Chromogenic diazirine: A new spectrophotometric approach for photoaffinity labeling

Hatanaka, Y.; Yoshida, Eiichi; Nakayama, Hitoshi; Kanaoka, Yuichi

doi:10.1016/0045-2068(89)90048-5

Cited by 17 publications

(10 citation statements)

References 8 publications

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“…The ethoxycarbonyl group of moiety C was modified by introducing hydrophilic groups to improve solubilities of compounds, and it was found that appropriate modification was tolerable. Based on the above information, a photophore was introduced to the ester group, which generated three compounds as potential photoaffinity labelling probes .…”

Section: Resultsmentioning

confidence: 99%

Indolizine Derivatives as HIV‐1 VIF–ElonginC Interaction Inhibitors

et al. 2013

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Compound 1 (VEC-5) was identified as a potent small-molecular HIV-1 viron infectivity factor inhibitor that targets the viron infectivity factor-ElonginC interaction. A structure-activity relationship study was carried out to develop compounds with improved efficacy against HIV-1 and 49 indolizine derivatives of three categories were designed and synthesized. We found that five compounds exhibited promising anti-HIV-1 activity, and the most active compound 2g had an IC50 value of 11.0 μm. These results provide new information to develop highly potent small-molecule HIV-1 viron infectivity factor inhibitors.

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Section: Resultsmentioning

confidence: 99%

Indolizine Derivatives as HIV‐1 VIF–ElonginC Interaction Inhibitors

et al. 2013

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“…The following compounds were prepared by literature methods: p - tert -butylphenyl 4,6-di- O -acetyl-2,3-dideoxy-α- d - erythro -hex-2-enopyranoside, p - tert -butyl phenyl 4,6-di- O -benzyl-2,3-dideoxy-α- d - erythro -hex-2-enopyranoside ( 1a ), p - tert -butylphenyl 4- O -benzyl-2,3,6-trideoxy-α- l - erythro -hex-2-enopyranoside ( 20 ), PdCl 2 (CH 3 CN) 2, PdCl 2 (dppf), NiCl 2 (dppe), NiCl 2 (dppp), NiCl 2 (dppb), NiCl 2 (dpppe), NiCl 2 (dppf), NiCl 2 (PPh 3 ) 2 , 1-bromo-4-[( tert -butyldimethylsilyl)oxy]benzene, 4-bromobenzaldehyde dimethyl acetal, and 1-bromo-4-(methoxymethoxy)benzene …”

Section: Methodsmentioning

confidence: 99%

Synthesis of α- and β-C-Aryl Δ²-Glycopyranosides from p-tert-Butylphenyl Δ²-Glycopyranosides via Grignard Reagents

1998

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Treatment of p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-alpha-D-erythro-hex-2-enopyranoside (1aalpha) or the 4,6-di-O-(tert-butyldimethylsilyl) analogue (1balpha) with various functionalized arylmagnesium bromides in the presence of a catalytic amount of PdCl(2)(dppf) at 25 degrees C in THF afforded the corresponding unsaturated C-arylglycosides 2-14 having the alpha-configuration in quite good yields. Benzyl-, allyl-, and vinylmagnesium bromides gave also the corresponding unsaturated alpha-C-glycosides 15-18, although in lower yields. When the same reaction was performed in the presence of NiCl(2)(dppe) as the catalyst at -40 degrees C, only the formation of the corresponding unsaturated C-arylglycosides having the beta-configuration was observed. As expected, reaction of phenylmagnesium bromide with p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-beta-D-erythro-hex-2-enopyranoside (1abeta) in the presence of NiCl(2)(dppe) gave only the unsaturated beta-C-phenylglycoside 2abeta, while palladium-catalyzed reaction led to the preponderant formation of C-phenylglycoside 2aalpha. Reaction of PhMgBr with p-tert-butylphenyl 4-O-benzyl-2,3,6-trideoxy-alpha-L-erythro-hex-2-enopyranoside (20) afforded stereospecifically the unsaturated alpha- and beta-C-phenylglycoside 25 in the presence of PdCl(2)(dppf) and NiCl(2)(dppe), respectively.

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“…7-{{cl-H}-{3-(trifluoromethyl)-3V{-diazirin-3-yljphenoxyacetyl) taxol [36].-Compound 35 (26 mg) was dissolved in 1.0 ml of 5 % HC1 in MeOH and stirred at room temperature for 15 min. The solution was diluted with CH2C12, washed successively with HzO and brine, dried over Na2S04, and concentrated to yield the crude product.…”

Section: Experimental General Experimentalmentioning

confidence: 99%

Modified Taxols, 9. Synthesis and Biological Evaluation of 7-Substituted Photoaffinity Analogues of Taxol

Rimoldi¹,

Kingston²,

Chaudhary³

et al. 1993

J. Nat. Prod.

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The 7-substituted taxol analogues 7, 19, 27, and 32 have been prepared as potential photoaffinity-labeled derivatives for studies of the nature of the binding site of taxol on polymerized tubulin. The analogue 32 has been prepared in both deuterium- and tritium-labeled versions. Tubulin-assembly studies were carried out with these compounds, and it was found that they showed some but not all of the properties of taxol. We conclude that these specific taxol analogues labeled at the 7 position are not ideal derivatives for photoaffinity labeling studies.

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Chromogenic diazirine: A new spectrophotometric approach for photoaffinity labeling

Cited by 17 publications

References 8 publications

Indolizine Derivatives as HIV‐1 VIF–ElonginC Interaction Inhibitors

Indolizine Derivatives as HIV‐1 VIF–ElonginC Interaction Inhibitors

Synthesis of α- and β-C-Aryl Δ²-Glycopyranosides from p-tert-Butylphenyl Δ²-Glycopyranosides via Grignard Reagents

Modified Taxols, 9. Synthesis and Biological Evaluation of 7-Substituted Photoaffinity Analogues of Taxol

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Chromogenic diazirine: A new spectrophotometric approach for photoaffinity labeling

Cited by 17 publications

References 8 publications

Indolizine Derivatives as HIV‐1 VIF–ElonginC Interaction Inhibitors

Indolizine Derivatives as HIV‐1 VIF–ElonginC Interaction Inhibitors

Synthesis of α- and β-C-Aryl Δ2-Glycopyranosides from p-tert-Butylphenyl Δ2-Glycopyranosides via Grignard Reagents

Modified Taxols, 9. Synthesis and Biological Evaluation of 7-Substituted Photoaffinity Analogues of Taxol

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Synthesis of α- and β-C-Aryl Δ²-Glycopyranosides from p-tert-Butylphenyl Δ²-Glycopyranosides via Grignard Reagents