40114-83-8Relevant articles and documents
An efficient multicomponent and stereoselective synthesis of new spiro[indeno[1,2-b]quinoxaline-11,2′-pyrrolidine] derivatives
Moemeni, Mehdi,Arvinnezhad, Hamid,Samadi, Saadi,Tajbakhsh, Mahmood,Jadidi, Khosrow,Khavasi, Hamid Reza
, p. 190 - 194 (2012)
New spiro[indeno[1,2-b]quinoxaline-11,2′-pyrrolidine] derivatives were prepared in high yield stereoselectively from an efficient multicomponent 1,3-dipolar cycloaddition reaction between ninhydrin, phenylenediamine, sarcosine, and chalcones. The regiochemistry and stereochemistry of resultant cycloadducts have been determined by several 2D NMR spectroscopic techniques and X-ray single crystal diffraction..
Design and synthesis of novel spirooxindole–indenoquinoxaline derivatives as novel tryptophanyl-tRNA synthetase inhibitors
Ren, Wen,Zhao, Qian,Yu, Meng,Guo, Li,Chang, Hongmei,Jiang, Xian,Luo, Youfu,Huang, Wei,He, Gu
, p. 1043 - 1063 (2020)
Abstract: In the current study, we used an integrated approach combining bioinformatics, rational drug design, one-pot synthesis, and biological experiments in vitro for the potential discovery of novel tryptophanyl-tRNA synthetase (TrpRS) inhibitors. Atom economic and diastereoselective syntheses were used to generate several Spirooxindole–indenoquinoxaline derivatives in situ from isatin and amino acids viz. proline, phenylglycine, and sarcosine through targeting the 1,3-dipolar cycloaddition of azomethine ylides. These compounds were assayed by biochemical TrpRS inhibition, using in vitro experiments to test against various gram-positive and gram-negative strains, and using diffuse large B cell lymphoma (DLBCL) cell lines. Compound 6e was found to be the most active in vitro with IC50 values of 225 and 74?nM for tests against hmTrpRS and ecTrpRS, respectively. We also found a MIC90 value of 4?μg/mL for tests against S. aureus and IC50 values which ranged from 2.9 to 4.8?μM for tests against proliferation of DLBCL cell lines. Moreover, compound 6e was remarkably good at inducing bacterial autolysis in MRSA strains. Our results suggested that such an integrated approach could be an attractive and viable strategy for the discovery of novel TrpRS inhibitors as potential lead compounds for antibiotics and as novel anticancer agents. Graphic abstract: Discovery of novel spirooxindole-indenoquinoxaline TrpRS inhibitors as potential lead compounds with antibacterial and antitumor activities.[Figure not available: see fulltext.].
Green synthesis of novel spiro-indenoquinoxaline derivatives and their cholinesterases inhibition activity
Maryamabadi, Ammar,Hasaninejad, Alireza,Nowrouzi, Najmeh,Mohebbi, Gholamhossein
, p. 2057 - 2064 (2017)
A convenient synthesis of substituted spiroindenoquinoxalines at mild and green conditions was developed. Multicomponent reaction of substituted phenylene diamines, ninhydrin, malononitrile and N,N′-substituted-2-nitroethene-1,1-diamines produced the targ
One-pot three-component synthesis of functionalized spirolactones by means of reaction between aromatic ketones, dimethyl acetylenedicarboxylate, and N-heterocycles
Maghsoodlou, Malek Taher,Habibi-Khorassani, Sayyed Mostafa,Moradi, Abbas,Hazeri, Nourallah,Davodi, Amir,Sajadikhah, Seyed Sajad
, p. 8492 - 8495 (2011)
A simple and convenient one-pot multi-component reaction has been described for the synthesis of functionalized spirolactones. This strategy demonstrated three-component reaction between aromatic ketones (11H-indeno[1,2-b]quinoxalin- 11-one) and dimethyl acetylenedicarboxylate (DMAD) in the presence of N-heterocycles, such as pyridine, quinoline, and isoquinoline in CH 2Cl2 at ambient temperature without use of any catalyst or activator.
