Crystal Structure of a Rearranged Cage Compound, 3-Hydroxy-4-aza-8-oxoheptacyclo [9.4.1.02,10.03,14.04,9.09,13.012,15]tetradecane

Prins, Louis H.A.; Vries, Armand de; Caira, Mino R.; Oliver, Douglas W.; Dyk, Sandra van; Malan, Sarel F.

doi:10.1007/s10870-008-9381-3

Cited by 3 publications

(3 citation statements)

References 7 publications

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“…Another class of stable hemiaminals constitute modified hydrocarbon polycyclic cages such as trishomocubane derivatives [21,22,23,24,25,26]. These compounds are interesting because of their biological activity such as modulation of cocaine-induced effects [21], inhibition of nitric oxide synthase [24] and improving of blood-brain barrier permeability for some non-steroidal anti-inflammatory drugs [23].…”

Section: Introductionmentioning

confidence: 99%

Stable Hemiaminals with a Cyano Group and a Triazole Ring

2014

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Under neutral conditions the reactions between 4-amino-1,2,4-triazole and cyano-substituted benzaldehyde derivatives yield stable hemiaminals. Addition of small amounts of acid catalyst promotes further step of dehydration resulting in formation of Schiff bases. Four new hemiaminals and the corresponding imines have been obtained. The molecular stability of the hemiaminal intermediates results from both the 1,2,4-triazole moiety and electron withdrawing substituents on the phenyl ring, so no further stabilisation by intramolecular interaction is required. Hemiaminal molecules possess stereogenic centres on carbon and nitrogen atoms. The chirality of these centres is strongly correlated with the conformation of the molecules due to heteroatom hyperconjugation effects.

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Section: Introductionmentioning

confidence: 99%

Stable Hemiaminals with a Cyano Group and a Triazole Ring

2014

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“…In order to obtain the ester prodrugs (2, 3), a tetradecane cage structure (1) was synthesised [15] and conjugated to acetylsalicylic acid and ibuprofen, respectively. Amantadine.HCl (4), a well known anti-Parkinsonian agent, was used to synthesise the amide prodrugs (5, 6) of the selected NSAIDs.…”

Section: Chemistrymentioning

confidence: 99%

“…A rearranged cage alcohol (1) was synthesised in order to effectively esterificate the relevant NSAIDs to the polycyclic cage (Scheme 1) [15]. Activation chemistry using N-(3-dimethylaminopropyl)-N 0 -ethylcarbodiimide hydrochloride (EDC.HCl), yielded the ester prodrugs of acetylsalicylic acid (2) and ibuprofen (3).…”

Section: Synthesismentioning

confidence: 99%