Use of <i>N</i>‐Methylpiperazine for the Preparation of Piperazine‐Based Unsymmetrical Bis‐Ureas as Anti‐HIV Agents

El‐Faham, Ayman; Armand‐Ugón, Mercedes; Esté, José A.; Alberício, Fernando

doi:10.1002/cmdc.200800059

Cited by 10 publications

(3 citation statements)

References 31 publications

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“…The drugs that contain imidazopyridine moiety such as zolimidine, saripidem, alpidem, necopidem, GSK812397 and zolpidem (Figure ) were clinically used, while piperazine moieties are significant pharmacophores in chemotherapy among various heterocycles for their various biological activities . Therefore, in the preset work we designed a novel series of imidazopyridine derivatives to investigate their anticancer activity against various cancer cell lines.…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Piperazine‐Linked Imidazo[1,2‐a]pyridine Derivatives as Potent Anticancer Agents

et al. 2019

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Designed, synthesized a series of novel imidazo[1,2-a]pyridine derivatives and evaluated for their in vitro cytotoxicity. Fluorine containing compounds, (2-fluorophenyl)(4-(2-(pyridin-2-yl)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)methanone (7 e),(4-(2-(pyridin-2-yl)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)(2-(trifluoromethyl)phenyl)methanone (7 h) and (3-fluorophenyl) (4-(2-(pyridin-2-yl)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)methanone (7 i) were found to have an effective cytotoxic profile against HepG2, HeLa and MDA-MB-231. Compounds 7 h (IC 50 = 5.8 μM) and 7 i (IC 50 = 3.5 μM) were found potent when compared with control Paclitaxel (IC 50 = 2.8 μM), against HeLa. Compound 7 h also found to be potent against HepG2 (IC 50 = 2.0 μM) and MDAMB-231(IC 50 = 6.9 μM) respectively, when compared with Paclitaxel (HepG2, IC 50 = 0.56 μM; MDAMB-231, IC 50 = 1.9 μM). Compound 7 e also found to be potent against HepG2 (IC 50 = 9.8 μM) cell lines. Synthesized piperazine linked imidazo[1,2-a]pyridine derivatives (7 i, IC 50 = 3.5 μM) and (7 h, IC 50 = 5.8 μM) showed 1.74 fold, 1.12 fold increase in antiproliferative activity than reported homopiperazine linked imidazo [1,2-a]pyrimidine derivatives (4-Fluorophenyl)(4-(2-(4fluorophenyl)imidazo[1,2-a]pyrimidin-7-yl)-1,4-diazepan-1-yl)methanone(10 f, IC 50 = 6.12 μM) and (4-(2-(4-Fluorophenyl)imidazo[1,2-a]pyrimidin-7-yl)-1,4-diazepan-1-yl)(3methoxyphenyl)methanone (12, IC 50 = 6.54 μM) against Hela cell lines. Molecular docking studies showed that designed compounds occupy at the active site of both colchicine and human estrogen receptor which demonstrated that the designed compounds were able to bind with multiple targets, the biological activity of these compounds hold promise to find application in considering for treatment protocol.[a] M.

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Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Piperazine‐Linked Imidazo[1,2‐a]pyridine Derivatives as Potent Anticancer Agents

et al. 2019

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“…Our first objective was to prepare the immonium salt shown in Figure , which contained an N- methylpiperazine moiety. However, during the preparation of this compound a side reaction took place, which led to unsymmetrical bis-ureas, which were found to have anti-HIV properties …”

Section: From Carbodiimide To Aminium Salts: the Importance Of 1-hydr...mentioning

confidence: 99%

“…However, during the preparation of this compound a side reaction took place, which led to unsymmetrical bis-ureas, which were found to have anti-HIV properties. 58 Next, we prepared new coupling reagents, including a morpholine moiety with HOBt, Cl-HOBt, and HOAt (Figure 8). 59 In all cases, the presence of the oxygen atom in the carbocation moiety conferred greater solubility to the reagent when compared with the tetramethyl derivatives (HXTU series).…”

Section: ■ Introductionmentioning

confidence: 99%

Choosing the Right Coupling Reagent for Peptides: A Twenty-Five-Year Journey

Alberício

El‐Faham

2018

Org. Process Res. Dev.

Self Cite

128

109

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This work is not a typical review that is trying to cover all coupling reagents in-depth. This is a personal accountit is written in the first personseeking to summarize the 25 years of collaboration that has brought the release of several products onto the market, together with strategies for the efficient synthesis of peptides and also other molecules of biological interest, broadly adopted by the scientific community.

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Bidirectional Effect of Triphala on Modulating Gut‐Brain Axis to Improve Cognition in the Murine Model of Alzheimer's Disease

Upadhyay,

Tyagi,

Agrawal

et al. 2023

Molecular Nutrition Food Res

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ScopeThe emerging role of gut microbiota and their metabolites in the modulation of the gut‐brain axis has received much attention as a new hope for the treatment of hard‐to‐treat chronic neurodegenerative diseases like Alzheimer's disease. The naturally occurring polyphenols can restore the gut‐brain axis by modulating gut microbiota and brain neurotransmitters. The Indian traditional medicine Triphala, a rich source of polyphenols, has been used on humans based on Prakriti or disease conditions for many years.Methods and resultsIn this study, the dual mode (morning and evening) action of Triphala is used to provide scientific evidence of its superior preventive and therapeutic efficacy in C57BL/6 and 5xFAD, APP/PS1 transgenic mouse model of Alzheimer's disease. The study observes that Triphala treatment has significantly improved cognitive function, by modulating the APP pathway, reducing inflammation, and restoring the gut‐brain axis by increasing the gut microbiota phyla of Bacteroides, Proteobacteria, Actinobacteria, etc., involved in maintaining the gut homeostasis.ConclusionsThe study paves a new path for using dual modes of Triphala alone or in combination to treat incurable AD.

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Use of N‐Methylpiperazine for the Preparation of Piperazine‐Based Unsymmetrical Bis‐Ureas as Anti‐HIV Agents

Cited by 10 publications

References 31 publications

Design and Synthesis of Piperazine‐Linked Imidazo[1,2‐a]pyridine Derivatives as Potent Anticancer Agents

Design and Synthesis of Piperazine‐Linked Imidazo[1,2‐a]pyridine Derivatives as Potent Anticancer Agents

Choosing the Right Coupling Reagent for Peptides: A Twenty-Five-Year Journey

Bidirectional Effect of Triphala on Modulating Gut‐Brain Axis to Improve Cognition in the Murine Model of Alzheimer's Disease

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