- Novel imidazo[4,5-b]pyridine derived acrylonitriles: A combined experimental and computational study of their antioxidative potential
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We describe the synthesis of novel unsubstituted and N-substituted imidazo[4,5-b]pyridine derived acrylonitriles, which were prepared by classical and microwave assisted organic synthesis. Their antioxidative potential was studied using spectroscopic DPPH
- Bo?ek, Ida,Star?evi?, Kristina,Novak Jovanovi?, Ivana,Vianello, Robert,Hranjec, Marijana
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- Cu-Catalyzed C-H Allylation of Benzimidazoles with Allenes
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CuH-catalyzed intramolecular cyclization and intermolecular allylation of benzimidazoles with allenes have been described. The reaction proceeded smoothly with the catalytic system of Cu(OAc)2/Xantphos and catalytic amount of (MeO)2MeSiH. This protocol features mild reaction conditions and a good tolerance of substrates bearing electron-withdrawing, electron-donating, or electron-neutral groups. A new catalytic mechanism was proposed for this copper hydride catalytic system.
- Dong, Yaxi,Breit, Bernhard
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p. 6765 - 6769
(2021/09/11)
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- SUBSTITUTED BENZIMIDAZOLE CARBOXAMIDES AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS
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The invention provides substituted benzimidazole carboxamides and related compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat a medical disorder, e.g., cancer, lysosomal storage disorder, neurodegenerative disorder, inflammatory disorder, in a patient.
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Paragraph 00295; 00373-00374; 00581
(2021/04/01)
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- Discovery of iminobenzimidazole derivatives as novel cytotoxic agents
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In our quest to identify inhibitors of the eukaryotic translation initiation factor 4F (eIF4F), we serendipitously discovered a novel cytotoxic agent. Even though this compound did not inhibit translation, we explored the structural requirements for its cytotoxicity due to its structural originality. A series of 1,3-disubstituted iminobenzimidazoles was synthesized and evaluated for their in vitro cytotoxicity. The structure-activity relationship studies demonstrate that hydrophobic substituent is essential for activity. The most active compounds displayed a cytotoxicity in KB, HL60 and HCT116 human cancer cells with an IC50 of about 1μM. These first-in-class series of low molecular weight synthetic molecules may provide the basis for the development of new anticancer drugs.
- Chouha, Nora,Hammoud, Hassan,Brogi, Simone,Campiani, Giuseppe,Welsch, Caroline,Robert, Caroline,Vagner, Stéphan,Cresteil, Thierry,Bentouhami, Embarek,Désaubry, Laurent
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- 5,10-Dihydropyrido-pyrazolo-triazine compounds and application thereof
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The invention relates to 5,10-dihydropyrido[2',3':5,6]pyrazolo[2,3-e][1,2,4]triazine compounds shown in general formula I, and their optical activators or racemates or their pharmaceutically acceptable salts, hydrates or solvates, wherein substituents R1,
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- The Chameleonic Nature of Platinum(II) Imidazopyridine Complexes
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The synthesis and characterization of cyclometalated C^C* platinum(II) complexes with unique photophysical properties, aggregation induced enhancement of the quantum yields with a simultaneous decrease of phosphorescence lifetimes, is reported. Additional
- Pinter, Piermaria,Pittkowski, Rebecca,Soellner, Johannes,Strassner, Thomas
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p. 14173 - 14176
(2017/10/07)
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- Palladium-Catalyzed Suzuki Cross-Coupling of 2-Halo-Deazapurines with Potassium Organotrifluoroborate Salts in the Regioselective Synthesis of Imidazo[4,5-b]pyridine Analogues
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In this paper, we report the use of potassium organotrifluoroborate salts as nucleophilic organoboron reagents in the Suzuki cross-coupling reactions of 2-halo deazapurines. Regio-isomeric C-2-substituted imidazo[4,5-b]pyridine analogues were synthesized by employing this protocol in good to excellent yields. Whereas aryl and heteroaryl trifluoroborates reacted readily to give the coupled products in high yields, alkyltrifluoroborates were found to be less reactive. The utilization of tetrabutylammonium acetate was found to play a substantial role in enhancing the reaction rates of the cross-coupling process. Also, a comparative study was performed between boronic acids and potassium organotrifluoroborate salts.
- Savitha, Bhaskaran,Sajith, Ayyiliath. M.,Joy, M. Nibin,Khader, K.K. Abdul,Muralidharan,Padusha, M. Syed Ali,Bodke, Yadav D.
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p. 618 - 630
(2016/07/06)
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- Probing the molecular and structural elements of ligands binding to the active site versus an allosteric pocket of the human farnesyl pyrophosphate synthase
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In order to explore the interactions of bisphosphonate ligands with the active site and an allosteric pocket of the human farnesyl pyrophosphate synthase (hFPPS), substituted indole and azabenzimidazole bisphosphonates were designed as chameleon ligands. NMR and crystallographic studies revealed that these compounds can occupy both sub-pockets of the active site cavity, as well as the allosteric pocket of hFPPS in the presence of the enzyme's Mg2+ ion cofactor. These results are consistent with the previously proposed hypothesis that the allosteric pocket of hFPPS, located near the active site, plays a feed-back regulatory role for this enzyme.
- Gritzalis, Dimitrios,Park, Jaeok,Chiu, Wei,Cho, Hyungjun,Lin, Yih-Shyan,De Schutter, Joris W.,Lacbay, Cyrus M.,Zielinski, Michal,Berghuis, Albert M.,Tsantrizos, Youla S.
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supporting information
p. 1117 - 1123
(2015/02/19)
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- Regioselective C2-arylation of imidazo[4,5-b]pyridines
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We show that N3-MEM-protected imidazo[4,5-b]pyridines undergo efficient C2-functionalisation via direct C-H arylation. Twenty-two substituted imidazo[4,5-b]pyridines are prepared and iterative, selective elaboration of functionalised imidazo[4,5-b]pyridin
- Macdonald, Jonathan,Oldfield, Victoria,Bavetsias, Vassilios,Blagg, Julian
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supporting information
p. 2335 - 2347
(2013/04/23)
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- PYRIDYL CARBENE PHOSPHORESCENT EMITTERS
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Organometallic compounds comprising an imidazole carbene ligand having a N-containing ring fused to the imidazole ring are provided. In particular, the N-containing ring fused to the imidazole ring may contain one nitrogen atom or more than one nitrogen a
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- PYRIDYL CARBENE PHOSPHORESCENT EMITTERS
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Organometallic compounds comprising an imidazole carbene ligand having a N- containing ring fused to the imidazole ring are provided. In particular, the N-containing ring fused to the imidazole ring may contain one nitrogen atom or more than one nitrogen
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Page/Page column 93-94
(2012/09/22)
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- FUSED HETEROCYCLIC COMPOUNDS
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The present invention provides a compound which has the effect of PDE inhibition, and which is useful as an agent for preventing or treating schizophrenia. The compound is represented by the formula (I): wherein the symbols are defined in the specification.
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- AZABENZIMIDAZOLYL COMPOUNDS
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Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula (I), as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.
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Page/Page column 57
(2008/06/13)
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- Imidazopyridines: A novel class of hNav1.7 channel blockers
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A series of imidazopyridines were evaluated as potential sodium channel blockers for the treatment of neuropathic pain. Several members were identified with good hNav1.7 potency and excellent rat pharmacokinetic profiles. Compound 4 had good efficacy (52% and 41% reversal of allodynia at 2 and 4 h post-dose, respectively) in the Chung rat spinal nerve ligation (SNL) model of neuropathic pain when dosed orally at 10 mg/kg.
- London, Clare,Hoyt, Scott B.,Parsons, William H.,Williams, Brande S.,Warren, Vivien A.,Tschirret-Guth, Richard,Smith, McHardy M.,Priest, Birgit T.,McGowan, Erin,Martin, William J.,Lyons, Kathryn A.,Li, Xiaohua,Karanam, Bindhu V.,Jochnowitz, Nina,Garcia, Maria L.,Felix, John P.,Dean, Brian,Abbadie, Catherine,Kaczorowski, Gregory J.,Duffy, Joseph L.
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p. 1696 - 1701
(2008/12/23)
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- 3-(Imidazolyl methyl)-3-aza-bicyclo[3.1.0]hexan-6-yl)methyl ethers: A novel series of mGluR2 positive allosteric modulators
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The synthesis and structure-activity relationship (SAR) of a novel series of 3-(imidazolyl methyl)-3-aza-bicyclo[3.1.0]hexan-6-yl)methyl ethers, derived from a high throughput screening (HTS), are described. Subsequent optimization led to identification of potent, metabolically stable and orally available mGluR2 positive allosteric modulators (PAMs).
- Zhang, Lei,Rogers, Bruce N.,Duplantier, Allen J.,McHardy, Stanley F.,Efremov, Ivan,Berke, Helen,Qian, Weimin,Zhang, Andy Q.,Maklad, Noha,Candler, John,Doran, Angela C.,Lazzaro Jr., John T.,Ganong, Alan H.
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scheme or table
p. 5493 - 5496
(2009/06/18)
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- Synthesis and mutagenic potency of structural isomers of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine
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(Chemical Equation Presented) Synthesis of 2-amino-1-methyl-6- phenylimidazo[4,5-b]pyridine (PhIP), three structural isomers, and two desphenyl PhIP congeners has been carried out. Mutagenic potency was evaluated using S. typhimurium strain TA98 in the Ames test. Mutagenic potency increased in relation to structural features in these heterocyclic amines that allow extended resonance between the phenyl and imidazo[4,5-b]pyridine N2-amino substituents. By contrast, PhIP isomers, whose substitution disallows involvement of the phenyl group in their ammoimidazo resonance hybrids, and desphenyl congeners were from 86- to 234-fold less mutagenic than PhIP.
- Chrisman,Knize,Tanga
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experimental part
p. 1641 - 1649
(2009/08/09)
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- Synthesis and evaluation of 3-anilino-quinoxalinones as glycogen phosphorylase inhibitors
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A series of 3-anilino-quinoxalinones has been identified as a new class of glycogen phosphorylase inhibitors. The lead compound 1 was identified through high throughput screening as well as through pharmacophore-based electronic screening. Modifications were made to the scaffold of 1 to produce novel analogues, some of which are 25 times more potent than the lead compound.
- Dudash Jr., Joseph,Zhang, Yongzheng,Moore, John B.,Look, Richard,Liang, Yin,Beavers, Mary Pat,Conway, Bruce R.,Rybczynski, Philip J.,Demarest, Keith T.
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p. 4790 - 4793
(2007/10/03)
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- Quinoxalinones
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The invention features quinoxalinones, pharmaceutical compositions containing them and methods of using them to treat, for example, diabetes.
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Page/Page column 12
(2010/02/12)
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- Heterocyclic compounds having anti-diabetic activity and their use
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Compounds of formula (I): STR1 [wherein: X represents an unsubstituted or substituted indolyl, indolinyl, azaindolyl, azaindolinyl, imidazopyridyl or imidazopyrimidinyl group; Y represents an oxygen or sulfur atom; Z represents a 2,4-dioxothiazolidin-5-ylidenylmethyl, 2,4-dioxothiazolidin-5-ylmethyl, 2,4-dioxooxazolidin-5-ylmethyl, 3,5-dioxooxadiazolidin-2-ylmethyl or N-hydroxyureidomethyl group; R represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a hydroxy group, a nitro group, an aralkyl group or a unsubstituted or substituted amino group; and m is an integer of from 1 to 5] have hypoglycemic and anti-diabetic activities.
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- Synthesis and CNS activities of pyridopyrazinone and pyridodiazepinone derivatives
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New tricyclic derivatives with cyclocondensed pyrido-pyrazine 7,10 and pyrido-diazepine 20a,20b skeletons were synthetized and biologically investigated. The compounds, preliminarily tested on explorative, muscle relaxing, antinociceptive, spontaneous motor activities and influence on the narcotic effect of Evipan, revealed interesting CNS depressant and analgesic activities. The pyrido[2,3-e]pyrrolo[1,2-a]pyrazine structure of 7 appeared the most promising for analgesic and neuroleptic activities. The above compounds were assayed also for their capacity to inhibit DNA synthesis in Ehrlich ascites tumor cells; 20a appeared to be able of inducing a significant inhibition.
- Savelli,Boido,Satta,Peana,Marzano
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p. 259 - 265
(2007/10/02)
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- The ortho effect in pyridines. Part XI(1). Substituent effects on basicity of 2- and 4-substituted 3-aminopyridines
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The substituent effects on the pKa values corresponding to the first protonation site of thirty 2- and 4-substituted 3-aminopyridines have been studied.It was found that the relative localized and delocalized effects are apparently sensitive to the variation of substituent position in the pyridine ring.An interaction of the 2-substituent with the protonation centre has mainly inductive character, whereas, the pKa values of 4-substituted 3-aminopyridines are highly affected by through-resonance.The steric effect was found to be insignificant.Keywords: substituent effects / 2- and 4-substituted 3-aminopyridines / basicity
- Rasala, D.
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- α-Mercaptophenylacetic acid derivatives of imidazole-containing compounds and analogues thereof
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α-Mercaptobenzylacetic acid derivatives of imidazole-containing compounds and analogues thereof, and their use as immunomodulating agents are disclosed.
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