Ultrasound-Assisted Synthesis of Novel α-Aminophosphonates and Their Biological Activity

The synthesis of a series of novel α‐aminosubstituted phosphonates was accomplished by the reaction of various substituted aldehydes with an amine amlodipine (3‐ethyl 5‐methyl (±)2‐((2‐aminoethoxy)methyl)‐4‐(2‐chlorophenyl)‐6‐methyl‐1,4‐dihydropyridene‐3,5‐dicarboxylate) followed by diethylphosphite...

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Bibliographic Details
Published in:Archiv der Pharmazie (Weinheim) 2012-04, Vol.345 (4), p.294-301
Main Authors: Rasheed, Syed, Venkataramana, Katla, Chandrasekhar, Kuruva, Fareeda, Gemmalamadugu, Raju, Chamarthi Naga
Format: Article
Language:English
Subjects:
Aminophosphonates
Anti-Infective Agents - chemical synthesis
Anti-Infective Agents - chemistry
Anti-Infective Agents - pharmacology
Antimicrobial activity
Antiviral activity
Microbial Sensitivity Tests - methods
Microbial Sensitivity Tests - statistics & numerical data
Molecular Structure
Organophosphonates - chemical synthesis
Organophosphonates - chemistry
Organophosphonates - pharmacology
Pudovik reaction
Sound
Structure-Activity Relationship
Ultrasound irradiation
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Summary:The synthesis of a series of novel α‐aminosubstituted phosphonates was accomplished by the reaction of various substituted aldehydes with an amine amlodipine (3‐ethyl 5‐methyl (±)2‐((2‐aminoethoxy)methyl)‐4‐(2‐chlorophenyl)‐6‐methyl‐1,4‐dihydropyridene‐3,5‐dicarboxylate) followed by diethylphosphite/dibutylphosphite in ethanol using SnCl2.2H2O as a Lewis acid catalyst, under conventional and ultrasonic irradiation. Their structures were established by analytical and spectral data. The title compounds showed good antibacterial, antifungal and antiviral activity depending on the nature of the bioactive groups at the α‐carbon. A new class of α‐aminosubstituted phosphonates was synthesized and evaluated for their antimicrobial and antiviral activity.
ISSN:0365-6233
1521-4184
DOI:10.1002/ardp.201100256