SrasV1, Main, Exploration, bibRecord, 000C95

Design, synthesis, docking studies and biological screening of 2-thiazolyl substituted -2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazines as potent HIV-1 reverse transcriptase inhibitors.

Identifieur interne : 000C95 ( Main/Exploration ); précédent : 000C94; suivant : 000C96

Design, synthesis, docking studies and biological screening of 2-thiazolyl substituted -2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazines as potent HIV-1 reverse transcriptase inhibitors.

Auteurs : Rakhi Gawali [Inde] ; Jay Trivedi [Inde] ; Sujit Bhansali [Inde] ; Raghunath Bhosale [Inde] ; Dhiman Sarkar [Inde] ; Debashis Mitra [Inde]

Source :

European journal of medicinal chemistry [ 1768-3254 ] ; 2018.

RBID : pubmed:30099253

Descripteurs français

English descriptors

KwdEn :
- Anti-HIV Agents (chemical synthesis), Anti-HIV Agents (chemistry), Anti-HIV Agents (pharmacology), Dose-Response Relationship, Drug, Drug Design, Drug Evaluation, Preclinical, HIV Reverse Transcriptase (antagonists & inhibitors), HIV Reverse Transcriptase (metabolism), HIV-1 (drug effects), Microbial Sensitivity Tests, Molecular Docking Simulation, Molecular Structure, Naphthalenes (chemical synthesis), Naphthalenes (chemistry), Naphthalenes (pharmacology), Oxazines (chemical synthesis), Oxazines (chemistry), Oxazines (pharmacology), Reverse Transcriptase Inhibitors (chemical synthesis), Reverse Transcriptase Inhibitors (chemistry), Reverse Transcriptase Inhibitors (pharmacology), Structure-Activity Relationship, Thiazoles (chemical synthesis), Thiazoles (chemistry), Thiazoles (pharmacology).
MESH :
- chemical , antagonists & inhibitors : HIV Reverse Transcriptase.
- chemical , chemical synthesis : Anti-HIV Agents, Naphthalenes, Oxazines, Reverse Transcriptase Inhibitors, Thiazoles.
- chemical , chemistry : Anti-HIV Agents, Naphthalenes, Oxazines, Reverse Transcriptase Inhibitors, Thiazoles.
- chemical , metabolism : HIV Reverse Transcriptase.
- chemical , pharmacology : Anti-HIV Agents, Naphthalenes, Oxazines, Reverse Transcriptase Inhibitors, Thiazoles.
- drug effects : HIV-1.
- Dose-Response Relationship, Drug, Drug Design, Drug Evaluation, Preclinical, Microbial Sensitivity Tests, Molecular Docking Simulation, Molecular Structure, Structure-Activity Relationship.

Abstract

1,3-oxazine nucleus and thiazolyl group features prominently in many biologically important natural products as well as bioactive molecules. A series of novel 2-thiazolyl substituted-2,3-dihydro-1H-naphtho [1,2-e][1,3]oxazine derivatives were designed and synthesized based on their structure-activity relationships (SARs) from 2-naphthol, substituted thiazolyl amines and formalin through ring closure by one-pot three component reaction. These derivatives were first evaluated for their inhibitory effect on HIV-1 Reverse Transcriptase (RT) enzyme activity. Out of 14 compounds, 4 showed potent inhibition of HIV-1 RT activity at significantly low concentration. Docking studies of these molecules revealed their high affinity binding to several amino acids of HIV-1 RT which are less sensitive to point mutations. Furthermore, anti-HIV activity of these molecules was analysed in a CD4⁺ T cell-line, which indicates that Therapeutic Index (TI) of some of these compounds is better than Zidovudine and Efavirenz, known HIV-1 RT inhibitors. Taken together, our studies report for the first time some novel naphthoxazine derivatives with significant TI, which is through inhibition of HIV-1 RT activity.

DOI: 10.1016/j.ejmech.2018.07.067
PubMed: 30099253

Affiliations:

Inde

Le document en format XML

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<term>Dose-Response Relationship, Drug</term>
<term>Drug Design</term>
<term>Drug Evaluation, Preclinical</term>
<term>HIV Reverse Transcriptase (antagonists & inhibitors)</term>
<term>HIV Reverse Transcriptase (metabolism)</term>
<term>HIV-1 (drug effects)</term>
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<term>Reverse Transcriptase Inhibitors (chemistry)</term>
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<term>Inhibiteurs de la transcriptase inverse ()</term>
<term>Inhibiteurs de la transcriptase inverse (pharmacologie)</term>
<term>Inhibiteurs de la transcriptase inverse (synthèse chimique)</term>
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<term>Oxazines (synthèse chimique)</term>
<term>Relation dose-effet des médicaments</term>
<term>Relation structure-activité</term>
<term>Simulation de docking moléculaire</term>
<term>Structure moléculaire</term>
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<term>Thiazoles (pharmacologie)</term>
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<term>Tests de sensibilité microbienne</term>
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<front><div type="abstract" xml:lang="en">1,3-oxazine nucleus and thiazolyl group features prominently in many biologically important natural products as well as bioactive molecules. A series of novel 2-thiazolyl substituted-2,3-dihydro-1H-naphtho [1,2-e][1,3]oxazine derivatives were designed and synthesized based on their structure-activity relationships (SARs) from 2-naphthol, substituted thiazolyl amines and formalin through ring closure by one-pot three component reaction. These derivatives were first evaluated for their inhibitory effect on HIV-1 Reverse Transcriptase (RT) enzyme activity. Out of 14 compounds, 4 showed potent inhibition of HIV-1 RT activity at significantly low concentration. Docking studies of these molecules revealed their high affinity binding to several amino acids of HIV-1 RT which are less sensitive to point mutations. Furthermore, anti-HIV activity of these molecules was analysed in a CD4<sup>+</sup>
 T cell-line, which indicates that Therapeutic Index (TI) of some of these compounds is better than Zidovudine and Efavirenz, known HIV-1 RT inhibitors. Taken together, our studies report for the first time some novel naphthoxazine derivatives with significant TI, which is through inhibition of HIV-1 RT activity.</div>
</front>
</TEI>
<affiliations><list><country><li>Inde</li>
</country>
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Design, synthesis, docking studies and biological screening of 2-thiazolyl substituted -2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazines as potent HIV-1 reverse transcriptase inhibitors.

Design, synthesis, docking studies and biological screening of 2-thiazolyl substituted -2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazines as potent HIV-1 reverse transcriptase inhibitors.

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Abstract

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