (IC50 = 4 μM) in comparison to allopurinol (IC50 = 11.10 μM) and febuxostat (IC50 = 0.025 μM). The basis of significant inhibition of xanthine oxidase by NP-19 was rationalized by its molecular docking at MTE binding site of xanthine oxidase.",

keywords = "Fluoroboric acid, Microwave, Naphthopyrans, Silica, Xanthine oxidase",

author = "Sahil Sharma and Kirti Sharma and Ritu Ojha and Dinesh Kumar and Gagandip Singh and Kunal Nepali and Bedi, {P. M.S.}",

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AU - Sharma, Sahil

AU - Sharma, Kirti

AU - Ojha, Ritu

AU - Kumar, Dinesh

AU - Singh, Gagandip

AU - Nepali, Kunal

AU - Bedi, P. M.S.

PY - 2014/1/15

Y1 - 2014/1/15

N2 - A series of naphthopyrans was synthesized employing silica supported fluoroboric acid under solvent free conditions in a microwave reactor. The catalytic influence of HBF4-SiO2 was investigated in detail to optimize the reaction conditions. The synthesised compounds were evaluated for in vitro xanthine oxidase inhibitory activity for the first time. Structure-activity relationship analyses have also been presented. Among the synthesised compounds, NP-17, NP-19, NP-20, NP-23, NP-24, NP-25 and NP-26 were the active inhibitors with an IC50 ranging from 4 to 17 μM. Compound NP-19 with a thiophenyl ring at position 1 emerged as the most potent xanthine oxidase inhibitor (IC50 = 4 μM) in comparison to allopurinol (IC50 = 11.10 μM) and febuxostat (IC50 = 0.025 μM). The basis of significant inhibition of xanthine oxidase by NP-19 was rationalized by its molecular docking at MTE binding site of xanthine oxidase.

AB - A series of naphthopyrans was synthesized employing silica supported fluoroboric acid under solvent free conditions in a microwave reactor. The catalytic influence of HBF4-SiO2 was investigated in detail to optimize the reaction conditions. The synthesised compounds were evaluated for in vitro xanthine oxidase inhibitory activity for the first time. Structure-activity relationship analyses have also been presented. Among the synthesised compounds, NP-17, NP-19, NP-20, NP-23, NP-24, NP-25 and NP-26 were the active inhibitors with an IC50 ranging from 4 to 17 μM. Compound NP-19 with a thiophenyl ring at position 1 emerged as the most potent xanthine oxidase inhibitor (IC50 = 4 μM) in comparison to allopurinol (IC50 = 11.10 μM) and febuxostat (IC50 = 0.025 μM). The basis of significant inhibition of xanthine oxidase by NP-19 was rationalized by its molecular docking at MTE binding site of xanthine oxidase.

KW - Fluoroboric acid

KW - Microwave

KW - Naphthopyrans

KW - Silica

KW - Xanthine oxidase

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Microwave assisted synthesis of naphthopyrans catalysed by silica supported fluoroboric acid as a new class of non purine xanthine oxidase inhibitors

Abstract

Keywords

ASJC Scopus subject areas

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