Diastereoselective synthesis and molecular docking studies of novel fused tetrahydropyridine derivatives as new inhibitors of HIV protease

Abstract

An efficient one-pot, catalyst-free, and four-components procedure for the synthesis of novel 10b-hydroxy-4-nitro-5-phenyl-2,3,5,5a-tetrahydro-1H-imidazo[1,2-a]indeno[2,1-e]pyridin-6(10bH)one derivatives from corresponding diamine, nitro ketene dithioacetal, aldehydes and 1,3-indandione in ethanol has been achieved upon a Knoevenagel condensation-Michael addition-tautomerismcyclisation sequence. All the newly synthesized compounds were screened for molecular docking studies. Molecular docking studies were carried out using the crystal structure of HIV protease enzyme. Some of the compounds obtain minimum binding energy and good affinity toward the active pocket of HIV protease enzyme in compare with Saquinavir as a standard HIV protease inhibitor.

N-methyl pyridinium tosylate (NMPyTs) and Ultrasound Promoted One-Pot Multicomponent Synthesis of Highly Functionalized of Tetrahydropyridine Derivatives

“…Further, intermediate ( 6) is produced by an intermolecular Mannich-type reaction between β-enaminone (4) and imine (5) in presence of NMPyTs. Next, intermediate (6) undergoes condensation with a second molecule of aryl aldehyde 3 leading to another intermediate (7). Intermediate (7) tautomerizes to (8) which on subsequent intramolecular Mannich type reaction gave intermediate (9).…”

“…It is a building block in the synthesis of various organic compounds, such as drugs and agrochemicals. The tetrahydropyridine moiety is a critical component of many biologically active compounds, and the importance of these molecules, such as anti-cancer [4], anti-microbial [5], anti-malarial [6], anti-HIV protease inhibitory [7],…”

Photocatalytic activity of Rose Bengal encapsulated in zeolitic imidazolate framework-8 (RB@ZIF-8): an innovative approach for the one pot synthesis of highly functionalized tetrahydropyridines and study of their anti-tubercular activity

“…2). They show a broad spectrum of pharmaceutical activities such as anti-hypertensive, 34 anti-bacterial, anti-malarial, 35 anti-inflammatory, 36 anti-convulsant, 37 and anti-Alzheimer 38 effects, anti-microbial, 39 anti-depresant and analgesic, 40 anti-cancer, 41 anti-HIV, 42 etc . Because of their great significance in natural and synthetic drugs, various approaches had been put forward for their synthesis.…”

An Efficient One‐Pot Three‐Component Synthesis of Some New 3‐(Benzo[d]thiazol‐2‐yl)‐2‐alkyl‐4(3H)‐quinazolinones Using Silica Sulfuric Acid as a Heterogeneous Catalyst

“…While numerous MCCs have been devised, relatively few processes that result in the formation of two or more intermolecular carbon–carbon bonds are known. Recently, we have reported the preparation of 2‐aryl‐3‐(phenylamino)quinazolin‐4(3 H )‐one , quinazolinediones , tetrahydropyridine , and bis(quinazolinon‐4(1 H )‐one) via MCR. In addition, we have reported the ability of silica sulfuric acid (SSA) as an effective catalyst in the synthesis of cis ‐isoquinolonic acid , pyrrole , and oxindole .…”