111787-82-7Relevant academic research and scientific papers
Enantioselective Synthesis of Nitrogen-Nitrogen Biaryl Atropisomers via Copper-Catalyzed Friedel-Crafts Alkylation Reaction
Guo, Chang-Qiu,Liu, Ren-Rong,Lu, Chuan-Jun,Wang, Xiao-Mei,Xu, Qi,Zhang, De-Bing,Zhang, Peng
supporting information, p. 15005 - 15010 (2021/09/30)
Nitrogen-nitrogen bonds containing motifs are ubiquitous in natural products and bioactive compounds. However, the atropisomerism arising from a restricted rotation around an N-N bond is largely overlooked. Here, we describe a method to access the first enantioselective synthesis of N-N biaryl atropisomers via a Cu-bisoxazoline-catalyzed Friedel-Crafts alkylation reaction. A wide range of axially chiral N-N bisazaheterocycle compounds were efficiently prepared in high yields with excellent enantioselectivities via desymmetrization and kinetic resolution. Heating experiments showed that the axially chiral bisazaheterocycle products have high rotational barriers.
An access to new N-pyrrolylcarboxylic acids as potential COX-2 inhibitors via Paal-Knorr cyclization
Vladimirova, Stanislava,Bijev, Atanas
, p. 111 - 115 (2014/07/07)
Twenty new N-pyrrolylcarboxylic acids were designed to assume the architecture of contemporary selective COX-2 inhibitors as potential anti-inflammatory agents. The targeted products were synthesized in 70-82% yields by Paal-Knorr cyclization of a set of
Synthesis, antimalarial activity, and cellular toxicity of new arylpyrrolylaminoquinolines
Casagrande, Manolo,Basilico, Nicoletta,Rusconi, Chiara,Taramelli, Donatella,Sparatore, Anna
experimental part, p. 6625 - 6633 (2010/10/18)
A set of nine new arylpyrrolyl derivatives of 7-chloro-4-aminoquinoline, characterized by different substituents on the phenyl ring or different distance between the pyrrolic nitrogen and the 4-aminoquinoline, has been synthesized and tested for their activity against D-10 (CQ-S) and W-2 (CQ-R) strains of Plasmodium falciparum. All compounds exhibited activity against the CQ-S strain in the low nM range, comparable to that of chloroquine. Some of them were also highly active against the CQ-R strain and not toxic against normal cells. The antimalarial activity of this new class of compounds seems to be related to the inhibition of heme detoxification process of parasites, as in the case of chloroquine.
Further optimization of novel pyrrole 3-carboxamides for targeting serotonin 5-HT2A, 5-HT2C, and the serotonin transporter as a potential antidepressant
Kang, Suk Youn,Park, Eun-Jung,Park, Woo-Kyu,Kim, Hyun Jung,Choi, Gildon,Jung, Myung Eun,Seo, Hee Jeong,Kim, Min Ju,Pae, Ae Nim,Kim, Jeongmin,Lee, Jinhwa
experimental part, p. 6156 - 6169 (2010/09/14)
In the continuing search for novel compounds targeting serotonin 5-HT 2A, 5-HT2C, and serotonin transporter, new arylpiperazine-containing pyrrole 3-carboxamide derivatives were synthesized and evaluated. Based on the lead reported previously, structural modifications regarding N-(3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propyl)-1,2-dimethyl-5- phenyl-1H-pyrrole-3-carboxamide 5, were accomplished for improvements in not only binding affinity against serotonin receptors and transporter, but also in hERG channel inhibition. Along the line, both the forced swimming tests and spontaneous locomotor activity tests were performed to distinguish between antidepressant activity and false positive results. As potential antidepressant agents, both 2,4-dimethyl-5-phenyl-1H-pyrrole-3-carboxamide and 5-tert-butyl-2-methyl-1H-pyrrole-3-carboxamide derivatives exhibited favorable in vitro and in vivo activities, warranting further investigation around these scaffolds.
Discovery of 4-(5-(4-chlorophenyl)-2-methyl-3-propionyl-1H-pyrrol-1-yl) benzenesulfonamide (A-867744) as a novel positive allosteric modulator of the α7 nicotinic acetylcholine receptor
Faghih, Ramin,Gopalakrishnan, Sujatha M.,Gronlien, Jens Halvard,Malysz, John,Briggs, Clark A.,Wetterstrand, Caroline,Ween, Hilde,Curtis, Michael P.,Sarris, Kathy A.,Gfesser, Gregory A.,El-Kouhen, Rachid,Robb, Holly M.,Radek, Richard J.,Marsh, Kennan C.,Bunnelle, William H.,Gopalakrishnan, Murali
experimental part, p. 3377 - 3384 (2010/03/31)
The discovery of a series of pyrrole-sulfonamides as positive allosteric modulators (PAM) of α7 nAChRs is described. Optimization of this series led to the identification of 19 (A-867744), a novel type II PAM with good potency and selectivity. Compound 19
Novel amodiaquine congeners as potent antimalarial agents
Casagrande, Manolo,Basilico, Nicoletta,Parapini, Silvia,Romeo, Sergio,Taramelli, Donatella,Sparatore, Anna
, p. 6813 - 6823 (2008/12/22)
To develop new classes of antimalarial agents, the possibility of replacing the phenolic ring of amodiaquine, tebuquine, and isoquine with other aromatic nuclei was investigated. Within a first set of pyrrole analogues, several compounds displayed high ac
PYRROLE DERIVATIVES AND THEIR METHODS OF USE
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Page/Page column 54, (2008/06/13)
The invention relates to a series of substituted pyrrole derivatives, compositions comprising the same, and methods of treating conditions and disorders using such compounds and compositions.
Ligand-based design, synthesis and primary in vivo screening of pyrrole derivatives as potential tricyclic anti-inflammatory agents
Bijev, Atanas,Yaneva, Diana,Bocheva, Adriana,Stoev, Georgi
, p. 753 - 759 (2007/10/03)
Twelve new compounds were designed as 5-aryl-1H-pyrrole analogs of celecoxib (CAS 169590-42-5) and were synthesized by Paal-Knorr cyclization in three series according to 1H-substitution: derivatives with salicylic acid, pyrazolone or isonicotinamide resi
