Derivatives of Imidazole. I. Synthesis and Reactions of Imidazo[1,2-α]pyridines with Analgesic, Antiinflammatory, Antipyretic, and Anticonvulsant Activity

Almirante, L; Polo, Luigi; Mugnaini, A; Provinciali, E; Rugarli, P. L.; Biancotti, Adriana; Gamba, A; Murmann, W

doi:10.1021/jm00327a007

Cited by 295 publications

(159 citation statements)

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“…One compound afforded protection against strychnine convulsions, while several of the compounds protected somewhat against electroshock and/or pentamethylenetetrazole seizures. Almirante et al (4) concluded that while interesting pharmacological activity had been uncovered, no satisfactory structure-activity relationships could be formulated, Further, they noted that none of these compounds was as active as the previously reported imidazo(l,2-a)-pyridines (5).…”

Section: Pharmacological Resultsmentioning

confidence: 98%

“…of crude product) and gave 1.17 g. (52.1% yield) of fine, emerald-green needles melting at 223.5-224.5 ' . (4).…”

Section: Methodsmentioning

confidence: 99%

“…Direct recrystallization of the free base from isopropyl alcohol also proved superior to literature procedures. 4 Neutralization of the reaction mixture with base, as would be customary when aqueous hydrochloric acid serves as the reaction solvent, resulted in loss of the nitroso group in early experiments. The use of aqueous acetic acid as the reaction solvent circumvents the necessity of adding base prior to filtration.…”

Section: Synthesis Of 3-nitroso-2-phenylimidazo(l2-a)pyrimidine (Com-mentioning

confidence: 99%

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Synthesis and Characterization of Some 3-Nitroso-2-arylimidazo (1,2-α) pyrimidines

Larocca

Gibson

Thompson³

1971

Journal of Pharmaceutical Sciences

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Section: Pharmacological Resultsmentioning

confidence: 98%

“…of crude product) and gave 1.17 g. (52.1% yield) of fine, emerald-green needles melting at 223.5-224.5 ' . (4).…”

Section: Methodsmentioning

confidence: 99%

Section: Synthesis Of 3-nitroso-2-phenylimidazo(l2-a)pyrimidine (Com-mentioning

confidence: 99%

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Synthesis and Characterization of Some 3-Nitroso-2-arylimidazo (1,2-α) pyrimidines

Larocca

Gibson

Thompson³

1971

Journal of Pharmaceutical Sciences

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“…Organic compounds containing the imidazo[1,2-a]-pyridine ring system have been shown to possess a broad range of useful pharmacological activities, including antibacterial, 1 antifungal, 2 anthelmintic, 3 antiviral, 4 antiprotozoal, 5 anti-inflammatory, 6 anticonvulsant, 7 anxiolytic (Alpidem), hypnotic (Zolpidem), 8 antiulcer (Zolmidine), 7 and immunomodulatory (Kifunensine) activities. 9 They have also been shown to be selective cyclin dependant kinase inhibitors, 10 GABA and benzodiazepine receptor antagonists, 11 and bradykinin B 2 receptor antagonists.…”

Section: Introductionmentioning

confidence: 99%

Tin(II) Chloride Dihydrate Catalyzed Groebke Condensation: An Efficient Protocol for the Synthesis of 3‐Aminoimidazo[1,2‐a]pyridines

Shaabani¹,

Soleimani²,

Sarvary³

et al. 2009

Chin. J. Chem.

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The ability of tin(II) chloride dihydrate as a catalyst to promote the three-component condensation reaction from a diversity of aromatic aldehydes, 2-aminopyridines and isonitriles at room temperature is described. This methodology affords a number of 3-aminoimidazo[1,2-a]pyridines in the presence of tin(II) chloride dihydrate as a new and mild Lewis acid catalyst in the multi-component reaction in reasonable yields and short reaction time without any significant optimization of the reaction conditions.

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“…6) As a result, numerous two-and three-component approaches for their synthesis have been reported. [7][8][9][10][11][12][13][14] Biopolymers, especially cellulose and its derivatives, 15) have some unique properties, which make them attractive alternatives for conventional organic or inorganic supports for catalytic applications.…”

mentioning

confidence: 99%

Cellulose Sulfuric Acid Catalyzed One-Pot Three-Component Synthesis of Imidazoazines

Shaabani

Maleki

Rad

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Imidazoazines have been synthesized by a one-pot three-component condensation reaction of an aldehyde, a 2-aminoazine and an isocyanide in the presence of the cellulose sulfuric acid, as an effective bio-supported catalyst in excellent yields. The reaction work-up is simple and the catalyst can be easily separated from the product and reused in several times.Key words cellulose sulfuric acid; bio-supported catalyst; imidazo[1,2-a]pyridine; isocyanide; multi-component reaction Imidazo[1,2-a]pyridines, as an important class of versatile pharmaceutically and biologically active compounds spanning applications in anti-inflammatory 1,2) and antibacterial agents, 3) inhibitors of gastric acids secretion, 4) calcium channel blockers, 5) and antiulcer based therapies. 6) As a result, numerous two-and three-component approaches for their synthesis have been reported. [7][8][9][10][11][12][13][14] Biopolymers, especially cellulose and its derivatives, 15) have some unique properties, which make them attractive alternatives for conventional organic or inorganic supports for catalytic applications. Among others, they are extremely inert, inexpensive, biodegradable and environmentally benign allowing various reaction conditions to be employed. Cellulose is the most abundant natural material in the world and it has been widely studied during the past decades because it is a biodegradable material and a renewable resource.In recent years, the emphasis of science and technology is shifting more towards environmentally friendly and sustainable resources and processes; in this regard, biopolymers are attractive candidates to explore for supported catalysis. 16,17) Several interesting biopolymers for example alginate, 18) gelatin, 19,20) starch 21) and chistosan 22) derivatives have been utilized as a support for catalytic applications.During the course of our studies on the development of new routes for the synthesis of organic compounds using solid acid catalysts in organic transformations [23][24][25][26][27] and our interest in isocyanide-based MCRs, [28][29][30][31] we developed the synthesis of imidazoazines 4a-j via the three-component condensation of an aldehyde 1, a 2-aminoazine 2 and an isocyanide 3 in the presence of catalytic amount of cellulose sulfuric acid at room temperature (Chart 1). ExperimentalApparatus Melting points were measured on an Electrothermal 9100 apparatus and are uncorrected. The elemental analyses were performed with an Elementar Analysensysteme GmbH VarioEL. Mass spectra were recorded on a FINNIGAN-MAT 8430 mass spectrometer operating at an ionization potential of 70 eV. IR spectra were recorded on a Shimadzu IR-470 spectrometer.1 H-and 13 C-NMR spectra were recorded on a BRUKER DRX-300 AVANCE spectrometer at 300.13 and 75.47 MHz, respectively. All the products (except 4g) are known compounds, which were identified by IR and 1 H-NMR spectral data and comparing their melting points with literature reports.Preparation of Cellulose Sulfuric Acid To a magnetically stirred mixture of 5.00 g of cellulos...

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Derivatives of Imidazole. I. Synthesis and Reactions of Imidazo[1,2-α]pyridines with Analgesic, Antiinflammatory, Antipyretic, and Anticonvulsant Activity

Cited by 295 publications

References 0 publications

Synthesis and Characterization of Some 3-Nitroso-2-arylimidazo (1,2-α) pyrimidines

Synthesis and Characterization of Some 3-Nitroso-2-arylimidazo (1,2-α) pyrimidines

Tin(II) Chloride Dihydrate Catalyzed Groebke Condensation: An Efficient Protocol for the Synthesis of 3‐Aminoimidazo[1,2‐a]pyridines

Cellulose Sulfuric Acid Catalyzed One-Pot Three-Component Synthesis of Imidazoazines

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