Synthesis and biological evaluation of novel C-indolylxylosides as sodium-dependent glucose co-transporter 2 inhibitors

Yao, Chun‐Hsu; Song, Jen‐Shin; Chen, Chiung‐Tong; Yeh, Teng‐Kuang; Hsieh, Tsung-Chih; Wu, Szu-Huei; Huang, Chen; Huang, Yuping; Wang, Min-Hsien; Liu, Yuwei; Tsai, Chi‐Hui; Kumar, Chidambaram Ramesh; Lee, Jinq‐Chyi

doi:10.1016/j.ejmech.2012.06.053

Cited by 43 publications

(24 citation statements)

References 15 publications

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“…29 Reduction of aldehyde 2 to alcohol 3 using NaBH 4 in EtOH proceeded almost quantitatively. 28 Chlorination of alcohol 3 with thionyl chloride afforded 4 in 81% yield.…”

Section: Resultsmentioning

confidence: 99%

“…32 N -methylation of 6 with methyl iodide and sodium hydride afforded 7 in 83% yield. 29 Mild hydrolysis (2 N HCl) afforded the α -substituted amino acid methyl ester 8 31 which was protected as the N VOC carbamate to yield 9 in 62% overall yield. 21 Methyl ester 9 was then hydrolyzed to afford the free acid which was subsequently treated with chloroacetonitrile to afford the requisite cyanomethyl ester 10 in 31% yield.…”

Section: Resultsmentioning

confidence: 99%

“…Initially, commercially available 4-azaindole was formylated to yield 12 which was N -tosylated with p -TsCl and NaH, affording 13 in 23% overall yield. 29 Reduction of aldehyde 13 with NaBH 4 in EtOH afforded alcohol 14 in 87% yield. 28 Chlorination of 14 with thionyl chloride then provided 15 .…”

Section: Resultsmentioning

confidence: 99%

“…Regioselective lithiation ( n -butyllithium, THF, −78°C) of the Schöllkopf reagent produced the lithium enolate which afforded adduct 16 in 62% yield with high diastereoselectivity. 31 Mild hydrolysis (2 N HCl) provided α -substituted amino acid methyl ester 17 29 which was protected as the N VOC carbamate to yield 18 in 33% overall yield. 21 N -Detosylation of 18 using cesium carbonate in 2:1 THF/MeOH afforded ester 19 .…”

Section: Resultsmentioning

confidence: 99%

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Tryptophan-based fluorophores for studying protein conformational changes

Talukder

Chen

Liu

et al. 2014

Bioorganic & Medicinal Chemistry

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With the continuing interest in deciphering the interplay between protein function and conformational changes, small fluorescence probes will be especially useful for tracking changes in the crowded protein interior space. Presently, we describe the potential utility of six unnatural amino acid fluorescence donors structurally related to tryptophan and show how they can be efficiently incorporated into a protein as fluorescence probes. We also examine the various photophysical properties of the new Trp analogues, which are significantly redshifted in their fluorescence spectra relative to tryptophan. In general, the Trp analogues were well tolerated when inserted into E. coli DHFR, and did not perturb enzyme activity, although substitution for Trp22 did result in a diminution in DHFR activity. Further, it was demonstrated that D and E at position 37 formed efficient FRET pairs with acridon-2-ylalanine (Acd) at position 17. The same was also true for a DHFR construct containing E at position 79 and Acd at position 17. Together, these findings demonstrate that these tryptophan analogues can be introduced into DHFR with minimal disruption of function, and that they can be employed for the selective study of targeted conformational or electrostatic changes in proteins, even in the presence of unmodified tryptophans.

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“…29 Reduction of aldehyde 2 to alcohol 3 using NaBH 4 in EtOH proceeded almost quantitatively. 28 Chlorination of alcohol 3 with thionyl chloride afforded 4 in 81% yield.…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Tryptophan-based fluorophores for studying protein conformational changes

Talukder

Chen

Liu

et al. 2014

Bioorganic & Medicinal Chemistry

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“…Pyrroloisoquinoline 4 was first formylated under Duff reaction conditions 14 to yield aldehyde 5 , the latter of which was subjected to N -tosylation with p -toluenesulfonyl chloride ( p -TsCl) and sodium hydride to afford 6 in 46% overall yield. 15 Reduction of aldehyde 6 to alcohol 7 using NaBH 4 in EtOH proceeded almost quantitatively. 14 Chlorination of alcohol 7 with thionyl chloride afforded 8 in 77% yield.…”

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confidence: 99%

Efficient Asymmetric Synthesis of Tryptophan Analogues Having Useful Photophysical Properties

et al. 2014

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Two new fluorescent probes of protein structure and dynamics have been prepared by concise asymmetric syntheses using the Schöllkopf chiral auxiliary. The site-specific incorporation of one probe into dihydrofolate reductase is reported. The utility of these tryptophan derivatives lies in their absorption and emission maxima which differ from those of tryptophan, as well as in their large Stokes shifts and high molar absorptivities.

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Ir(I)‐Catalyzed C−H Glycosylation for Synthesis of 2‐Indolyl‐C‐Deoxyglycosides

Liu

Xie

et al. 2021

Adv Synth Catal

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The construction of 2‐deoxy‐C‐glycosides has gradually become a hotspot of carbohydrate chemistry in recent years. In this work, we present an efficient, regioselective, stereoselective and widely applicable strategy for the synthesis of 2‐indolyl‐C‐deoxyglycosides via Ir(I)‐catalyzed, pyridine‐group‐directed C−H functionalization. This method exhibits high tolerance for the functional groups of indoles and the protecting groups of carbohydrates. Moreover, this protocol has good stereoselectivity and mainly produces β‐configuration products. Gram‐scale synthesis and several practical transformations were conducted for further applications. Meantime, we also explored the mechanism of this method and proposed a catalytic cycle

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Synthesis and biological evaluation of novel C-indolylxylosides as sodium-dependent glucose co-transporter 2 inhibitors

Cited by 43 publications

References 15 publications

Tryptophan-based fluorophores for studying protein conformational changes

Tryptophan-based fluorophores for studying protein conformational changes

Efficient Asymmetric Synthesis of Tryptophan Analogues Having Useful Photophysical Properties

Ir(I)‐Catalyzed C−H Glycosylation for Synthesis of 2‐Indolyl‐C‐Deoxyglycosides

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