Anti-human immunodeficiency activity of novel 2-arylpyrrolidine analogs

Martirosyan, A. O.; Gasparyan, S. P.; Alexanyan, M. V.; Harutyunyan, G.; Panosyan, Henry A.; Schinazi, Raymond F.

doi:10.1007/s00044-016-1731-7

Cited by 7 publications

(7 citation statements)

References 9 publications

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“…Such enantio-enriched b-alkylamine-containing pyrrolidines have great potential for applications in asymmetric synthesis and medicinal chemistry. [56][57][58][59][60][61][62]…”

Section: The Bigger Picturementioning

confidence: 99%

“…The structure of 7 is the core component of many biologically active compounds ( Figure S2). [56][57][58][59][60]73 Pyrrolidine tethered with a tertiary amine moiety has been widely used as powerful organocatalysts. 61,62,[74][75][76][77][78] To further demonstrate the potential of the resulting a-tertiary pyrrolidine-derived diamine as organocatalyst, the asymmetric Michael reaction of b-nitrostyrene with propionaldehyde was investigated as a model reaction.…”

Section: Transformation and Applicationmentioning

confidence: 99%

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Catalytic Asymmetric Radical Diamination of Alkenes

Wang

Dong

Lin

et al. 2017

Chem

125

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Liu and colleagues describe the asymmetric radical diamination of alkenes triggered by intermolecular addition of dialkylaminyl or azidyl radical to the alkene under Cu(I)/chiral phosphoric acid dual catalysis. This reaction enables direct incorporation of alkylamine moieties and provides convenient and practical access to a wide range of highly enantio-enriched b-alkylamine-containing pyrrolidines. Moreover, the resulting a-tertiary pyrrolidine-derived diamine proves to significantly promote the enantioselectivity of an asymmetric Michael reaction.

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“…Such enantio-enriched b-alkylamine-containing pyrrolidines have great potential for applications in asymmetric synthesis and medicinal chemistry. [56][57][58][59][60][61][62]…”

Section: The Bigger Picturementioning

confidence: 99%

Section: Transformation and Applicationmentioning

confidence: 99%

Catalytic Asymmetric Radical Diamination of Alkenes

Wang

Dong

Lin

et al. 2017

Chem

125

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“…By acylation, corresponding 2-aryl-2-(arylamino acetonitriles with 3-chloropropanoyl chloride and further intramolecular cyclization under phase transfer catalytic conditions were prepared 1,2-diaryl substituted pyrrolidine carbonitriles 1a-j (Fig. 2) [17][18][19][20][21].…”

Section: Resultsmentioning

confidence: 99%

“…Different substituted pyrrolidine carbonitriles were reduced to corresponding aminomethyl pyrrolidines 2a-g according to the method developed by us, using NaBH 4 / PEG-400/ CoCl 2 system [19,21]. The pyrrolidine carboxamides 3a and 3b were synthesized from corresponding pyrrolidine carbonitriles via reaction with conc.…”

Section: Resultsmentioning

confidence: 99%

Design, antihuman immunodeficiency activity and molecular docking studies of synthesized 2-aryl and 2-pyrimidinyl pyrrolidines

et al. 2020

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A series of thirty-one new compounds were synthesized and evaluated for their anti-HIV-1 and cytotoxicity activity. Of these, twelve were found to be inhibitors of HIV replications in primary human lymphocytes with median effective concentration (EC 50 ) values < 20 μM. However, most of the compounds demonstrated cytotoxicity in different cells. Our structure activity relationship study identified different patterns. In the series of 2-aryl pyrrolidines, comparing the activity of the compounds containing 2-aryl substituents we observed that compounds 1c, 1f-j, 2f,g with benzyloxyphenyl and isopropoxy groups were more potent. Compounds 1g-j, 2f,g, in which the 1 aryl moiety contained a methyl group in 3,5-or 4-positions also showed high activity. In the series of compounds containing the amide, aminomethyl and nitrile groups we observed an increase in activity with C(O)NH 2 < CH 2 NH 2 < CN. In the series of 2-pyrimidinyl pyrrolidines, the best results were demonstrated with derivatives 5e and 5f, in which the presence of a benzyl fragment in 1st and aniline fragment in 6th positions of pyrimidine ring we observed an increase in anti-HIV activity. Molecular docking studies of synthesized compounds with HIV-1 reverse transcriptase enzyme were performed. Binding energies of ligands were estimated, and the interacting amino acids of HIV-1 reverse transcriptase protein were shown. Based on corroborative results of the molecular docking studies and in vitro experiments, we suggest that three groups of synthesized ligands (1c, 1f-i), (2f,g), (5e,f, 7) are of high interest for further research on new drugs against HIV.

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“…16,17 Comprehensive literatures have reported that pyrrolidinone and its derivatives display a broad range of biological activities, such as HIV-1 integrase inhibitors, antimicrobial, anti-inflammatory and anticancer properties. [18][19][20][21][22][23] Our interest in these types of molecules continues from when we discovered that a synthesized pyrrolidinone derivative exhibited good inhibitory activity against MRSA with MIC values between 7.8 and 31.3 𝜇g/ml. 1,2 This bioactivity value is very much comparable in terms of its biological activity with the commercialized antibiotic In addition, oxazepanone is a seven-membered heterocyclic compound with a nitrogen and oxygen atom, with some compounds containing this structural motif displaying potent biological activities including antibacterial, antifungal and anticonvulsant properties.…”

Section: Introductionmentioning

confidence: 99%

Concise strategy for diastereoselective annulation to afford fused [5:7] oxazepanone γ-lactams

Rashid¹,

Mohammat²,

Mansor³

et al. 2021

Arkivoc

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A series of novel potentially biologically active fused [5:7] oxazepanone γ-lactams were synthesized and described. A series of functional group transformations, namely amination, syn-hydrogenation and intramolecular annulation reactions were used to obtain the [5:7] oxazepanone γ-lactams in reasonable yields. In the diastereoselective fused-annulation for the formation of the secondary ring, steric constrain and cisgeometrical configuration of C-3 and C-4 substituents were observed as the predetermined factors. These ring annulations were purposely constructed to suit the physicochemical enhancement of the biological activity of the title compounds via SAR study of γ-lactams.

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Anti-human immunodeficiency activity of novel 2-arylpyrrolidine analogs

Cited by 7 publications

References 9 publications

Catalytic Asymmetric Radical Diamination of Alkenes

Catalytic Asymmetric Radical Diamination of Alkenes

Design, antihuman immunodeficiency activity and molecular docking studies of synthesized 2-aryl and 2-pyrimidinyl pyrrolidines

Concise strategy for diastereoselective annulation to afford fused [5:7] oxazepanone γ-lactams

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