Related Experiment Video
Updated: Jun 12, 2026

Development of a Backbone Cyclic Peptide Library as Potential Antiparasitic Therapeutics Using Microwave Irradiation
Published on: January 26, 2016
Bicyclic Lactams From Chiral Imines: Synthesis, Structural Optimization, and Biological Evaluation of Promising
Siga Sagne1,2, Sandrine Cojean3,4, Ramata Ousmane Diallo1
1Laboratoire de Chimie et Physique des Matériaux (LCPM), Université Assane Seck de Ziguinchor, Ziguinchor, Senegal.
Abstract:
In this study, a bicyclic lactam derived from piperidine was synthesized via an asymmetric Michael reaction using a chiral imine 3. In addition, twenty-four nitrogen-modulated analogues were synthesized, including 20 benzylated (9a-k(S) and ent-9a-j(R)) and 4 acylated (12(S) and 13a-c(S)) derivatives. All compounds were evaluated for their antileishmanial activity against axenic and intramacrophage amastigotes of Leishmania major (cutaneous leishmaniasis) and L. donovani (visceral leishmaniasis). Several derivatives displayed potent activity with low toxicity toward macrophages and MRC-5 cell lines. Notably, compounds ent-9b (IC50 values of 0.33 and 0.78 μM against intramacrophage amastigote forms of L. major and L. donovani, respectively), ent-9d (IC50 = 0.69 and 1.12 μM), ent-9e (IC50 = 0.21 and 0.43 μM), ent-9h (IC50 = 0.68 and 1.54 μM), and 13b (IC50 = 0.97 and 0.88 μM) exhibited remarkable activity and favorable selectivity indices compared with the reference drug miltefosine (IC50 = 2.74 and 1.03 μM). Pharmacokinetic (ADME) analyses were conducted to assess their drug-likeness and identify promising candidates for further development. Ligand-based inverse virtual screening suggested L. major phosphodiesterase B1 and L. donovani cAMP-specific phosphodiesterase as potential molecular targets. These compounds represent promising leads for further development in the fight against leishmaniasis.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
11:04Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Related Concept Videos
Antiprotozoal Agents
Antifungal Agents
Prochirality
Basicity of Heterocyclic Aromatic Amines
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Amides to Amines: LiAlH4 Reduction
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.