Structural analogs of umifenovir 2*. The synthesis and antiHIV activity study of new regioisomeric (trans-2-phenylcyclopropyl)-1Н-indole derivatives

Schols, Dominique; Ручко, Е. А.; Лавренов, С. Н.; Качала, В. В.; Nawrozkij, M. B.; Babushkin, A. S.

doi:10.1007/s10593-016-1807-9

Cited by 12 publications

(4 citation statements)

References 13 publications

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“…As umifenovir analogs have been reported to possess a broad-spectrum antiviral activity, the conformationally restricted structural analogs of umifenovir are studied and their anti-HIV activity is evaluated using umifenovir and rac-MC-1501 as reference compounds. 41 Cyclopropyl phenyl analogs have demonstrated stronger anti-HIV activity compared to umifenovir but the activity is inferior compared to rac-MC-1501. The presence of the cyclopropyl phenyl motif at the indole 2-position in compound 37 (Fig.…”

Section: Hiv Inhibitorsmentioning

confidence: 99%

Indole – a promising pharmacophore in recent antiviral drug discovery

Dorababu¹

2020

RSC Med. Chem.

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Section: Hiv Inhibitorsmentioning

confidence: 99%

Indole – a promising pharmacophore in recent antiviral drug discovery

Dorababu¹

2020

RSC Med. Chem.

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“…Especially, reactions of N-aryl-substituted enaminoesters at low temperatures are known to generate 6-hydroxyindoles [41]. O-acylated 4,5-dihydroxyindoles are Besides 5-hydroxyindoles and benzofurans, a diverse range of alternative reaction products, including 6-hydroxyindoles [32][33][34], O-acylated 4,5-dihydroxyindoles [33,[35][36][37][38], pyrroloindoles [39], furo [2,3-f ]benzofurans [40], and dimeric indoles [35], have been isolated (Scheme 2). Moreover, 6-hydroxyindoles are formed in the so-called 'anti-Nenitzescu reaction' which occurs via a 1,2-addition followed by an intramolecular Michael addition [15,23].…”

Section: Introductionmentioning

confidence: 99%

“…Especially, reactions of N-aryl-substituted enaminoesters at low temperatures are known to generate 6-hydroxyindoles [41]. O-acylated 4,5-dihydroxyindoles are com-mon (by)products in acetic or propanoic acid [33,[35][36][37][38], and are formed by the nucleophilic attack of the carboxylate on 5-hydroxyindole intermediate I4 [33,[35][36][37][38]. Pyrroloindoles and furo [2,3-f ]benzofurans derive from the addition of a second enamine to enamino quinone I2 or hemiaminal I3 and have been isolated from the reaction of N-substituted enamines with p-benzoquinone [39,40,42].…”

Section: Introductionmentioning

confidence: 99%

Exploration of the Divergent Outcomes for the Nenitzescu Reaction of Piperazinone Enaminoesters

et al. 2023

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The Nenitzescu reaction is a condensation reaction between an enamine and a quinone, which can give rise to a wide variety of reaction products depending on the nature of the starting material and the reaction conditions. The most commonly observed products are 5-hydroxyindoles and 5-hydroxybenzofurans. Both classes are of interest since they are known to possess a variety of promising bioactivities. Despite the high chemodivergency for this reaction, it remains an interesting synthetic strategy thanks to the mild reaction conditions, easily accessible starting materials and simple reaction procedures. For these reasons, our research group investigated the Nenitzescu reaction of piperazinone enaminoesters, resulting in the unexpected formation of rearranged 2-imidazolidinone benzofurans. In this work, we aimed to develop reaction conditions that favor the formation of 5-hydroxyindoles via an extensive, multivariate optimization study. This led to valuable insights into the parameters that influence regio- and chemoselectivity. Furthermore, two novel products were obtained, a pyrrolo[2,3-f]indole and a benzofuranone, both of which are rarely reported in the literature.

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“…It belongs to the category of fusion inhibitors. [1][2][3][4] It inhibits membrane fusion and prevents contact between virus and target host cells. [5,6] Annapurna et al established stability indicting ultrafast liquid chromatographic (LC) method for the determination of UMI in tablets [7] and Wang et al identified the metabolites present in human urine with the help of fragmentation patterns with LC-mass spectrometry LC-MS. [8] In the present study, the authors have developed a validated LC method for the quantification of UMI in the presence of Eplerenone as internal standard (IS).…”

Section: Introductionmentioning

confidence: 99%

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Narendra¹

2018

AJP

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Introduction:A new liquid chromatographic method has been developed for the determination of Arbidol in capsules. Arbidol is the brand name for the anti-viral drug Umifenovir. Umifenovir is used for the treatment for influenza infections. Materials and Methods: SHIMADZU HPLC system with Agilent column (150 mm × 4.6 mm i.d., 3.5 µm particle size) was used for the chromatographic study of Umifenovir on isocratic mode. A mixture of 10 mM tetra butyl ammonium hydrogen sulphate and acetonitrile (50: 50, v/v) was used as mobile phase with flow rate 0.8 mL/min. for the chromatographic separation of Umifenovir. PDA detector was used (UV detection: at 223 nm) and the total run time was 10 mins. Results and Discussion: Umifenovir has obeyed Beer-Lambert's law 0.5-50 µg/mL with correlation coefficient 0.9999. The LOD and LOQ are found to be 0.1581 µg/mL and 0.4829 µg/mL respectively. Conclusions: The method is simple, precise and accurate and can be used for the determination of Umifenovir. The method was validated as per ICH guidelines.

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Structural analogs of umifenovir 2*. The synthesis and antiHIV activity study of new regioisomeric (trans-2-phenylcyclopropyl)-1Н-indole derivatives

Cited by 12 publications

References 13 publications

Indole – a promising pharmacophore in recent antiviral drug discovery

Indole – a promising pharmacophore in recent antiviral drug discovery

Exploration of the Divergent Outcomes for the Nenitzescu Reaction of Piperazinone Enaminoesters

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