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Synthesis and biological evaluation of (acyl)hydrazones and thiosemicarbazones obtained via in situ condensation of iminium salts with nitrogen-containing nucleophiles
by
De Maria, Monica
, Delogu, Ilenia
, Caneva, Chiara
, Ibba, Cristina
, Alfei, Silvana
, Spallarossa, Andrea
, Loddo, Roberta
in
Antiviral Agents - chemical synthesis
/ Antiviral Agents - pharmacology
/ Biochemistry
/ Biomedical and Life Sciences
/ Cell Proliferation - drug effects
/ Cell Survival - drug effects
/ Cytotoxins - chemical synthesis
/ Cytotoxins - pharmacology
/ Full-Length Paper
/ Hydrazones - chemical synthesis
/ Hydrazones - pharmacology
/ Life Sciences
/ Molecular Structure
/ Nitrogen
/ Nitrogen - chemistry
/ Organic Chemistry
/ Pharmacy
/ Polymer Sciences
/ Salts
/ Thiosemicarbazones - chemical synthesis
/ Thiosemicarbazones - pharmacology
2015
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Synthesis and biological evaluation of (acyl)hydrazones and thiosemicarbazones obtained via in situ condensation of iminium salts with nitrogen-containing nucleophiles
by
De Maria, Monica
, Delogu, Ilenia
, Caneva, Chiara
, Ibba, Cristina
, Alfei, Silvana
, Spallarossa, Andrea
, Loddo, Roberta
in
Antiviral Agents - chemical synthesis
/ Antiviral Agents - pharmacology
/ Biochemistry
/ Biomedical and Life Sciences
/ Cell Proliferation - drug effects
/ Cell Survival - drug effects
/ Cytotoxins - chemical synthesis
/ Cytotoxins - pharmacology
/ Full-Length Paper
/ Hydrazones - chemical synthesis
/ Hydrazones - pharmacology
/ Life Sciences
/ Molecular Structure
/ Nitrogen
/ Nitrogen - chemistry
/ Organic Chemistry
/ Pharmacy
/ Polymer Sciences
/ Salts
/ Thiosemicarbazones - chemical synthesis
/ Thiosemicarbazones - pharmacology
2015
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Synthesis and biological evaluation of (acyl)hydrazones and thiosemicarbazones obtained via in situ condensation of iminium salts with nitrogen-containing nucleophiles
by
De Maria, Monica
, Delogu, Ilenia
, Caneva, Chiara
, Ibba, Cristina
, Alfei, Silvana
, Spallarossa, Andrea
, Loddo, Roberta
in
Antiviral Agents - chemical synthesis
/ Antiviral Agents - pharmacology
/ Biochemistry
/ Biomedical and Life Sciences
/ Cell Proliferation - drug effects
/ Cell Survival - drug effects
/ Cytotoxins - chemical synthesis
/ Cytotoxins - pharmacology
/ Full-Length Paper
/ Hydrazones - chemical synthesis
/ Hydrazones - pharmacology
/ Life Sciences
/ Molecular Structure
/ Nitrogen
/ Nitrogen - chemistry
/ Organic Chemistry
/ Pharmacy
/ Polymer Sciences
/ Salts
/ Thiosemicarbazones - chemical synthesis
/ Thiosemicarbazones - pharmacology
2015
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Synthesis and biological evaluation of (acyl)hydrazones and thiosemicarbazones obtained via in situ condensation of iminium salts with nitrogen-containing nucleophiles
Journal Article
Synthesis and biological evaluation of (acyl)hydrazones and thiosemicarbazones obtained via in situ condensation of iminium salts with nitrogen-containing nucleophiles
2015
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Overview
An unprecedented, highly convergent, high-yielding, one-pot synthesis of (acyl)hydrazones and thiosemicarbazones was carried out by the in situ condensation of isolable iminium chlorides of imidazolidin-2-(thio)one, tetrahydropyrimidin-2-thione and indole derivatives with nitrogen nucleophiles in the presence of a base. The developed reaction procedure is largely advantageous. It is highly parallelizable, no intermediates need to be isolated and minimal sample handling is required during the purification steps. Some relevant reaction parameters including reaction temperature and p
K
a
of the base are discussed. NMR analysis was carried out to assess the stereochemistry of the obtained compounds. The stereochemical outcome of the reaction was found to be affected by the nature of the nitrogen-containing nucleophile being the majority of the derivatives isolated as single geometric isomers. The cytotoxicity and antiviral activities of the prepared compounds have been preliminary assessed. In cell-based screenings some of the derivatives proved to be cytotoxic at low micromolar concentrations and interesting anti-Reo-1 properties have been detected.
Publisher
Springer International Publishing,Springer Nature B.V
Subject
Antiviral Agents - chemical synthesis
/ Antiviral Agents - pharmacology
/ Biomedical and Life Sciences
/ Cell Proliferation - drug effects
/ Cell Survival - drug effects
/ Cytotoxins - chemical synthesis
/ Hydrazones - chemical synthesis
/ Nitrogen
/ Pharmacy
/ Salts
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