Natural products as templates for bioactive compound libraries. 3*. novel heterocycles and peptidomimetics generated from anabasine by isocyanide-based multicomponent reactions

Diastereoselective Ugi reaction of chiral 1,3-aminoalcohols derived from an organocatalytic Mannich reaction

“…From the point of view of atom- and step-economy, the use of chiral amines that are retained in the final products will be more valuable [27]. In this case they are not "chiral auxiliaries" and are not removed after the multicomponent reaction, and they contribute to the diversity of the final products.…”

The Groebke‐Blackburn‐Bienaymé Reaction

“…Overview of GBB catalysts that performed best in reported catalyst screenings (single hits were omitted for clarification). TiO 2 NPs (nanopowders) [170] TMSCl 7 [37,38,53,152,155,169,176] ZnO NPs [116] Montmorillonite K-10 clay 6 [19,64,65,70,121,192] Methanesulfonic acid [52] Magnesium chloride (MgCl 2 ) 5 [134,136,193,194] Zeolite HY [195] Ytterbium triflate (Yb(OTf) 3 ) 4 HCl dioxane 4 [72,73,84,117] Bromodimethylsulfonium bromide (BDMS) [69] Indium triflate (In(OTf) 3 ) 3 [108,109,122] γ-Fe 2 O 3 @SiO 2 -OSO 3 H [71] Trifluoroacetic acid (TFA) 2 [82,165] Cationic polyurethane dispersions (CPUDs) [76] Bismuth chloride (BiCl 3 ) 2 [81,91] pTsCl [77] Silica sulfuric acid 2 [126,148] Iodine [135] Lanthanum chloride (LaCl 3 •7H 2 O) 2 [92,104] (TBBDA) [83] Piperidine 2 [162,163] (PBBS)…”

“…Targeting this family of neurotransmission receptors could lead to drugs for the treatment of associated with PD, AD, schizophrenia and depression. [176] The five GBB-3CR products were synthesized in low to moderate yields 20-53 %, employing various isocyanides, modified anabasine 2-aminopyridine and substituted benzaldehydes in MeCN, 70°C using an stoichiometric amount of TMSCl as Lewis acid promoter (Scheme 33). The use of a alkynylbenzaldehydes 83 in the GBB-3CR allows for post modifications such as metal catalyzed intramolecular cyclization yielding a library of compounds, some with strong cytotoxicity against the HeLa cell line, due to binding affinity with the G-quadruplex DNA motif, thus exhibiting anti-proliferative activity as described by Shen et al [206] The cyclization to the tricyclic compounds, such as 84, was performed in a domino one pot approach of the Yb(OTf ) 3 catalyzed GBB-3CR between 2-aminopyridines, isocyanides and 2-alkynylbenzaldehyde followed by a AgOTf catalyzed intramolecular cyclization (Scheme 34).…”

Novel approach to the design of potential bioactive alkaloid anabasine conjugates using click chemistry methodology

“…During last three decades, the search for type‐selective ligands for nAChRs is very intensive and particular attention in this field is directed on pyridine alkaloid anabasine and its derivatives. By now, a great deal of functionalized anabasine derivatives are synthesized and majority of them possess biological activity . However, the search for therapy of socially significant mental illnesses, such as Alzheimer's disease, is still in progress, and therefore, the development of synthetic approaches to novel anabasine derivatives is of high importance and actuality.…”

“…By now, a great deal of functionalized anabasine derivatives are synthesized and majority of them possess biological activity. [7][8][9] However, the search for therapy of socially significant mental illnesses, such as Alzheimer's disease, is still in progress, and therefore, the development of synthetic approaches to novel anabasine derivatives is of high importance and actuality.…”