4290-78-2Relevant articles and documents
Synthesis of 6-aminopropyl-6H-indolo[2,3-b]quinoxaline derivatives
Shibinskaya, Marina O.,Kutuzova, Nina A.,Mazepa, Alexandr V.,Lyakhov, Sergey A.,Andronati, Sergey A.,Zubritsky, Mykhayl Ju.,Galat, Valerij F.,Lipkowski, Janusz,Kravtsov, Victor Ch.
, p. 678 - 682 (2012)
A series of 6-(3-aminopropyl)-6H-indolo[2,3-b]quinoxalines were synthesized with high yields by the reaction of 6-(3-chloropropyl)-6H-indolo[2,3-b] quinoxaline and corresponding amines in presence of tetrabutylammonium iodide in boiling toluene or dimethylformamide at room temperature. It was found that boiling of 6-(3-chloropropyl)-6H-indolo[2,3-b]quinoxaline in acetone with sodium iodide or in acetic acid lead to intramolecular cyclization product.
Synthesis, cytotoxicity, antiviral activity and interferon inducing ability of 6-(2-aminoethyl)-6H-indolo[2,3-b]quinoxalines
Shibinskaya, Marina O.,Lyakhov, Sergey A.,Mazepa, Alexander V.,Andronati, Sergey A.,Turov, Alexander V.,Zholobak, Nadezhda M.,Spivak, Nikolay Ya.
, p. 1237 - 1243 (2010)
New 6-(2-aminoethyl)-6H-indolo[2,3-b]quinoxalines were synthesized with high yields using bromoethylisatin and 6-(2-bromoethyl)-6H-indolo[2,3-b]quinoxaline as intermediates. These compounds were screened for the cytotoxicity, antiviral activity and interferon inducing ability. It was shown, that tested 6-(2-aminoethyl)-6H-indolo[2,3-b]quinoxalines are low toxic potent interferon inducers and antivirals. Morpholine and 4-methyl-piperidine derivatives appeared as the most active antivirals and the least cytotoxic in the investigated series.
Design, synthesis and in vitro anti-mycobacterial activities of homonuclear and heteronuclear bis-isatin derivatives
Xu, Yan,Guan, Jianguo,Xu, Zhi,Zhao, Shijia
, p. 383 - 386 (2018)
A series of novel homonuclear and heteronuclear bis-isatin derivatives tethered through ethylene were designed, synthesized and evaluated for their in vitro anti-mycobacterial activities against MTB H37Rv and MDR-TB. All hybrids exhibited potential anti-mycobacterial activities against MTB H37Rv and MDR-TB with MIC ranging from 16 to 256 μg/mL. In particular, the heteronuclear bis-isatin 4i (MIC: 25 and 16 μg/mL) was most active against MTB H37Rv and MDR-TB strains, and could act as a lead for further optimization.
Rapid assembly of heterocycle grafted macrocycles via tandem one-pot double 1,3-dipolar cycloaddition reaction
Prasanna,Purushothaman,Raghunathan
, p. 9375 - 9383 (2014)
Synthesis of triazole linked macrocycles grafted with glycospiroheterocycle was accomplished by stereo- and regioselective tandem double 1,3-dipolar cycloaddition (1,3-DC) reaction. By this method we could construct complex chiral macrocycles in good yields from the easily available starting materials and we could achieve the synthesis of two heterocyclic rings involving simultaneous formation of five bonds in one-pot reaction. The structures of the macrocycles were confirmed by spectroscopic methods and single crystal XRD. This journal is
Isatin-derived azoles as new potential antimicrobial agents: Design, synthesis and biological evaluation
Tangadanchu, Vijai Kumar Reddy,Sui, Yan-Fei,Zhou, Cheng-He
, (2021)
Novel antibiotics are forced to be developed on account of multidrug-resistant bacteria with serious threats to human health. This work developed isatin-derived azoles as new potential antimicrobial agents. Bioactive assay revealed that isatin hybridized 1,2,4-triazole 7a exhibited excellent inhibitory activity against E. coli ATCC 25,922 with an MIC value of 1 μg/mL, which was 8-fold more potent than reference drug norfloxacin. The active molecule 7a possessed the ability to kill some bacteria and fungi as well as displayed low propensity to induce resistance towards E. coli ATCC25922. Preliminary mechanism investigation indicated that hybrid 7a might block deoxyribonucleic acid (DNA) replication by intercalating with DNA and possibly interacting with DNA polymerase III, thus exerting its antimicrobial potency.
Isatin-linked 4,4-dimethyl-5-methylene-4,5-dihydrothiazole-2-thiols for inhibition of acetylcholinesterase
Davis, Sydney M.,Eckroat, Todd J.
, p. 2289 - 2300 (2021/10/25)
A series of novel isatin-linked 4,4-dimethyl-5-methylene-4,5-dihydrothiazole-2-thiols (IT2Ts) 1a–1g were designed as acetylcholinesterase (AChE) inhibitors capable of interacting with both the catalytic active site (CAS) and peripheral anionic site (PAS) of the enzyme simultaneously. The target IT2Ts were prepared through a short synthesis in moderate yield. The most potent inhibitors of this series 1b and 1c (IC50 = 18.2 and 27.5 μM, respectively) outperformed rivastigmine and were comparable to galantamine, both clinically used AChE inhibitors. Furthermore, 1b displayed non-competitive inhibition patterns in kinetic studies, whereas molecular modeling predicted a simultaneous interaction with both the CAS and PAS. In silico methods predicted several promising drug-like characteristics of 1b. Taken together, these results indicate 1b warrants further investigation as a multitarget-directed ligand for AChE inhibition. [Figure not available: see fulltext.]
Azide-alkyne cycloaddition en route to ferrocenyl-methoxy-methyl-isatin-conjugates: Synthesis, anti-breast cancer activities and molecular docking studies
Rani, Anu,Singh, Gurjot Inder,Kaur, Ramandeep,Palma, Gabriella,Perumal, Shanen,Kaur, Mandeep,Ebenezer, Oluwakemi,Awolade, Paul,Singh, Parvesh,Kumar, Vipan
, (2019/12/23)
A series of 1H-1,2,3-triazole linked Ferrocenyl-methoxy-methyl-Isatin conjugates was synthesized and assayed for their anti-proliferative activities against estrogen-responsive as well as estrogen non-responsive cell lines. The non-cytotoxic conjugate 7l, with an optimum combination of octyl chain as spacer and methyl-substituent at the C-5 position of isatin, proved to be a promising hit with an IC50 value of 14.62 μM against MCF-7 and 79.63 μM against MDA-MB-231 cells, respectively. The observed anti-proliferative activities of active conjugates were further corroborated via docking studies carried out on estrogen receptor subtypes α and β.
