Design, synthesis, and antiviral activity of a series of CD4-mimetic small-molecule HIV-1 entry inhibitors

Curreli, Francesca; Ahmed, Shahad; Victor, Sofia M. Benedict; Iusupov, Ildar R.; Spiridonov, Evgeny A.; Belov, Dmitry S.; Altieri, Andrea; Kurkin, Alexander V.; Debnath, Asim K.

doi:10.1016/j.bmc.2021.116000

Cited by 11 publications

(10 citation statements)

References 58 publications

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“…15 c was obtained according to the experimental procedure described earlier for a similar derivative [9,25] . Purification by chromatography, eluent: hexane/EtOAc from 1:0 to 30 : 1, Rf=0.5 in hexane.…”

Section: Methodsmentioning

confidence: 99%

“…15 d was obtained according to the earlier experimental procedure for a similar derivative. [9,25] Purification by chromatography, eluent: hexane/EtOAc…”

Section: -Tert-butyl 2-methyl 5-(2-fluoro-4-(trifluoromethyl)phenyl)-...mentioning

confidence: 99%

“…15 e was obtained according to the earlier experimental procedure for a similar derivative. [9,25] Purification chromatography, eluent: hexane-EtOAc from 20 : 1 to 5 : 1, Rf = 0.4-05 in hexane/EtOAc 5 : 1. M = 4.31 g. Yield = 93 %.…”

Section: Methyl 5-(2-fluoro-4-(trifluoromethyl)phenyl)-3-methyl-1hpyr...mentioning

confidence: 99%

“…Compounds 14-fR (NBD-14378) and 14-fS (F45-90-fS; NBD-14379) were obtained following the general procedure A and B from amine 8 and the 5-[2-fluoro-4-(trifluoromethyl)phenyl]-1H-pyrrole-2-carboxylic acid. [25] The desired compounds were purified using column chromatography on silica gel. Eluent CHCl 3 /MeOH saturated with NH 3 (10 : 1 and 5 : 1).…”

Section: N-(2-amino-1-(2-(hydroxymethyl)thiazol-4-yl)ethyl)-5-(2-fluo...mentioning

confidence: 99%

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Design, Synthesis, and Antiviral Activity of the Thiazole Positional Isomers of a Potent HIV‐1 Entry Inhibitor NBD‐14270

Kurkin¹,

Curreli

Iusupov³

et al. 2022

ChemMedChem

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The envelope glycoprotein gp120 of human immunodeficiency virus type 1 (HIV‐1) plays a critical role in virus entry to the cells by binding to the host cellular protein CD4. Earlier, we reported the design and discovery of a series of highly potent small‐molecule entry antagonists containing a thiazole ring (Scaffold A). Since this thiazole ring connected with an ethyl amide linkage represents the molecule‘s flexible part, we decided to explore substituting Scaffold A with two other positional isomers of the thiazole ring (Scaffold B and C) to evaluate their effect on the antiviral potency and cellular toxicity. Here we report the novel synthesis of two sets of positional thiazole isomers of the NBD‐14270 by retrosynthetic analysis approach, their anti‐HIV‐1 activity, cellular toxicity, and structure‐activity relationships. The study revealed that Scaffold A provided the best HIV‐1 inhibitors with higher potency and better selectivity index (SI).

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Section: Methodsmentioning

confidence: 99%

“…15 d was obtained according to the earlier experimental procedure for a similar derivative. [9,25] Purification by chromatography, eluent: hexane/EtOAc…”

Section: -Tert-butyl 2-methyl 5-(2-fluoro-4-(trifluoromethyl)phenyl)-...mentioning

confidence: 99%

Section: Methyl 5-(2-fluoro-4-(trifluoromethyl)phenyl)-3-methyl-1hpyr...mentioning

confidence: 99%

Section: N-(2-amino-1-(2-(hydroxymethyl)thiazol-4-yl)ethyl)-5-(2-fluo...mentioning

confidence: 99%

See 2 more Smart Citations

Design, Synthesis, and Antiviral Activity of the Thiazole Positional Isomers of a Potent HIV‐1 Entry Inhibitor NBD‐14270

Kurkin¹,

Curreli

Iusupov³

et al. 2022

ChemMedChem

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show abstract

“…Debnath, and coworkers. 13 They designed and synthesized a series of CD4-mimetic small molecules as potential HIV-1 entry inhibitors. The best thiazole analog displayed the greatest antiviral activity and selectivity against HIV-1 HXB2 .…”

mentioning

confidence: 99%

Current trends in designing antiviral agents against emerging and re-emerging RNA viruses

Silva-Júnior

Zhan

2022

Bioorganic & Medicinal Chemistry

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The anti-HIV potential of imidazole, oxazole and thiazole hybrids: A mini-review

Deng

Yan

Wang

et al. 2022

Arabian Journal of Chemistry

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Design, synthesis, and antiviral activity of a series of CD4-mimetic small-molecule HIV-1 entry inhibitors

Cited by 11 publications

References 58 publications

Design, Synthesis, and Antiviral Activity of the Thiazole Positional Isomers of a Potent HIV‐1 Entry Inhibitor NBD‐14270

Design, Synthesis, and Antiviral Activity of the Thiazole Positional Isomers of a Potent HIV‐1 Entry Inhibitor NBD‐14270

Current trends in designing antiviral agents against emerging and re-emerging RNA viruses

The anti-HIV potential of imidazole, oxazole and thiazole hybrids: A mini-review

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