2019
DOI: 10.1016/j.bmcl.2019.05.014
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Synthesis and structure-activity relationship of 4-alkoxy-thieno[2,3-b]pyridine derivatives as potent alkaline phosphatase enhancers for osteoporosis treatment

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Cited by 12 publications
(6 citation statements)
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“…13 C NMR (100 MHz, DMSO-d6): δ = 161.9 (C-8a), 159.4 (C=O), 154.6 (C-7), 145.0 (C-2), 143.9 (C-9b), 139.9 (C-5), 136.6 (C-4a), 130.3 (C-3a), 121.2 (C-6), 120.0 (C-4b), 107.3 (C-3), 99.7 (C-9a), 52.2 (COOCH3), 24.0 (7-CH3), 20.0 (5-CH3). (20), 300 [M] + (100), 269 (6), 257 (11), 242 (8).…”
Section: -Azido-46-dimethyl-2-[4-(morpholin-4ylsulfonyl)phenyl]thieno...mentioning
confidence: 99%
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“…13 C NMR (100 MHz, DMSO-d6): δ = 161.9 (C-8a), 159.4 (C=O), 154.6 (C-7), 145.0 (C-2), 143.9 (C-9b), 139.9 (C-5), 136.6 (C-4a), 130.3 (C-3a), 121.2 (C-6), 120.0 (C-4b), 107.3 (C-3), 99.7 (C-9a), 52.2 (COOCH3), 24.0 (7-CH3), 20.0 (5-CH3). (20), 300 [M] + (100), 269 (6), 257 (11), 242 (8).…”
Section: -Azido-46-dimethyl-2-[4-(morpholin-4ylsulfonyl)phenyl]thieno...mentioning
confidence: 99%
“…1 H NMR (400 MHz, CDCl3): δ =7.80 (2H, d, J = 8.5 Hz, H-3,5 Ar), 7.75 (2H, d, J = 8.5 Hz, H-2,6 Ar),6.98 (1H, s, H-5), 5.25 (2H, s, NH2), 3.63 (4H, s, O-CH2), 2.89 (4H, s, N-CH2), 2.75 (3H, s, 4-CH3), 2.47 (3H, s, 6-CH3) 13. C NMR (100 MHz, CDCl3): δ = 159.09 (C-7a), 156.60 (C-6), 143.79 (C-4), 139.70 (C-3), 138.22 (C-4 Ar), 131.74 (C-1 Ar), 128.98 (2C, C-3,5-Ar), 128.57 (2C, C2,6 Ar), 125.34 (C-3a), 122.44 (C-5), 107.92 (C-2), 65.76 (2C, O-CH2), 46.32 (2C, N-CH2), 24.06 (6-CH3), 20.25 (4-CH3).…”
mentioning
confidence: 99%
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“…In addition, oral medication has a higher rate of treatment compliance than parenteral medications. Thus, an unmet medical need for orally active bone anabolic agents attracted researchers to develop small molecules [8][9][10][11] including phytoand natural molecules 12 which became an ideal choice for modern chemical biology and drug discovery. Almost 84% of small molecule drugs approved by the US FDA have at least one nitrogen atom in them, and 59% drugs contain some sort of nitrogen heterocycles.…”
Section: Introductionmentioning
confidence: 99%
“…26 4-Aminothienopyridine-3carbonitriles 3 or their derivatives showed good activity against Staphylococcus epidermidis, 27 Leishmania amazonensis, 28 and Mayaro virus 29 and were also recognized as protein kinase C θ (PKCθ) inhibitors 30−32 for treatment of autoimmune and inflammatory diseases. Several thienopyridines have been developed as bone anabolic agents 33 (4, Figure 1), inhibitors of 15-prostaglandin dehydrogenase 5 useful for tissue regeneration, 34,35 alkaline phosphatase enhancers 6 for osteoporosis treatment, 36 hepatitis C virus inhibitors 7, 37 anti-HIV agents 8, 38 highly selective 5-hydroxytryptamine (5-HT) 4 receptor agonists and memory enhancers such as PRX-03140 (9), 39,40 and negative allosteric modulators of metabotropic GluR5 receptors (10). 41 A series of 3-amino-4methylthieno [2,3-b]pyridine-2-carboxamides 11−14 were reported 42−53 as selective muscarinic acetylcholine receptor 4 (M 4 ) positive allosteric modulators that displayed in vivo efficacy in preclinical models of antispsychotic drug effects.…”
Section: ■ Introductionmentioning
confidence: 99%