scholarly journals Synthesis and Anti-HIV Activity of Carbamates of Antiviral Agent Stavudine

2002 ◽  
Vol 13 (5) ◽  
pp. 289-297
Author(s):  
TK Venkatachalam ◽  
P Samuel ◽  
IV Kourinov ◽  
FM Uckun
Keyword(s):  
Biological Activity ◽  
Antiviral Agent ◽  
Heterocyclic Amines ◽  
Efficient Synthesis ◽  
Hiv Replication ◽  
Derivatives Of ◽  
Anti Hiv

An efficient synthesis of carbamate analogues of the NRTI compound stavudine, has been achieved in five steps starting from commercially available thymidine. The synthesis involves conversion of thymidine into stavudine followed by condensation with carbaimidazole derivative obtained from various aromatic and heterocyclic amines in dimethylformamide solvent. The analogues thus obtained were further purified by crystallization to furnish analytically pure products. Examination of biological activity of these carbamate derivatives of stavudine showed that they inhibited HIV replication only at micro-molar concentrations.

Phosphoramidate Derivatives of AZT as Inhibitors of HIV: Studies on the Carboxyl Terminus

1993 ◽  
Vol 4 (2) ◽  
pp. 97-101 ◽  
Author(s):  
C. McGuigan ◽  
R. N. Pathirana ◽  
S. S.-M. Choi ◽  
D. Kinchington ◽  
T. J. O'Connor
Keyword(s):  
Amino Acids ◽  
Biological Activity ◽  
Carboxyl Terminus ◽  
Amino Ester ◽  
Carboxy Terminus ◽  
Free Nucleotides ◽  
Derivatives Of ◽  
Anti Hiv ◽  
Ester Lead

Novel phosphoramidate derivatives of the anti-HIV nucleoside analogue AZT have been prepared by phosphorochloridate chemistry. These materials carry carboxy-protected, amino acids, and are designed to act as membrane-soluble prodrugs of the bio-active free nucleotides. In vitro evaluation revealed the compounds to have a pronounced, selective antiviral activity. In particular, variation in the carboxy terminus region is studied. For alkyl phosphates small changes in the structure of the amino ester lead to marked changes in biological activity. However, for analogous aryl phosphates there is little dependence on the structure of the ester. This suggests a different mechanism of action for these two categories of phosphate prodrug.

Haloalkyl Phosphate Derivatives of AZT as Inhibitors of HIV: Studies in the Phosphate Region

1994 ◽  
Vol 5 (3) ◽  
pp. 162-168 ◽  
Author(s):  
C. McGuigan ◽  
S. Turner ◽  
S. R. Nicholls ◽  
T. J. O'Connor ◽  
D. Kinchington
Keyword(s):  
Biological Activity ◽  
Alkyl Chain ◽  
Antiviral Action ◽  
Alkyl Phosphate ◽  
Free Nucleotides ◽  
Order Of Magnitude ◽  
Derivatives Of ◽  
Anti Hiv ◽  
Hiv 1

Novel haloalkyl phosphate derivatives of the anti-HIV nucleoside analogue AZT were prepared by phosphorochloridate chemistry. These materials were designed to act as labile membrane-soluble prodrugs of the bio-active free nucleotides. In vitro evaluation revealed the compounds to have a pronounced and selective antiviral action, which varied greatly with the structure of the phosphate moiety. By comparison to simple dialkyl phosphates, which are inactive against HIV-1, the introduction of halogen atoms into the alkyl (phosphate) chains led to anti-HIV activity. Although halogen substitution in just one alkyl chain was sufficient for biological activity, substitution in the second alkyl chain further enhanced activity. Conversely, stabilization of the second chain, by conversion to a phosphonate, led to a reduction in activity. In one case, the diastereo-isomers resulting from mixed stereochemistry at the phosphate centre were separated, and found to differ in activity by one order of magnitude. Lastly, the bis(mono- and di-chloroethyl) phosphates were prepared and found to display moderate anti-HIV activity.

Synthesis and anti-HIV evaluation of some phosphoramidate derivatives of AZT: Studies on the effect of chain elongation on biological activity

1990 ◽  
Vol 14 (6) ◽  
pp. 345-356 ◽  
Author(s):  
Duncan Curley ◽  
Christopher McGuigan ◽  
Kevin G. Devine ◽  
Timothy J. O'Connor ◽  
Donald J. Jeffries ◽  
...  
Keyword(s):  
Biological Activity ◽  
Chain Elongation ◽  
Derivatives Of ◽  
Anti Hiv

scholarly journals Phosphoramidates as Potent Prodrugs of anti-HIV Nucleotides: Studies in the Amino Region

1996 ◽  
Vol 7 (1) ◽  
pp. 31-36 ◽  
Author(s):  
C. McGuigan ◽  
D. Cahard ◽  
A. Salgado ◽  
E. De Clercq ◽  
J. Balzarini
Keyword(s):  
Amino Acid ◽  
Vital Role ◽  
Nucleoside Analogues ◽  
Acid Moiety ◽  
Hiv Replication ◽  
Amino Acid Moiety ◽  
Free Nucleotides ◽  
Derivatives Of ◽  
Anti Hiv

Novel phosphoramidate derivatives of the anti-HIV nucleoside analogues AZT and d4T have been prepared by phosphorochloridate chemistry. These materials are designed to act as labile membrane-soluble prodrugs of the bio-active free nucleotides. All compounds were fully characterised by a range of methods and were subjected to evaluation in vitro of their anti-HIV efficacy. A notable feature of the current study was that any attempt to replace the amino acid moiety of the phosphoramidate with a simple amine lead to a marked, virtually total loss of activity. Such simple phenyl alkylamino phosphate derivatives of either d4T or AZT inhibit HIV replication at cytotoxic concentrations and have no detectable antiviral selectivity. This clearly highlights the vital role played by the amino acid in the antiviral efficacy of the blocked phosphoramidates.

scholarly journals 3,4-dihydro-2H-1,3-benzoxazines and their oxo-derivatives chemistry and bioactivities

2020 ◽  
pp. 1-1 ◽  
Author(s):  
El-Din Sharaf
Keyword(s):  
Biological Activity ◽  
Bioactive Compounds ◽  
Biological Activities ◽  
Anti Inflammatory ◽  
Derivatives Of ◽  
Anti Hiv ◽  
Significant Class

3,4-Dihydro-2H-1,3-benzoxazines derivatives are a significant class of heterocycles with a particular awareness due to their remarkable biological activities in humans, plant as well as in animals and also, they are naturally occurrence. Because of alteration in the benzoxazines skeleton, beside their comparative chemical simplicity and accessibility, make these compounds to be suitable sources of other bioactive compounds. Resulting in the discovery of a wide set of these compounds that have a broad biological activity such as antifungal, antibacterial, anti-HIV, anticancer, anticonvulsant, anti-inflammatory and so on. Subsequently, this review herein gives a brief overview of derivatives of 3,4-dihydro-2H-1,3-benzoxazines monomers and their oxo-derivatives chemistry and bioactivities.

scholarly journals A New Type of Synthesis of 1,2,3-Thiadiazole and 1,2,3-Diazaphosphole Derivatives Via-Hurd-Mori Cyclization

2012 ◽  
Vol 9 (3) ◽  
pp. 1276-1287 ◽  
Author(s):  
Mona A. Hosny ◽  
Taghreed H. El-Sayed ◽  
Emtithal El-Sawi
Keyword(s):  
Biological Activity ◽  
Large Scale ◽  
High Potential ◽  
Efficient Synthesis ◽  
Anticancer Effect ◽  
Potential Biological Activity ◽  
Large Scale Preparation ◽  
New Type ◽  
Scale Preparation ◽  
Derivatives Of

We present a short and efficient synthesis of the title compounds starting with cheap and readily available camphor and derivatives of acetophenone. The optimized sequence allows the large-scale preparation of this new type of synthesis in a few steps. New 1,2,3-thiadiazole and 1,2,3-diazaphosphole derivatives 11-20, were prepared from the ketones 1-5 via the corresponding semicarbazones 6-10. The Hurd-Mori and Lalezari methods were used, respectively, for the preparation of these 1,2,3-thiadiazole and 1,2,3-diazaphospholene derivatives. These derivatives exhibit anticancer effect due to their high potential biological activity.

Synthesis and Biological Potentials of Quinoline Analogues: A Review of Literature

2019 ◽  
Vol 16 (7) ◽  
pp. 653-688 ◽  
Author(s):  
Leena Kumari ◽  
Salahuddin ◽  
Avijit Mazumder ◽  
Daman Pandey ◽  
Mohammad Shahar Yar ◽  
...  
Keyword(s):  
Biological Activity ◽  
Heterocyclic Compounds ◽  
Building Blocks ◽  
Vital Role ◽  
Review Of Literature ◽  
Drug Discovery Process ◽  
Active Compounds ◽  
Lead Compounds ◽  
Synthetic Approaches ◽  
Derivatives Of

Heterocyclic compounds are well known for their different biological activity. The heterocyclic analogs are the building blocks for synthesis of the pharmaceutical active compounds in the organic chemistry. These derivatives show various type of biological activity like anticancer, antiinflammatory, anti-microbial, anti-convulsant, anti-malarial, anti-hypertensive, etc. From the last decade research showed that the quinoline analogs plays a vital role in the development of newer medicinal active compounds for treating various type of disease. Quinoline reported for their antiviral, anticancer, anti-microbial and anti-inflammatory activity. This review will summarize the various synthetic approaches for synthesis of quinoline derivatives and to check their biological activity. Derivatives of quinoline moiety plays very important role in the development of various types of newer drugs and it can be used as lead compounds for future investigation in the field of drug discovery process.

Synthesis and Biological Activity of 28-Amide Derivatives of 23-Hydroxy Betulinic Acid as Antitumor Agent Candidates

2013 ◽  
Vol 9 (7) ◽  
pp. 920-925 ◽  
Author(s):  
Yi Bi ◽  
Jinyi Xu ◽  
Fei Sun ◽  
Xiaoming Wu ◽  
Wencai Ye ◽  
...  
Keyword(s):  
Biological Activity ◽  
Betulinic Acid ◽  
Antitumor Agent ◽  
Amide Derivatives ◽  
Derivatives Of
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