52068-30-1Relevant articles and documents
Design, synthesis and evaluation of tetrahydrocarbazole derivatives as potential hypoglycemic agents
Chen, Rui,Cheng, Fei,Cui, Xing,Du, Yao,Fan, Ling-Ling,Guo, Bing,Li, Shu-Min,Tang, Lei,Wang, Jian-Ta,Wang, Li-Li,Wu, Hao-Shu,Yang, Sheng-Gang,Zhang, Ji-Quan,Zhang, Na-Na
, (2021/07/28)
Two series of tetrahydrocarbazole derivatives have been designed and synthesized based on ZG02, a promising candidate developed in our previous studies. The newly prepared compounds were screened for glucose consumption activity in HepG2 cell lines. Aza-tetrahydrocarbazole compound 12b showed the most potent hypoglycemic activity with a 45% increase in glucose consumption when compared to the solvent control, which had approximately 1.2-fold higher activity than the positive control compounds (metformin and ZG02). An investigation of the potential mechanism indicated that 12b may exhibit hypoglycemic activity via activation of the AMPK pathway. Metabolic stability assays revealed that 12b showed good stability profiles in both artificial gastrointestinal fluids and blood plasma from SD rats. An oral glucose tolerance test (OGTT) was performed and the results further confirmed that 12b was a potent hypoglycemic agent.
Synthesis, antiproliferative and pro-apoptotic activity of 2-phenylindoles
Kelly, Patrick M.,Bright, Sandra A.,Fayne, Darren,Pollock, Jade K.,Zisterer, Daniela M.,Williams, D. Clive,Meegan, Mary J.
, p. 4075 - 4099 (2016/08/23)
Breast cancer is the second most common cancer worldwide after lung cancer with the vast majority of early stage breast cancers being hormone-dependent. One of the major therapeutic advances in the clinical treatment of breast cancer has been the introduction of selective estrogen receptor modulators (SERMs). We describe the design and synthesis of novel SERM type ligands based on the 2-arylindole scaffold to selectively target the estrogen receptor in hormone dependent breast cancers. Some of these novel compounds are designed as bisindole type structures, while others are conjugated to a cytotoxic agent based on combretastatin A4 (CA4) which is a potent inhibitor of tubulin polymerisation. The indole compounds synthesised within this project such as 31 and 86 demonstrate estrogen receptor (ER) binding and strong antiproliferative activity in the ER positive MCF-7 breast cancer cell line with IC50values of 2.71?μM and 1.86?μM respectively. These active compounds induce apoptotic activity in MCF-7 cells with minimal effects on normal peripheral blood cells. Their strong anti-cancer effect is likely mediated by the presence of two ER binding ligands for 31 and an ER binding ligand combined with a cytotoxic agent for 86.
Functional group transformations in derivatives of 6-oxoverdazyl
Jasinski, Marcin,Gerding, Jason S.,Jankowiak, Aleksandra,Geibicki, Krzysztof,Romanski, Jaroslaw,Jastrzeibska, Katarzyna,Sivaramamoorthy, Ajan,Mason, Kristein,Evans, Donavan H.,Celeda, Malgorzata,Kaszynski, Piotr
, p. 7445 - 7454 (2013/09/02)
Transformations of functional groups, such as OCH2Ph, OCOPh, NO2 and I, in 1,3,5-triphenyl-6-oxoverdazyls 1a-1e were investigated in order to expand the range of synthetic tools for incorporation of the verdazyl system into more complex molecular architectures and to increase spin delocalization. Thus, Pd-catalyzed debenzylation of the OCH2Ph group or basic hydrolysis of the OCOPh group gave the phenol functionality, which was acylated, but could not be alkylated. Orthogonal deprotection of diphenol functionality was also demonstrated in radical 1c. Pt-catalyzed reduction of the NO2 group led to the aniline derivative, which was acylated. Attempted C-C coupling reactions to iodophenyl derivatives 1e and 5e were unsuccessful. Selected verdazyl radicals were characterized by EPR and electronic absorption spectroscopy, and results were analyzed with the aid of DFT computational methods.
