Studies on Organophosphorus Compounds Reactions of 1,3,2,4-Dithiadiphosphetane-2,4-Disulfides and Alkyl Phosphites With Coumarin Derivatives

Fahmy, A. A.; Hafez, T. S.; El‐Farargy, Ahmed F.; Hamad, M. M.

doi:10.1080/10426509108038852

Cited by 10 publications

(2 citation statements)

References 7 publications

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“…We successfully replaced the CdO with a CdS in the presence of thionation reagent. 30 Scheme 4 illustrates the practical strategies used to achieve this replacement. The hydroxyl group(s) was protected by a tosyl 31 group when the oxygen atom was substituted under P 2 S 5 or Lawesson's reagent in either method.…”

Section: Chemistrymentioning

confidence: 99%

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Chemical Library and Structure–Activity Relationships of 11-Demethyl-12-oxo Calanolide A Analogues as Anti-HIV-1 Agents

Liu

Xue

et al. 2008

J. Med. Chem.

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(+)-Calanolide A ( 1) as a natural product was previously found as an inhibitor of HIV-1 reverse transcriptase. In our further investigation of its template, racemic 11-demethyl-12-oxo calanolide A ( 15), which had two fewer chiral carbon centers at the C-11 and C-12 positions than (+)-calanolide A, had a comparably inhibitory activity and better therapeutic index (EC 50 = 0.11 microM, TI = 818) against HIV-1 in vitro. A library based on its structural core was then designed and synthesized with introduction of nine diversity points in this article. The evaluations of anti-HIV-1 activity in vitro concluded their structure-activity relationships (SARs). A novel compound (10-bromomethyl-11-demethyl-12-oxo calanolide A, 123) was identified to have much higher inhibitory potency and therapeutic index (EC 50 = 2.85 nM, TI > 10,526) than those of the class compound against HIV-1. This finding provided a very important clue that modifications of the C ring at the C-10 position may be conducted to obtain drug candidates with better activity against HIV-1.

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Section: Chemistrymentioning

confidence: 99%

“…The replacement of the CO of the ester with CS in ring B was first explored. We successfully replaced the CO with a CS in the presence of thionation reagent . Scheme illustrates the practical strategies used to achieve this replacement.…”

Section: Chemistrymentioning

confidence: 99%

Chemical Library and Structure–Activity Relationships of 11-Demethyl-12-oxo Calanolide A Analogues as Anti-HIV-1 Agents

Liu

Xue

et al. 2008

J. Med. Chem.

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The Synthesis and Reactions of Thio‐ and Seleno‐Phosphonic and ‐Phosphinic Acids

Edmundson¹

2009

Patai's Chemistry of Functional Groups

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Introduction The Synthesis of Monothio‐ and Monoseleno‐Phosphonic and ‐Phosphinic Acids and their Derivatives Interconversions of the Monothio(or Seleno) ‐Phosphonic and ‐Phosphinic Acids and Their Derivatives Syntheses and Reactions of Di‐ and Tri‐Thio(Seleno)‐Phosphonic Acids and Dithio(Seleno)Phosphinic Acids

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Functions Containing a Chalcogen and Any Other Heteroatoms Other Than a Halogen

Rice¹

1995

Comprehensive Organic Functional Group Transformations

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Studies on Organophosphorus Compounds Reactions of 1,3,2,4-Dithiadiphosphetane-2,4-Disulfides and Alkyl Phosphites With Coumarin Derivatives

Cited by 10 publications

References 7 publications

Chemical Library and Structure–Activity Relationships of 11-Demethyl-12-oxo Calanolide A Analogues as Anti-HIV-1 Agents

Chemical Library and Structure–Activity Relationships of 11-Demethyl-12-oxo Calanolide A Analogues as Anti-HIV-1 Agents

The Synthesis and Reactions of Thio‐ and Seleno‐Phosphonic and ‐Phosphinic Acids

Functions Containing a Chalcogen and Any Other Heteroatoms Other Than a Halogen

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