The Experts below are selected from a list of 228 Experts worldwide ranked by ideXlab platform
Andrzej Stańczak - One of the best experts on this subject based on the ideXlab platform.
-
Cinnoline Scaffold—A Molecular Heart of Medicinal Chemistry?
Molecules (Basel Switzerland), 2019Co-Authors: Marta Szumilak, Andrzej StańczakAbstract:The Cinnoline nucleus is a very important bicyclic heterocycle that is used as the structural subunit of many compounds with interesting pharmaceutical properties. Cinnoline derivatives exhibit broad spectrum of pharmacological activities such as antibacterial, antifungal, antimalarial, anti-inflammatory, analgesic, anxiolytic and antitumor activities. Some of them are under evaluation in clinical trials. In the present review, we have compiled studies focused on the biological properties of Cinnoline derivatives conducted by many research groups worldwide between 2005 and 2019. Comprehensive and target oriented information clearly indicate that the development of Cinnoline based molecules constitute a significant contribution to the identification of lead compounds with optimized pharmacodynamic and pharmacokinetic properties.
-
Cinnoline scaffold a molecular heart of medicinal chemistry
Molecules, 2019Co-Authors: Marta Szumilak, Andrzej StańczakAbstract:The Cinnoline nucleus is a very important bicyclic heterocycle that is used as the structural subunit of many compounds with interesting pharmaceutical properties. Cinnoline derivatives exhibit broad spectrum of pharmacological activities such as antibacterial, antifungal, antimalarial, anti-inflammatory, analgesic, anxiolytic and antitumor activities. Some of them are under evaluation in clinical trials. In the present review, we have compiled studies focused on the biological properties of Cinnoline derivatives conducted by many research groups worldwide between 2005 and 2019. Comprehensive and target oriented information clearly indicate that the development of Cinnoline based molecules constitute a significant contribution to the identification of lead compounds with optimized pharmacodynamic and pharmacokinetic properties.
-
Synthesis and Biological Activity of Some 4‐Amino‐3‐Cinnolinecarboxylic Acid Derivatives. Part 5. Pyrimido[5,4‐c]Cinnolines and Triazepino[7,6‐c]Cinnoline.
ChemInform, 2010Co-Authors: Andrzej Stańczak, Z. B. Ochocki, W. PakulskaAbstract:A series of substituted 3-aminopyrimido[5,4-c]Cinnolines 3, 7 was prepared. 6,7-Substituted 4-amino-3-Cinnolinecarboxylic acid 1 were condensed with acetic anhydride to give the respective 1,3-oxazino[5,4-c]Cinnolines 2. The obtained derivatives reacted with hydrazines and gave 3-aminopyrimido[5,4-c]Cinnolines. Reaction of the esters 5 with hydrazines produced hydrazides 6, which upon treatment with N,N-dimethylformamide dimethyl acetal gave 3-aminopyrimido[5,4-c]Cinnolines 7. Treatment of 6b with bromocyan produced 2-amino-3,4-dihydro-3,10-dimethyl-5 H-1,3,4-triazepino[7,6-c]cinnolin-5-on (8b). Some of the synthesized compounds were screened for their effect on the CNS.
-
Cinnoline Derivatives with Biological Activity
ChemInform, 2007Co-Authors: Wieslawa Lewgowd, Andrzej StańczakAbstract:Although Cinnoline belongs to a family of fairly well known heterocycles, the interest in the study of its derivatives continues. Cinnoline compounds demonstrate interesting bioactivity and many research papers have discussed the biological property, structure-activity relationship, and applications in medicinal science. Attention has been paid to the synthesis of heterocyclic compounds bearing a Cinnoline moiety, mainly because of the interest in their broad spectrum of pharmacological activities. This chronological work summarizes almost all synthetic papers and patents concerning the biological properties of 107 Cinnoline derivatives published over the last 50 years with 117 references.
-
Synthesis and biological activity of some 4-amino-3-Cinnolinecarboxylic acid derivatives. Part 5: Pyrimido[5,4-c]Cinnolines and triazepino[7,6-c]Cinnoline.
Die Pharmazie, 1998Co-Authors: Andrzej Stańczak, Z. B. Ochocki, W. PakulskaAbstract:A series of substituted 3-aminopyrimido[5,4-c]Cinnolines 3, 7 was prepared. 6,7-Substituted 4-amino-3-Cinnolinecarboxylic acid 1 were condensed with acetic anhydride to give the respective 1,3-oxazino[5,4-c]Cinnolines 2. The obtained derivatives reacted with hydrazines and gave 3-aminopyrimido[5,4-c]Cinnolines. Reaction of the esters 5 with hydrazines produced hydrazides 6, which upon treatment with N,N-dimethylformamide dimethyl acetal gave 3-aminopyrimido[5,4-c]Cinnolines 7. Treatment of 6b with bromocyan produced 2-amino-3,4-dihydro-3,10-dimethyl-5 H-1,3,4-triazepino[7,6-c]cinnolin-5-on (8b). Some of the synthesized compounds were screened for their effect on the CNS.
Mark J Kurth - One of the best experts on this subject based on the ideXlab platform.
-
quinoxalino 2 3 c Cinnolines and their 5 n oxide alkoxylation of methyl substituted quinoxalino 2 3 c Cinnolines to acetals and orthoesters
Journal of Organic Chemistry, 2011Co-Authors: Makhluf J Haddadin, Mirna Elkhatib, Tharallah A Shoker, Christine M Beavers, Marilyn M Olmstead, James C Fettinger, Kelli M Farber, Mark J KurthAbstract:We report the alkoxylation of methyl-substituted quinoxalino[2,3-c]Cinnolines to give acetals and orthoesters in high yields. Routes to the precursors of this alkoxylation reaction as well as other quinoxalino[2,3-c]Cinnoline and their 5-oxide derivatives are reported. Most of these quinoxalino[2,3-c]Cinnolines were prepared by cyclization of the corresponding 2-amino-3-(2-nitrophenyl)quinoxaline, which, in turn, result from an unusual Beirut reaction from benzofurazan oxides plus 2-nitrobenzylcyanides. Mechanistic explanations for these intriguing reactions are presented.
Claudia Vergelli - One of the best experts on this subject based on the ideXlab platform.
-
Cinnoline derivatives as human neutrophil elastase inhibitors
Journal of Enzyme Inhibition and Medicinal Chemistry, 2016Co-Authors: Maria Paola Giovannoni, Igor A. Schepetkin, Letizia Crocetti, Giovanna Ciciani, Agostino Cilibrizzi, Gabriella Guerrini, Andrei I. Khlebnikov, Mark T. Quinn, Claudia VergelliAbstract:AbstractCompounds that can effectively inhibit the proteolytic activity of human neutrophil elastase (HNE) represent promising therapeutics for treatment of inflammatory diseases. We present here the synthesis, structure–activity relationship analysis, and biological evaluation of a new series of HNE inhibitors with a Cinnoline scaffold. These compounds exhibited HNE inhibitory activity but had lower potency compared to N-benzoylindazoles previously reported by us. On the other hand, they exhibited increased stability in aqueous solution. The most potent compound, 18a, had a good balance between HNE inhibitory activity (IC50 value = 56 nM) and chemical stability (t1/2 = 114 min). Analysis of reaction kinetics revealed that these Cinnoline derivatives were reversible competitive inhibitors of HNE. Furthermore, molecular docking studies of the active products into the HNE binding site revealed two types of HNE inhibitors: molecules with cinnolin-4(1H)-one scaffold, which were attacked by the HNE Ser195 hydr...
-
Cinnoline derivatives as human neutrophil elastase inhibitors
2016Co-Authors: Maria Paola Giovannoni, Igor A. Schepetkin, Letizia Crocetti, Giovanna Ciciani, Agostino Cilibrizzi, Gabriella Guerrini, Andrei I. Khlebnikov, Mark T. Quinn, Claudia VergelliAbstract:Compounds that can effectively inhibit the proteolytic activity of human neutrophil elastase (HNE) represent promising therapeutics for treatment of inflammatory diseases. We present here the synthesis, structure–activity relationship analysis, and biological evaluation of a new series of HNE inhibitors with a Cinnoline scaffold. These compounds exhibited HNE inhibitory activity but had lower potency compared to N-benzoylindazoles previously reported by us. On the other hand, they exhibited increased stability in aqueous solution. The most potent compound, 18a, had a good balance between HNE inhibitory activity (IC50 value = 56 nM) and chemical stability (t1/2 = 114 min). Analysis of reaction kinetics revealed that these Cinnoline derivatives were reversible competitive inhibitors of HNE. Furthermore, molecular docking studies of the active products into the HNE binding site revealed two types of HNE inhibitors: molecules with cinnolin-4(1H)-one scaffold, which were attacked by the HNE Ser195 hydroxyl group at the amido moiety, and Cinnoline derivatives containing an ester function at C-4, which is the point of attack of Ser195.
W. Pakulska - One of the best experts on this subject based on the ideXlab platform.
-
Synthesis and Biological Activity of Some 4‐Amino‐3‐Cinnolinecarboxylic Acid Derivatives. Part 5. Pyrimido[5,4‐c]Cinnolines and Triazepino[7,6‐c]Cinnoline.
ChemInform, 2010Co-Authors: Andrzej Stańczak, Z. B. Ochocki, W. PakulskaAbstract:A series of substituted 3-aminopyrimido[5,4-c]Cinnolines 3, 7 was prepared. 6,7-Substituted 4-amino-3-Cinnolinecarboxylic acid 1 were condensed with acetic anhydride to give the respective 1,3-oxazino[5,4-c]Cinnolines 2. The obtained derivatives reacted with hydrazines and gave 3-aminopyrimido[5,4-c]Cinnolines. Reaction of the esters 5 with hydrazines produced hydrazides 6, which upon treatment with N,N-dimethylformamide dimethyl acetal gave 3-aminopyrimido[5,4-c]Cinnolines 7. Treatment of 6b with bromocyan produced 2-amino-3,4-dihydro-3,10-dimethyl-5 H-1,3,4-triazepino[7,6-c]cinnolin-5-on (8b). Some of the synthesized compounds were screened for their effect on the CNS.
-
Synthesis and biological activity of some 4-amino-3-Cinnolinecarboxylic acid derivatives. Part 5: Pyrimido[5,4-c]Cinnolines and triazepino[7,6-c]Cinnoline.
Die Pharmazie, 1998Co-Authors: Andrzej Stańczak, Z. B. Ochocki, W. PakulskaAbstract:A series of substituted 3-aminopyrimido[5,4-c]Cinnolines 3, 7 was prepared. 6,7-Substituted 4-amino-3-Cinnolinecarboxylic acid 1 were condensed with acetic anhydride to give the respective 1,3-oxazino[5,4-c]Cinnolines 2. The obtained derivatives reacted with hydrazines and gave 3-aminopyrimido[5,4-c]Cinnolines. Reaction of the esters 5 with hydrazines produced hydrazides 6, which upon treatment with N,N-dimethylformamide dimethyl acetal gave 3-aminopyrimido[5,4-c]Cinnolines 7. Treatment of 6b with bromocyan produced 2-amino-3,4-dihydro-3,10-dimethyl-5 H-1,3,4-triazepino[7,6-c]cinnolin-5-on (8b). Some of the synthesized compounds were screened for their effect on the CNS.
Aijun Lin - One of the best experts on this subject based on the ideXlab platform.
-
Rh(III)‐Catalyzed Redox‐Neutral Annulation of Azo and Diazo Compounds: One‐Step Access to Cinnolines.
ChemInform, 2016Co-Authors: Peng Sun, Yue Huang, Hequan Yao, Aijun LinAbstract:Reported herein is a Rh-catalyzed redox-neutral annulation reaction between azo and diazo compounds, thus leading to the direct synthesis of Cinnolines under mild conditions. The procedure exhibited a broad substrate scope, scalability and step economy, obviating the pre-functionalization of substrates and the use of oxidants. Further utilization of the resulting Cinnolines provided efficient routes to some bioactive structures, such as 4-amino-Cinnoline and 1-aminoindole.
-
rh iii catalyzed redox neutral annulation of azo and diazo compounds one step access to Cinnolines
ChemInform, 2016Co-Authors: Peng Sun, Yue Huang, Hequan Yao, Aijun LinAbstract:Reported herein is a Rh-catalyzed redox-neutral annulation reaction between azo and diazo compounds, thus leading to the direct synthesis of Cinnolines under mild conditions. The procedure exhibited a broad substrate scope, scalability and step economy, obviating the pre-functionalization of substrates and the use of oxidants. Further utilization of the resulting Cinnolines provided efficient routes to some bioactive structures, such as 4-amino-Cinnoline and 1-aminoindole.