A facile synthetic approach to 6-pyrrolo[3,2,1-]acridines has been developed by using cascade -nucleophilic addition-cyclic Michael addition process of arynes and indoles substituted with Michael acceptors under metal-free conditions. Additionally, photophysical studies of a few of the newly synthesized pyrroloacridine compounds indicated good fluorescence emission properties.
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http://dx.doi.org/10.1021/acs.joc.3c00462 | DOI Listing |
J Org Chem
July 2023
Department of Chemical Sciences, Indian Institute of Science Education and Research Berhampur, Transit Campus, Govt. ITI Building, NH 59, Engineering School Road, Ganjam-District, Berhampur, Odisha 760 010, India.
A facile synthetic approach to 6-pyrrolo[3,2,1-]acridines has been developed by using cascade -nucleophilic addition-cyclic Michael addition process of arynes and indoles substituted with Michael acceptors under metal-free conditions. Additionally, photophysical studies of a few of the newly synthesized pyrroloacridine compounds indicated good fluorescence emission properties.
View Article and Find Full Text PDFJ Org Chem
June 2014
Department of Chemistry and Department of Medicinal Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 4790, United States.
FR901464 (1) and spliceostatin A (2) are potent inhibitors of spliceosomes. These compounds have shown remarkable anticancer activity against multiple human cancer cell lines. Herein, we describe efficient, enantioselective syntheses of FR901464, spliceostatin A, six corresponding diastereomers and an evaluation of their splicing activity.
View Article and Find Full Text PDFJ Am Chem Soc
March 2011
Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, PR China.
An efficient method for synthesis of polysubstituted cyclobutenones, which are not readily available from traditional methods due to the intrinsic ring strain, is described. The reaction of 2,3-allenoates and organozinc reagents proceeds via a tandem Michael addition/cyclic 1,2-addition/elimination mechanism with the functional groups from the organozinc reagents being introduced to the 3-position of the cyclobutenone products regiospecifically in moderate to excellent yields. Application to the synthesis of stereodefined β,γ-unsaturated enones is demonstrated.
View Article and Find Full Text PDFJ Org Chem
January 2010
Department of Chemistry, Zhejiang University (Xixi Campus), Hangzhou 310028, People's Republic of China.
A facile synthesis of xanthenes and acridines based on a cascade nucleophilic addition-cyclic Michael addition process of arynes and phenols/anilines substituted with alpha,beta-unsaturated groups at the ortho positions is described. The reaction has also been successfully extended to the synthesis of 9-spiro-xanthene and acridine derivatives with potential biochemical interest.
View Article and Find Full Text PDFAm Rev Respir Dis
June 1992
Department of Medicine, Veterans Affairs Medical Center, Salt Lake City, Utah.
We investigated cellular mechanisms that may be involved in controlling cytosol calcium and pulmonary artery pressure during hypoxia and normoxia in isolated blood-perfused ferret lungs. Alveolar hypoxia in ferret lungs causes an active increase in pulmonary vascular resistance. Hypoxic pulmonary vasoconstriction directly correlates with extracellular calcium ([Ca2+]o), and the absence of [Ca2+]o in the perfusate markedly attenuates the hypoxemia-induced pulmonary vasoconstriction.
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