13761-32-5Relevant articles and documents
Two-photon uncaging of bioactive thiols in live cells at wavelengths above 800 nm
Hammers, Matthew D.,Hodny, Michael H.,Bader, Taysir K.,Mahmoodi, M. Mohsen,Fang, Sifei,Fenton, Alexander D.,Nurie, Kadiro,Trial, Hallie O.,Xu, Feng,Healy, Andrew T.,Ball, Zachary T.,Blank, David A.,Distefano, Mark D.
, p. 2213 - 2223 (2021)
Photoactivatable protecting groups (PPGs) are useful for a broad range of applications ranging from biology to materials science. In chemical biology, induction of biological processesviaphotoactivation is a powerful strategy for achieving spatiotemporal control. The importance of cysteine, glutathione, and other bioactive thiols in regulating protein structure/activity and cell redox homeostasis makes modulation of thiol activity particularly useful. One major objective for enhancing the utility of photoactivatable protecting groups (PPGs) in living systems is creating PPGs with longer wavelength absorption maxima and efficient two-photon (TP) absorption. Toward these objectives, we developed a carboxyl- and dimethylamine-functionalized nitrodibenzofuran PPG scaffold (cDMA-NDBF) for thiol photoactivation, which has a bathochromic shift in the one-photon absorption maximum fromλmax= 315 nm with the unfunctionalized NDBF scaffold toλmax= 445 nm. While cDMA-NDBF-protected thiols are stable in the presence of UV irradiation, they undergo efficient broad-spectrum TP photolysis at wavelengths as long as 900 nm. To demonstrate the wavelength orthogonality of cDMA-NDBF and NDBF photolysis in a biological setting, caged farnesyltransferase enzyme inhibitors (FTI) were prepared and selectively photoactivated in live cells using 850-900 nm TP light for cDMA-NDBF-FTI and 300 nm UV light for NDBF-FTI. These experiments represent the first demonstration of thiol photoactivation at wavelengths above 800 nm. Consequently, cDMA-NDBF-caged thiols should have broad applicability in a wide range of experiments in chemical biology and materials science.
One pot synthesis of diarylfurans from aryl esters and PhI(OAc)2 via palladium-associated iodonium ylides
Bao, Yong-Sheng,Bao, Agula,Bao, Zhaorigetu,Jia, Meilin,Baiyin, Menghe
, p. 4179 - 4182 (2015)
The example of palladium-catalyzed intermolecular cyclization for the synthesis of various diarylfurans in which one of the aromatic rings originates from the phenolic part of the starting ester and the other one from PhI(OAc)2 has been reported. The reaction is carried out through two steps: the rearrangement of palladium-associated iodonium ylides to form o-iodo diaryl ether and then palladium catalyzed intramolecular direct arylation. This reaction can tolerate a variety of functional groups and is alternative or complementary to the previous methods for the synthesis of diarylfurans.
Palladium-catalyzed acetylation of arylbromides
Ariki, Zach,Garg, Neil K.,Kaiser, Daniel,Kelleghan, Andrew V.,Mehta, Milauni M.
, p. 68 - 83 (2021/04/14)
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Pyrazoles: 'one-pot' synthesis from arenes and carboxylic acids
Gong, Ming,Kim, Jung Keun,Kovalev, Vladimir V.,Kovaleva, Olga V.,Shokova, Elvira A.,Tafeenko, Viktor A.,Wu, Yangjie
supporting information, p. 5625 - 5638 (2020/08/21)
A rapid and efficient method for 'one-pot' synthesis of pyrazoles from (hetero)arenes and carboxylic acids via successive formation of ketones and β-diketones followed by heterocyclization with hydrazine has been developed. The utility of the RCOOH/TfOH/TFAA acylation system for intermediate production of ketones and 1,3-diketones is a key feature of this approach. The preliminary evaluation of the anticancer activity of the synthesized pyrazoles is performed.