Synthesis of Acyclo-<i>C</i>-nucleosides in the Imidazo[1,2-<i>a</i>]pyridine and Pyrimidine Series as Antiviral Agents

A dialkylaminomethylation reaction (the Mannich reaction) of 3,4 bis(indol 1 yl) maleimides and 3 (indol 1 yl) 4 (indolin 1 yl)maleimides leads to mono and di(dimethyl amino) derivatives at position 3 of one or two indole rings. A series of 3,4 bis(indol 1 yl) maleimides and 3 (indol 1 yl) 4 (indolin 1 yl)maleimides containing ω hydroxyalkyloxy methyl substituents at position 3 of the indole ring was obtained by the reaction of iodomethyl ates of these compounds with ethylene glycol and other α,ω alkanediols. The reaction of quaternary salts of bis(3 dimethylaminomethylindol 1 yl)maleimides with α,ω alkanediols resulted in the isolation of 3,4 bis(3 ω hydroxyalkyloxymethylindol 1 yl)maleimides. Upon heating iodomethylate of 3 (3 dimethylaminoindol 1 yl) 4 (indolin 1 yl)maleimide in pyri dine, 5,6 dihydro 10 methyl 1H indolo [1´,7a´,7´:4,5,6]pyrrolo[3´,4´:2,3] [1,4]diazepino[1,7 a] indole 1,3(2H) dione was obtained due to the intramolecular alkylation and formation of the bond between position 2 of the indole and position 7 of the indoline rings.

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“…It should be noted that cyclization of maleimides 1a,b (6) Reagents and conditions: 1) MeI, THF; 2) R´H, pyridine, reflux.…”

Section: Compoundmentioning

confidence: 99%

Nucleophilic substitution and cyclization reactions involving quaternized 3-dimethylaminomethyl derivatives of 3,4-bis(indol-l-yl)maleimide and 3-(indol-l-yl)-4-(indolin-l-yl)maleimide

et al. 2010

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“…78 Some imidazo[1,2-a]pyridine and pyrimidine derivatives (52, 53) proved quite promising anti-HCMV and anti-VZV agents. 79 SAR studies de®ned the nature of the thioether side chain which must contain an aromatic cyclic ring. 80 The fact that they show selective activity against these two viruses suggests that they are preferentially metabolized by the virus infected cells and/or show particular af®nity for virus-speci®c enzymes.…”

Section: Nonnucleoside Hcmv Inhibitorsmentioning

confidence: 99%

Recent strategies in the development of new human cytomegalovirus inhibitors

Martı́nez¹,

Castro²,

Gil³

et al. 2001

Medicinal Research Reviews

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Human cytomegalovirus (HCMV) is one of the most common opportunistic infections in immunucompromised individuals, such as AIDS patients and organ transplant recipients, and is the most frequent congenital viral infection in humans. Despite a reduction of the incidence of AIDS‐related opportunistic infections in patients under highly active antiretroviral treatment, attention should be paid to the HCMV risk factor in these individuals. Furthermore, HCMV may have an important role in atherosclerosis. Existing antiviral treatments for the HCMV infection suffer from poor bioavailability, toxicity, and limited effectiveness, mainly due to the development of drug resistance. Fortunately there are novel and potentially very effective new compounds undergoing pre‐clinical and clinical evaluation. This review provides an overview in the last five years of new HCMV inhibitors (chemical structures, SAR, and new mechanisms of action) with the aim to provide new clues for the development of future drugs against this opportunistic virus. © 2001 John Wiley & Sons, Inc. Med Res Rev, 21, No. 3, 227–244, 2001

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“…Imidazo [1,2-a]pyrimidine structural moieties are important as benzodiazepine receptor agonists [2], antiviral agents [3], antibacterials [4], antifungal agents [5], and calcium channel blockers [6]. Significant effort has been devoted to new synthetic methods and chemical reactivities regarding these ring systems [7,8].…”

Section: Introductionmentioning

confidence: 99%

A rapid and efficient method for synthesis of pyrimido[1,2‐a]‐benzimidazole derivatives under microwave irradiation

Zhuang¹,

Li²,

Tu³

et al. 2008

Journal of Heterocyclic Chem

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Synthesis of Acyclo-C-nucleosides in the Imidazo[1,2-a]pyridine and Pyrimidine Series as Antiviral Agents

Abstract: The synthesis and the antiviral activities of C-3 acyclic nucleoside analogues of imidazo[1,2-a]pyridine and pyrimidine are reported. From these compounds, 20, 21, 22, 23, 28, and 34 showed a specific activity against cytomegalovirus and/or varicella-zoster virus.

Cited by 157 publications

References 15 publications

Nucleophilic substitution and cyclization reactions involving quaternized 3-dimethylaminomethyl derivatives of 3,4-bis(indol-l-yl)maleimide and 3-(indol-l-yl)-4-(indolin-l-yl)maleimide

Nucleophilic substitution and cyclization reactions involving quaternized 3-dimethylaminomethyl derivatives of 3,4-bis(indol-l-yl)maleimide and 3-(indol-l-yl)-4-(indolin-l-yl)maleimide

Recent strategies in the development of new human cytomegalovirus inhibitors

A rapid and efficient method for synthesis of pyrimido[1,2‐a]‐benzimidazole derivatives under microwave irradiation

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