190912-67-5Relevant academic research and scientific papers
On the Relocation of the Amino Functionality to the Ethyl Side Chain in Aminoglutethimide: Synthesis and Aromatase-inhibitory Activity of 3-(2′-N,N-Diethylamino)ethyl-3-phenylpiperidine-2,6-dione
Moniz, George A.,Hammond, Gerald B.
, p. 649 - 652 (1997)
Aminoglutethimide [3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione] has been used clinically in the treatment of metastatic breast carcinoma. Inhibition of tumor growth is due to interference with estrogen biosynthesis. However, its action is not specific and its metabolism gives rise to toxic and non-inhibitory metabolites. We sought to explore the impact of relocating the amino group in aminoglutethimide to the ethyl side chain. To that end, we now report the synthesis and aromatase-inhibitory activity of 3-(2′-N,N-diethylamino)ethyl-3-phenylpiperidine-2,6-dione 5. The introduction of the amino functionality on the ethyl group is accomplished via reductive amination of aldehyde 8, prepared in three steps from benzyl cyanide, The synthetic route presented can be used for the preparation of related derivatives of azninoglutethimide.
1-Phenylalkylpiperazines
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Page/Page column 25-26, (2010/02/06)
Described are novel 1-phenylalkylpiperazines having affinity for serotonergic receptors. These compounds and their enantiomers, diastereoisomers, N-piperazine oxides, polymorphs, solvates and pharmaceutically acceptable salts are useful in the treatment o
1-PHENYLALKYL-PIPERAZINES
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Page 50, (2010/02/04)
Compounds of formula (I) (R and R1 are a wide range of substituents, Q is CO, CHOH or CHOR2, R2 is alkyl, alkenyl, alkynyl or cycloalkyl group, each of which is optionally substituted, or is alkanoyl, alkanoyoxy, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl or dialkylaminothiocarbonyl, R3 is H, alkyl, -alkenyl, alkynyl, cycloalkyl, aryl or heterocyclic group, each of which is optionally substituted, n is 1 or 2, A is a bond or a methylene or ethylene group and R4 is an aryl or heteroaryl group, either of which is optionally substituted) have affinity for serotoninergic receptors. These compounds and their enantiomers, diastereoisomers, N-piperazine oxides, polymorphs, solvates and pharmaceutically acceptable salts are useful in the treatment of patients with neuromuscular dysfunction of the lower urinary tract and diseases related to 5-HT1A receptor activity.
