Derivatives of imidazole. III. Synthesis and pharmacological activities of nitriles, amides, and carboxylic acid derivatives of imidazo[1,2-a]pyridine

Almirante, L; Mugnaini, A; Rugarli, P. L.; Gamba, A; Zefelippo, Enzo; Toma, Nicola De; Murmann, W

doi:10.1021/jm00301a031

Cited by 33 publications

(14 citation statements)

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“…Following the classical procedure for the preparation of imidazo[1,2-a]pyridines, 11) the cyclization of a-bromo-4-methylacetophenone 3 with methyl 2-aminopyridine-5-carboxylate 4 gave the imidazopyridine 5. Substitution on C-3 by a tert-butyl acetate group was completed with tert-butyl diazoacetate/Cu in toluene at reflux.…”

Section: Resultsmentioning

confidence: 99%

Major Metabolites of Zolpidem: Expeditious Synthesis and Mass Spectra

Klupsch

Houssin

Humbert³

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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An expeditious route to the two major metabolites of Zolpidem-and readily applicable to the synthesis of the drug-was established via a cyclization reaction between a 2-aminopyridine and a suitable a a-bromoacetophenone. The structures of the target compounds were confirmed from a 2D 1 H-15 N NMR correlation. Their mass spectra contribute to a reliable toxicological identification of the drug in the case of drug-facilitated crimes.

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Section: Resultsmentioning

confidence: 99%

Major Metabolites of Zolpidem: Expeditious Synthesis and Mass Spectra

Klupsch

Houssin

Humbert³

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Based upon structural features similarities and certain chemistry behavior resemblance of the imidazo[1,2-a]pyridine system with the indole nucleus, some investigators have proposed the synthesis and pharmacological evaluation of a number of indole acetic acid and indomethacin analogs (Almirante et al, 1968).…”

Section: Resultsmentioning

confidence: 99%

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

et al. 2011

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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 DG 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.

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“…Close analogs thereof are 2-phenylimidazo[1,2-a]pyridine derivatives [211][212][213]. This includes compound 18 in Fig.…”

Section: Peripheral Benzodiazepine Receptor Agonistsmentioning

confidence: 99%

Inhibition of Insulin Secretion as a New Drug Target in the Treatment of Metabolic Disorders

Hansen¹,

Arkhammar²,

Bödvarsdóttir³

et al. 2004

CMC

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The pattern of insulin release is crucial for regulation of glucose and lipid haemostasis. Deficient insulin release causes hyperglycemia and diabetes, whereas excessive insulin release can give rise to serious metabolic disorders, such as nesidioblastosis (Persistent Hyperinsulinemic Hypoglycemia of Infancy, PHHI) and might also be closely associated with development of type 2 diabetes and obesity. Type 2 diabetes is characterized by fasting hyperinsulinemia, insulin resistance and impaired insulin release, i.e. reduced first phase insulin release and decreased insulin pulse mass. The beta cell function of patients with type 2 diabetes slowly declines and will ultimately result in beta cell failure and increasing degrees of hyperglycemia. Type 2 diabetes, in combination with obesity and cardiovascular disorders, forms the metabolic syndrome. It has been possible to improve beta cell function and viability in preclinical models of type 1 and type 2 diabetes by reducing insulin secretion to induce beta cell rest. Clinical studies have furthermore indicated that inhibitors of insulin release will be of benefit in treatment or prevention of diabetes and obesity. Pancreatic beta cells secrete insulin in response to increased metabolism and by stimulation of different receptors. The energy status of the beta cell controls insulin release via regulation of open probability of the ATP sensitive potassium (K(ATP)) channels to affect membrane potential and the intracellular calcium concentration [Ca(2+)](i). Other membrane bound receptors and ion channels and intracellular targets that modulate [Ca(2+)](i)will affect insulin release. Thus, insulin release is regulated by e.g. somatostatin receptors, GLP-1 receptors, muscarinic receptors, cholecystokinin receptors and adrenergic receptors. Although the relationship between hyperinsulinemia and certain metabolic diseases has been known for decades, only a few inhibitors of insulin release have been characterized in vitro and in vivo. These include the K(ATP) channel openers diazoxide and NN414 and the somatostatin receptor agonist octreotide.

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Derivatives of imidazole. III. Synthesis and pharmacological activities of nitriles, amides, and carboxylic acid derivatives of imidazo[1,2-a]pyridine

Cited by 33 publications

References 0 publications

Major Metabolites of Zolpidem: Expeditious Synthesis and Mass Spectra

Major Metabolites of Zolpidem: Expeditious Synthesis and Mass Spectra

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

Inhibition of Insulin Secretion as a New Drug Target in the Treatment of Metabolic Disorders

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