25410-78-0Relevant academic research and scientific papers
Regioselective Cross-Coupling of Isatogens with Boronic Acids to Construct 2,2-Disubstituted Indolin-3-one Derivatives
Song, Qiuling,Xu, Hetao,Yang, Kai,Ye, Mingxing
supporting information, p. 7776 - 7780 (2021/10/25)
Herein we present a transition-metal-free cross-coupling reaction of isatogens with boronic acids through a 1,4-metalate shift of a boron "ate"complex. This coupling reaction provides a feasible method to deliver valuable 2,2-disubstituted indolin-3-one d
C-H alkenylation/cyclization and sulfamidation of 2-phenylisatogens using: N -oxide as a directing group
Guo, Lingmei,Tang, Baolan,Nie, Ruifang,Liu, Yanzhao,Lv, Shan,Wang, Huijing,Guo, Li,Hai, Li,Wu, Yong
supporting information, p. 10623 - 10626 (2019/09/06)
The first example of transition-metal-catalyzed C-H activations of 2-phenylisatogens with alkynes and sulfonyl azides has been developed using N-oxide as the directing group. Ru(ii)-Catalyzed C-H alkenylation/cyclization and Ir(iii)-catalyzed direct C-H sulfamidation proceeded with good yields and excellent functional group tolerance. Importantly, these two transformations provided straightforward routes for the synthesis of indol-3-one derivatives and sulfamidated 2-phenylisatogens respectively, which might be of considerable bioactivities.
One-Pot Au[III]-/Lewis Acid Catalyzed Cycloisomerization of Nitroalkynes and [3 + 3]Cycloaddition with Donor-Acceptor Cyclopropanes
Dhote, Pawan S.,Ramana, Chepuri V.
supporting information, p. 6221 - 6224 (2019/08/26)
A one-pot protocol for the synthesis of a tricyclic pseudoindoxyl scaffold from 2-nitroalkynylbenzenes, comprising of an Au(III)-catalyzed nitroalkyne cycloisomerization leading to isatogen and its [3 + 3]-cycloaddition with donor-acceptor cyclopropanes m
2-Aryl-3H-indol-3-ones: Synthesis, electrochemical behaviour and antiplasmodial activities
Najahi, Ennaji,Valentin, Alexis,Fabre, Paul-Louis,Reybier, Karine,Nepveu, Fran?oise
, p. 269 - 274 (2014/04/17)
The synthesis of indolone derivatives and their antiplasmodial activity in vitro against Plasmodium falciparum at the blood stage are described. The 2-aryl-3H-indol-3-ones were synthesized via deoxygenation of indolone-N-oxides. Electrochemical behaviour, antiplasmodial activity and cytotoxicity on human tumor cell lines were compared to those of indolone-N-oxides. The antiplasmodial IC50 (concentrations at 50% inhibition) of these compounds ranged between 49 and 1327 nM. Among them, the 2-(4-dimethylaminophenyl)-5-methoxy- indol-3-one, 7, had the best antiplasmodial activity in vitro (IC50 = 49 nM; FcB1 strain) and selectivity index (SI (CC50 MCF7/IC 50 FcB1) = 423.4). Thus, the hits identified in this deoxygenated series correspond to their structural homologs in the N-oxide series with comparable electrochemical behaviour at the nitrogen-carbon double bond.
A combined experimental and density functional theory study on the Pd-mediated cycloisomerization of o-alkynylnitrobenzenes - Synthesis of isatogens and their evaluation as modulators of ROS-mediated cell death
Ramana, Chepuri V.,Patel, Pitambar,Vanka, Kumar,Miao, Benchun,Degterev, Alexei
, p. 5955 - 5966 (2011/03/17)
Highly selective cycloisomerization of o-alkynylnitrobenzenes, leading to isatogens, has been achieved by employment of a PdII complex. This reaction is very general and functional-group-tolerant. The possible mechanism of this reaction was inv
Synthesis and antiplasmodial activity of new indolone N-Oxide derivatives
Nepveu, Fran?oise,Kim, Sothea,Boyer, Jeremie,Chatriant, Olivier,Ibrahim, Hany,Reybier, Karine,Monje, Marie-Carmen,Chevalley, Severine,Perio, Pierre,Lajoie, Barbora H.,Bouajila, Jalloul,Deharo, Eric,Sauvain, Michel,Tahar, Rachida,Basco, Leonardo,Pantaleo, Antonella,Turini, Francesco,Arese, Paolo,Valentin, Alexis,Thompson, Eloise,Vivas, Livia,Petit, Serge,Nallet, Jean-Pierre
experimental part, p. 699 - 714 (2010/07/09)
A series of 66 new indolone-N-oxide derivatives was synthesized with three different methods. Compounds were evaluated for in vitro activity against CQ-sensitive (3D7), CQ-resistant (FcB1), and CQ and pyrimethamine cross-resistant (K1) strains of Plasmodium falciparum (P.f.), aswell as for cytotoxic concentration (CC50) on MCF7 and KB human tumor cell lines. Compound 26 (5-methoxy-indolone-N-oxide analogue) had the most potent antiplasmodial activity in vitro (50 MCF7/IC50 FcB1: 14623; CC50 KB/IC50 3D7: 198823). In in vivo experiments, compound 1 (dioxymethylene derivatives of the indolone-N-oxide) showed the best antiplasmodial activity against Plasmodium berghei, 62% inhibition of the parasitaemia at 30 mg/kg/day. 2009 American Chemical Society.
AuBr3-catalyzed cyclization of o-(alkynyl)nitrobenzenes. Efficient synthesis of isatogens and anthranils
Asao, Naoki,Sato, Kenichiro,Yamamoto, Yoshinori
, p. 5675 - 5677 (2007/10/03)
The cyclization of o-(arylalkynyl)nitrobenzenes was catalyzed by AuBr3 to produce the corresponding isatogens in good to high yields together with small amounts of anthranils. On the other hand, anthranils were obtained selectively when the AuB
Oxygenation of 2,3-dihydroindoles
Sl?tt, Johnny,Bergman, Jan
, p. 9187 - 9191 (2007/10/03)
Isatogens (3-oxo-3H-indole 1-oxides) possess interesting biological properties and development of a general method to construct these derivatives has now been developed. Indolines (2,3-dihydroindoles) and isatogens have been prepared in an efficient route starting from indoles substituted in position 2. Reduction of the 2-substituted indoles was performed with tin and hydrochloric acid to give racemic indolines, which were converted to isatogens by 3-chloroperoxybenzoic acid (m-CPBA).
Antitubercular Agents : Part III - Synthesis of Substituted 2-Arylisatogens
Sahasrabudhe, A. B.,Kamath, H. V.,Bapat, B. V.,Kulkarni, Sheshgiri N.
, p. 230 - 232 (2007/10/02)
A number of 2-arylisatogens (VII) have been prepared starting from o-nitroacetophenones (I).Condensation of I with different aromatic aldehydes (II) gives the corresponding o-nitrochalkones (III) which on epoxidation followed by treatment with BF3-etherat
