Molecules

136 KiB

Open AccessReview

Review of the Molecule of the Month Website in 1997

by Paul May

Molecules 1998, 3(1), 16-19; https://doi.org/10.3390/30100016 - 25 Jan 1999

Cited by 3 | Viewed by 8172

This review describes the history of the "Molecule of the Month" Website, along with a short summary of some of the molecules which featured during 1997. Full article

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28 KiB

Open AccessCommunication

Nucleophilic Additions of 2-Furyllithium to Carbonyl Derivatives of L-Serine. Formal Synthesis of (2R,3R)-β-Hydroxy Aspartic Acid

by P. Merino, S. Franco, F. L. Merchan and T. Tejero

Molecules 1998, 3(1), 26-30; https://doi.org/10.3390/30100026 - 25 Jan 1998

Cited by 3 | Viewed by 8651

Abstract

The nucleophilic addition of 2-furyllithium to esters derived from L-serine is described. The obtained furyl ketone 5 is stereoselectively reduced (ds≥95%) with sodium borohydride to afford the corresponding syn aminoalcohol 12 in enantiomerically pure form. Compound 12 was further converted into valuable α-hydroxy-β-amino [...] Read more.

The nucleophilic addition of 2-furyllithium to esters derived from L-serine is described. The obtained furyl ketone 5 is stereoselectively reduced (ds≥95%) with sodium borohydride to afford the corresponding syn aminoalcohol 12 in enantiomerically pure form. Compound 12 was further converted into valuable α-hydroxy-β-amino acids by means of the furan-to-acid equivalence. Full article

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45 KiB

Open AccessArticle

Synthesis and Biological Evaluation of 14 -Methoxy Digitalis Derivatives

by M. Gobbini, N. Almirante, A. Cerri, G. Padoani and P. Melloni

Molecules 1998, 3(1), 20-25; https://doi.org/10.3390/30100020 - 25 Jan 1998

Cited by 4 | Viewed by 8778

Abstract

The synthesis and biological evaluation of 14β-methoxy derivatives of digitoxigenin and of other digitalis-like compounds are reported. These compounds have a 14β-oxygen, which can be a hydrogen bonding acceptor, as is the case of 14β,15β-epoxide derivatives, but not a hydrogen bonding donor as [...] Read more.

The synthesis and biological evaluation of 14β-methoxy derivatives of digitoxigenin and of other digitalis-like compounds are reported. These compounds have a 14β-oxygen, which can be a hydrogen bonding acceptor, as is the case of 14β,15β-epoxide derivatives, but not a hydrogen bonding donor as is the case of 14β-hydroxy derivatives. All the new 14β-methoxy derivatives show a considerable reduced binding affinity on Na⁺,K⁺-ATPase when compared with the 14β-hydroxy analogues and also with the 14β,15β-epoxy derivatives. These results could mean that the digitalis receptor does not permit the presence of a bulky substituent in the 14β region, even of relatively small volume like the methyl group Full article

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150 KiB

Open AccessArticle

Synthesis and Intramolecular [4+2] Cycloaddition Reactions of 4-Pyridazinecarbonitriles with Alkyne Side Chains

by Günther Fülep and Norbert Haider

Molecules 1998, 3(1), 10-15; https://doi.org/10.3390/30100010 - 25 Jan 1998

Cited by 1 | Viewed by 7456

Abstract

The preparation of a series of new 3-(alkynyl-X)-substituted 4-pyridazinecarbonitriles 2-5 (X = O, NH) is described. The compounds are shown to undergo thermally induced intramolecular Diels-Alder reactions with inverse electron demand, affording the fused benzonitriles 6-8. Incorporation of a 1,2-phenylene unit into the [...] Read more.

The preparation of a series of new 3-(alkynyl-X)-substituted 4-pyridazinecarbonitriles 2-5 (X = O, NH) is described. The compounds are shown to undergo thermally induced intramolecular Diels-Alder reactions with inverse electron demand, affording the fused benzonitriles 6-8. Incorporation of a 1,2-phenylene unit into the side chain, as in the case of compounds 10 and 13, results in a more favorable conformation of the dienophilic substructure and thus to a pronounced acceleration of the [4+2] cycloaddition reaction. Full article

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