Study of alkaloids of the Siberian and Altai flora 14. Synthesis of alkaloid-based tertiary N-(3-arylprop-2-ynyl)amines

Abstract

3 Arylprop 2 ynylamines containing the key fragment of known alkaloids of the Altai flora were synthesized by the Sonogashira and Mannich reactions.

Identification of Novel Human Dipeptidyl Peptidase-IV Inhibitors of Natural Origin (Part II): In Silico Prediction in Antidiabetic Extracts

“…These compounds are (+)-pseudoephedrine (CAS number 90-82-4) and (−)-ephedrine (CAS number 299-42-3), and both have also been reported to have hypoglycemic activity [33] . Both molecules are found in several Ephedra species ( Ephedra alata [34] , Ephedra distachya [35] , Ephedra equisetina [36] , Ephedra gerardiana [35] , Ephedra shennungiana [37] , Ephedra sinica , Ephedra vulgaris and Ephedra pflanze ). However, Ephedra distachya and Ephedra alata are the only species reported to have antidiabetic properties [33] , [38] ; therefore, we proposed that the remaining Ephedra species may be new sources of antidiabetic extracts.…”

An Efficient Access to 3,5‐Disubstituted Isoxazoles with Anthranilate Ester Moiety: Alkaloid Lappaconitine – Aryl Conjugates with an Isoxazole Linker

“…For providing a most powerful approach to compound 4 by limited number of reaction steps, we assumed that two‐step Pd‐catalyzed Sonogashira coupling and subsequent addition of hydroxylamine could be carried out in a one‐pot manner. By Sonogashira reaction of methyl N‐acetyl‐5‐ethynylantranilate 7 [26] with 4‐methoxybenzoyl chloride 8 a in benzene for 2 h (TLC‐control), evaporation the solvent and subsequent reaction of the crude alkynone with hydroxylamine hydrochloride in MeCN in the presence of a base we were able to obtained compound 4 in the yield 69% (Table 1, Entry 8).…”

Design, Synthesis and Antibacterial Activity of Coumarin-1,2,3-triazole Hybrids Obtained from Natural Furocoumarin Peucedanin

“…Peucedanin ( 1 ) was isolated from Peucedanum morisonii according to [31]. Peuruthenicin ( 2 ) [32], umbelliferone carboxylic acid 3 [19], azidobenzoic acids 7а – с [33], methyl ether of 9-aminopelargonic acid hydrochloride [34], D,L-2-aminobutyric acid and L-phenylalanine hydrochlorides [35], methyl 2-(prop-2-ynylamino)butanoate ( 14 ), and ( S )-methyl 3-phenyl-2-(prop-2-ynylamino)propanoate ( 15 ) [36], methyl ethynylantranilate ( 23 ) [37] and 2-azidooreoselone ( 35 ) [14] were synthesized according to published procedures. Solvents (CH 2 Cl 2 , CHCl 3 , MeCN, DMF, THF, benzene, dioxane) and Et 3 N were purified by standard methods and distilled under a stream of argon just before use.…”