- Simple synthesis of imidazo[1,2-A]pyridine derivatives bearing 2-aminonicotinonitrile or 2-aminochromene moiety
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A simple and general method for the synthesis of new imidazopyridines bearing an aminopyridinyl, chromenyl, or quinolinyl moiety in the C2 position was developed. The Knoevenagel reaction between imidazo[1,2-a]pyridine-2-carbaldehyde 1 and malononitrile resulted in the formation of starting material 2. Subsequently, intramolecular cyclization between the cyano group of 2 and acetophenones, naphtols, hydroxyquinolines, or phenols, gave 3, 4, 5, and 6 compounds, respectively. This is a simple, reproducible, and environmentally friendly method of synthesizing substituted imidazopyridines using water as a solvent or under solvent-free conditions.
- Haouchine, Arslane-Larbi,Kabri, Youssef,Bakhta, Saléha,Curti, Christophe,Nedjar-Kolli, Bellara,Vanelle, Patrice
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- Toward the Synthesis of Sceptrin and Benzosceptrin: Solvent Effect in Stereo- and Regioselective [2+2] Photodimerization and Easy Access to the Fully Substituted Benzobutane
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By simply switching solvents, two sets of conditions for the total regio- and stereoselective photodimerization of (E)-3-(imidazo[1,2-a]pyrimidin-2-yl)acrylic acid [(E)-7a] have been found. In acetonitrile in the presence of benzophenone as photosensitizer or in cyclohexane, the head-to-head cis-trans-cis isomer 8a was the only observable cycloadduct. In DMSO, the head-to-head trans-trans-trans isomer 10a was obtained as the unique cycloadduct. The diester 9a, derived from 8a, was cyclized to the challenging, fully substituted diimidazobenzobutane system 13 present in benzosceptrins.
- Binh Nguyen, Thanh,Anh Nguyen, Le,Corbin, Mathilde,Retailleau, Pascal,Ermolenko, Ludmila,Al-Mourabit, Ali
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- Diversity-Oriented Synthesis of β-Lactams and γ-Lactams by Post-Ugi Nucleophilic Cyclization: Lewis Acids as Regioselective Switch
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Heterocyclic fused α-methylene β-lactams were successfully synthesized by a post-Ugi InIII-catalyzed intramolecular addition reaction. Switching from InCl3 to AlCl3 led to the regioselective synthesis of α,β-unsaturated γ-lactams. Moreover, replacing terminal alkynes by substituted alkynes in the Ugi adducts resulted in the exclusive formation of γ-lactams with both catalytic systems. A regioselective approach for the synthesis of heterocyclic fused α-methylene β-lactams and α,β-unsaturated γ-lactams by employing a Ugi reaction followed by InIII- or AlIII-catalyzed intramolecular nucleophilic addition is reported.
- Li, Zhenghua,Sharma, Upendra Kumar,Liu, Zhen,Sharma, Nandini,Harvey, Jeremy N.,Van Der Eycken, Erik V.
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- Inhibition of the Cysteine Protease Human Cathepsin L by Triazine Nitriles: Amide???Heteroarene π-Stacking Interactions and Chalcogen Bonding in the S3 Pocket
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We report an extensive “heteroarene scan” of triazine nitrile ligands of the cysteine protease human cathepsin L (hCatL) to investigate π-stacking on the peptide amide bond Gly67–Gly68 at the entrance of the S3 pocket. This heteroarene???peptide bond stacking was supported by a co-crystal structure of an imidazopyridine ligand with hCatL. Inhibitory constants (Ki) are strongly influenced by the diverse nature of the heterocycles and specific interactions with the local environment of the S3 pocket. Binding affinities vary by three orders of magnitude. All heteroaromatic ligands feature enhanced binding by comparison with hydrocarbon analogues. Predicted energetic contributions from the orientation of the local dipole moments of heteroarene and peptide bond could not be confirmed. Binding of benzothienyl (Ki=4 nm) and benzothiazolyl (Ki=17 nm) ligands was enhanced by intermolecular C?S???O=C interactions (chalcogen bonding) with the backbone C=O of Asn66 in the S3 pocket. The ligands were also tested for the related enzyme rhodesain.
- Giroud, Maude,Ivkovic, Jakov,Martignoni, Mara,Fleuti, Marianne,Trapp, Nils,Haap, Wolfgang,Kuglstatter, Andreas,Benz, J?rg,Kuhn, Bernd,Schirmeister, Tanja,Diederich, Fran?ois
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p. 257 - 270
(2017/02/15)
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- GLUCOSYLCERAMIDE SYNTHASE INHIBITORS FOR THE TREATMENT OF DISEASES
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Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).
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Paragraph 000822
(2015/04/15)
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- HETEROARYL COMPOUNDS AND METHODS OF USE THEREOF
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Provided herein are heteroaryl compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. In one embodiment, the compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, such as CNS disorders and metabolic disorders, including, but not limited to, e.g., neurological disorders, psychosis, schizophrenia, obesity, and diabetes.
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Page/Page column 49
(2012/07/27)
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- CHEMICAL COMPOUNDS
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The present invention provides compounds of formula (I) including salts, solvates, and pharmaceutically acceptable derivatives thereof, pharmaceutical formulations containing them, processes for their preparation, and methods of treatment using them.
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Page/Page column 47
(2010/11/28)
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- CHEMCIAL COMPOUNDS
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The present invention provides novel compounds that demonstrate protective effects on target cells from HIV infection in a manner as to bind specifically to the chemokine receptor, and which affect the binding of the natural ligand or chemokine to a receptor such as CXCR4 and/or CCR5 of a target cell.
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Page/Page column 39
(2010/10/20)
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- INHIBITORS OF HEPATITIS C VIRUS RNA-DEPENDENT RNA POLYMERASE, AND COMPOSITIONS AND TREATMENTS USING THE SAME
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The invention relates to compounds of the formula (I) and to pharmaceutically acceptable salts, solvates, prodrugs and metabolites thereof, wherein W, Z, R1and R2, are as defined herein. The invention also relates to methods of treating Hepatitis C virus in mammals by administering the compounds of formula (I), and to pharmaceutical compositions for treating such disorders, which contain the compounds of formula (I). The invention also relates to methods of preparing the compounds of formula (I).
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