Synthesis and biological activity of anabasine and cytisine derivatives of monothiooxamides

Indolizidine and quinolizidine alkaloids

“…113 The cytisinium salts of xylosyland glucosyl-benzyldithiocarbamic acids showed good in vitro fungicidal activity against Fusarium oxysporum. 114 Novel N(12)-substituted derivatives of cytisine include (b-chlorob-phenylvinyl)phosphinic esters, 115 monothiooxamides, 116 Npropargyl and related compounds 117 and, more exotically, numerous N-coumarinyloxyacetyl and furocoumarinalkanoyl derivatives. 118,119 The C-substituted cytisine derivatives 386 and 387, prepared for testing as agonists for neuronal nicotinic acetylcholine receptors (nAChRs), showed substantial increases in selectivity for the a4b2 over the a3b4 subtype (3000-fold and 900-fold, respectively) compared with cytisine itself.…”

Solanum Alkaloids and their Pharmaceutical Roles: A Review

“…Kulakov et al, 62 synthesised thiourea derivatives of anabasine and evaluated its antifungal and antibacterial properties. Parallely, Bakbardina et al, 63 chemically synthesised alkaloid anabasine and cytisine derivatives of monothiooxamides and determined its biological activity in terms of aphicidal and fungicidal properties. Anabasine showed strong insecticidal properties against Lepidopterous larvae (Pieris rapae larval bioassay).…”

Structure–Activity Relationship Investigations Of Leishmanicidal N‐Benzylcytisine Derivatives

“…This is achieved by either C3 halogenation of the pyridone ring or N‐substitution by residues that could modify and improve the lipophilicity of the parent alkaloid (9–12). Remarkably, as evidenced by literature survey, cytisine, N ‐methylcytisine, and some other related tricyclic quinolizidine alkaloids also showed good potential when subjected to the evaluation of their nematicidal, antimicrobial, antibiotic, insecticidal activity, and toxicity (13–17). However, as mentioned above, these early studies were mainly of an episodic nature, lacking systematic studies performed for the series of congeneric cytisine derivatives followed by in‐depth SAR discussion.…”