13606-10-5Relevant academic research and scientific papers
Bis-Acetyl Carbazole: A Photoremovable Protecting Group for Sequential Release of Two Different Functional Groups and Its Application in Therapeutic Release
Venkatesh, Yarra,Nandi, Surajit,Shee, Maniklal,Saha, Biswajit,Anoop, Anakuthil,Pradeep Singh
, p. 6121 - 6130 (2017/11/15)
In this paper, we present fluorescent photoremovable protecting groups (FPRPG) based on bis-acetyl carbazole for the release of two different functional groups such as carboxylic acids, alcohols, thiols, and amines in a sequential fashion. Dual-arm caged bis-acetyl carbazoles with different combinations of two unlike functional groups were synthesized. Photophysical studies showed that caged bis-acetyl carbazoles are blue fluorescent and their emission properties are sensitive to the environment. Sequential photorelease of two different functional groups by bis-acetyl carbazole was analyzed by HPLC, UV and emission spectroscopy. The mechanism of the dual release by bis-acetyl carbazole was investigated and supported by TD-DFT calculations. To demonstrate the applicability of the dual release ability of bis-acetyl carbazole FPRPG, we synthesized a drug delivery system (DDS) in which one arm of bis-acetyl carbazole is linked to the carboxylic functional group of chlorambucil (CBL) and the other arm is attached to the hydroxyl group of ferulic acid ethyl ester (FAEE). In vitro studies showed that our DDS presents excellent properties such as photoregulated dual drug delivery, cellular uptake, and biocompatibility.
The Kinetics and Mechanism of the Thallium(III) Ion-promoted Hydrolysis of Thiolurethanes in Aqueous Solution. A Metal Ion-promoted Elimination
Satchell, Derek P. N.,Satchell, Rosemary S.,Wassef, Wasfy N.
, p. 1199 - 1202 (2007/10/02)
The hydrolysis of thiolurethanes R1C6H4NHCOSC6H4R2 (1), in dilute aqueous perchloric acid, under conditions where the spontaneous hydrolysis is negligible, is promoted by Ti3+ ions.The organic products are the corresponding anilinium ion and the thalium salt of the thiophenol.The effects of substituent changes (R1,R2) of changes in +>, temperature, ionic strength, and of replacement of the NH proton by Me, are all compatible with hydrolysis occurring by elimination-addition mechanisms via the isocyanate as a reactive intermediate; thalium ion-promoted E1 cb and E2 routes are implicated.In effect the elimination-addition type of mechanism which is important for these esters at higher pH has been made available at low pH by complexation with Tl3+ ions.With the thiolurethanes RC6H4NHCOSEt, (2) which are less susceptible to the spontaneous and base-catalysed elimination-addition mechanisms of hydrolysis than are thiolurethanes (1), the presence of Tl3+ ions can also lead to promoted hydrolysis via elimination, but an AAc1-like route (with Tl3+ taking the role of H+) seems to be available to the N-Me derivatives.
