ChemInform Abstract: STUDIES ON THE SYNTHESIS OF SOME 1‐(P‐FLUOROPHENYL)‐1‐PYRID‐2′‐YLBUTYLAMINES

Schliemann, Willibald; Buege, A.; Reppel, L

doi:10.1002/chin.198025227

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“…Also for the preparation of piperazinyl derivatives 8 and 9 , two different strategies were employed. In the first route (Scheme ), 1-(2-chloroethyl)piperazine 30 and 1-(3-chloropropyl)piperazine 31 (as bishydrochloride salts) were joined to 15 by use of triethylamine in N , N ‘-dimethylformamide to furnish the intermediates 32 and 33 , respectively. Only for the latter compound ( 33 ) did the reaction with silver nitrate in the standard conditions furnish the nitro ester ( 9 ) in a good yield, while for derivative 32 the reaction with silver nitrate did not furnish the desired product ( 8 ), due to a probable intramolecular S N 2 reaction of the chloroethylamino moiety, with the generation of a chemically reactive species (an aziridinium ion) corresponding to compound 34 (Scheme ).…”

Section: Chemistrymentioning

confidence: 99%

Synthesis of Nitro Esters of Prednisolone, New Compounds Combining Pharmacological Properties of Both Glucocorticoids and Nitric Oxide

et al. 2003

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Glucocorticoids (GC) are widely used in therapy for their many pharmacological properties including antiinflammatory and immunosuppressive actions. However, their use over long periods is hampered by a number of severe side effects. Given the biological properties of nitric oxide (NO) and previous experience with nonsteroidal antiinflammatory agents, we synthesized new chemical entities combining both NO and GC properties. Here we report the synthesis of nitro esters of prednisolone obtained through the esterification, with different linkers, on the hydroxy group at C-21 position of the corticosteroid structure. The alkyl chain, as of the nitrooxy derivative (2), or aromatic linkers, as of o-, m-, and p-nitrooxymethylbenzoate derivatives (3-5), respectively, furnish stable compounds that release NO and inhibit the GC receptors in biological assays. To improve solubility we introduced a more water-soluble linker such as the nitrooxyalkylpiperidine or -piperazine group (6-9). Also these compounds retained properties of both NO and prednisolone. Compound 5 (NCX 1015) was selected for its better profile: enhanced antiinflammatory properties and reduced side effects compared with prednisolone. NCX 1015 is currently under preclinical development.

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Section: Chemistrymentioning

confidence: 99%

Synthesis of Nitro Esters of Prednisolone, New Compounds Combining Pharmacological Properties of Both Glucocorticoids and Nitric Oxide

et al. 2003

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ChemInform Abstract: STUDIES ON THE SYNTHESIS OF SOME 1‐(P‐FLUOROPHENYL)‐1‐PYRID‐2′‐YLBUTYLAMINES

Abstract: Auf verschiedenen Wegen wird die Synthese von p‐Fluorbenzylpyridin (IIIa) durchgeführt, wobei die Darstellung aus Fluorbenzol (I) und dessen Chlormethylierung zu (II) sowie anschließende Umsetzung mit Pyridinhydrochlorid am günstigsten ist.

Cited by 1 publication

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Synthesis of Nitro Esters of Prednisolone, New Compounds Combining Pharmacological Properties of Both Glucocorticoids and Nitric Oxide

Synthesis of Nitro Esters of Prednisolone, New Compounds Combining Pharmacological Properties of Both Glucocorticoids and Nitric Oxide

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