ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
We present a novel and facile route to functionalised isoquinolinones and isoquinolines in good y... more We present a novel and facile route to functionalised isoquinolinones and isoquinolines in good yields.
This is a repository copy of Catalytic bimetalic [Pd(0)/Ag(I) Heck-1,3-dipolar cycloaddition casc... more This is a repository copy of Catalytic bimetalic [Pd(0)/Ag(I) Heck-1,3-dipolar cycloaddition cascade reactions accessing spiro-oxindoles. Concomitant in situ generation of azomethine ylides and dipolarophile.
To overcome numerous health disorders, heterocyclic structures of synthetic or natural origin are... more To overcome numerous health disorders, heterocyclic structures of synthetic or natural origin are utilized, and notably, the emergence of various side effects of existing drugs used for treatment or the resistance of disease-causing microorganisms renders drugs ineffective. Therefore, the discovery of potential therapeutic agents that utilize different modes of action is of utmost significance to circumvent these constraints. Pyrrolidines, pyrrolidine-alkaloids, and pyrrolidinebased hybrid molecules are present in many natural products and pharmacologically important agents. Their key roles in pharmacotherapy make them a versatile scaffold for designing and developing novel biologically active compounds and drug candidates. This review aims to provide an overview of recent advancements (especially during 2015-2023) in the exploration of pyrrolidine derivatives, emphasizing their significance as fundamental components of the skeletal structure. In contrast to previous reviews that have predominantly focused on a singular biological activity associated with these molecules, this review consolidates findings from various investigations encompassing a wide range of important activities (antimicrobial, antiviral, anticancer, anti-inflammatory, anticonvulsant, cholinesterase inhibition, and carbonic anhydrase inhibition) exhibited by pyrrolidine derivatives. This study is also anticipated to serve as a valuable resource for drug research and development endeavors, offering significant insights and guidance.
Diastereoselective Synthesis of β 2-Amino Acids.-A general route to β 2-amino acids is presented,... more Diastereoselective Synthesis of β 2-Amino Acids.-A general route to β 2-amino acids is presented, involving highly diastereoselective alkylation of a chiral sultam β-alaninate derivative (IV) as the key step. Alkylation must be performed below-45 • C to avoid elimination via ketene formation. β 2-Homophenylalanine (VI),-homoalanine (IXa) and-homoleucine derivatives (IXb) are prepared using this technique. Starting with (-)-sultam (II), the (R)-β 2-amino acids are obtained, while the corresponding (S)-enantiomers arise from (+)-sultam.-(
Some novel cyclic α-aminoacid esters and potential bioactive compounds were prepared via thermal ... more Some novel cyclic α-aminoacid esters and potential bioactive compounds were prepared via thermal 1,2-prototropy-and 1,3-APT oxime nitrone-l,3-dipolar cycloaddition cascades reactions. This substrate allows the influence of the new stereocentres on the cascade to be assessed with respect to the configuration of the nitrone that is generated and the facial selectivity of the subsequent cycloaddition.
Imines of (1S,9S)-t-butyl-9-amino-octahydro-6,10-dioxo-6H-pyridazino[1,2-a][1,2]diazepine-1-carbo... more Imines of (1S,9S)-t-butyl-9-amino-octahydro-6,10-dioxo-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate undergo thermal (toluene, 1108C) or LiBr-DBU catalysed (MeCN, room temperature) regio-and stereo-specific cycloaddition to a range of chiral dipolarophiles giving enantiopure spiro-cycloadducts in excellent yield. The reactions proceed via intermediate NH azomethine ylides and litho azomethine ylides, respectively and results in the multiplication of chiral centres from 2 (one of which is lost in the process) to 5.
Palladium catalysed three component cascade process, involving coupling of 2-iodobenzoates,-benza... more Palladium catalysed three component cascade process, involving coupling of 2-iodobenzoates,-benzaldehydes, or acetophenones with substituted allenes and ammonium 65 75
Carbophilic 3-Component Cascades: Access to Complex Bioactive Cyclopropyl Diindolylmethanes.-Cycl... more Carbophilic 3-Component Cascades: Access to Complex Bioactive Cyclopropyl Diindolylmethanes.-Cycloisomerization of nitrogen-tethered 1,6-dienynes is catalyzed by PtCl2 and affords the corresponding azabicyclo[4.1.0]hept-4-enes [viz. (II), (IV), (VI)]. Substrates bearing 3-pyridyl substituents fail to react. Three component reaction of 1,6-enynes and indoles proceeds under the same reaction conditions and afford biologically relevant diindolylmethane derivatives [viz. (VIII), (XII)]. In the case of internal alkyne substrates as (Ia) monoindolyl adduct (X) is isolated as well. Diindolyl methanes (VIIId) and (XIIb) are tested for their activity against prostate cancer cell lines and show some selectivity but are poorly soluble in the culture medium. Their derivatization into oximes greatly improve their aqueous solubility and activity against the LNCaP and PC3 cell lines.-(GROOME, N. M.
International Journal of Analytical Chemistry, 2014
The acid dissociation constants of potential bioactive fused ring thiohydantoin-pyrrolidine compo... more The acid dissociation constants of potential bioactive fused ring thiohydantoin-pyrrolidine compounds were determined by potentiometric titration in 20% (v/v) ethanol-water mixed at 25 ± 0.1 ∘ C, at an ionic background of 0.1 mol/L of NaCl using the HYPERQUAD computer program. Proton affinities of potential donor atoms of the ligands were calculated by AM1 and PM3 semiempiric methods. We found, potentiometrically, three different acid dissociation constants for 1a-f. We suggest that these acid dissociation constants are related to the carboxyl, enol, and amino groups.
ÐOximes possessing g-and d-alkenyl substituents are cyclised by N-bromo-or N-iodosuccinimide, iod... more ÐOximes possessing g-and d-alkenyl substituents are cyclised by N-bromo-or N-iodosuccinimide, iodine or ICl to the corresponding cyclic nitrones or their dimeric H-bonded hydroiodide salts in good yield; facially speci®c cycloaddition of these nitrones, and others derived by cyclisation of d,d-bis(alkenyl) ketoximes or by iodine induced addition of acetaldoxime to cyclohexene, furnish isoxazolidines.
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
We present a novel and facile route to functionalised isoquinolinones and isoquinolines in good y... more We present a novel and facile route to functionalised isoquinolinones and isoquinolines in good yields.
This is a repository copy of Catalytic bimetalic [Pd(0)/Ag(I) Heck-1,3-dipolar cycloaddition casc... more This is a repository copy of Catalytic bimetalic [Pd(0)/Ag(I) Heck-1,3-dipolar cycloaddition cascade reactions accessing spiro-oxindoles. Concomitant in situ generation of azomethine ylides and dipolarophile.
To overcome numerous health disorders, heterocyclic structures of synthetic or natural origin are... more To overcome numerous health disorders, heterocyclic structures of synthetic or natural origin are utilized, and notably, the emergence of various side effects of existing drugs used for treatment or the resistance of disease-causing microorganisms renders drugs ineffective. Therefore, the discovery of potential therapeutic agents that utilize different modes of action is of utmost significance to circumvent these constraints. Pyrrolidines, pyrrolidine-alkaloids, and pyrrolidinebased hybrid molecules are present in many natural products and pharmacologically important agents. Their key roles in pharmacotherapy make them a versatile scaffold for designing and developing novel biologically active compounds and drug candidates. This review aims to provide an overview of recent advancements (especially during 2015-2023) in the exploration of pyrrolidine derivatives, emphasizing their significance as fundamental components of the skeletal structure. In contrast to previous reviews that have predominantly focused on a singular biological activity associated with these molecules, this review consolidates findings from various investigations encompassing a wide range of important activities (antimicrobial, antiviral, anticancer, anti-inflammatory, anticonvulsant, cholinesterase inhibition, and carbonic anhydrase inhibition) exhibited by pyrrolidine derivatives. This study is also anticipated to serve as a valuable resource for drug research and development endeavors, offering significant insights and guidance.
Diastereoselective Synthesis of β 2-Amino Acids.-A general route to β 2-amino acids is presented,... more Diastereoselective Synthesis of β 2-Amino Acids.-A general route to β 2-amino acids is presented, involving highly diastereoselective alkylation of a chiral sultam β-alaninate derivative (IV) as the key step. Alkylation must be performed below-45 • C to avoid elimination via ketene formation. β 2-Homophenylalanine (VI),-homoalanine (IXa) and-homoleucine derivatives (IXb) are prepared using this technique. Starting with (-)-sultam (II), the (R)-β 2-amino acids are obtained, while the corresponding (S)-enantiomers arise from (+)-sultam.-(
Some novel cyclic α-aminoacid esters and potential bioactive compounds were prepared via thermal ... more Some novel cyclic α-aminoacid esters and potential bioactive compounds were prepared via thermal 1,2-prototropy-and 1,3-APT oxime nitrone-l,3-dipolar cycloaddition cascades reactions. This substrate allows the influence of the new stereocentres on the cascade to be assessed with respect to the configuration of the nitrone that is generated and the facial selectivity of the subsequent cycloaddition.
Imines of (1S,9S)-t-butyl-9-amino-octahydro-6,10-dioxo-6H-pyridazino[1,2-a][1,2]diazepine-1-carbo... more Imines of (1S,9S)-t-butyl-9-amino-octahydro-6,10-dioxo-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate undergo thermal (toluene, 1108C) or LiBr-DBU catalysed (MeCN, room temperature) regio-and stereo-specific cycloaddition to a range of chiral dipolarophiles giving enantiopure spiro-cycloadducts in excellent yield. The reactions proceed via intermediate NH azomethine ylides and litho azomethine ylides, respectively and results in the multiplication of chiral centres from 2 (one of which is lost in the process) to 5.
Palladium catalysed three component cascade process, involving coupling of 2-iodobenzoates,-benza... more Palladium catalysed three component cascade process, involving coupling of 2-iodobenzoates,-benzaldehydes, or acetophenones with substituted allenes and ammonium 65 75
Carbophilic 3-Component Cascades: Access to Complex Bioactive Cyclopropyl Diindolylmethanes.-Cycl... more Carbophilic 3-Component Cascades: Access to Complex Bioactive Cyclopropyl Diindolylmethanes.-Cycloisomerization of nitrogen-tethered 1,6-dienynes is catalyzed by PtCl2 and affords the corresponding azabicyclo[4.1.0]hept-4-enes [viz. (II), (IV), (VI)]. Substrates bearing 3-pyridyl substituents fail to react. Three component reaction of 1,6-enynes and indoles proceeds under the same reaction conditions and afford biologically relevant diindolylmethane derivatives [viz. (VIII), (XII)]. In the case of internal alkyne substrates as (Ia) monoindolyl adduct (X) is isolated as well. Diindolyl methanes (VIIId) and (XIIb) are tested for their activity against prostate cancer cell lines and show some selectivity but are poorly soluble in the culture medium. Their derivatization into oximes greatly improve their aqueous solubility and activity against the LNCaP and PC3 cell lines.-(GROOME, N. M.
International Journal of Analytical Chemistry, 2014
The acid dissociation constants of potential bioactive fused ring thiohydantoin-pyrrolidine compo... more The acid dissociation constants of potential bioactive fused ring thiohydantoin-pyrrolidine compounds were determined by potentiometric titration in 20% (v/v) ethanol-water mixed at 25 ± 0.1 ∘ C, at an ionic background of 0.1 mol/L of NaCl using the HYPERQUAD computer program. Proton affinities of potential donor atoms of the ligands were calculated by AM1 and PM3 semiempiric methods. We found, potentiometrically, three different acid dissociation constants for 1a-f. We suggest that these acid dissociation constants are related to the carboxyl, enol, and amino groups.
ÐOximes possessing g-and d-alkenyl substituents are cyclised by N-bromo-or N-iodosuccinimide, iod... more ÐOximes possessing g-and d-alkenyl substituents are cyclised by N-bromo-or N-iodosuccinimide, iodine or ICl to the corresponding cyclic nitrones or their dimeric H-bonded hydroiodide salts in good yield; facially speci®c cycloaddition of these nitrones, and others derived by cyclisation of d,d-bis(alkenyl) ketoximes or by iodine induced addition of acetaldoxime to cyclohexene, furnish isoxazolidines.
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