23772-61-4Relevant academic research and scientific papers
Stereoselective synthesis of 3-alkylideneoxindoles by rhodium-catalyzed cyclization reaction of 2-alkynylaryl isocyanates with aryland alkenylboronic acids
Miura, Tomoya,Takahashi, Yusuke,Murakami, Masahiro
, p. 5075 - 5077 (2007)
The rhodium-catalyzed cyclization reaction of 2-alkynylaryl isocyanates with aryl- and alkenylboronic acids furnishes 3-alkylideneoxindoles in a stereoselective manner. The reaction allows arrangement of various substituents on the exocyclic double bond a
Influence of the terminal amide fragment geometry in some 3-arylideneindolin-2(1H)-ones on their 5-HT1A/5-HT2A receptor activity1
Mokrosz, Maria J.,Charakchieva-Minol, Sijka,Koziol, Aneta,Klodzinska, Aleksandra,Chojnacka-Wojcik, Ewa
, p. 1229 - 1231 (2001)
Several 1,4-disubstituted arylpiperazine derivatives of 3-arylideneindolin-2(1H)-one (Z and E isomers) were tested for their 5-HT1A and 5-HT2A receptor activity in vitro and in vivo. It was shown that introduction of 3-arylidene subs
Alkyne hydroarylation with Au N-heterocyclic carbene catalysts
Tubaro, Cristina,Baron, Marco,Biffis, Andrea,Basato, Marino
, p. 246 - 253 (2013)
Mono- and dinuclear gold complexes with N-heterocyclic carbene (NHC) ligands have been employed as catalysts in the intermolecular hydroarylation of alkynes with simple unfunctionalised arenes. Both mono- and dinuclear gold(III) complexes were able to catalyze the reaction; however, the best results were obtained with the mononuclear gold(I) complex IPrAuCl. This complex, activated with one equivalent of silver tetrafluoroborate, exhibited under acidic conditions at room temperature much higher catalytic activity and selectivity compared to more commonly employed palladium(II) catalysts. Moreover, the complex was active, albeit to a minor extent, even under neutral conditions, and exhibited lower activity but higher selectivity compared to the previously published complex AuCl(PPh3). Preliminary results on intramolecular hydroarylations using this catalytic system indicate, however, that alkyne hydration by traces of water may become a serious competing reaction.
Metal-Organic Framework Derived Metal Oxide Clusters in Porous Aluminosilicates: A Catalyst Design for the Synthesis of Bioactive aza-Heterocycles
Martín, Nuria,Dusselier, Michiel,De Vos, Dirk E.,Cirujano, Francisco G.
, p. 44 - 48 (2019)
Simple solid-state mixing and calcination of catalytic amounts of metal-organic frameworks (MOFs) in the presence of aluminosilicates allow for the generation of active and robust supported metal oxide nanoparticles that catalyze C-C and C-N bond formatio
Electrochemical Umpolung C-H Functionalization of Oxindoles
Pastor, Miryam,Vayer, Marie,Weinstabl, Harald,Maulide, Nuno
supporting information, p. 606 - 612 (2022/01/12)
Herein, we present a general electrochemical method to access unsymmetrical 3,3-disubstituted oxindoles by direct C-H functionalization where the oxindole fragment behaves as an electrophile. This Umpolung approach does not rely on stoichiometric oxidants and proceeds under mild, environmentally benign conditions. Importantly, it enables the functionalization of these scaffolds through C-O, and by extension to C-C or even C-N bond formation.
Pharmacophore based drug design and synthesis of oxindole bearing hybrid as anticancer agents
Ali, Abuzer,Devaraji, Vinod,Dewangan, Rikeshwer Prasad,Haider, Kashif,Pandey, Vivek,Pathak, Ankita,Raj Pokharel, Yuba,Saad, Suma,Shahar Yar, M.,Siddiqui, Nadeem
, (2021/09/22)
Dual TK inhibitors have shown significant clinical effects against many tumors, but with unmanageable side effects. Design approach and selectivity of these inhibitors plays substantial role in their potency and side-effects. Understanding the homology of binding sites in targeted receptors, and involvement of signaling proteins after the inhibition might help in producing less toxic but effective inhibitors. Herein, we designed benzylideneindolon-2-one derivatives based on homology modeling in binding sites of VEGFR-2 and EGFR receptors as dual- inhibitor potent anticancer compounds with high selectivity. The benzylideneindolon-2-one derivatives were found to possess conformational switch in form of oxindole, substituted at 2-benzimidazole. Within synthesized compounds, 5b was found most active in in-vitro enzyme inhibition assay against VEGFR-2 and EGFR with highest IC50 value of 6.81 ± 2.55 and 13.04 ± 4.07 nM, respectively. Interestingly, cytotoxicity studies revealed selective toxicity of compound 5b against proliferation of A-431 cell lines (over expressed VEGFR-2 and EGFR) with GI50 value of 0.9 ± 0.66 μM. However, the compounds showed mild to moderate activity in all other cancer cell line in the range of 0.2–100 μM. Further mode of action studies by flow cytometry and western blot on A-431 indicated that they work via apoptosis at S- phase following Bcl/Bax pathway, and cell migration via MMP9. 5b not only suppressed tumor growth but also improved vandetanib associated with weight loss toxicity. Moreover, 5b was found safer than sunitinib and erlotinib with LD50 of 500 mg/kg body weight. These results propose 5b as potential anti-tumor drug with safer profile of conventional inhibitors of VEGFR-2 and EGFR for solid tumors.
Oxidative electro-organic synthesis of dimeric hexahydropyrrolo-[2,3-: B] indole alkaloids involving PCET: Total synthesis of (±)-folicanthine
Bisai, Alakesh,Khatua, Arindam,Paul, Amit,Sharma, Sulekha,Shaw, Kundan
supporting information, p. 9390 - 9395 (2021/11/17)
An efficient electrochemical oxidation strategy for the total synthesis of a dimeric hexahydropyrrolo[2,3-b]indole alkaloid, (±)-folicanthine (1b), has been envisioned. Control experiments suggest that a PCET pathway involving stepwise electron transfer f
E - Z isomerization of 3-benzylidene-indolin-2-ones using a microfluidic photo-reactor
Ganesh, Veeramalla,Raji Reddy, Chada,Singh, Ajay K.
, p. 28630 - 28634 (2020/08/25)
Here, we report controlled E-Z isomeric motion of the functionalized 3-benzylidene-indolin-2-ones under various solvents, temperature, light sources, and most importantly effective enhancement of light irradiance in microfluidic photoreactor conditions. S
Selective C3-alkenylation of oxindole with aldehydes using heterogeneous CeO2 catalyst
Rashed, Md. Nurnobi,Touchy, Abeda Sultana,Chaudhari, Chandan,Jeon, Jaewan,Siddiki, S.M.A. Hakim,Toyao, Takashi,Shimizu, Ken-ichi
, p. 970 - 976 (2020/01/31)
We report herein that a commercially available CeO2 is an active and reusable catalyst for the C3-selective alkenylation of oxindole with aldehydes under solvent-free conditions. This catalytic method is generally applicable to different aromatic and aliphatic aldehydes, giving 3-alkyledene-oxindoles in high yields (87%–99%) and high stereoselectivities (79%–93% to E-isomers). This is the first example of the catalytic synthesis of 3-alkenyl-oxindoles from oxindole and various aliphatic aldehydes. The Lewis acid-base interaction between Lewis acid sites on CeO2 and benzaldehyde was studied by in situ IR. The structure-activity relationship study using CeO2 catalysts with different sizes suggests that defect-free CeO2 surface is the active site for this reaction.
Activity-directed expansion of a series of antibacterial agents
Chow, Shiao,Clarke, Justin E.,Leggott, Abbie,Nelson, Adam,O'Neill, Alex J.,Warriner, Stuart L.
, p. 8047 - 8050 (2020/08/03)
The feasibility of using activity-directed synthesis to drive antibacterial discovery was investigated. An array of 220 Pd-catalysed microscale reactions was executed, and the crude product mixtures were evaluated for activity against Staphylococcus aureus. Scale-up of the hit reactions, purification and evaluation, enabled expansion of a class of antibacterial quinazolinones. The novel antibacterials had MICs from 0.016 μg mL-1 (i.e. 38 nM) to 2-4 μg mL-1 against S. aureus ATCC29213. This journal is
