Exploration of pyrrole derivatives to find an effective potassium-competitive acid blocker with moderately long-lasting suppression of gastric acid secretion

Nishida, Haruyuki; Fujimori, Ikuo; Arikawa, Yasuyoshi; Hirase, Keizo; Ono, Koji; Nakai, Kengo; Inatomi, Nobuhiro; Hori, Yasunobu; Matsukawa, Jun; Fujioka, Yasushi; Imanishi, Akihito; Fukui, Hirokazu; Itoh, Fumio

doi:10.1016/j.bmc.2017.04.034

Cited by 8 publications

(2 citation statements)

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“…Direct deoxyfluorination of sulfonic acids 28 with SF 4 was also reported. [227] Another related approach relies on oxidative chlorination of thiols 30 [228][229][230][231][232][233][234] or sulfides 31 [235,236] (Cl 2 , NaClO, or N-chlorosuccinimide, NCS), followed by nucleophilic substitution with fluoride (KHF 2 , BnNMe 3 + F À , etc.). A recently published method relied on using N-arylsulfenyl phthalimides, which could be obtained from aryl halides.…”

Section: Synthesis Of (Hetero)aromatic Sulfonyl Fluoridesmentioning

confidence: 99%

Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances

2021

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Current medicinal chemistry relies heavily on the quality of building blocks, i. e. reagents used to introduce chemical diversity into the target molecules. The last decade witnessed an emergence of many novel (or well-overlooked old) chemotypes for drug discovery, which is related to adapting new synthetic methodologies, designing new sp 3 -enriched bioisosteres, paying attention to previously underrated (or even unwanted) structural motifs, or combination thereof. In this review with 532 references, a survey of selected chemotypes that emerged recently in medicinal chemistry is provided, with a focus on the synthesis of the corresponding building blocks. Thus, saturated (hetero)aliphatic boronates, sulfonyl fluorides, sulfinates, non-classical sp 3 -enriched benzene isosteres, bicyclic morpholine/piperidine/piperazine analogs, as well as gemdifluorinated cycloalkanes (as an example of emerging fluorinated motifs) are discussed.

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Section: Synthesis Of (Hetero)aromatic Sulfonyl Fluoridesmentioning

confidence: 99%

Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances

2021

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“…• electrophilic substitution using fluorosulfonic acid; [23,24] • reaction of sulfonyl chlorides with fluorine anion source (KHF 2 , [5] KF, [25] TBAF, [26] NH 4 F, [27,28] or [ 18 F]KF -2.2.2-cryptand, [5,26] ); • oxidative chlorination of thiols, [29][30][31][32][33][34] sulfides [35,36] (Cl 2 , Na-ClO, NCS), followed by in situ nucleophilic substitution by fluorine anion (KHF 2 or BnNMe 3 + F -); • electrophilic fluorination of sulfinates or sulfonyl hydrazides. [37] A recently developed modification of this approach relies on in situ generation of sulfinate via palladium-catalyzed reaction of the corresponding aryl halides with DABSO, followed by oxidation with Selectfluor or NFSI; [38,39] • cycloaddition and heterocyclization reactions.…”

Section: Introductionmentioning

confidence: 99%

Hetaryl Bromides Bearing the SO₂F Group – Versatile Substrates for Palladium‐Catalyzed C–C Coupling Reactions

et al. 2018

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Synthesis of novel five‐ and six‐membered heteroaromatic sulfonyl fluorides bearing bromine atom at various positions of the heterocyclic ring is described. The synthetic utility of these compounds is demonstrated by the Suzuki, Stille, and Negishi cross‐coupling reactions, which proceeded chemoselectively at the aryl bromide moiety with 69–98 % yields. The tolerance of the SO2F group towards the coupling reaction conditions was confirmed in most of the experiments. The proposed method was efficient for either sp2–sp2 or sp2–sp3 C–C couplings. The developed procedure provides rapid access to various substituted heterocyclic sulfonyl fluorides.

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Pyridine‐3‐sulfonic Acid

Park¹

2022

Encyclopedia of Reagents for Organic Synthesis

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Exploration of pyrrole derivatives to find an effective potassium-competitive acid blocker with moderately long-lasting suppression of gastric acid secretion

Cited by 8 publications

References 20 publications

Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances

Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances

Hetaryl Bromides Bearing the SO₂F Group – Versatile Substrates for Palladium‐Catalyzed C–C Coupling Reactions

Pyridine‐3‐sulfonic Acid

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Exploration of pyrrole derivatives to find an effective potassium-competitive acid blocker with moderately long-lasting suppression of gastric acid secretion

Cited by 8 publications

References 20 publications

Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances

Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances

Hetaryl Bromides Bearing the SO2F Group – Versatile Substrates for Palladium‐Catalyzed C–C Coupling Reactions

Pyridine‐3‐sulfonic Acid

Contact Info

Product

Resources

About

Hetaryl Bromides Bearing the SO₂F Group – Versatile Substrates for Palladium‐Catalyzed C–C Coupling Reactions