Hydrocarbon analogs of the type II photoeliminations of ketones. Photochemistry of 1-substituted 4-phenyl-4-pentenes

Hornback, Joseph M.; Proehl, Gary S.

doi:10.1021/ja00518a039

Cited by 10 publications

(1 citation statement)

References 7 publications

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“…Sir: Photocyclization via intramolecular hydrogen transfer (e.g., type II cyclization) is one of the most important reactions in the photochemistry of ketones,1 thioketones,2 and olefins.3 45Recently, intramolecular hydrogen-transfer reactions of olefins have received considerable attention. 3,4 In the case of acyclic olefins these reactions are quite inefficient, and the inefficiency has been attributed to the presence of competitive processes such as cis-trans isomerization.4 Thus, photocyclization of olefins via intramolecular hydrogen transfer has been limited to cyclic olefins.…”

Section: Communicationsmentioning

confidence: 99%

Epoxidation of 2,3-dimethyl-2-butene by 3-bromo-4,5-dihydro-5-hydroperoxy-4,4-dimethyl-3,5-diphenyl-3H-pyrazole

Baumstark¹,

Chrisope²,

Landis³

1981

J. Org. Chem.

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Section: Communicationsmentioning

confidence: 99%

Epoxidation of 2,3-dimethyl-2-butene by 3-bromo-4,5-dihydro-5-hydroperoxy-4,4-dimethyl-3,5-diphenyl-3H-pyrazole

Baumstark¹,

Chrisope²,

Landis³

1981

J. Org. Chem.

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ChemInform Abstract: HYDROCARBON ANALOGS OF THE TYPE II PHOTOELIMINATIONS OF KETONES. PHOTOCHEMISTRY OF 1‐SUBSTITUTED 4‐PHENYL‐4‐PENTENES

Hornback¹,

Proehl²

1980

Chemischer Informationsdienst

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A New Class of Inhibitors for the Metalloprotease Neprilysin Based on a Central Imidazole Scaffold

Sahli

Stump

Welti

et al. 2005

Helvetica Chimica Acta

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Neprilysin (NEP; neutral endopeptidase EC 3.4.24.11) is a Zn II -dependent, membrane-bound endopeptidase. NEP is widely distributed in the organs, particularly in the kidneys and lungs, and it is involved in the metabolism of a number of smaller regulatory peptides. Inhibition of NEP has been proposed as a potential target for analgesic and antihypertensive therapies. In this study, new nonpeptidic inhibitors of neprilysin ((AE)-1, (AE)-43, (AE)-45, and (AE)-46; Table) were designed, based on the X-ray crystal structure of NEP complexed to phosphoramidon (Fig. 1). They feature an imidazole ring as the central scaffold, acting as a peptide bond isoster to undergo H-bonding with the side chains of Asn542 and Arg717 (Fig. 2). The scaffold is decorated with a thiol group to ligate to the Zn II ion and two aromatic residues to bind into the hydrophobic S1' and S2' pockets. The synthesis of the new inhibitors was approached by two routes (Schemes 1 ± 4 and 5 ± 8), with the second one involving a double directed ortho-metallation of the imidazole platform and a Stille cross-coupling, providing the desired target molecules as hydrochloride salts. In a fluorescence assay, inhibitors (AE)-1, (AE)-43, (AE)-45, and (AE)-46 all exhibit IC 50 values in the single-digit micromolar activity range (2 ± 4 mm, Table), which validates the binding mode postulated by modeling. Useful guidelines for a next lead optimization cycle were obtained in several control runs.

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Hydrocarbon analogs of the type II photoeliminations of ketones. Photochemistry of 1-substituted 4-phenyl-4-pentenes

Cited by 10 publications

References 7 publications

Epoxidation of 2,3-dimethyl-2-butene by 3-bromo-4,5-dihydro-5-hydroperoxy-4,4-dimethyl-3,5-diphenyl-3H-pyrazole

Epoxidation of 2,3-dimethyl-2-butene by 3-bromo-4,5-dihydro-5-hydroperoxy-4,4-dimethyl-3,5-diphenyl-3H-pyrazole

ChemInform Abstract: HYDROCARBON ANALOGS OF THE TYPE II PHOTOELIMINATIONS OF KETONES. PHOTOCHEMISTRY OF 1‐SUBSTITUTED 4‐PHENYL‐4‐PENTENES

A New Class of Inhibitors for the Metalloprotease Neprilysin Based on a Central Imidazole Scaffold

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