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Literature DB >> 24346942

[2+2+2] Cycloadditions of siloxy alkynes with 1,2-diazines: from reaction discovery to identification of an antiglycolytic chemotype.

Timothy J Montavon¹, Yunus E Türkmen, Noumaan A Shamsi, Christopher Miller, Chintan S Sumaria, Viresh H Rawal, Sergey A Kozmin.

Abstract

Cycloaddition uncovered: The title reaction produces novel polycyclic compounds with high efficiency and excellent diastereoselectivity under mild reaction conditions. A small-molecule library, synthesized using this reaction, yielded a novel chemotype which inhibited glycolytic ATP production by blocking glucose uptake in CHO-K1 cells. DMF=N,N-dimethylformamide, Tf=trifluoromethanesulfonyl, TIPS=triisopropylsilyl.

Entities: CellLine Chemical Disease Species

Keywords: cycloaddition; inhibitor; polycycles; siloxyalkynes; synthetic methods

Mesh：

Substances：
Alkynes

Year: 2013 PMID： 24346942 PMCID： PMC3996828 DOI： 10.1002/anie.201305711

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

16 in total

1. Recent advances in [2+2+2] cycloaddition reactions.

Authors: Gema Domínguez; Javier Pérez-Castells
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2. Highly stereoselective synthesis of homoallylic amines based on addition of allyltrichlorosilanes to benzoylhydrazones.

Authors: R Hirabayashi; C Ogawa; M Sugiura; S Kobayashi
Journal: J Am Chem Soc Date: 2001-10-03 Impact factor: 15.419

3. Brønsted acid-promoted cyclizations of 1-siloxy-1,5-diynes.

Authors: Jianwei Sun; Sergey A Kozmin
Journal: J Am Chem Soc Date: 2005-10-05 Impact factor: 15.419

Review 4. N-acylhydrazones as versatile electrophiles for the synthesis of nitrogen-containing compounds.

Authors: Masaharu Sugiura; Shū Kobayashi
Journal: Angew Chem Int Ed Engl Date: 2005-08-19 Impact factor: 15.336

5. Formation and reactivity of silacyclopropenes derived from siloxyalkynes: stereoselective formation of 1,2,4-triols.

Authors: Timothy B Clark; K A Woerpel
Journal: Org Lett Date: 2006-08-31 Impact factor: 6.005

6. A pairwise chemical genetic screen identifies new inhibitors of glucose transport.

Authors: Olesya A Ulanovskaya; Jiayue Cui; Stephen J Kron; Sergey A Kozmin
Journal: Chem Biol Date: 2011-02-25

7. Metal triflimidates: better than metal triflates as catalysts in organic synthesis--the effect of a highly delocalized counteranion.

Authors: Sylvain Antoniotti; Vincent Dalla; Elisabet Duñach
Journal: Angew Chem Int Ed Engl Date: 2010-10-18 Impact factor: 15.336

8. Stereoselective synthesis of both syn- and anti-N-tert-alkylamines using highly stereospecific crotylation of ketone-derived acylhydrazones with crotyltrichlorosilanes.

Authors: Chikako Ogawa; Masaharu Sugiura; Shū Kobayashi
Journal: J Org Chem Date: 2002-07-26 Impact factor: 4.354

3. Non-precious metals catalyze formal [4 + 2] cycloaddition reactions of 1,2-diazines and siloxyalkynes under ambient conditions.

Authors: Chintan S Sumaria; Yunus E Türkmen; Viresh H Rawal
Journal: Org Lett Date: 2014-06-09 Impact factor: 6.005

3 in total