Synthesis, anti-HIV activity, integrase enzyme inhibition and molecular modeling of catechol, hydroquinone and quinol labdane analogs

Pawar, Rohan; Das, Tiyasa; Mishra, S. K.; Nutan,; Pancholi, Boskey; Gupta, Seema; Bhat, Sujata V.

doi:10.1016/j.bmcl.2013.11.014

Cited by 7 publications

(6 citation statements)

References 22 publications

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“…TZM‐bl cells (5.0 × 10 4 /well) were seeded in 24‐well cell culture plate (Greiner Bio‐One, GmbH, Frickenhausen, Germany) and cultured overnight at 37°C in the presence of 75% relative humidity and 5% CO 2 . In separate vials, HIV‐1 NL4.3 (CXCR4 using virus) at a multiplicity of infection (MOI) of 0.05 was treated with various synthetic compounds or solvent for 1 hr at 37°C . Subsequently, pretreated viruses were added in duplicates to TZM‐bl cells and cultured for 4 hr.…”

Section: Methodsmentioning

confidence: 99%

N‐hydroxy‐substituted 2‐aryl acetamide analogs: A novel class of HIV‐1 integrase inhibitors

et al. 2017

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An in silico method has been used to discover N-hydroxy-substituted 2-aryl acetamide analogs as a new class of HIV-1 integrase inhibitors. Based on the molecular requirements of the binding pocket of catalytic active site, two molecules (compounds 2 and 4b) were designed as fragments. These were further synthesized and biologically evaluated. In vitro potency along with docking studies highlighted compound 4b as an active fragment which was further used to synthesize new leads as HIV-1 integrase inhibitors. Finally, six promising compounds (compounds 5b, 5c, 5e, 6-2c, 6-3b, and 6-5b) were identified by integrase inhibition assay (>50% inhibition). Based on in vitro anti-HIV-1 activity in a reporter gene-based cell assay system, compounds 5d, 6s, and 6k were found as novel HIV-1 integrase inhibitors due to its better selectivity index. Additionally, docking study revealed the importance of H-bond as well as hydrophobic interactions with Asn155, Lys156, and Lys159 which were required for their anti-HIV-1 activity.

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Section: Methodsmentioning

confidence: 99%

N‐hydroxy‐substituted 2‐aryl acetamide analogs: A novel class of HIV‐1 integrase inhibitors

et al. 2017

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“…86 Labdane-based analogues having an o-quinol moiety are generally synthesized from compound 65 via Diels-Alder reaction with myrcene 66 and ocimene 70, respectively. 82 Compound 65 treated with myrcene 66, as presented in Fig. 8, results in the formation of compound 67, a major…”

Section: Labdane Analogsmentioning

confidence: 96%

In search of therapeutic candidates for HIV/AIDS: rational approaches, design strategies, structure–activity relationship and mechanistic insights

Kumar

Shabu

et al. 2021

RSC Adv.

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“…8 Moreover, they are active against viruses, as in the case of rhinovirus, 9 HIV-1 integrase, 10,11 HIV-1 reverse transcriptase, 12 and coronavirus. 13 The biological activity of catechols is associated to their antioxidant property, that is the capacity of transferring singleelectron and/or hydrogen-atom to reactive free radicals, 14,15,16 as well as, to binding pro-oxidant metal ions.…”

Section: Introductionmentioning

confidence: 99%

Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses

Botta

Bizzarri

Garozzo

et al. 2015

Bioorganic & Medicinal Chemistry

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Hydroxytyrosol and dihydrocaffeoyl catechols with lipophilic properties have been synthesized in high yield using tyrosinase immobilized on multi-walled carbon nanotubes by the Layer-by-Layer technique. All synthesized catechols were evaluated against a large panel of DNA and RNA viruses, including Poliovirus type 1, Echovirus type 9, Herpes simplex virus type 1 (HSV-1), Herpes simplex virus type 2 (HSV-2), Coxsackievirus type B3 (Cox B3), Adenovirus type 2 and type 5 and Cytomegalovirus (CMV). A significant antiviral activity was observed in the inhibition of HSV-1, HSV-2, Cox B3 and CMV. The mechanism of action of the most active dihydrocaffeoyl derivative was investigated against a model of HSV-1 infection.

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Synthesis, anti-HIV activity, integrase enzyme inhibition and molecular modeling of catechol, hydroquinone and quinol labdane analogs

Cited by 7 publications

References 22 publications

N‐hydroxy‐substituted 2‐aryl acetamide analogs: A novel class of HIV‐1 integrase inhibitors

N‐hydroxy‐substituted 2‐aryl acetamide analogs: A novel class of HIV‐1 integrase inhibitors

In search of therapeutic candidates for HIV/AIDS: rational approaches, design strategies, structure–activity relationship and mechanistic insights

Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses

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