Synthesis and pharmacological evaluation of potential metabolites of the potassium-competitive acid blocker BYK405879

Palmer, Andreas Marc; Münch, Gabriela; Grobbel, Burkhard; Kromer, W.

doi:10.1016/j.tetlet.2009.04.070

Cited by 3 publications

(1 citation statement)

References 8 publications

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“…The synthesis of the 2-hydroxymethyl analogue 140 of the candidate 4 has been described previously. 35 The corresponding 2-methoxymethyl-substituted benzimidazole derivative 142 was prepared by activation of the hydroxy function of 140 with thionyl chloride and subsequent nucleophilic substitution of the chloro atom of intermediate 141 with methanol (Scheme 5).…”

Section: Chemistrymentioning

confidence: 99%

Tetrahydrochromenoimidazoles as Potassium-Competitive Acid Blockers (P-CABs): Structure−Activity Relationship of Their Antisecretory Properties and Their Affinity toward the hERG Channel

Palmer¹,

Chiesa²,

Schmid³

et al. 2010

J. Med. Chem.

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Potassium-competitive acid blockers (P-CABs) constitute a new therapeutic option for the treatment of acid-related diseases that are widespread and constitute a significant economical burden. Enantiomerically pure tetrahydrochromenoimidazoles were prepared using the readily available candidate 4 (BYK 405879) as starting material or the Noyori asymmetric reduction of ketones as key reaction. A comprehensive SAR regarding the influence of the 5-carboxamide and the 8-aryl residue on in vitro activity, acid-suppression in the Ghosh Schild rat, and affinity toward the hERG channel was established. In addition, efficacy and duration of the antisecretory action was examined for the most promising target compounds by 24 h pH-metry in the fistula dog and a significantly different SAR was observed as compared to the Ghosh Schild rat. Several tetrahydrochromenoimidazoles were identified that possessed a comparable profile as the candidate 4.

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Section: Chemistrymentioning

confidence: 99%

Tetrahydrochromenoimidazoles as Potassium-Competitive Acid Blockers (P-CABs): Structure−Activity Relationship of Their Antisecretory Properties and Their Affinity toward the hERG Channel

Palmer¹,

Chiesa²,

Schmid³

et al. 2010

J. Med. Chem.

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Total Synthesis of (−) and (+)-Zingibergingerols A

Shet,

Ramana

2024

J. Org. Chem.

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The first total synthesis of both of the enantiomers of Zingibergingerol A has been accomplished. The distinctive 3,7,9trioxabicyclo[4.2.1]nonane skeleton is crafted through goldcatalyzed alkynol cycloisomerization. The synthesis comprises sequential C−C bond formations at both ends of epichlorohydrin: first opening the epoxide with eugenol-derived alkyne, followed by subsequent epoxide installation, and again opening with a Grignard reagent. The resulting alkynol with a fixed C5 stereochemistry was subjected to O-allylation, followed by dihydroxylation and alkynol cycloisomerization.Note pubs.acs.org/joc

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Asymmetric Total Synthesis of Dragonbloodins A1 and A2

2018

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The first asymmetric total synthesis of dragonbloodins A1 and A2, a pair of unprecedented chalcone-flavan heterotrimmers, has been achieved through a series of rationally designed or bioinspired transformations. Key elements of the synthesis include a highly efficient heterotrimerization reaction to assemble the two chalcone units and one flavan unit in one pot and a tandem oxidative dearomatization/cyclization/oxygenation reaction to forge the polycyclic core of dragonbloodins A1 and A2. The present synthesis unambiguously confirms the biogenetic relationship and absolute stereochemistry of dragonbloodins A1 and A2.

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Synthesis and pharmacological evaluation of potential metabolites of the potassium-competitive acid blocker BYK405879

Cited by 3 publications

References 8 publications

Tetrahydrochromenoimidazoles as Potassium-Competitive Acid Blockers (P-CABs): Structure−Activity Relationship of Their Antisecretory Properties and Their Affinity toward the hERG Channel

Tetrahydrochromenoimidazoles as Potassium-Competitive Acid Blockers (P-CABs): Structure−Activity Relationship of Their Antisecretory Properties and Their Affinity toward the hERG Channel

Total Synthesis of (−) and (+)-Zingibergingerols A

Asymmetric Total Synthesis of Dragonbloodins A1 and A2

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