Docking simulations, synthesis, and anti-inflammatory activity evaluation of 2-(N-alkyl)amino-3-nitroimidazo[1,2-a]pyridines

Yazmín K. Márquez-Flores; Ma Elena Campos-Aldrete; Héctor Salgado-Zamora; José Correa-Basurto; Ma Estela Meléndez-Camargo

doi:10.1007/s00044-011-9585-5

Docking simulations, synthesis, and anti-inflammatory activity evaluation of 2-(N-alkyl)amino-3-nitroimidazo[1,2-a]pyridines

Yazmín K. Márquez-Flores, Ma Elena Campos-Aldrete, Héctor Salgado-Zamora, José Correa-Basurto, Ma Estela Meléndez-Camargo

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

21 Scopus citations

Abstract

A set of imidazo[1,2-a]pyridine derivatives was submitted to a docking analysis on COX-1 and COX-2. Although most of the compounds showed affinity for both COX-1 and COX-2, compound 1h showed a higher COX-1 affinity while 1i was more selective to COX-2. None of them had ΔG value higher than indomethacin. Compounds 1b, 1c, and 1g were synthesized and evaluated as potential anti-inflammatory agents. Compound 2-(N-cyclopropyl) amino-3-nitroimidazo[1,2-a]pyridine (1c) which gave a very poor affinity for either COX-1 or COX-2, showed anti-inflammatory activity (20 mg/kg) on the cotton pellet granuloma bioassay, with no induction of gastrointestinal damage.

Original language	English
Pages (from-to)	775-782
Number of pages	8
Journal	Medicinal Chemistry Research
Volume	21
Issue number	6
DOIs	https://doi.org/10.1007/s00044-011-9585-5
State	Published - Jun 2012

Keywords

Anti-inflammatory
Cyclooxygenase
Docking
Imidazo[1,2-a]pyridines

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title = "Docking simulations, synthesis, and anti-inflammatory activity evaluation of 2-(N-alkyl)amino-3-nitroimidazo[1,2-a]pyridines",

abstract = "A set of imidazo[1,2-a]pyridine derivatives was submitted to a docking analysis on COX-1 and COX-2. Although most of the compounds showed affinity for both COX-1 and COX-2, compound 1h showed a higher COX-1 affinity while 1i was more selective to COX-2. None of them had ΔG value higher than indomethacin. Compounds 1b, 1c, and 1g were synthesized and evaluated as potential anti-inflammatory agents. Compound 2-(N-cyclopropyl) amino-3-nitroimidazo[1,2-a]pyridine (1c) which gave a very poor affinity for either COX-1 or COX-2, showed anti-inflammatory activity (20 mg/kg) on the cotton pellet granuloma bioassay, with no induction of gastrointestinal damage.",

keywords = "Anti-inflammatory, Cyclooxygenase, Docking, Imidazo[1,2-a]pyridines",

author = "M{\'a}rquez-Flores, {Yazm{\'i}n K.} and Campos-Aldrete, {Ma Elena} and H{\'e}ctor Salgado-Zamora and Jos{\'e} Correa-Basurto and Mel{\'e}ndez-Camargo, {Ma Estela}",

note = "Funding Information: Acknowledgment This study was partially supported by the Sec-retar{\'i}a de Investigaci{\'o}n y de Posgrado, COFAA, (IPN). ICyTDF and CONACYT Grant No. 49937, 62488, 91426.",

year = "2012",

month = jun,

doi = "10.1007/s00044-011-9585-5",

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volume = "21",

pages = "775--782",

journal = "Medicinal Chemistry Research",

issn = "1054-2523",

number = "6",

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T1 - Docking simulations, synthesis, and anti-inflammatory activity evaluation of 2-(N-alkyl)amino-3-nitroimidazo[1,2-a]pyridines

AU - Márquez-Flores, Yazmín K.

AU - Campos-Aldrete, Ma Elena

AU - Salgado-Zamora, Héctor

AU - Correa-Basurto, José

AU - Meléndez-Camargo, Ma Estela

N1 - Funding Information: Acknowledgment This study was partially supported by the Sec-retaría de Investigación y de Posgrado, COFAA, (IPN). ICyTDF and CONACYT Grant No. 49937, 62488, 91426.

PY - 2012/6

Y1 - 2012/6

N2 - A set of imidazo[1,2-a]pyridine derivatives was submitted to a docking analysis on COX-1 and COX-2. Although most of the compounds showed affinity for both COX-1 and COX-2, compound 1h showed a higher COX-1 affinity while 1i was more selective to COX-2. None of them had ΔG value higher than indomethacin. Compounds 1b, 1c, and 1g were synthesized and evaluated as potential anti-inflammatory agents. Compound 2-(N-cyclopropyl) amino-3-nitroimidazo[1,2-a]pyridine (1c) which gave a very poor affinity for either COX-1 or COX-2, showed anti-inflammatory activity (20 mg/kg) on the cotton pellet granuloma bioassay, with no induction of gastrointestinal damage.

AB - A set of imidazo[1,2-a]pyridine derivatives was submitted to a docking analysis on COX-1 and COX-2. Although most of the compounds showed affinity for both COX-1 and COX-2, compound 1h showed a higher COX-1 affinity while 1i was more selective to COX-2. None of them had ΔG value higher than indomethacin. Compounds 1b, 1c, and 1g were synthesized and evaluated as potential anti-inflammatory agents. Compound 2-(N-cyclopropyl) amino-3-nitroimidazo[1,2-a]pyridine (1c) which gave a very poor affinity for either COX-1 or COX-2, showed anti-inflammatory activity (20 mg/kg) on the cotton pellet granuloma bioassay, with no induction of gastrointestinal damage.

KW - Anti-inflammatory

KW - Cyclooxygenase

KW - Docking

KW - Imidazo[1,2-a]pyridines

UR - http://www.scopus.com/inward/record.url?scp=84861918771&partnerID=8YFLogxK

U2 - 10.1007/s00044-011-9585-5

DO - 10.1007/s00044-011-9585-5

M3 - Artículo

SN - 1054-2523

VL - 21

SP - 775

EP - 782

JO - Medicinal Chemistry Research

JF - Medicinal Chemistry Research

IS - 6

ER -

Docking simulations, synthesis, and anti-inflammatory activity evaluation of 2-(N-alkyl)amino-3-nitroimidazo[1,2-a]pyridines

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