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Kinetic investigation of phenylselenoetherification of some Δ4-alkenols in presence of catalytic amount of CoCl2
The phenylselenoetherification of unsaturated alcohols is the one of the most rapid and convenient methods for formation of THF and THP type of rings. The convenient position of a double bond and a hydroxyl group in an alkenol can easily lead to formation of corresponding cyclization product. The reaction of selenium electrophiles with alkenols is a stereospecific anti addition where the nucleophile (pendant hydroxyl group) attacks usually at higher substituted carbon atom (Markownikoff stere...
The phenylselenoetherification of unsaturated alcohols is the one of the most rapid and convenient methods for formation of THF and THP type of rings. The convenient position of a double bond and a hydroxyl group in an alkenol can easily lead to formation of corresponding cyclization product. The reaction of selenium electrophiles with alkenols is a stereospecific anti addition where the nucleophile (pendant hydroxyl group) attacks usually at higher substituted carbon atom (Markownikoff stere...
Biological evaluation of the 3,4-dihydro-2(1H)-quinoxalinones and 3,4-dihydro-1,4-benzoxazin-2-ones
In order to investigate new potential therapeutically active agents, we investigated the biological properties of two small libraries of quinoxalinones and 3,4-dihydro-2(1H)-quinoxalinones (Fig. 1). The results obtained showed that compounds 5, 9–11 have good cytotoxic activity against HeLa cells where the lowest IC50 ǀalue ;ϭϬ.ϰϲ ± Ϭ.ϴϮ μM/ŵLͿ ǁas measured for compound 10. Additionally, the most active compounds (5, 9–11) showed much better selectivity for MRC-5 cells (up to 17.4) compared...
In order to investigate new potential therapeutically active agents, we investigated the biological properties of two small libraries of quinoxalinones and 3,4-dihydro-2(1H)-quinoxalinones (Fig. 1). The results obtained showed that compounds 5, 9–11 have good cytotoxic activity against HeLa cells where the lowest IC50 ǀalue ;ϭϬ.ϰϲ ± Ϭ.ϴϮ μM/ŵLͿ ǁas measured for compound 10. Additionally, the most active compounds (5, 9–11) showed much better selectivity for MRC-5 cells (up to 17.4) compared...
Synthesis of a Pt(II) complex with 2-(phenylselanylmethyl)oxolane as a ligand
Transition metal complexes with organoselenium compounds as ligands have attracted considerable interest due to their biological and biomedical applications. They can display cytotoxic, antimalarian, antileukemic and antitumor properties.1 In our previous work we have screened 2-(phenylselanylmethyl)oxolane (L) for its antioxidant and antiproliferative effect on colon cancer cell line HCT-116 and breast cancer cell line MDA-MB-231. 2 Coordinating L to Pd(II) gave complex which exhibits cytost...
Transition metal complexes with organoselenium compounds as ligands have attracted considerable interest due to their biological and biomedical applications. They can display cytotoxic, antimalarian, antileukemic and antitumor properties.1 In our previous work we have screened 2-(phenylselanylmethyl)oxolane (L) for its antioxidant and antiproliferative effect on colon cancer cell line HCT-116 and breast cancer cell line MDA-MB-231. 2 Coordinating L to Pd(II) gave complex which exhibits cytost...
Application of acyl pyruvates in synthetic chemistry
Acyl piruvates (1) represent a class of molecules that have attracted a considerable interest in synthetic chemistry.1 These molecules were used as a starting compounds in synthesis small libraries of novel M(II) complexes (2), quinoxalin-2(1H)-ones (3), benzo[b][1,4]oxazin-2-ones (4) and 2-hydroxy-pyrimidines (5). Yields were good-to excellent for all compounds.
Acyl piruvates (1) represent a class of molecules that have attracted a considerable interest in synthetic chemistry.1 These molecules were used as a starting compounds in synthesis small libraries of novel M(II) complexes (2), quinoxalin-2(1H)-ones (3), benzo[b][1,4]oxazin-2-ones (4) and 2-hydroxy-pyrimidines (5). Yields were good-to excellent for all compounds.
Regioselectivity and kinetics of cobalt(II) chloride catalyzed phenylselenocyclization of 6-methyl-hept-5-en-2-ol
Selenocyclization reactions are probably the most useful utilization of the electrophilic selenium(II) reagents. Addition of the reagents to the double bond triggers the nucleophilic attack of the suitably positioned pendant group resulting in the generation of a cyclic product. Due to the great diversity and versatility of pendant nuclephiles that can be used, these reactions have found widespread usage in some natural product synthesis, where the selenocyclization reaction represents the ke...
Selenocyclization reactions are probably the most useful utilization of the electrophilic selenium(II) reagents. Addition of the reagents to the double bond triggers the nucleophilic attack of the suitably positioned pendant group resulting in the generation of a cyclic product. Due to the great diversity and versatility of pendant nuclephiles that can be used, these reactions have found widespread usage in some natural product synthesis, where the selenocyclization reaction represents the ke...
Kinetic and mechanistic studies of triethylamine-catalyzed phenylselenolactonization of 4-pentenoic acid
The aim of this work is exploration of kinetic and mechanistic aspects of triethylaminecatalyzed phenylselenolactonization of 4-pentenoic acid by means of phenylselenenyl halides (PhSeCl and PhSeBr). The major product of these reactions is Ȗ-lactone with PhSefunctionalizated side chain, which can be easily transformed in numerous useful functional groups by very simple chemical reactions. In addition, the importance of Ȗ-lactones is reflected in the fact that a large number of these molecules...
The aim of this work is exploration of kinetic and mechanistic aspects of triethylaminecatalyzed phenylselenolactonization of 4-pentenoic acid by means of phenylselenenyl halides (PhSeCl and PhSeBr). The major product of these reactions is Ȗ-lactone with PhSefunctionalizated side chain, which can be easily transformed in numerous useful functional groups by very simple chemical reactions. In addition, the importance of Ȗ-lactones is reflected in the fact that a large number of these molecules...
Kinetic studie of phenylselenoetherification of 2,6-dimethyl-hept-5-en-2-ol in the presence of some catalysts
Tetrahydropyran- and tetrahydrofuran types of ethers are structural fragments of many natural products that can exibit significant biological activity. One of the most effective methods for their synthesis is cyclofunctionalization of unsaturated alcohols with phenylselenylhalides as reagents. Use of certain catalysts in these reactions increases yields and influences very high regio- and stereoselectivity. So far, small accomplishment has been achieved in the area of kinetics and mechanism ...
Tetrahydropyran- and tetrahydrofuran types of ethers are structural fragments of many natural products that can exibit significant biological activity. One of the most effective methods for their synthesis is cyclofunctionalization of unsaturated alcohols with phenylselenylhalides as reagents. Use of certain catalysts in these reactions increases yields and influences very high regio- and stereoselectivity. So far, small accomplishment has been achieved in the area of kinetics and mechanism ...
Kinetic investigation of cyclization reactions of some terpenic alcohols
Substituted tetrahydrofuran and tetrahydropyran ring systems are common structural units found in many bioactive natural products. Intramolecular heterocyclization of Δ4- and Δ5- alkenols is one of the fastest and easiest ways for obtaining cyclic ethers with very high structural diversity and possibility for further functionalization. In this work we investigated the influence of some Lewis bases (triethylamine, pyridine, quinoline, 2, 2’-bipyridne and piperidine) on rate constants of the e...
Substituted tetrahydrofuran and tetrahydropyran ring systems are common structural units found in many bioactive natural products. Intramolecular heterocyclization of Δ4- and Δ5- alkenols is one of the fastest and easiest ways for obtaining cyclic ethers with very high structural diversity and possibility for further functionalization. In this work we investigated the influence of some Lewis bases (triethylamine, pyridine, quinoline, 2, 2’-bipyridne and piperidine) on rate constants of the e...
NMR and UV- Vis Kinetic Study of the CoCl2-Catalyzed Phenylselenoetherification of Nerolidol
Nerodilol represents acyclic sesquiteprenic alkenol with rich medical potential, as well as with potential to serve as fragrant and flavor constituent in food.1 Numerous biological activities have been expressed by the nerolidol, such as antimalarian, antiulcer and antiparasitic.2 The phenylselenyl halideinduced oxyselenocyclization of the nerolidol present an important pathway for the synthesis of the substituted oxygen heterocycles (five- or six membered cyclic ethers) which are structural ...
Nerodilol represents acyclic sesquiteprenic alkenol with rich medical potential, as well as with potential to serve as fragrant and flavor constituent in food.1 Numerous biological activities have been expressed by the nerolidol, such as antimalarian, antiulcer and antiparasitic.2 The phenylselenyl halideinduced oxyselenocyclization of the nerolidol present an important pathway for the synthesis of the substituted oxygen heterocycles (five- or six membered cyclic ethers) which are structural ...
Solvent Effects on the Kinetics and Mechanism of Phenylselenoetherification of Some Δ4 – Alkenols
Solvent-solute interactions can play a key role in organic synthesis. These interactions are commonly described as non-specific (van der Waals, dipole-dipole, etc.) and specific (hydrogen bonding). Through the solvation, reactants, reaction products or intermediates can be stabilized, but also these interactions can modify energy barriers thereby altering transition states and possible reaction pathways. Depending on the solvent, reaction rates can vary by orders of magnitude and as well as p...
Solvent-solute interactions can play a key role in organic synthesis. These interactions are commonly described as non-specific (van der Waals, dipole-dipole, etc.) and specific (hydrogen bonding). Through the solvation, reactants, reaction products or intermediates can be stabilized, but also these interactions can modify energy barriers thereby altering transition states and possible reaction pathways. Depending on the solvent, reaction rates can vary by orders of magnitude and as well as p...
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