Solvent-free mechanochemical modification of lappaconitine and piroxicam

Solvent-free mechanochemical modification of lappaconitine and piroxicam Full article

Journal

Materials and Manufacturing Processes
ISSN: 1042-6914

Output data

Year: 2008, Volume: 23, Number: 6, Pages: 561-565 Pages count : 5 DOI: 10.1080/10426910802157870

Tags

lappaconitine N(20)-oxide; lappaconitine; mechanochemistry; N(20) deethyllappaconitine; piroxicam 4-nitrobenzoate; piroxicam; solvent-free synthesis

Authors

Pankrushina N. ^1,2 , Nikitina I. ^1,2 , Chernjak E. ¹ , Myz C. ^2,3 , Shakhtshneider T. ^2,3 , Boldyrev V. ^2,3

Affiliations

1	(Данные Web of science) Novosibirsk Organ Chem Inst, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Mol Design & Ecologically Safe Technol Res & Educ, Novosibirsk 630090, Russia
3	(Данные Web of science) Inst Solid State Chem & Mechanochem, Novosibirsk, Russia

A mechanochemical procedure of ball milling was applied to a solvent-free synthesis of natural alkaloid lappaconitine derivatives. A mixture of purely solid lappaconitine and 3-Cl-perbenzoic acid reacted to give lappaconitine N(20)-oxide with a good isolated yield (57percnt after workup). The ball milling of solid lappaconitine and N-bromosuccinimide affords N(20)-deethyllappaconitine with an acceptable (42percnt) yield. The mechanochemical approach was also applied for acylation of the anti-inflammatory drug piroxicam to improve its therapeutical properties. Consequently piroxicam 4-nitrobenzoate was obtained under the solvent-free reaction conditions with a moderate yield as a result of mechanical activation of the reaction between piroxicam and 4-nitrobenzoyl chloride in the presence of the aluminum oxide impregnated with thriethylamine. The reaction mixtures were analyzed after ball milling by HPLC in the proposed conditions.

Pankrushina N. , Nikitina I. , Chernjak E. , Myz C. , Shakhtshneider T. , Boldyrev V.
Solvent-free mechanochemical modification of lappaconitine and piroxicam
Materials and Manufacturing Processes. 2008. V.23. N6. P.561-565. DOI: 10.1080/10426910802157870 WOS Scopus РИНЦ

Published print:

Jul 4, 2008

Web of science	WOS:000257472500005
Scopus	2-s2.0-47049113642
Elibrary	13579281
OpenAlex	W2062113238