Synthesis and antiviral activities of adamantane spiro compounds. 1. Adamantane and analogous spiro-3'-pyrrolidines

Lundahl, K.; Schut, J.; Schlatmann, J. L. M. A.; Paerels, G. B.; Peters, A.

doi:10.1021/jm00272a003

Cited by 103 publications

(49 citation statements)

References 5 publications

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“…25 Compound 1 was previously used as the precursor in the synthesis of adamantane-based α-amino acid, (adamant-2-yl)glycine, and it is also known as a precursor of adamantane spiro-3'-pyrrolidines which show antiviral acitivities. 18 The crystal structure of ethyl adamant-2-ylidenecyanoacetate (1) was determined and is described in this paper for the first time.…”

Section: Resultsmentioning

confidence: 99%

An Efficient Synthesis of Novel Adamantane β-Amino Acid: 2-(Adamant-2-yl)-3-aminopropanoic Acid

Peroković¹,

Ribić²,

Prugovečki³

et al. 2012

Croat. Chem. Acta

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Abstract. Novel adamantane-containing β-amino acid, 2-(adamant-2-yl)-3-aminopropanoic acid, interesting from the aspect of medicinal chemistry, was prepared and characterized. It was synthesized in a sequence of three steps with very good overall yield. In the first step ethyl adamant-2-ylidenecyanoacetate was prepared and its crystal structure was determined. Reduction of this unsaturated cyanoacetate by catalytic hydrogenation gave the ethyl ester of the desired amino acid. 2-(Adamant-2-yl)-3-aminopropanoic acid was obtained following ester hydrolysis. (doi: 10.5562/cca2122)

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Section: Resultsmentioning

confidence: 99%

An Efficient Synthesis of Novel Adamantane β-Amino Acid: 2-(Adamant-2-yl)-3-aminopropanoic Acid

Peroković¹,

Ribić²,

Prugovečki³

et al. 2012

Croat. Chem. Acta

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“…In a field where so little has been achieved, the study of chemically allied substances in an attempt to define structure-activity relationships seems to be worth a special effort. This has recently proved possible because of the synthesis of a number of new adamantanes (15), and the one which we have described in this paper, a spiroadamantane, is one of the most active and is appreciably more potent than 1-amino adamantane hydrochloride.…”

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confidence: 90%

“…One of these is 1-aminoadamantane hydrochloride (amantadine), which has been shown to be partly effective in influenza A infections of man (10,19,22,25). As a consequence, a number of secondarily substituted adamantanes have now been produced for a study of structure-activity relationships (15). A compound, 1'-methyl spiro (adamantane-2, 3-pyrrolidine) maleate (1: 1) ( Fig.…”

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confidence: 99%

In Vitro Antiviral Activity and Preliminary Clinical Trials of a New Adamantane Compound

Mathur

Beare

Reed

1973

Antimicrob Agents Chemother

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A compound, 1′-methyl spiro (adamantane-2,3′-pyrrolidine) maleate, chemically related to the antiviral drug amantadine, was tested for activity in vitro against a number of human respiratory viruses. By a variety of techniques, it was shown to be active against a wide range of human and animal influenza A viruses. The effect was, however, variable and ranged from high activity against two 1957 Asian strains to no observable activity against a 1971 strain. Like amantadine, the drug did not inhibit the growth of influenza B viruses. It was also inactive against a number of paramyxoviruses. Unlike amantadine, the drug did inhibit rhinoviruses, but to a lesser extent than myxoviruses. The coronavirus 229E was also sensitive to the action of the drug in vitro. Although an earlier trial in volunteers showed that, when given orally from 2 days before until 5 days after virus challenge, the drug was protective against infection with influenza A/Hong Kong/68 virus, a similar trial in volunteers challenged with rhinoviruses 2 and 9 revealed no useful activity against rhinoviruses in man.

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“…The research was conducted to investigate the availability of different C–H bonds in the homoadamantane skeleton for the homolytic activation, that is, abstraction by the phthalimide. The research was, furthermore, sparked by the discovery that numerous poly-azaheterocyclic adamantane derivatives show antiviral activity [53–55]. Thus, photoproducts derived from 5 may also exhibit antiviral activity, although that is yet to be substantiated.…”

Section: Introductionmentioning

confidence: 99%

Photoinduced homolytic C–H activation inN-(4-homoadamantyl)phthalimide

Cindro¹,

Horvat²,

Mlinarić‐Majerski³

et al. 2011

Beilstein J. Org. Chem.

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Summary N-(4-homoadamantyl)phthalimide (5) on excitation and population of the triplet excited state underwent intramolecular H-abstractions and gave products 6 and 7. The major product, exo-alcohol 6 was a result of the regioselective δ H-abstraction and the stereoselective cyclization of the 1,5-biradical. Minor products 7 were formed by photoinduced γ H-abstractions, followed by ring closure to azetidinols and ring enlargement to azepinediones. The observed selectivity to exo-alcohol 6 was explained by the conformation of 5 and the best orientation and the availability of the δ-H for the abstraction.

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Synthesis and antiviral activities of adamantane spiro compounds. 1. Adamantane and analogous spiro-3'-pyrrolidines

Cited by 103 publications

References 5 publications

An Efficient Synthesis of Novel Adamantane β-Amino Acid: 2-(Adamant-2-yl)-3-aminopropanoic Acid

An Efficient Synthesis of Novel Adamantane β-Amino Acid: 2-(Adamant-2-yl)-3-aminopropanoic Acid

In Vitro Antiviral Activity and Preliminary Clinical Trials of a New Adamantane Compound

Photoinduced homolytic C–H activation inN-(4-homoadamantyl)phthalimide

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