Selenium heterocycles. XXVIII . Synthesis of pyrrolo[3,2‐<i>d</i>]selenazole and pyrrolo[3,2‐<i>d</i>|thiazole. Two novel heterocycles

Shafiee, Abbas; Mazloumi, A.; Cohen, Victor Israel

doi:10.1002/jhet.5570160809

Cited by 43 publications

(24 citation statements)

References 11 publications

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“…The synthesis of thiazole aldehyde C 28 began with the reaction of aldehyde 2 29 with β-ketophosphonate 3 (Scheme 2). 30 These precursors underwent the Paterson modification31 of the Horner-Emmons-Wadsworth reaction using barium hydroxide and provided the desired enone 4 with >20:1 E:Z selectivity.…”

Section: Resultsmentioning

confidence: 99%

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Total Synthesis and Evaluation of C26-Hydroxyepothilone D Derivatives for Photoaffinity Labeling of β-Tubulin

et al. 2009

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Three photaffinity labeled derivatives of epothilone D were prepared by total synthesis, using efficient novel asymmetric synthesis methods for the preparation of two important synthetic building blocks. The key step for the asymmetric synthesis of (S,E)-3-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methylthiazol-4-yl)pent-4-enal involved a ketone reduction with (R)-Me-CBSoxazaborolidine. For the synthesis of (5S)-5,7-di-[(tert-butyldimethylsilyl)oxy]-4,4-dimethylheptan-3-one an asymmetric Noyori reduction of a β-ketoester was employed. The C26 hydroxyepothilone D derivative was constructed following a well-established total synthesis strategy and the photoaffinity labels were attached to the C26 hydroxyl group. The photoaffinity analogues were tested in a tubulin assembly assay and for cytotoxicity against MCF-7 and HCT-116 cancer cell lines. The 3-and 4-azidobenzoic acid analogues were found to be as active as epothilone B in a tubulin assembly assay, but demonstrated significantly reduced cellular cytotoxicity compared to epothilone B. The benzophenone analogue was inactive in both assays. Docking and scoring studies were conducted that suggested that the azide analogues can bind to the epothilone binding site, but that the benzophenone analogue undergoes a sterically driven ligand rearrangement that interrupts all hydrogen bonding and therefore protein binding. Photoaffinity labeling studies with the 3-azidobenzoic acid derivative did not identify any covalently labeled peptide fragments, suggesting that the phenylazido side chain was predominantly solvent-exposed in the bound conformation.

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Section: Resultsmentioning

confidence: 99%

“…The mixture was then cooled to 0 °C and aldehyde 2 29 (6.40 g, 50.2 mmol, 1.00 equiv) dissolved in THF (143 mL) and water (3.27 mL) was added dropwise. The reaction mixture was stirred at 0 °C for two hours.…”

Section: Methodsmentioning

confidence: 99%

Total Synthesis and Evaluation of C26-Hydroxyepothilone D Derivatives for Photoaffinity Labeling of β-Tubulin

et al. 2009

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“…Heating of the azidoacrylate 80 formed here in xylene leads to the pyrrolothiazole 81 with an overall yield of 9% [61]. The aminopyrrole 83, obtained by reduction of the nitropyrrole 82, was transformed into the pyrrolothiourea 84, subsequent cyclization of which gave the condensed system 85 with a yield of about 50% calculated on the initial nitro compound 82 [62].…”

Section: Pyrrolothiazolesmentioning

confidence: 99%

Synthesis of condensed thiazoles. (Review)

Smirnova

Заварзин

Krayushkin

2006

Chem Heterocycl Compd

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“…39 Table 1 Comp. Condensation of compounds 10 and 11 with methyl azidoacetate under the condition reported above, afforded methyl α-azido-β- [1-(2'-carbomethoxybiphenyl-4-yl)methyl]-2-alkyl-5-imidazolyl]acrylates (12) and methyl α-azido-β- [1-(2'-carbomethoxybiphenyl-4-yl)methyl]-2-alkyl-4-imidazolyl]acrylates (13).…”

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confidence: 99%

Syntheses of substituted pyrrolo[2,3‐d]imidazole‐5‐carboxylates and substitued pyrrolo[3,2‐d]imidazole‐5‐carboxylates

Shafiee

Mojarrad

Jalili

et al. 2002

Journal of Heterocyclic Chem

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Starting from readily available p-substituted-benzylamines a series of ethyl 2-alkylthio-1-substituted-benzylpyrrolo[2,3-d]imidazole-5-carboxylates was prepared. In addition, starting from 2-alkyl-4(or 5)-formylimidazoles and methyl 4'-bromomethylbiphenyl-2-carboxylate a series of methyl substitutedpyrrolo[2,3-d]imidazole-5-carboxylates and methyl substituted-pyrrolo[3,2-d]imidazole-5-carboxylates was prepared.

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Selenium heterocycles. XXVIII . Synthesis of pyrrolo[3,2‐d]selenazole and pyrrolo[3,2‐d|thiazole. Two novel heterocycles

Abstract: Aus den Selenoamiden (I) und Dichloraceton (II) entstehen die Selenazole (IIIa), die zu den Carbinolen (IIIb) verseift und dann zu den Aldehyden (IV) oxidiert werden.

Cited by 43 publications

References 11 publications

Total Synthesis and Evaluation of C26-Hydroxyepothilone D Derivatives for Photoaffinity Labeling of β-Tubulin

Total Synthesis and Evaluation of C26-Hydroxyepothilone D Derivatives for Photoaffinity Labeling of β-Tubulin

Synthesis of condensed thiazoles. (Review)

Syntheses of substituted pyrrolo[2,3‐d]imidazole‐5‐carboxylates and substitued pyrrolo[3,2‐d]imidazole‐5‐carboxylates

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