5-Substituted 1H-pyrrolo[3,2-b]pyridines as inhibitors of gastric acid secretion☆

Palmer, Andreas Marc; Münch, Gabriela; Brehm, Christof; Zimmermann, Peter Jan; Buhr, Wilm; Feth, Martin P.; Simon, W.

doi:10.1016/j.bmc.2007.10.017

Cited by 30 publications

(11 citation statements)

References 29 publications

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“…Compounds synthesized by literature procedures: 2a, 4 2b, 4 6, 5 and 8. 6 4-Bromo-6-chloro-1H-pyrrolo[2, 3-b]pyridine 13b was also synthesized according to the literature 7 and isolated as an inseparable mixture (77:23) of 13b and the 4,6-dichloro analog. Activities against Mtb H 37 Rv (ATCC #27294) (MABA and LORA assay), 3e,11,12 and VERO cells 2 were determined as reported before.…”

Section: Methodsmentioning

confidence: 99%

“…The product was purified by flash chromatography on silica gel eluting with hexane followed by CH 2 Cl 2 -hexane (3:7); yield 70 mg (43%), yellow wax. 1 H NMR (Me 2 CO-d 6 (6), 77 (6); HRMS Found 303.1252, calcd for C 20 H 17 NO 2 303.1259.…”

Section: Pyridine (18b)mentioning

confidence: 97%

“…The product was purified by flash chromatography on silica gel eluting with hexane followed by EtOAc-hexane (1:5) and finally EtOAc-hexane (1:4); yield 435 mg (97%), mp 119-120°C, yellow solid. 1 H NMR (Me 2 CO-d 6 (95), 277 (100), 189 (30), 145 (24), 121 (70) …”

Section: -(Furan-2-yl)-n-(4-methoxybenzyl)-3-nitropyridin-2-amine (3a)mentioning

confidence: 99%

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Synthesis and antimycobacterial activities of non-purine analogs of 6-aryl-9-benzylpurines: Imidazopyridines, pyrrolopyridines, benzimidazoles, and indoles

Khoje

Charnock

Wan

et al. 2011

Bioorganic & Medicinal Chemistry

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6,9-Disubstituted purines and 7-deazapurines are known to be powerful inhibitors of Mycobacterium tuberculosis (Mtb) in vitro. Analogs modified in the six-membered ring (imidazopyridines, pyrrolopyridines, benzimidazoles, and indoles) were synthesized and evaluated as Mtb inhibitors. The targets were prepared by functionalization on the bicyclic heterocycle or from simple pyridines. The results reported herein, indicate that the purine N-1, but not N-3, is important for binding to the unknown target. The 3-deazapurines appears to be slightly more active compared to the parent purines and slightly less active than their 7-deazapurine isomers. Removal of both the purine N-3 and N-7 did not result in further enhanced antimycobacterial activity but the toxicity towards mammalian cells was increased. Both 3-deaza and 3,7-dideazapurines exhibited a modest activity against of the Mtb isolate in the state of non-replicating persistence.

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Section: Methodsmentioning

confidence: 99%

Section: Pyridine (18b)mentioning

confidence: 97%

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Synthesis and antimycobacterial activities of non-purine analogs of 6-aryl-9-benzylpurines: Imidazopyridines, pyrrolopyridines, benzimidazoles, and indoles

Khoje

Charnock

Wan

et al. 2011

Bioorganic & Medicinal Chemistry

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“…6, 128.4, 127.8, 127.2, 126.8, 125.5, 116.1 (d, J = 21.3 Hz), 115.9 (d,J = 21.3 Hz),110.4,103.1,41.8,38.7,36.7,21.6 198.5, 188.3, 149.6, 146.6, 136.6, 133.4, 130.6 (t, J = 17.5 Hz, CF 3 ), 130. 1, 128.9, 128.8, 128.6, 128.2, 127.8, 127.2, 125.4, 110.1, 103.1, 41.9, 38.7, 36.8, 21.6 2, 139.5, 136.8, 133.2, 131.0, 130.5, 129.1, 129.0, 128.9, 128.5, 128.1, 125.9, 115.4 (d, J = [4][5][6][7][8]2,3, (d,J = 7.5 Hz,2H,ArH),7.48 (t,J = 7.3 Hz,1H,ArH),7H,ArH),7.22 (d,J = 8.2 Hz, 2H, ArH), 6.96 (d, J = 8.2 Hz, 2H, ArH), 3.71 (t, J = 5.6 Hz, 2H, NCH 2 ), 3.68 (s, 2H, ArCOCH 2 ), 3.47-3.53 (m, 2H, NCH 2 ), 2.03-2.09 (m, 2H, CH 2 ); 13 C NMR (125 MHz, CDCl 3 ): δ = 198. 7, 188.8, 149.4 141.6, 136.8, 134.9, 133.3, 130.9, 130.5, 130.3, 128.9, 128.7, 128.6, 128.4, 128.2, 128.0, 110.4, 103.2, 41.9, 38.7, 36.8, 21.6 2,3, [1,2-a] (d, J = 7.3 Hz, 1H, ArH), 6.97-7.03 (m, 3H, ArH), 6.80-6.84 (m, 1H, ArH), 6.64-6.68 (m, 1H, ArH), 3.63-3.72 (m, 3H, NCH 2 ), 3.54-3.58 (m, 1H, NCH 2 ), 3.53 (s, 2H, ArCOCH 2 ), 2.08-2.14 (m, 2H, CH 2 ); 13 C NMR (125 MHz, CDCl 3 ): δ = 197.…”

Section: General Procedures For the Synthesis Of Compounds 4a-umentioning

confidence: 99%

“…Members of this class of compounds possess diverse pharmacological activities ( Fig. 1), including inhibition of Janus kinases, 3 PI3K, 4 dihydrofolate reductase (DHFR), 5 glycosidase, 6 firefly luciferase, 7 gastric acid pumps, 8 adenosine A1 receptor, 9 and human topoisomerase I (Lamellarin D, Fig. 1) 10 as well as antibacterial, 11 antiviral, 12 antiprotozoal, 13 antitumor, 14 anti-inflammatory, 15 antifungal, 16 and anti-microbial activities.…”

Section: ．Introductionmentioning

confidence: 99%

Catalyst-free three-component domino reactions for regioselective synthesis of multi-functional fused pyrroles

Chen

Yan

et al. 2015

Tetrahedron

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The Barton‐McCombie Reaction

2012

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Deoxygenations of alcohols, i.e., processes that replace a hydroxyl group with hydrogen at a saturated carbon, find applications in both total synthesis and the systematic modifications of natural products. They may also be employed to introduce deuterium or tritium in a site‐specific manner. Reductive methods that involve ionic or highly polarized reagents or intermediates can be limited in their applicability: for example, competing reaction pathways including cationic rearrangements and anionic eliminations may be encountered in sterically hindered systems with substrates bearing heteroatoms close to the center undergoing reduction. As evidenced by developments over the last few decades, methods that involve the generation and direct quenching via hydrogen atom abstraction of the derived, carbon‐centered radical typically show the greatest tolerance for the presence of other functional groups and for variations in both the steric acid and the electronic environment in the vicinity of the center undergoing deoxygenation. Derivatization of the hydroxyl is a prerequisite, the determinant factors for efficient formation of the deoxygenated product lies in the ability of the combination of the substrate and reagents to induce homolysis of the C‐O bond coupled with the induction of homolysis to rapidly reduce a free radical by hydrogen donation, thereby propagating an efficient chain process. A high‐yielding way to realize this sequence was first described by Barton McCombie using the free‐radical chain reaction of O ‐thioacyl derivatives of secondary alcohols with tri‐ n ‐butylstannane. This chapter provides a detailed description and comparison of the combinations of substrates and reagents that will bring about these processes and provides a summary and evaluation of alternative deoxygenation methods. Mechanistic and stereochemical issues set out the scope and limitations of these processes with respect to both the thioacylation and reduction steps and exemplify some applications to both total synthesis and the modification of natural products.

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5-Substituted 1H-pyrrolo[3,2-b]pyridines as inhibitors of gastric acid secretion☆

Cited by 30 publications

References 29 publications

Synthesis and antimycobacterial activities of non-purine analogs of 6-aryl-9-benzylpurines: Imidazopyridines, pyrrolopyridines, benzimidazoles, and indoles

Synthesis and antimycobacterial activities of non-purine analogs of 6-aryl-9-benzylpurines: Imidazopyridines, pyrrolopyridines, benzimidazoles, and indoles

Catalyst-free three-component domino reactions for regioselective synthesis of multi-functional fused pyrroles

The Barton‐McCombie Reaction

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