Synthesis of N-Acylamino-Acid Derivatives of Cytisine

Semisynthesis of novel N‐acyl/sulfonyl derivatives of 5(3,5)‐(di)halogenocytisines/cytisine and their pesticidal activities against Mythimna separata Walker, Tetranychus cinnabarinus Boisduval, and Sitobion avenae Fabricius

“…), isolated from plants of the family Leguminosae, is a prevalent quinolizidine alkaloid. Cytisine and its derivatives exhibit a variety of biological properties such as antineoplastic, anti‐inflammatory and nootropic activity, they are agonists of α4β2 nicotinic acetylcholine receptors, inhibitors of hydroxysteroid 17‐β‐dehydrogenase‐4, inhibitors of the menin–mixed lineage leukemia (MLL) interaction, and show insecticidal activity . However, we previously investigated halogenation of the E‐ring of podophyllotoxins and prepared a series of 4α‐acyloxy‐2′(2′,6′)‐(di)halogenopodophyllotoxins ( I , Fig.…”

“…Cytisine and its derivatives exhibit a variety of biological properties such as antineoplastic, anti-inflammatory and nootropic activity, they are agonists of 4 2 nicotinic acetylcholine receptors, inhibitors of hydroxysteroid 17--dehydrogenase-4, inhibitors of the menin-mixed lineage leukemia (MLL) interaction, and show insecticidal activity. [17][18][19][20][21][22][23][24][25] However, we previously investigated halogenation of the E-ring of podophyllotoxins and prepared a series of 4 -acyloxy-2 ′ (2 ′ ,6 ′ )-(di)halogenopodophyllotoxins (I, Fig. 1), 26 2 -chloro-4 -acyloxy-2 ′ (2 ′ ,6 ′ )-(di)halogenopicropodophyllotoxins (II, Fig.…”

Synthesis of N-Arylcytisine Derivatives Using the Copper-Catalyzed Chan-Lam Coupling

“…31 N 3 -Acylcytisines are another small group, including sulfonyl-, carbamyl-, and thiocarbamyl derivatives, and N 3 -acyl amino-acid derivatives have been reported reacting cytisine with methyl esters of amino-acid isocyanates. 32 N 3 -Aryl cytisine derivatives are quite rare, prepared either via nucleophilic substitution on electron-deficient aromatics 33−37 or more recently by constructing the benzene ring bonded to nitrogen using two different approaches: a multicomponent reaction to obtain the 3-methoxycarbonyl-5-phenyl derivative and a photochemical dehydrogenative methodology to obtain the p-methylphenyl derivative (Scheme 1). 38,39 In addition, some N-alkyl reduced cytisine derivatives are of interest as chiral ligands in asymmetric deprotonations and racemate resolution acting as (+)-sparteine surrogates.…”