Identification of novel 1,2,3,6-tetrahydropyridyl-substituted benzo[ d ]thiazoles: Lead generation and optimization toward potent and orally active EP 1 receptor antagonists

Umei, Kentaro; Nishigaya, Yosuke; Tatani, Kazuya; Kohno, Yasushi; Tanaka, Nobuyuki; Seto, Shigeki

doi:10.1016/j.bmc.2017.04.028

Cited by 5 publications

(2 citation statements)

References 25 publications

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“…Arenes with 8-aminoquinoline (bidentate, NHQ)-directing groups ( 25a – 30a ) were also mono- or dichlorinated, but in slightly lower yields (58–80%). Compounds 25b – 27b are important synthetic intermediates of active EP 1 antagonists 67 and positive allosteric modulators 68 . In general, the excess PVC employed in the reaction is to ensure high product yields and does not affect the selectivity for ortho -di- or monochloride products.…”

Section: Resultsmentioning

confidence: 99%

Tandem catalysis enables chlorine-containing waste as chlorination reagents

Liu,

Wu,

Dyson

2024

Nat. Chem.

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Chlorinated compounds are ubiquitous. However, accumulation of chlorine-containing waste has a negative impact on human health and the environment due to the inapplicability of common disposal methods, such as landfill and incineration. Here we report a sustainable approach to valorize chlorine-containing hydrocarbon waste, including solids (chlorinated polymers) and liquids (chlorinated solvents), based on copper and palladium catalysts with a NaNO3 promoter. In the process, waste is oxidized to release the chlorine in the presence of N-directing arenes to afford valuable aryl chlorides, such as the FDA-approved drug vismodegib. The remaining hydrocarbon component is mineralized to afford CO, CO2 and H2O. Moreover, the CO and CO2 generated could be further utilized directly. Thus, chlorine-containing hydrocarbon waste, including mixed waste, can serve as chlorination reagents that neither generate hazardous by-products nor involve specialty chlorination reagents. This tandem catalytic approach represents a promising method for the viable management of a wide and diverse range of chlorine-containing hydrocarbon wastes.

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Section: Resultsmentioning

confidence: 99%

Tandem catalysis enables chlorine-containing waste as chlorination reagents

Liu,

Wu,

Dyson

2024

Nat. Chem.

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“…The thiazole nucleus is present in some already approved medicines like: xanthine oxidase inhibitors (Febuxostat), NSAIDs (meloxicam), H 2 receptor antagonists (nizatidine), leukotriene receptor antagonists (cinalukast), dopamine agonists (pramipexol) as well as a series of antimicrobial agents (abafungin, acinitrazole, aztreonam, ceftriaxone) or antineoplastic drugs (bleomycin, tiazofurin) [2,3]. However, a great deal of interested is still bestowed upon this molecular moiety by current research [4] that aims at identifying new lead compounds to act as: antineoplastic agents [5][6][7][8][9], prostaglandin receptor antagonists [10], antiprotozoal drugs [11,12] or antimicrobial agents [13]. Alongside thiazole, oxadiazole is also a versatile moiety present in a series of antimicrobial agents [14,15].…”

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confidence: 99%

Synthesis and Antimicrobial Assessment of Some New 2-(Thiazol-5-yl)-1,3,4-oxadiazoles

Araniciu¹,

Oniga²,

Stoica³

et al. 2019

Rev. Chim.

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Considering the promising antimicrobial activity of compounds bearing the thiazole or the oxadiazole rings in their structures, we set out to obtain new antimicrobial molecules bearing the 2-(thiazol-5-yl)-1,3,4-oxadiazole schaffold. The structures of the 8 new compounds obtained was confirmed by physicochemical characterization including: 1H-NMR, MS and elemental analysis. Antimicrobial activity was investigated against 5 Gram-positive bacterial strains, 2 Gram-negative bacterial strains and 2 fungal strains. The newly synthesized compounds showed modest antimicrobial activity.

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Development of Synthetic Route for 3‐Amino‐5‐halo‐2‐iodobenzoates: Versatile Starting Materials in Pharmaceuticals Synthesis

Park,

Seo,

Cheon

2024

Asian J Org Chem

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A novel synthetic route to 3‐amino‐5‐halo‐2‐iodobenzoates, which are used as versatile starting materials in the synthesis of pharmaceuticals, was developed using commercially available 2‐aminobenzoates bearing a suitable halogen atom at the C5 position as the starting material. Synthesis was initiated with the introduction of a nitro group at the C3 position of the appropriate 2‐aminobenzoates, forming 2‐amino‐3‐nitrobenzoates with a C5‐halogen atom. The subsequent conversion of the C2‐amino group to an iodide yielded 5‐halo‐2‐iodo‐3‐nitrobenzoates, which were further converted into the desired 3‐amino‐5‐halo‐2‐iodobenzoates by reducing the C3‐nitro group to an amino group. It is worth noting that this transformation can be conducted on a 50 mmol scale, and the desired benzoate compounds were obtained in good yield, demonstrating the practical applicability of this protocol.

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Identification of novel 1,2,3,6-tetrahydropyridyl-substituted benzo[ d ]thiazoles: Lead generation and optimization toward potent and orally active EP 1 receptor antagonists

Cited by 5 publications

References 25 publications

Tandem catalysis enables chlorine-containing waste as chlorination reagents

Tandem catalysis enables chlorine-containing waste as chlorination reagents

Synthesis and Antimicrobial Assessment of Some New 2-(Thiazol-5-yl)-1,3,4-oxadiazoles

Development of Synthetic Route for 3‐Amino‐5‐halo‐2‐iodobenzoates: Versatile Starting Materials in Pharmaceuticals Synthesis

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