QSAR and docking studies of coumarin derivatives as potent HIV-1 integrase inhibitors

Srivastav, Vijay Kumar; Tiwari, Mayank

doi:10.1016/j.arabjc.2013.01.015

Cited by 19 publications

(8 citation statements)

References 30 publications

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“…The 1 H-and 13 C-NMR spectra ( Table 1) of 2 were very similar to those of 1 except for the absence of a signal for H-C(5) and the presence of signals for an additional prenyl group, suggesting 2 to be a doubly prenylated analogue of 1. The HMBCs from H-C(1 0 ) of the first prenyl group to C(5), C(6), and C(10) and from H-C(1″) of the second prenyl group to C(5), C (6). and C (7) indicated the attachment of the prenyl groups to C(5) and C(6) of the coumarin skeleton ( Fig.…”

Section: Resultsmentioning

confidence: 98%

“…Coumarins have been obtained from a variety of plants which produce them through the general phenylpropanoid pathway and are further subjected to various modifications. Coumarins have attracted considerable interest owing to their pharmacological properties such as antibacterial, anticholinesterase, antioxidant, anti‐inflammatory, and anti‐HIV activities . In particular, ortho ‐dihydroxycoumarins such as esculetin (6,7‐dihydroxycoumarin) and daphnetin (7,8‐dihydroxycoumarin) have been reported to exhibit antitumor and antimetastatic activities and are used in the clinical treatment of coagulation disorders, rheumatoid arthritis, and lumbago, and to reduce fever …”

Section: Introductionmentioning

confidence: 99%

“…Coumarins have attracted considerable interest owing to their pharmacological properties such as antibacterial, [2] anticholinesterase, [3] antioxidant, [4] anti-inflammatory, [5] and anti-HIV activities. [6] In particular, ortho-dihydroxycoumarins such as esculetin (6,7-dihydroxycoumarin) and daphnetin (7,8-dihydroxycoumarin) have been reported to exhibit antitumor and antimetastatic activities [7] and are used in the clinical treatment of coagulation disorders, rheumatoid arthritis, and lumbago, and to reduce fever. [8] [9] The genus Ficus of the Moraceae family has over 800 species, commonly found in warm-temperate and tropical regions.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

New Prenylated ortho‐Dihydroxycoumarins from the Fruits of Ficus nipponica

Akihara

Ohta

Nehira

et al. 2017

Chemistry & Biodiversity

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Two new prenylated ortho-dihydroxycoumarins, designated fipsomin (1) and fipsotwin (2), were isolated from the fruits of Ficus nipponica together with a known prenylated coumarin, apigravin (3). Their structures were established by spectroscopic data and X-ray crystallographic analysis. Compound 1 exhibited antibacterial activity against Bacillus subtilis with an MIC value of 61 μm, while 2 and 3 showed very weak activity.

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Section: Resultsmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

New Prenylated ortho‐Dihydroxycoumarins from the Fruits of Ficus nipponica

Akihara

Ohta

Nehira

et al. 2017

Chemistry & Biodiversity

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show abstract

“…Two coumarin motif attached by an aryl linker were found to be very crucial for the anti-HIV-integrase activity. In this coumarin derivative, lipophilicity of aromatic ring of the linker was responsible for the inhibitory activity [47]. Another research group studied the therapeutic potential of synthesized coumarin carbohydrazide derivatives.…”

Section: Anti-hivmentioning

confidence: 99%

Coumarin: An emerging antiviral agent

Mishra

Pandey

Manvati

2020

Heliyon

183

117

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Viral infections are responsible for many illnesses, and recent outbreaks have raised public health concerns. Despite the availability of many antiviral drugs, they are often unsuccessful due to the generation of viral mutants and less effective against their target virus. Identifying novel antiviral drugs is therefore of critical importance and natural products are an excellent source for such discoveries. Coumarin is one such natural compound that is a potential drug candidate owing to its properties of stability, solubility, and low toxicity. There are numerous evidences showing its inhibitory role against infection of various viruses such as HIV, Influenza, Enterovirus 71 (EV71) and coxsackievirus A16 (CVA16). The mechanisms involve either inhibition of proteins essential for viral entry, replication and infection or regulation of cellular pathways such as Akt-Mtor (mammalian target of rapamycin), NF-κB (nuclear factor kappa-light-chain-enhancer of activated B cells), and anti-oxidative pathway including NrF-2 (The nuclear factor erythroid 2 (NFE2)-related factor 2). This review summarizes the present state of understanding with a focus on coumarin's antiviral effect and their possible molecular mechanisms against Influenza virus, HIV, Hepatitis virus, Dengue virus and Chikungunya virus.

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“…Due to wide range of biological activity, synthesis of coumarins in laboratory has now become the prime interest of medicinal chemists. Previously, several coumarin derivatives were designed as antiHIV agents by quantitative structure-activity relationship (QSAR) and docking studies [21,22] . The present study explores the synthesis and antiretroviral activity of 6-acetylcoumarin derivatives against HIV infection.…”

Section: Research Papermentioning

confidence: 99%

Synthesis and Antiretroviral Activity of 6-Acetyl-coumarin Derivatives against HIV-1 Infection

Srivastav¹,

Tiwari²,

X³

et al. 2018

pharmaceutical-sciences

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Srivastav, et al.: Synthesis and Antiretroviral Activity of 6-Acetyl-coumarin Derivatives A series of 6-acetyl-coumarin derivatives (2a-n) were synthesized and evaluated for antiretroviral activity in C8166 T-cell line infected with HxBru-Gluc strain of human immunodeficiency virus-1. Michael Addition followed by re-aromatization and subsequent acid-induced elimination of water leads to the formation of coumarin intermediate, which undergoes Claisen-Schmidt condensation with substituted bezaldehydes using silica sulphuric acid as a catalyst to form 6-acetyl-coumarin derivatives, 2a-n. In silico absorption, distribution, metabolism, excretion and toxicity parameters of compounds 2a-n were found within their reference limits. All synthesized compounds were devoid of cytotoxicity as they have shown cell viability count more than 80 % in cytotoxicity assay. Compounds 2a, 2g and 2h showed potent inhibitory activity against human immunodeficiency virus infection with IC 50 value of 4.7, 4.5 and 0.35 µM, respectively. It was found that electron-withdrawing group at phenyl ring, attached to the coumarin nucleus was crucial for activity against human immunodeficiency virus. The present study may be helpful in the development of some potent antiretroviral agents.

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QSAR and docking studies of coumarin derivatives as potent HIV-1 integrase inhibitors

Cited by 19 publications

References 30 publications

New Prenylated ortho‐Dihydroxycoumarins from the Fruits of Ficus nipponica

New Prenylated ortho‐Dihydroxycoumarins from the Fruits of Ficus nipponica

Coumarin: An emerging antiviral agent

Synthesis and Antiretroviral Activity of 6-Acetyl-coumarin Derivatives against HIV-1 Infection

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