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Synthesis, structure and biological properties of active spirohydantoin derivatives
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| Zeitschriftentitel: | Chemical Industry |
|---|---|
| Personen und Körperschaften: | , , , , |
| In: | Chemical Industry, 70, 2016, 2, S. 177-199 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
National Library of Serbia
|
| Schlagwörter: |
| author_facet |
Lazic, Anita Valentic, Natasa Trisovic, Nemanja Petrovic, Slobodan Uscumlic, Gordana Lazic, Anita Valentic, Natasa Trisovic, Nemanja Petrovic, Slobodan Uscumlic, Gordana |
|---|---|
| author |
Lazic, Anita Valentic, Natasa Trisovic, Nemanja Petrovic, Slobodan Uscumlic, Gordana |
| spellingShingle |
Lazic, Anita Valentic, Natasa Trisovic, Nemanja Petrovic, Slobodan Uscumlic, Gordana Chemical Industry Synthesis, structure and biological properties of active spirohydantoin derivatives General Chemical Engineering General Chemistry |
| author_sort |
lazic, anita |
| spelling |
Lazic, Anita Valentic, Natasa Trisovic, Nemanja Petrovic, Slobodan Uscumlic, Gordana 0367-598X 2217-7426 National Library of Serbia General Chemical Engineering General Chemistry http://dx.doi.org/10.2298/hemind150205025l <jats:p>Spirohidantoins represent an pharmacologically important class of heterocycles since many derivatives have been recognized that display interesting activities against a wide range of biological targets. First synthesis of cycloalkanespiro-5-hydantoins was performed by Bucherer and Lieb 1934 by the reaction of cycloalkanone, potassium cyanide and ammonium-carbonate at reflux in a mixture of ethanol and water. QSAR (Quantitative Structure-Activity Relationship) studies showed that a wide range of biological activities of spirohydantoin derivatives strongly depend upon their structure. This paper describes different methods of synthesis of spirohydantoin derivatives, their physico-chemical properties and biological activity. It emphasizes the importance of cycloalkanespiro-5-hydantoins with anticonvulsant, antiproliferative, antipsychotic, antimicrobial and antiinflammatory properties as well as their importance in the treatment of diabetes. Numerous spirohydantoin compounds exhibit physiological activity such as serotonin and fibrinogen antagonist, inhibitors of the glycine binding site of the NMDA receptor also, antagonist of leukocyte cell adhesion, acting as allosteric inhibitors of the protein-protein interactions. Some spirohydantoin derivatives have been identified as antitumor agents. Their activity depends on the substituent presented at position N-3 of the hydantoin ring and increases in order alkene > ester > ether. Besides that, compounds that contain two electron withdrawing groups (e.g. fluorine or chlorine) on the third and fourth position of the phenyl ring are better antitumor agents than compounds with a single electron withdrawing group.</jats:p> Synthesis, structure and biological properties of active spirohydantoin derivatives Chemical Industry |
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| title |
Synthesis, structure and biological properties of active spirohydantoin derivatives |
| title_unstemmed |
Synthesis, structure and biological properties of active spirohydantoin derivatives |
| title_full |
Synthesis, structure and biological properties of active spirohydantoin derivatives |
| title_fullStr |
Synthesis, structure and biological properties of active spirohydantoin derivatives |
| title_full_unstemmed |
Synthesis, structure and biological properties of active spirohydantoin derivatives |
| title_short |
Synthesis, structure and biological properties of active spirohydantoin derivatives |
| title_sort |
synthesis, structure and biological properties of active spirohydantoin derivatives |
| topic |
General Chemical Engineering General Chemistry |
| url |
http://dx.doi.org/10.2298/hemind150205025l |
| publishDate |
2016 |
| physical |
177-199 |
| description |
<jats:p>Spirohidantoins represent an pharmacologically important class of
heterocycles since many derivatives have been recognized that display
interesting activities against a wide range of biological targets. First
synthesis of cycloalkanespiro-5-hydantoins was performed by Bucherer and Lieb
1934 by the reaction of cycloalkanone, potassium cyanide and
ammonium-carbonate at reflux in a mixture of ethanol and water. QSAR
(Quantitative Structure-Activity Relationship) studies showed that a wide
range of biological activities of spirohydantoin derivatives strongly depend
upon their structure. This paper describes different methods of synthesis of
spirohydantoin derivatives, their physico-chemical properties and biological
activity. It emphasizes the importance of cycloalkanespiro-5-hydantoins with
anticonvulsant, antiproliferative, antipsychotic, antimicrobial and
antiinflammatory properties as well as their importance in the treatment of
diabetes. Numerous spirohydantoin compounds exhibit physiological activity
such as serotonin and fibrinogen antagonist, inhibitors of the glycine
binding site of the NMDA receptor also, antagonist of leukocyte cell
adhesion, acting as allosteric inhibitors of the protein-protein
interactions. Some spirohydantoin derivatives have been identified as
antitumor agents. Their activity depends on the substituent presented at
position N-3 of the hydantoin ring and increases in order alkene > ester >
ether. Besides that, compounds that contain two electron withdrawing groups
(e.g. fluorine or chlorine) on the third and fourth position of the phenyl
ring are better antitumor agents than compounds with a single electron
withdrawing group.</jats:p> |
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| author | Lazic, Anita, Valentic, Natasa, Trisovic, Nemanja, Petrovic, Slobodan, Uscumlic, Gordana |
| author_facet | Lazic, Anita, Valentic, Natasa, Trisovic, Nemanja, Petrovic, Slobodan, Uscumlic, Gordana, Lazic, Anita, Valentic, Natasa, Trisovic, Nemanja, Petrovic, Slobodan, Uscumlic, Gordana |
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| description | <jats:p>Spirohidantoins represent an pharmacologically important class of heterocycles since many derivatives have been recognized that display interesting activities against a wide range of biological targets. First synthesis of cycloalkanespiro-5-hydantoins was performed by Bucherer and Lieb 1934 by the reaction of cycloalkanone, potassium cyanide and ammonium-carbonate at reflux in a mixture of ethanol and water. QSAR (Quantitative Structure-Activity Relationship) studies showed that a wide range of biological activities of spirohydantoin derivatives strongly depend upon their structure. This paper describes different methods of synthesis of spirohydantoin derivatives, their physico-chemical properties and biological activity. It emphasizes the importance of cycloalkanespiro-5-hydantoins with anticonvulsant, antiproliferative, antipsychotic, antimicrobial and antiinflammatory properties as well as their importance in the treatment of diabetes. Numerous spirohydantoin compounds exhibit physiological activity such as serotonin and fibrinogen antagonist, inhibitors of the glycine binding site of the NMDA receptor also, antagonist of leukocyte cell adhesion, acting as allosteric inhibitors of the protein-protein interactions. Some spirohydantoin derivatives have been identified as antitumor agents. Their activity depends on the substituent presented at position N-3 of the hydantoin ring and increases in order alkene > ester > ether. Besides that, compounds that contain two electron withdrawing groups (e.g. fluorine or chlorine) on the third and fourth position of the phenyl ring are better antitumor agents than compounds with a single electron withdrawing group.</jats:p> |
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| institution | DE-Pl11, DE-Rs1, DE-105, DE-14, DE-Ch1, DE-L229, DE-D275, DE-Bn3, DE-Brt1, DE-Zwi2, DE-D161, DE-Gla1, DE-Zi4, DE-15 |
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| physical | 177-199 |
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| spelling | Lazic, Anita Valentic, Natasa Trisovic, Nemanja Petrovic, Slobodan Uscumlic, Gordana 0367-598X 2217-7426 National Library of Serbia General Chemical Engineering General Chemistry http://dx.doi.org/10.2298/hemind150205025l <jats:p>Spirohidantoins represent an pharmacologically important class of heterocycles since many derivatives have been recognized that display interesting activities against a wide range of biological targets. First synthesis of cycloalkanespiro-5-hydantoins was performed by Bucherer and Lieb 1934 by the reaction of cycloalkanone, potassium cyanide and ammonium-carbonate at reflux in a mixture of ethanol and water. QSAR (Quantitative Structure-Activity Relationship) studies showed that a wide range of biological activities of spirohydantoin derivatives strongly depend upon their structure. This paper describes different methods of synthesis of spirohydantoin derivatives, their physico-chemical properties and biological activity. It emphasizes the importance of cycloalkanespiro-5-hydantoins with anticonvulsant, antiproliferative, antipsychotic, antimicrobial and antiinflammatory properties as well as their importance in the treatment of diabetes. Numerous spirohydantoin compounds exhibit physiological activity such as serotonin and fibrinogen antagonist, inhibitors of the glycine binding site of the NMDA receptor also, antagonist of leukocyte cell adhesion, acting as allosteric inhibitors of the protein-protein interactions. Some spirohydantoin derivatives have been identified as antitumor agents. Their activity depends on the substituent presented at position N-3 of the hydantoin ring and increases in order alkene > ester > ether. Besides that, compounds that contain two electron withdrawing groups (e.g. fluorine or chlorine) on the third and fourth position of the phenyl ring are better antitumor agents than compounds with a single electron withdrawing group.</jats:p> Synthesis, structure and biological properties of active spirohydantoin derivatives Chemical Industry |
| spellingShingle | Lazic, Anita, Valentic, Natasa, Trisovic, Nemanja, Petrovic, Slobodan, Uscumlic, Gordana, Chemical Industry, Synthesis, structure and biological properties of active spirohydantoin derivatives, General Chemical Engineering, General Chemistry |
| title | Synthesis, structure and biological properties of active spirohydantoin derivatives |
| title_full | Synthesis, structure and biological properties of active spirohydantoin derivatives |
| title_fullStr | Synthesis, structure and biological properties of active spirohydantoin derivatives |
| title_full_unstemmed | Synthesis, structure and biological properties of active spirohydantoin derivatives |
| title_short | Synthesis, structure and biological properties of active spirohydantoin derivatives |
| title_sort | synthesis, structure and biological properties of active spirohydantoin derivatives |
| title_unstemmed | Synthesis, structure and biological properties of active spirohydantoin derivatives |
| topic | General Chemical Engineering, General Chemistry |
| url | http://dx.doi.org/10.2298/hemind150205025l |