14135-70-7Relevant academic research and scientific papers
Biologically Active Compounds through Catalysis: Efficient Synthesis of N-(Heteroarylcarbonyl)-N′-(arylalkyl)piperazines
Kumar, Kamal,Michalik, Dirk,Castro, Ivette Garcia,Tillack, Annegret,Zapf, Alexander,Arlt, Michael,Heinrich, Timo,Boettcher, Henning,Beller, Matthias
, p. 746 - 757 (2007/10/03)
A practical route for the synthesis of new biologically active 5-HT 2A receptor antagonists has been developed. In only three catalytic steps, this class of central nervous system (CNS) active compounds can be synthesized efficiently with high diversity. As the initial step, an anti-Markovnikov addition of amines to styrenes provides an easy route to N-(arylalkyl)piperazines, which constitute the core structure of the active molecules. Here, base-catalyzed hydroamination reactions of styrenes with benzylated piperazine proceeded in high yield even at room temperature. After catalytic debenzylation, the free amines were successfully carbonylated with different aromatic and heteroaromatic halides and carbon monoxide to yield the desired compounds in good to excellent yields. The two key reactions, base-catalyzed hydroamination of styrenes and palladium-catalyzed aminocarbonylation of haloarenes/heterocycles, showed tolerance towards various functional groups, thereby demonstrating the potential to synthesize a wide variety of new derivatives of this promising class of pharmaceuticals.
SYNTHESIS OF 4-METHOXYPHENOXYACETIC AND 3,4,5-TRIMETHOXYPHENOXYACETIC ACID AMIDES AND HYDRAZIDES AS POTENTIAL NEUROTROPIC AND CARDIOVASCULAR AGENTS
Valenta, Vladimir,Holubek, Jiri,Svatek, Emil,Protiva, Miroslav
, p. 3013 - 3023 (2007/10/02)
4-Methoxyphenoxyacetyl chloride, 3,4,5-trimethoxyphenoxyacetic acid and its methyl ester were reacted with 2-phenylethylamine, 1-benzylpiperazine, 1-(2-phenylethyl)piperazine, 1-(1-phenyl-2-propyl)piperazine, isopropylhydrazine, 1-aminopiperidine, and 4-aminomorpholine and afforded the amides and hydrazides Iab-IVab and Vb-VIIIb. 1-Amino-4-methylpiperazine and 1-amino-4-phenylpiperazine were transformed to the hydrazones XV and XVI, and to the quaternary salts XVII and XVIII.Pharmacological screening showed indications of thymoleptic acitivity with compounds Ia-IIIa, anorectic effect with IIa and IIIb, antiarrhytmic activity with IIIa, XVII, and XVIII, and myorelaxant effect with XVII and XVIII.Antimicrobial and anthelmintic effects were also noted.
