Development of novel β-carboline-based hydroxamate derivatives as HDAC inhibitors with antiproliferative and antimetastatic activities in human cancer cells

Synthesis, Characterization and Energetic Performance of Oxalyl Diazide, Carbamoyl Azide, and N,N’‐Bis(azidocarbonyl)hydrazine

“…The low stability of acyl azides limits reports on the synthesis and the characterization of such compounds [3] . Today, the Curtius rearrangement forming isocyanate intermediates and subsequent reaction with water, is a common method to convert carbonyl azides to amines [4–6] . The number of carbonyl azides, which have been both spectroscopically and structurally characterized has slightly increased in recent years.…”

“…[3] Today, the Curtius rearrangement forming isocyanate intermediates and subsequent reaction with water, is a common method to convert carbonyl azides to amines. [4][5][6] The number of carbonyl azides, which have been both spectroscopically and structurally characterized has slightly increased in recent years. In 1992, Willner and coworkers characterized fluorocarbonyl azide by gas electron diffraction.…”

“…[20][21][22] In this work, methanol was used which reacted with the isocyanate intermediate, and surprisingly, hydrazoic acid was eliminated by methanol and dimethyl iminodicarbonate (4) was formed. Furthermore, using oxetan-3-ol and 2amino-2H-tetrazole as reagents, oxetan-3-yl-N-azidocarbonylcarbamate (5) and N-azidocarbonyl-N'-(2H-tetrazol-2-yl)-urea (6) were obtained. Subsequently, several oxidative coupling reactions were attempted to convert 2 into 3, using different oxidizing agents.…”

Novel β‐carboline‐based indole‐4,7‐quinone derivatives as NAD(P)H: Quinone‐oxidoreductase‐1 inhibitor with potent antitumor activities by inducing reactive oxygen species, apoptosis, and DNA damage

“…Some indolequinones and their derivatives are cytotoxic to cancer cell lines which overexpress NQO1, and induce high‐level ROS (Jiho et al, 2019; Reigan et al, 2007; Sasaki et al, 2014; Xu et al, 2017). Moreover, according to structure‐activity relationship (SAR) analysis of quinone derivatives, the amino substituent on quinone ring moiety favorably impacts binding to the active site of NQO1 and ROS induction in various cancer cells (Jiho et al, 2019; Ling, Guo, et al, 2018; Ling, Yang, et al, 2018; Parkinson, Bair, Cismesia, & Hergenrother, 2013; Sasaki et al, 2014; Valderrama, Ibacache, Arancibia, Rodriguez, & Theoduloz, 2009). Many quinone analogs bearing alkyl amino substitutions have been reported to have improved antitumor activities against different tumor cell lines, however, the antitumor activities of some are modest (Kumar et al, 2019; Nishiyama et al, 2017; Parkinson & Hergenrother, 2015; Salvador et al, 2017).…”

Design, Synthesis, and Biological Evaluation of Novel N-Acylhydrazone Bond Linked Heterobivalent β-Carbolines as Potential Anticancer Agents

“…A large number of β-carboline derivatives have been prepared in search of more potent antitumor agents. The structure–activity relationships (SARs) of these β-carbolines have been extensively investigated [3,4,5,6,7,8,9,10]. Research has indicated that this class of compounds exert their antitumor effects through multiple mechanisms of action, including intercalating into DNA [11,12,13] and inhibiting topoisomerases I and II [14,15], cyclin-dependent kinase (CDK) [16,17], polo-like kinase 1 (PLK1) [18], kinesin-like protein Eg5 [19], and IκB kinases [20].…”