Utility of amino acid coupled 1,2,4-triazoles in organic synthesis: synthesis of some new antileishmainal agents

Starting from 3-amino-5-(2-hydroxyphenyl) amino acid coupled triazoles 1a-e, new 3-(2-hydroxyphenyl)-3H-imidazo[2,1-c][1,2,4]triazol-6(5H)-one 2a,b, 3b,d, 6a and 3-N-arly(alkyl) amino acid coupled triazoles 4b,d, 7a,c,d,e have been synthesized as potential antileishmanial agents. The structures of the newly synthesized compounds were confirmed using elemental and spectral analyses (FT-IR, 1H-NMR, 13C-NMR and MS). The in vitro antileishmanial potency of the synthesized compounds was evaluated compared to Amphotericin B deoxycholate and miltefosine as lead references. Compounds 2b, 7d and 7e showed perfect IC50 values corresponding to amphotericin B and more patent than miltefosine against L. aethiopica promastigotes.               KEY WORDS: Amino acids, Coupled, Imidazo-1,2,4-Triazole, Promatigote, Antileishmanial Bull. Chem. Soc. Ethiop. 2018, 32(3), 559-570.DOI: https://dx.doi.org/10.4314/bcse.v32i3.1

Design, Synthesis and Antibacterial Evaluation of some new 3,5-Diphenylcyclohex-2-en-1-one Derivatives

The moiety of cyclohexene has been showed highly antibacterial activity. New compounds were synthesized from diphenylcyclohexenone via reaction with a variety of reagents to afford branched chain of 1,3-diphenylcyclohexene or fused heterocyclic systems including pyrazole, chromen and pyrrole derivatives. Cyclic ketoketene s,s-acetal can be prepared by reaction with CS2/MeI under PTC conditions which in turn used as starting material for the synthesis of pyrazolyl and benzothiszolyl derivatives. Most of new synthesized compounds were characterized by using spectral data and were screened for their antibacterial activity

Eco-Friendly Synthesis, Biological Evaluation, and In Silico Molecular Docking Approach of Some New Quinoline Derivatives as Potential Antioxidant and Antibacterial Agents

A new series of quinoline derivatives 5–12 were efficiently synthesized via one-pot multicomponent reaction (MCR) of resorcinol, aromatic aldehydes, β-ketoesters, and aliphatic/aromatic amines under solvent-free conditions. All products were obtained in excellent yields, pure at low-cost processing, and short time. The structures of all compounds were characterized by means of spectral and elemental analyses. In addition, all the synthesized compounds 5–12 were in vitro screened for their antioxidant and antibacterial activity. Moreover, in silico molecular docking studies of the new quinoline derivatives with the target enzymes, human NAD (P)H dehydrogenase (quinone 1) and DNA gyrase, were achieved to endorse their binding affinities and to understand ligand–enzyme possible intermolecular interactions. Compound 9 displayed promising antioxidant and antibacterial activity, as well as it was found to have the highest negative binding energy of -9.1 and -9.3 kcal/mol for human NAD (P)H dehydrogenase (quinone 1) and DNA gyrase, respectively. Further, it complied with the Lipinski’s rule of five, Veber, and Ghose. Therefore, the quinoline analogue 9 could be promising chemical scaffold for the development of future drug candidates as antioxidant and antibacterial agents

A-Alkenoyl Ketene S,S- and N,S-Acetals As Starting For Unexpected and Novel Synthesis of N-Heterocycles

A series of N-heterocycles such as diazaspiro-[4.5]decane,  pyrazolo[4,3-d][1,2]-diazepine, imidazo[3,2,1ij][1,8]naphthyridine derivatives or  pyrazolo[3,4-b]pyridin-4-ol were synthesized using a-alkenoyl-, a,a-dialkenoyl ketene-(S,S)-acetals 2a-d, 3a-c or a-dialkenoyl ketene-(N,S)-acetal 12 as starting materials. The biological activity of some new synthesized compounds have been investigated.&nbsp

Synthesis and Reactions of Five-Membered Heterocycles Using Phase Transfer Catalyst (PTC) Techniques

Phase transfer catalysts (PTCs) have been widely used for the synthesis of organic compounds particularly in both liquid-liquid and solid-liquid heterogeneous reaction mixtures. They are known to accelerate reaction rates by facilitating formation of interphase transfer of species and making reactions between reagents in two immiscible phases possible. Application of PTC instead of traditional technologies for industrial processes of organic synthesis provides substantial benefits for the environment. On the basis of numerous reports it is evident that phase-transfer catalysis is the most efficient way for generation and reactions of many active intermediates. In this review we report various uses of PTC in syntheses and reactions of five-membered heterocycles compounds and their multifused rings

Synthesis, Structural Stability Calculation, and Antibacterial Evaluation of Novel 3,5-Diphenylcyclohex-2-en-1-one Derivatives

<div><p></p><p>Starting with 3,5-diphenylcyclohex-2-en-1-one, 3,5-diphenylcyclohex-2-en-1-semicarbazone, 1-chloro-3,5-diphenylcyclohex-2-en-2-carbaldehyde, and 3,5-diphenylcyclohex-2-en-1-hydrazone were synthesized via the reactions with semicarbazide hydrochloride, POCl₃/ dimethylformamide, and hydrazine hydrate, respectively. These products were used as key intermediates for the preparation of novel series of tetrahydrobenzothiadiazol-1-oxide, indazole, benzo-thiazepines, pentahydroxyhexylidene and N-thiazines. Some of these derivatives exhibit high antibacterial activity against Gram-positive bacteria.</p></div