Abstract:These data further establish that rotamers of acyclic carbohydrate derivatives that involve an eclipsed 1,3 interaction between substituents are energetically disfavored, a situation that is generally alleviated by rotation about an internal carbon-carbon bond to a different, gauche rotamer (sickle form). The short (three carbon) chains are more prone to populate more than one conformational state to a substantial extent, whereas prolongation of the chain tends to cause the molecule to favor one conformation m… Show more
“…1-(1-Adamantylcarbonyl)-2-pyrrolidinone ( 24 ) was obtained from the reaction of 1-adamantanecarbonyl chloride with 1-(trimethylsilyl)-2-pyrrolidinone ( 23 ) . Dry distillation of the N -acylpyrrolidinone 24 in the presence of CaO − led to the 2-(1-adamantanyl)-1-pyrroline ( 25 ). Reduction of pyrroline 25 with NaBH 4 resulted in the 2-(1-adamantanyl)pyrrolidine ( 6a ), which was converted to the desired N -substituted derivatives 6b − d via suitable alkylations. 3 …”
The synthesis of some new aminoadamantane derivatives is described. The new compounds were evaluated against a wide range of viruses [influenza A H1N1, influenza A H2N2, influenza A H3N2, influenza B, parainfluenza 3, herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2), thymidine kinase-deficient (TK-) HSV-1, vaccinia, vesicular stomatitis, polio 1, Coxsackie B4, Sindbis, Semliki forest, Reo 1, varicella-zoster virus (VZV), TK- VZV, human cytomegalovirus (HCMV), and human immunodeficiency virus type 1 (HIV-1) and type 2 (HIV-2)]. Some of them proved markedly active against the influenza A H2N2 (compounds 4a,b, 5a, 6a, and 7a), H3N2 (compounds 5a, 6a, and 7a), and H1N1 (compounds 4b,c and 6d). Since compounds 5a, 6a, and 7a, amantadine, and rimantadine showed the same comparative pattern of potency against influenza strains H2N2, H3N2, and B, it may postulated that they act according to a similar mechanism, with regard to their "amine" effect, on the M2 ion channel of influenza A (H1N1, H2N2, or H3N2). In general, no significant activity was noted with any of the new compounds against any of the other viruses tested, making their activity against influenza virus more specific and striking. Borderline activity was noted with some of the compounds (4b,c, 5a-c, and 8a) against HIV-1.
“…1-(1-Adamantylcarbonyl)-2-pyrrolidinone ( 24 ) was obtained from the reaction of 1-adamantanecarbonyl chloride with 1-(trimethylsilyl)-2-pyrrolidinone ( 23 ) . Dry distillation of the N -acylpyrrolidinone 24 in the presence of CaO − led to the 2-(1-adamantanyl)-1-pyrroline ( 25 ). Reduction of pyrroline 25 with NaBH 4 resulted in the 2-(1-adamantanyl)pyrrolidine ( 6a ), which was converted to the desired N -substituted derivatives 6b − d via suitable alkylations. 3 …”
The synthesis of some new aminoadamantane derivatives is described. The new compounds were evaluated against a wide range of viruses [influenza A H1N1, influenza A H2N2, influenza A H3N2, influenza B, parainfluenza 3, herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2), thymidine kinase-deficient (TK-) HSV-1, vaccinia, vesicular stomatitis, polio 1, Coxsackie B4, Sindbis, Semliki forest, Reo 1, varicella-zoster virus (VZV), TK- VZV, human cytomegalovirus (HCMV), and human immunodeficiency virus type 1 (HIV-1) and type 2 (HIV-2)]. Some of them proved markedly active against the influenza A H2N2 (compounds 4a,b, 5a, 6a, and 7a), H3N2 (compounds 5a, 6a, and 7a), and H1N1 (compounds 4b,c and 6d). Since compounds 5a, 6a, and 7a, amantadine, and rimantadine showed the same comparative pattern of potency against influenza strains H2N2, H3N2, and B, it may postulated that they act according to a similar mechanism, with regard to their "amine" effect, on the M2 ion channel of influenza A (H1N1, H2N2, or H3N2). In general, no significant activity was noted with any of the new compounds against any of the other viruses tested, making their activity against influenza virus more specific and striking. Borderline activity was noted with some of the compounds (4b,c, 5a-c, and 8a) against HIV-1.
“…The bromination of isoquinoline is reported to give 4bromoisoquinoline under drastic conditions.4 A mechanism involving the addition of bromine followed by the elimination of hydrogen bromide has been postulated.5 The dibromide has eluded isolation and characterisation. l-Cyano-2-p-toluenesulfonyl-l,2-dihydroisoquinoline (1) was prepared according to the method described by Wefer, et ale The bromination of 1 took place readily to give l-cyano-3,4-cis-dibromo-2-p-toluenesulfonyl-l, 2,3,4tetrahydroisoquinoline (2), which could be isolated and characterized. The analytical values and the spectral data were in agreement with structure 2.…”
“…Myosmine is one of the alkaloids found in tobacco, and has been synthesized by different groups. [43][44][45] The amathaspiramides are a family of marine alkaloids containing a spirobicylic core consisting of pyrroline, pyrrolidine, or pyrrolidinone rings as well as a dibromomethoxyphenyl ring. 46 To date, only amathaspiramide F has been synthesized.…”
This work reviews the reactivity of oxazolones and their application in the synthesis of natural products. In particular, the focus is on the development and scope of oxazolone-mediated enetype reactions, 1,3-dipolar cycloadditions, and a novel Claisen-type rearrangement. The utility of these reactions towards natural product synthesis is described.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
