Preparation of Furo[3,2‐c]coumarins from 3‐Cinnamoyl‐4‐hydroxy‐2H‐chromen‐2‐ones and Acyl Chlorides: A Bu3P‐Mediated C‐Acylation/Cyclization Sequence

Lee, Chia‐Jui; Tsai, Cheng-Che; Hong, Shao-Hao; Chang, Geng-Hua; Yang, Mei‐Chun; Möhlmann, Lennart; Lin, Wenwei

doi:10.1002/ange.201502789

Cited by 7 publications

(1 citation statement)

References 32 publications

(8 reference statements)

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“…Coumarin compound LM-021 [15] was synthesized and analyzed as described [19]. LMDS-1 and LMDS-2 [17] were obtained from Enamine (Kyiv, Ukraine).…”

Section: Compoundsmentioning

confidence: 99%

Investigating the Therapeutic Effects of Novel Compounds Targeting Inflammasome and IL-1β and IL-6 Signaling Pathways in Spinocerebellar Ataxia Type 3

Chen

Chang

et al. 2023

Preprint

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At least seven dominantly inherited spinocerebellar ataxias (SCA) are caused by expansions of polyglutamine (polyQ)-encoding CAG repeat. The misfolded and aggregated polyQ-expanded proteins increase reactive oxygen species (ROS), cellular toxicity and neuroinflammation in the disease pathogenesis. In this study, we evaluated the anti-inflammatory potentials of coumarin derivatives LM-021, LMDS-1 and LMDS-2, and pharmacological chaperone tafamidis that stabilizes the correctly folded tetrameric transthyretin protein, using mouse BV-2 microglia and SCA3 ATXN3/Q75-GFP SH-SY5Y cells. The four tested compounds displayed anti-inflammatory activity by suppressing NO, IL-1β, IL-6 and TNF-α production and CD68, MHCII expression in LPS/IFN-γ-stimulated BV-2 microglia. In retinoic acid-differentiated ATXN3/Q75-GFP-expressing SH-SY5Y cells inflamed with LPS/IFN-γ-primed BV-2 conditioned medium, treatment with test compounds mitigated the increased caspase 1 activity and lactate dehydrogenase release, reduced ROS and ATXN3/Q75 aggregation, and promoted neurite outgrowth. Examination of inflammasome, IL-1β and IL-6-mediated signaling pathways revealed that LM-021, LMDS-1, LMDS-2 and tafamidis decreased NLRP1, JNK/JUN, IκBα/P65, P38/STAT1 and/or JAK2/STAT3 signaling. The study results suggest the potential of LM-021, LMDS-1, LMDS-2 and tafamidis in treating SCA3 and probable other polyQ diseases.

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“…Coumarin compound LM-021 [15] was synthesized and analyzed as described [19]. LMDS-1 and LMDS-2 [17] were obtained from Enamine (Kyiv, Ukraine).…”

Section: Compoundsmentioning

confidence: 99%

Investigating the Therapeutic Effects of Novel Compounds Targeting Inflammasome and IL-1β and IL-6 Signaling Pathways in Spinocerebellar Ataxia Type 3

Chen

Chang

et al. 2023

Preprint

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Phosphine‐Mediated Rauhut‐Currier‐Type/Acyl Transfer/Wittig Strategy for Synthesis of Spirocyclopenta[c]chromene‐Indolinones

et al. 2021

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A phosphine-mediated reaction for the construction of spirocyclopenta[c]chromene-indolinones is reported via a Rauhut-Currier (RC)-type/ acyl transfer/Wittig sequence. This methodology attributes the chemoselective phosphine addition to the alkynoate which generates the phosphorus zwitterion via RC-type reaction, and that further undergoes O-acylation to form the seven-membered betaine intermediate with acyl chloride in the presence of base. Extensive investigations reveal that the exceptional δ-acylation occurs through the CÀ O bond cleavage upon the seven-membered betaine, and the subsequent Wittig reaction preferentially result in the aforementioned spiro compounds. Furthermore, our protocol could also be applicable to different alkynoates to provide a series of spirocyclopenta[c]chromenones bearing privileged skeletons.

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Four‐Component Synthesis of Phosphonium Salts: Application Toward an Alternative Approach to Cross‐Coupling for the Synthesis of Bis‐Heteroarenes

et al. 2017

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As eries of stable phosphonium salts have been synthesized via an ovel four-component reaction of an arene nucleophile,2 -heteroatom substituted aryl aldehyde,a nd phosphine in presence of an acid. The phosphonium salts thus obtained were utilized for the synthesis of avariety of bisheteroarenes,p roviding an efficient alternative method to the classical cross-coupling strategies.Scheme 2. Proposed retrosynthetic approach for the synthesis of bisheteroarenes.

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Preparation of Furo[3,2‐c]coumarins from 3‐Cinnamoyl‐4‐hydroxy‐2H‐chromen‐2‐ones and Acyl Chlorides: A Bu₃P‐Mediated C‐Acylation/Cyclization Sequence

Cited by 7 publications

References 32 publications

Investigating the Therapeutic Effects of Novel Compounds Targeting Inflammasome and IL-1β and IL-6 Signaling Pathways in Spinocerebellar Ataxia Type 3

Investigating the Therapeutic Effects of Novel Compounds Targeting Inflammasome and IL-1β and IL-6 Signaling Pathways in Spinocerebellar Ataxia Type 3

Phosphine‐Mediated Rauhut‐Currier‐Type/Acyl Transfer/Wittig Strategy for Synthesis of Spirocyclopenta[c]chromene‐Indolinones

Four‐Component Synthesis of Phosphonium Salts: Application Toward an Alternative Approach to Cross‐Coupling for the Synthesis of Bis‐Heteroarenes

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