Shahriar Khadem - Academia.edu (original) (raw)
Papers by Shahriar Khadem
Bulletin of The Korean Chemical Society, Jun 20, 2011
Under solvent-free conditions and in one-pot, a series of 2-amino-4-aryl-3-cyano-6-(3,4-dimethoxy... more Under solvent-free conditions and in one-pot, a series of 2-amino-4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)pyridines and 4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)-2(1H)-pyridinones were prepared using 3,4dimethoxyacetophenone, an aldehyde, malononitrile (or ethyl cyanoacetate), and ammonium acetate in the presence of 3-methyl-1-(4-sulfonylbutyl)imidazolium hydrogen sulfate [HO 3 S(CH 2) 4 MIM][HSO 4 ] (a Brønsted acidic ionic liquid) as the catalyst in very short reaction time. The preference for the formation of more stable tautomers was consistence with the theoretical calculation using the Gaussian 03 program at the B3LYP hybrid density functional level.
Planta Medica, Mar 1, 2011
Pure and Applied Chemistry, 2005
Due to the growing interest in small molecules that could help in understanding protein–protein i... more Due to the growing interest in small molecules that could help in understanding protein–protein interactions based on signal transduction, the demand for the generation of small-molecule libraries that are inspired by bioactive natural products has grown significantly. Many of these pathways are highly complex and present tremendous challenges with the use of classical tools. A rapid access to natural product-like small molecules having structural complexity and diversity is crucial for systematically dissecting the functions of complex protein networking and understanding cell signaling pathways. The complex nature, the three-dimensional architecture, and the number of protein binding functional groups presented in three-dimensional arrays are some of the attractive features to incorporate in small-molecule chemical probes to be used as modulators of protein function.
ChemInform, Sep 29, 2011
Experimental and Theoretical Studies on the Tautomerism in 2-Aminopyridines and 2(1H)-Pyridinones... more Experimental and Theoretical Studies on the Tautomerism in 2-Aminopyridines and 2(1H)-Pyridinones: Synthesis of 2-Amino-4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)pyridines and 4-Aryl-3-cyano-6-(3,4-dimethoxyphenyl)-2(1H)-pyridinones.-The reaction is conducted under solvent free conditions. The experimental results are consistent with the theoretical calculation regarding the formation of more stable tautomers.
Under solvent-free conditions and in one-pot, a series of 2-amino-4-aryl-3-cyano-6-(3,4-dimethoxy... more Under solvent-free conditions and in one-pot, a series of 2-amino-4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)-pyridines and 4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)-2(1H)-pyridinones were prepared using 3,4-dimethoxyacetophenone, an aldehyde, malononitrile (or ethyl cyanoacetate), and ammonium acetate in the presence of 3-methyl-1-(4-sulfonylbutyl)imidazolium hydrogen sulfate [HO3S(CH2)4MIM][HSO4] (a Brønsted acidic ionic liquid) as the catalyst in very short reaction time. The preference for the formation of more stable tautomers was consistence with the theoretical calculation using the Gaussian 03 program at the B3LYP hybrid density functional level. Key Words: Brønsted-acidic ionic liquids, 3-Cyanopyridines, 3-Cyanopyridinones, Multicomponent reac-tions, Tautomerism
Among the wide diversity of naturally occurring phenolic acids, at least 30 hydroxy-and polyhydro... more Among the wide diversity of naturally occurring phenolic acids, at least 30 hydroxy-and polyhydroxybenzoic acids have been reported in the last 10 years to have biological activities. The chemical structures, natural occurrence throughout the plant, algal, bacterial, fungal and animal kingdoms, and recently described bioactivities of these phenolic and polyphenolic acids are reviewed to illustrate their wide distribution, biological and ecological importance, and potential as new leads for the development of pharmaceutical and agricultural products to improve human health and nutrition.
Over the years, it has been shown that natural products which are capable of acting as modulators... more Over the years, it has been shown that natural products which are capable of acting as modulators (i.e., activators or inhibitors) of protein-protein interactions are highly complex and possess three-dimensional architectures with several chiral centers and a diverse range of protein-binding elements. These features appear to be required when it comes to dissecting protein functions with the help of small molecules. Therefore, it is not surprising that an interest in developing natural product-like small molecules, which could aid in understanding proteinprotein interactions-based cellular signaling pathways, is growing. The success of the chemical genomics program that is aimed toward understanding complex protein networking and its roles in cellular signaling pathways depends on the availability of a diverse range of such chemical probes (Chapter 1). Tetrahydroquinoline-derived natural products have long been utilized as modulators of protein functions and belong to an important f...
Chem Rev, 2009
Born in India, Jyoti Prokash Nandy completed his Ph.D. under the supervision of Prof. Javed Iqbal... more Born in India, Jyoti Prokash Nandy completed his Ph.D. under the supervision of Prof. Javed Iqbal from the Indian Institute of Technology, Kanpur (IITK), in 2002 and joined Prof. Albert Eschenmoser's group as a postdoctoral fellow in the Scripps Research Institute, La Jolla, California. In ...
ChemInform, 2010
Having α,β-Unsaturated γ-Lactam and δ-Lactone Functionalities. -Substrates (II) and (IV) are prep... more Having α,β-Unsaturated γ-Lactam and δ-Lactone Functionalities. -Substrates (II) and (IV) are prepared from alcohol (I) and used for the synthesis of the natural product skeletons (III) and (VI). -(KHADEM*, S.; UDACHIN, K. A.; ARYA, P.; Synlett 2010, 2, 199-202; Steacie Inst. Mol. Sci., Natl. Res. Counc. Can., Ottawa, Ont. K1A 0R6, Can.; Eng.) -Mais 22-133
Born in India, Jyoti Prokash Nandy completed his Ph.D. under the supervision of Prof. Javed Iqbal... more Born in India, Jyoti Prokash Nandy completed his Ph.D. under the supervision of Prof. Javed Iqbal from the Indian Institute of Technology, Kanpur (IITK), in 2002 and joined Prof. Albert Eschenmoser's group as a postdoctoral fellow in the Scripps Research Institute, La Jolla, California. In ...
ChemInform
Under solvent-free conditions and in one-pot, a series of 2-amino-4-aryl-3-cyano-6-(3,4-dimethoxy... more Under solvent-free conditions and in one-pot, a series of 2-amino-4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)pyridines and 4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)-2(1H)-pyridinones were prepared using 3,4-dimethoxyacetophenone, an aldehyde, malononitrile (or ethyl cyanoacetate), and ammonium acetate in the presence of 3-methyl-1-(4-sulfonylbutyl)imidazolium hydrogen sulfate [HO(3)S(CH(2))(4)MIM][HSO(4)] (a Bronsted acidic ionic liquid) as the catalyst in very short reaction time. The preference for the formation of more stable tautomers was consistence with the theoretical calculation using the Gaussian 03 program at the B3LYP hybrid density functional level.
![Research paper thumbnail of ChemInform Abstract: One-Pot Construction of Isoindolo[2,1-a]quinoline System](https://attachments.academia-assets.com/66737747/thumbnails/1.jpg)
](ChemInform, 2010
One-Pot Construction of Isoindolo[2,1-a]quinoline System. -Application of Povarov's three-compone... more One-Pot Construction of Isoindolo[2,1-a]quinoline System. -Application of Povarov's three-component reaction to o-carboxybenzaldehydes results in a following condensation in the same pot to cause stereo-and regioselective formation of polycyclic isoindolo-[2,1-a]quinoline derivatives. -(KHADEM*, S.; UDACHIN, K. A.; ENRIGHT, G. D.; PRAKESCH, M.; ARYA, P.; Tetrahedron Lett. 50 (2009) 48, 6661-6664; Steacie Inst. Mol. Sci., Natl. Res. Counc. Can., Ottawa, Ont. K1A 0R6, Can.; Eng.) -Mais 11-158
![Research paper thumbnail of One-pot construction of isoindolo[2,1-a]quinoline system](https://attachments.academia-assets.com/66737740/thumbnails/1.jpg)
](Tetrahedron Letters, 2009
Polycyclic compounds bearing isoindolo[2,1-a]quinoline system were easily prepared stereo-and reg... more Polycyclic compounds bearing isoindolo[2,1-a]quinoline system were easily prepared stereo-and regioselectively, and in one-pot, in a tandem fashion containing Povarov's multicomponent and condensation reactions. Involving a stepwise route for the aza Diels-Alder reaction within the synthesis was suggested.
Synlett, 2010
Vous avez des questions? Nous pouvons vous aider. Pour communiquer directement avec un auteur, co... more Vous avez des questions? Nous pouvons vous aider. Pour communiquer directement avec un auteur, consultez la première page de la revue dans laquelle son article a été publié afin de trouver ses coordonnées. Si vous n'arrivez pas à les repérer, communiquez avec nous à PublicationsArchive-ArchivesPublications@nrc-cnrc.gc.ca.
Molecules, 2010
Among the wide diversity of naturally occurring phenolic acids, at least 30 hydroxy-and polyhydro... more Among the wide diversity of naturally occurring phenolic acids, at least 30 hydroxy-and polyhydroxybenzoic acids have been reported in the last 10 years to have biological activities. The chemical structures, natural occurrence throughout the plant, algal, bacterial, fungal and animal kingdoms, and recently described bioactivities of these phenolic and polyphenolic acids are reviewed to illustrate their wide distribution, biological and ecological importance, and potential as new leads for the development of pharmaceutical and agricultural products to improve human health and nutrition.
Molecules, 2011
The chromone and flavonoid alkaloids represent an unusual group of structurally diverse secondary... more The chromone and flavonoid alkaloids represent an unusual group of structurally diverse secondary metabolites, derived from the convergence of multiple biosynthetic pathways that are widely distributed through the plant and animal kingdoms. Many of them have been discovered through bioassay-guided chemical investigations of traditional medicines, suggesting potential therapeutic significance. Their unique structures and varied pharmacological activities may provide important new leads for the discovery of drugs with novel mechanisms of action. Potential therapeutic indications are as diverse as cancer and viral infections, inflammation and immunomodulation, neurological and psychiatric conditions, and diabetes.
Journal of Chemical & Engineering Data, 2010
The structures of all of the chemical species involved in the prototropic tautomerism and acid−ba... more The structures of all of the chemical species involved in the prototropic tautomerism and acid−base dissociation equilibria of N-(2-oxo-2H-chromen-3-yl)acetamide were determined both experimentally and theoretically. Using the calculated acidity constants, the ...
Bulletin of The Korean Chemical Society, Jun 20, 2011
Under solvent-free conditions and in one-pot, a series of 2-amino-4-aryl-3-cyano-6-(3,4-dimethoxy... more Under solvent-free conditions and in one-pot, a series of 2-amino-4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)pyridines and 4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)-2(1H)-pyridinones were prepared using 3,4dimethoxyacetophenone, an aldehyde, malononitrile (or ethyl cyanoacetate), and ammonium acetate in the presence of 3-methyl-1-(4-sulfonylbutyl)imidazolium hydrogen sulfate [HO 3 S(CH 2) 4 MIM][HSO 4 ] (a Brønsted acidic ionic liquid) as the catalyst in very short reaction time. The preference for the formation of more stable tautomers was consistence with the theoretical calculation using the Gaussian 03 program at the B3LYP hybrid density functional level.
Planta Medica, Mar 1, 2011
Pure and Applied Chemistry, 2005
Due to the growing interest in small molecules that could help in understanding protein–protein i... more Due to the growing interest in small molecules that could help in understanding protein–protein interactions based on signal transduction, the demand for the generation of small-molecule libraries that are inspired by bioactive natural products has grown significantly. Many of these pathways are highly complex and present tremendous challenges with the use of classical tools. A rapid access to natural product-like small molecules having structural complexity and diversity is crucial for systematically dissecting the functions of complex protein networking and understanding cell signaling pathways. The complex nature, the three-dimensional architecture, and the number of protein binding functional groups presented in three-dimensional arrays are some of the attractive features to incorporate in small-molecule chemical probes to be used as modulators of protein function.
ChemInform, Sep 29, 2011
Experimental and Theoretical Studies on the Tautomerism in 2-Aminopyridines and 2(1H)-Pyridinones... more Experimental and Theoretical Studies on the Tautomerism in 2-Aminopyridines and 2(1H)-Pyridinones: Synthesis of 2-Amino-4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)pyridines and 4-Aryl-3-cyano-6-(3,4-dimethoxyphenyl)-2(1H)-pyridinones.-The reaction is conducted under solvent free conditions. The experimental results are consistent with the theoretical calculation regarding the formation of more stable tautomers.
Under solvent-free conditions and in one-pot, a series of 2-amino-4-aryl-3-cyano-6-(3,4-dimethoxy... more Under solvent-free conditions and in one-pot, a series of 2-amino-4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)-pyridines and 4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)-2(1H)-pyridinones were prepared using 3,4-dimethoxyacetophenone, an aldehyde, malononitrile (or ethyl cyanoacetate), and ammonium acetate in the presence of 3-methyl-1-(4-sulfonylbutyl)imidazolium hydrogen sulfate [HO3S(CH2)4MIM][HSO4] (a Brønsted acidic ionic liquid) as the catalyst in very short reaction time. The preference for the formation of more stable tautomers was consistence with the theoretical calculation using the Gaussian 03 program at the B3LYP hybrid density functional level. Key Words: Brønsted-acidic ionic liquids, 3-Cyanopyridines, 3-Cyanopyridinones, Multicomponent reac-tions, Tautomerism
Among the wide diversity of naturally occurring phenolic acids, at least 30 hydroxy-and polyhydro... more Among the wide diversity of naturally occurring phenolic acids, at least 30 hydroxy-and polyhydroxybenzoic acids have been reported in the last 10 years to have biological activities. The chemical structures, natural occurrence throughout the plant, algal, bacterial, fungal and animal kingdoms, and recently described bioactivities of these phenolic and polyphenolic acids are reviewed to illustrate their wide distribution, biological and ecological importance, and potential as new leads for the development of pharmaceutical and agricultural products to improve human health and nutrition.
Over the years, it has been shown that natural products which are capable of acting as modulators... more Over the years, it has been shown that natural products which are capable of acting as modulators (i.e., activators or inhibitors) of protein-protein interactions are highly complex and possess three-dimensional architectures with several chiral centers and a diverse range of protein-binding elements. These features appear to be required when it comes to dissecting protein functions with the help of small molecules. Therefore, it is not surprising that an interest in developing natural product-like small molecules, which could aid in understanding proteinprotein interactions-based cellular signaling pathways, is growing. The success of the chemical genomics program that is aimed toward understanding complex protein networking and its roles in cellular signaling pathways depends on the availability of a diverse range of such chemical probes (Chapter 1). Tetrahydroquinoline-derived natural products have long been utilized as modulators of protein functions and belong to an important f...
Chem Rev, 2009
Born in India, Jyoti Prokash Nandy completed his Ph.D. under the supervision of Prof. Javed Iqbal... more Born in India, Jyoti Prokash Nandy completed his Ph.D. under the supervision of Prof. Javed Iqbal from the Indian Institute of Technology, Kanpur (IITK), in 2002 and joined Prof. Albert Eschenmoser's group as a postdoctoral fellow in the Scripps Research Institute, La Jolla, California. In ...
ChemInform, 2010
Having α,β-Unsaturated γ-Lactam and δ-Lactone Functionalities. -Substrates (II) and (IV) are prep... more Having α,β-Unsaturated γ-Lactam and δ-Lactone Functionalities. -Substrates (II) and (IV) are prepared from alcohol (I) and used for the synthesis of the natural product skeletons (III) and (VI). -(KHADEM*, S.; UDACHIN, K. A.; ARYA, P.; Synlett 2010, 2, 199-202; Steacie Inst. Mol. Sci., Natl. Res. Counc. Can., Ottawa, Ont. K1A 0R6, Can.; Eng.) -Mais 22-133
Born in India, Jyoti Prokash Nandy completed his Ph.D. under the supervision of Prof. Javed Iqbal... more Born in India, Jyoti Prokash Nandy completed his Ph.D. under the supervision of Prof. Javed Iqbal from the Indian Institute of Technology, Kanpur (IITK), in 2002 and joined Prof. Albert Eschenmoser's group as a postdoctoral fellow in the Scripps Research Institute, La Jolla, California. In ...
ChemInform
Under solvent-free conditions and in one-pot, a series of 2-amino-4-aryl-3-cyano-6-(3,4-dimethoxy... more Under solvent-free conditions and in one-pot, a series of 2-amino-4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)pyridines and 4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)-2(1H)-pyridinones were prepared using 3,4-dimethoxyacetophenone, an aldehyde, malononitrile (or ethyl cyanoacetate), and ammonium acetate in the presence of 3-methyl-1-(4-sulfonylbutyl)imidazolium hydrogen sulfate [HO(3)S(CH(2))(4)MIM][HSO(4)] (a Bronsted acidic ionic liquid) as the catalyst in very short reaction time. The preference for the formation of more stable tautomers was consistence with the theoretical calculation using the Gaussian 03 program at the B3LYP hybrid density functional level.
ChemInform, 2010
One-Pot Construction of Isoindolo[2,1-a]quinoline System. -Application of Povarov's three-compone... more One-Pot Construction of Isoindolo[2,1-a]quinoline System. -Application of Povarov's three-component reaction to o-carboxybenzaldehydes results in a following condensation in the same pot to cause stereo-and regioselective formation of polycyclic isoindolo-[2,1-a]quinoline derivatives. -(KHADEM*, S.; UDACHIN, K. A.; ENRIGHT, G. D.; PRAKESCH, M.; ARYA, P.; Tetrahedron Lett. 50 (2009) 48, 6661-6664; Steacie Inst. Mol. Sci., Natl. Res. Counc. Can., Ottawa, Ont. K1A 0R6, Can.; Eng.) -Mais 11-158
Tetrahedron Letters, 2009
Polycyclic compounds bearing isoindolo[2,1-a]quinoline system were easily prepared stereo-and reg... more Polycyclic compounds bearing isoindolo[2,1-a]quinoline system were easily prepared stereo-and regioselectively, and in one-pot, in a tandem fashion containing Povarov's multicomponent and condensation reactions. Involving a stepwise route for the aza Diels-Alder reaction within the synthesis was suggested.
Synlett, 2010
Vous avez des questions? Nous pouvons vous aider. Pour communiquer directement avec un auteur, co... more Vous avez des questions? Nous pouvons vous aider. Pour communiquer directement avec un auteur, consultez la première page de la revue dans laquelle son article a été publié afin de trouver ses coordonnées. Si vous n'arrivez pas à les repérer, communiquez avec nous à PublicationsArchive-ArchivesPublications@nrc-cnrc.gc.ca.
Molecules, 2010
Among the wide diversity of naturally occurring phenolic acids, at least 30 hydroxy-and polyhydro... more Among the wide diversity of naturally occurring phenolic acids, at least 30 hydroxy-and polyhydroxybenzoic acids have been reported in the last 10 years to have biological activities. The chemical structures, natural occurrence throughout the plant, algal, bacterial, fungal and animal kingdoms, and recently described bioactivities of these phenolic and polyphenolic acids are reviewed to illustrate their wide distribution, biological and ecological importance, and potential as new leads for the development of pharmaceutical and agricultural products to improve human health and nutrition.
Molecules, 2011
The chromone and flavonoid alkaloids represent an unusual group of structurally diverse secondary... more The chromone and flavonoid alkaloids represent an unusual group of structurally diverse secondary metabolites, derived from the convergence of multiple biosynthetic pathways that are widely distributed through the plant and animal kingdoms. Many of them have been discovered through bioassay-guided chemical investigations of traditional medicines, suggesting potential therapeutic significance. Their unique structures and varied pharmacological activities may provide important new leads for the discovery of drugs with novel mechanisms of action. Potential therapeutic indications are as diverse as cancer and viral infections, inflammation and immunomodulation, neurological and psychiatric conditions, and diabetes.
Journal of Chemical & Engineering Data, 2010
The structures of all of the chemical species involved in the prototropic tautomerism and acid−ba... more The structures of all of the chemical species involved in the prototropic tautomerism and acid−base dissociation equilibria of N-(2-oxo-2H-chromen-3-yl)acetamide were determined both experimentally and theoretically. Using the calculated acidity constants, the ...