Synthesis and evaluation of 3-hydroxy-3-phenylpropanoate ester–AZT conjugates as potential dual-action HIV-1 Integrase and Reverse Transcriptase inhibitors

Manyeruke, Meloddy H.; Olomola, Temitope O.; Majumder, Swarup; Abrahams, Shaakira; Isaacs, Michelle; Mautsa, Nicodemus; Mosebi, Salerwe; Mnkandhla, Dumisani; Hewer, Raymond; Hoppe, Heinrich C.; Klein, Rosalyn; Kaye, Perry T.

doi:10.1016/j.bmc.2015.10.039

Cited by 12 publications

(1 citation statement)

References 23 publications

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“…Compounds 23 and 24 showed a simultaneous inhibition of RT (73.7% for both compounds) and IN (42.2% and 72.2% for 23 and 24 respectively) enzymes. These compounds were found to be cytoprotective with 56.4% cell viability for most toxic compound) [38]. The importance of click chemistry in drug synthesis is that it leads to the production of new compounds under very mild conditions [39].…”

Section: Modifications At Azido Groupmentioning

confidence: 99%

Zidovudine: Structural Modifications and Their Impact on Biological Activities and Pharmacokinetic Properties

Mohsin

Ahmed

Irfan

2019

J. Chil. Chem. Soc.

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Zidovudine was the first drug approved for the treatment of Acquired Immuno Deficiency Syndrome (AIDS). Its chemical name is azidothymidine (AZT). AZT use is associated with bone marrow toxicity. Shorter half-life and inability to penetrate the blood-brain barrier are the pharmacokinetic problems of this important drug molecule. Various modifications have been carried out in the structure of AZT. These include modification of hydroxyl and azido group, thymidine ring, preparation of phosphate and phosphonate derivatives, attachment of polymers and synthesis of hybrid molecules. Some of these changes produced compounds with significantly increased activity and less toxicity. This review highlights the various structural modifications of AZT and their influence on biological activities and pharmacokinetic properties.

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Section: Modifications At Azido Groupmentioning

confidence: 99%

Zidovudine: Structural Modifications and Their Impact on Biological Activities and Pharmacokinetic Properties

Mohsin

Ahmed

Irfan

2019

J. Chil. Chem. Soc.

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Organocatalysis in the Synthesis of 1,2,3‐Triazoyl‐zidovudine Derivatives: Synthesis and Preliminary Antioxidant Activity

et al. 2020

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We describe herein the organocatalyzed synthesis and preliminary results of antioxidant activities of a range of 1,2,3-triazoylzidovudine derivatives. These hybrid compounds were synthesized in moderate to excellent yields by reacting zidovudine 1 with a variety of functionalized keto compounds 2, such as βketo-esters, β-diketones, β-keto-amides, α-keto-nitriles, and βketo-sulfones, in the presence of a catalytic amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (10 mol %). Furthermore, the synthesized compounds were screened for their in vitro antioxidant activity. Compounds 3 a, 3 d, 3 g, and 3 l inhibited the formation of reactive oxygen species (ROS) and lipid peroxidation in the prefrontal cortex and hippocampus of mice with similar potency and efficacy.

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Advances in rationally designed dual inhibitors of HIV-1 reverse transcriptase and integrase

Xue

et al. 2016

Bioorganic & Medicinal Chemistry

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Synthesis and evaluation of 3-hydroxy-3-phenylpropanoate ester–AZT conjugates as potential dual-action HIV-1 Integrase and Reverse Transcriptase inhibitors

Cited by 12 publications

References 23 publications

Zidovudine: Structural Modifications and Their Impact on Biological Activities and Pharmacokinetic Properties

Zidovudine: Structural Modifications and Their Impact on Biological Activities and Pharmacokinetic Properties

Organocatalysis in the Synthesis of 1,2,3‐Triazoyl‐zidovudine Derivatives: Synthesis and Preliminary Antioxidant Activity

Advances in rationally designed dual inhibitors of HIV-1 reverse transcriptase and integrase

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