199.21 | - Indole Building Blocks

Kadikova, Gulnara N. et al. published their research in Molecules in 2021 | CAS: 14396-90-8

2-(But-3-yn-1-yl)isoindoline-1,3-dione (cas: 14396-90-8) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.HPLC of Formula: 14396-90-8

Synthesis of new functionally substituted 9-azabicyclo[4.2.1]nona-2,4,7-trienes by cobalt(I)-Catalyzed [6蟺 + 2蟺]-cycloaddition of N-carbocholesteroxyazepine to alkynes was written by Kadikova, Gulnara N.;D’yakonov, Vladimir A.;Dzhemilev, Usein M.. And the article was included in Molecules in 2021.HPLC of Formula: 14396-90-8 This article mentions the following:

Catalytic [6蟺 + 2蟺]-cycloaddition of N-carbocholesteroxyazepine with functionally substituted terminal alkynes and 1,4-butynediol was performed for the first time under the action of the Co(acac)₂(dppe)/Zn/ZnI₂ three-component catalytic system. The reaction gave previously undescribed but promising 9-azabicyclo[4.2.1]nona-2,4,7-trienes I (n-Bu, (CH₂)₂CN, 1-naphthyl, etc.) (in 79-95% yields), covalently bound to a natural metabolite, cholesterol. In the experiment, the researchers used many compounds, for example, 2-(But-3-yn-1-yl)isoindoline-1,3-dione (cas: 14396-90-8HPLC of Formula: 14396-90-8).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Cheval, Nicolas P. et al. published their research in Tetrahedron in 2018 | CAS: 14396-90-8

2-(But-3-yn-1-yl)isoindoline-1,3-dione (cas: 14396-90-8) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Reference of 14396-90-8

Vinyl nosylates as partner in copper and silver co-catalyzed Sonogashira cross-coupling reactions was written by Cheval, Nicolas P.;Hoffmann, Barbara;Dikova, Anna;Sirindil, Fatih;Bertus, Philippe;Blanc, Aurelien;Weibel, Jean-Marc;Pale, Patrick. And the article was included in Tetrahedron in 2018.Reference of 14396-90-8 This article mentions the following:

Vinyl nosylates, readily obtained from 尾-dicarbonyl derivatives, could be efficiently engaged in Sonogashira cross-coupling reactions, co-catalyzed by either copper or silver salts. The para-nitrobenzenesulfonate (nosylate) group allows this coupling to be performed under very mild conditions (room temperature). This new leaving group and mild conditions could be applied to the synthesis of acetylenic coumarinyl derivatives and to the total synthesis of an acetylenic monoterpene natural product, cleviolide. In the experiment, the researchers used many compounds, for example, 2-(But-3-yn-1-yl)isoindoline-1,3-dione (cas: 14396-90-8Reference of 14396-90-8).

Pisaneschi, Federica et al. published their research in Bioconjugate Chemistry in 2017 | CAS: 14396-90-8

2-(But-3-yn-1-yl)isoindoline-1,3-dione (cas: 14396-90-8) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). SDS of cas: 14396-90-8

Automated, Resin-Based Method to Enhance the Specific Activity of Fluorine-18 Clicked PET Radiotracers was written by Pisaneschi, Federica;Kelderhouse, Lindsay E.;Hardy, Amanda;Engel, Brian J.;Mukhopadhyay, Uday;Gonzalez-Lepera, Carlos;Gray, Joshua P.;Ornelas, Argentina;Takahashi, Terry T.;Roberts, Richard W.;Fiacco, Stephen V.;Piwnica-Worms, David;Millward, Steven W.. And the article was included in Bioconjugate Chemistry in 2017.SDS of cas: 14396-90-8 This article mentions the following:

Radiolabeling of substrates with 2-[¹⁸F]fluoroethylazide exploits the rapid kinetics, chem. selectivity, and mild conditions of the copper-catalyzed azide-alkyne cycloaddition reaction. While this methodol. has proven to result in near-quant. labeling of alkyne-tagged precursors, the relatively small size of the fluoroethylazide group makes separation of the ¹⁸F-labeled radiotracer and the unreacted precursor challenging, particularly with precursors >500 Da (e.g., peptides). We have developed an inexpensive azide-functionalized resin to rapidly remove unreacted alkyne precursor following the fluoroethylazide labeling reaction and integrated it into a fully automated radiosynthesis platform. We have carried out 2-[¹⁸F]fluoroethylazide labeling of four different alkynes ranging from <300 Da to >1700 Da and found that >98% of the unreacted alkyne was removed in less than 20 min at room temperature to afford the final radiotracers at >99% radiochem. purity with specific activities up to >200 GBq/渭mol. We have applied this technique to label a novel cyclic peptide previously evolved to bind the Her2 receptor with high affinity, and demonstrated tumor-specific uptake and low nonspecific background by PET/CT. This resin-based methodol. is automated, rapid, mild, and general allowing peptide-based fluorine-18 radiotracers to be obtained with clin. relevant specific activities without chromatog. separation and with only a minimal increase in total synthesis time. In the experiment, the researchers used many compounds, for example, 2-(But-3-yn-1-yl)isoindoline-1,3-dione (cas: 14396-90-8SDS of cas: 14396-90-8).

Cheval, Nicolas P. et al. published their research in Tetrahedron in 2018 | CAS: 14396-90-8

Vinyl nosylates, readily obtained from β-dicarbonyl derivatives, could be efficiently engaged in Sonogashira cross-coupling reactions, co-catalyzed by either copper or silver salts. The para-nitrobenzenesulfonate (nosylate) group allows this coupling to be performed under very mild conditions (room temperature). This new leaving group and mild conditions could be applied to the synthesis of acetylenic coumarinyl derivatives and to the total synthesis of an acetylenic monoterpene natural product, cleviolide. In the experiment, the researchers used many compounds, for example, 2-(But-3-yn-1-yl)isoindoline-1,3-dione (cas: 14396-90-8Reference of 14396-90-8).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Pisaneschi, Federica et al. published their research in Bioconjugate Chemistry in 2017 | CAS: 14396-90-8

Radiolabeling of substrates with 2-[¹⁸F]fluoroethylazide exploits the rapid kinetics, chem. selectivity, and mild conditions of the copper-catalyzed azide-alkyne cycloaddition reaction. While this methodol. has proven to result in near-quant. labeling of alkyne-tagged precursors, the relatively small size of the fluoroethylazide group makes separation of the ¹⁸F-labeled radiotracer and the unreacted precursor challenging, particularly with precursors >500 Da (e.g., peptides). We have developed an inexpensive azide-functionalized resin to rapidly remove unreacted alkyne precursor following the fluoroethylazide labeling reaction and integrated it into a fully automated radiosynthesis platform. We have carried out 2-[¹⁸F]fluoroethylazide labeling of four different alkynes ranging from <300 Da to >1700 Da and found that >98% of the unreacted alkyne was removed in less than 20 min at room temperature to afford the final radiotracers at >99% radiochem. purity with specific activities up to >200 GBq/μmol. We have applied this technique to label a novel cyclic peptide previously evolved to bind the Her2 receptor with high affinity, and demonstrated tumor-specific uptake and low nonspecific background by PET/CT. This resin-based methodol. is automated, rapid, mild, and general allowing peptide-based fluorine-18 radiotracers to be obtained with clin. relevant specific activities without chromatog. separation and with only a minimal increase in total synthesis time. In the experiment, the researchers used many compounds, for example, 2-(But-3-yn-1-yl)isoindoline-1,3-dione (cas: 14396-90-8SDS of cas: 14396-90-8).

Pisaneschi, Federica et al. published their research in Bioconjugate Chemistry in 2017 | CAS: 14396-90-8

Radiolabeling of substrates with 2-[¹⁸F]fluoroethylazide exploits the rapid kinetics, chem. selectivity, and mild conditions of the copper-catalyzed azide-alkyne cycloaddition reaction. While this methodol. has proven to result in near-quant. labeling of alkyne-tagged precursors, the relatively small size of the fluoroethylazide group makes separation of the ¹⁸F-labeled radiotracer and the unreacted precursor challenging, particularly with precursors >500 Da (e.g., peptides). We have developed an inexpensive azide-functionalized resin to rapidly remove unreacted alkyne precursor following the fluoroethylazide labeling reaction and integrated it into a fully automated radiosynthesis platform. We have carried out 2-[¹⁸F]fluoroethylazide labeling of four different alkynes ranging from <300 Da to >1700 Da and found that >98% of the unreacted alkyne was removed in less than 20 min at room temperature to afford the final radiotracers at >99% radiochem. purity with specific activities up to >200 GBq/μmol. We have applied this technique to label a novel cyclic peptide previously evolved to bind the Her2 receptor with high affinity, and demonstrated tumor-specific uptake and low nonspecific background by PET/CT. This resin-based methodol. is automated, rapid, mild, and general allowing peptide-based fluorine-18 radiotracers to be obtained with clin. relevant specific activities without chromatog. separation and with only a minimal increase in total synthesis time. In the experiment, the researchers used many compounds, for example, 2-(But-3-yn-1-yl)isoindoline-1,3-dione (cas: 14396-90-8SDS of cas: 14396-90-8).

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