887750-89-2Relevant academic research and scientific papers
Synthesis of 1,4-dihydropyrazolo[4,3-b]indoles via intramolecular C(sp2)-N bond formation involving nitrene insertion, DFT study and their anticancer assessment
Kaur, Manpreet,Mehta, Vikrant,Abdullah Wani, Aabid,Arora, Sahil,Bharatam, Prasad V.,Sharon, Ashoke,Singh, Sandeep,Kumar, Raj
, (2021/07/19)
We herein report a new synthetic route for a series of unreported 1,4-dihydropyrazolo[4,3-b]indoles (6–8) via deoxygenation of o-nitrophenyl-substituted N-aryl pyrazoles and subsequent intramolecular (sp2)-N bond formation under microwave irradiation expedite modified Cadogan condition. This method allows access to NH-free as well as N-substituted fused indoles. DFT study and controlled experiments highlighted the role of nitrene insertion as one of the plausible reaction mechanisms. Furthermore, the target compounds exhibited cytotoxicity at low micromolar concentration against lung (A549), colon (HCT-116), and breast (MDA-MB-231, and MCF-7) cancer cell lines, induced the ROS generation and altered the mitochondrial membrane potential of highly aggressive MDA-MB-231 cells. Further investigations revealed that these compounds were selective Topo I (6h) or Topo II (7a, 7b) inhibitors.
Application of modified Pictet-Spengler reaction for the synthesis of thiazolo- and pyrazolo-quinolines
Duggineni, Srinivas,Sawant, Devesh,Saha, Biswajit,Kundu, Bijoy
, p. 3228 - 3241 (2007/10/03)
Two new thiazole and pyrazole-based arylamine substrate have been used for the Pictet-Spengler reaction. This is in contrast to the traditionally used indole/imidazole-based aliphatic amine substrates that has remained in use for the last ~100 years. The
