243-59-4Relevant academic research and scientific papers
The Condensation of Isatin with o-Phenylenediamine
Niume, Kazuma,Kurosawa, Shigeru,Toda, Fujio,Hasegawa, Masaki,Iwakura, Yoshio
, p. 2293 - 2294 (1982)
The condensation of isatin with o-phenylenediamine has been studied in various kind of solvents.The reaction gave pure indoloquinoxaline (1) in acidic solvents, while it gave a mixture containing at least two out three compounds, 1, an anil and a spiro compound, in neutral or basic organic solvents.The anil and spiro compounds were converted to 1 in the presence of acid or by heating them above their melting points.The mechanism of the formation of these compounds and the conversion could be explained by the presence of the intermediate of the adduct formed between the amino groups of o-phenylenediamine and the β-carbonyl of isatin.
Self-assembled quinoxaline derivative: Insight into disaggregation induced selective detection of nitro-aromatics in aqueous medium and live cell imaging
Basak, Megha,Bhattacharjee, Basu,Das, Gopal,Ramesh, Aiyagari
, (2021)
Advancement in fluorescent chemosensor for discriminative and precise detection of picric acid (PA) in aqueous medium is highly desirable owing to its alarming impact on the natural environment via soil and groundwater pollution. To this end, we have successfully fabricated a quinoxaline-based receptor (Probe 1) to detect PA in 100% aqueous medium. Probe 1 self-assembled to form leaf-like structures in pure water as micro aggregates (～940 nm) and transformed entirely into smaller spherical shape (～354 nm) upon addition of PA. DFT analysis and lifetime experiment validated that both PET and FRET from the electron-rich Probe 1 to electron-deficient PA are concurrently responsible for effective fluorescence quenching. The self-assembled probe exhibited excellent selectivity towards PA (Ksv of 22.6 × 106 M?1) with a ～56 ppb detection limit. Importantly, PA detection on solution-coated paper strips was achieved at the picogram level. Furthermore, to evaluate the practical usefulness, the probe has been used to detect PA in actual water and soil samples. Interestingly, Probe 1 was non-toxic to cultured HeLa cells and rendered detection of intracellular picric acid through live cell imaging.
β-cyclodextrin mediated synthesis of indole derivatives: reactions of isatins with 2-amino(or 2-thiole)anilines by supramolecular catalysis in water
Shivhare, Km Neha,Siddiqui
, p. 52 - 61 (2019)
An elegant, mild, and straightforward strategy for the synthesis of indole derivatives have been accomplished by the biomimetic catalysis for the first time in water under neutral conditions. This supramolecular catalyst oriented methodology provides a sustainable and green protocol for the synthesis of 6H-indolo[2,3-b]quinoxalines and 3H-spiro[benzo[d]thiazole-2,3’-indolin]-2’-one by the reaction of isatin derivatives with 1,2-difunctionalized benzene using β-cyclodextrin (β-CD) as a recoverable and reusable supramolecular catalyst.
Cu doped CdS nanoparticles: A versatile and recoverable catalyst for chemoselective synthesis of indolo[2,3-b]quinoxaline derivatives under microwave irradiation
Dandia, Anshu,Parewa, Vijay,Maheshwari, Shuchi,Rathore, Kuldeep S.
, p. 244 - 252 (2014)
CdS and Cu doped CdS NPs has been obtained successfully using safe agents through a simple aqueous chemical method and characterized by XRD, TEM, SEM, EDAX, UV/VIS and ICP-AES. These investigations revealed that the particle size of the synthesized materi
Preparation and structure of tetrakis(indolo[2,3-b]quinoxalinato)dinickel(II)
Takekuma, Shin-Ichi,Katayama, Satoshi,Takekuma, Hideko
, p. 614 - 615 (2000)
Treatment of 6H-indolo[2,3-b]quinoxaline (1) with NaBH4 in ethanol at 82 °C for 10 min under argon gives the reactive anion species 2 (generated by deprotonation of N-6 position of 1), which upon reaction with Ni(OAc)2·4H2O in ethanol at 82 °C for 6 h under argon forms the title dinuclear nickel(II) complex 3. The molecular structure of the novel complex 3, indicating the Ni-Ni distance of 2.618(1) A, is reported.
3-Oxo 3H-Indole from Dioxygen Copper-Catalyzed Oxidation of Indole: One-Flask Synthesis of 2-Dialkylamino 3-Oxo 3H-Indoles.
Capdevielle, Patrice,Maumy, Michel
, p. 2953 - 2956 (1993)
Cu(I)Cl-catalyzed oxidation of indole 1 by dioxygen in anhydrous acetonitrile leads to highly reactive 3-oxo 3H-indole 2, which provides directly 2-dialkylamino 3-oxo 3H-indoles 3 in presence of dialkylamines.Amidines 3, previously difficult to prepare, are potentially useful synthons in the field of heterocyclic chemistry. Key Words: Copper-catalyzed oxidation; dioxygen; indole; 2-dialkylamino 3-oxo 3H-indoles.
Indoloquinoxaline derivatives as promising multi-functional anti-Alzheimer agents
Kanhed, Ashish M.,Patel, Dushyant V.,Patel, Nirav R.,Sinha, Anshuman,Thakor, Priyanka S.,Patel, Kishan B.,Prajapati, Navnit K.,Patel, Kirti V.,Yadav, Mange Ram
, p. 2498 - 2515 (2020/11/02)
To confront a disease like Alzheimer’s disease having complex pathogenesis, development of multitarget-directed ligands has emerged as a promising drug discovery approach. In our endeavor towards the development of multitarget-directed ligands for Alzheimer’s disease, a series of indoloquinoxaline derivatives were designed and synthesized. In vitro cholinesterase inhibition studies revealed that all the synthesized compounds exhibited moderate to good cholinesterase inhibitory activity. 6-(6-(Piperidin-1-yl)hexyl)-6H-indolo[2,3-b]quinoxaline 9f was identified as the most potent and selective BuChE inhibitor (IC50 = 0.96 μM, selectivity index = 0.17) that possessed 2 fold higher BuChE inhibitory activity compared to the commercially approved reference drug donepezil (IC50 = 1.87 μM). Moreover, compound 9f is also endowed with self-induced Aβ1-42 aggregation inhibitory activity (51.24% inhibition at 50 μM concentration). Some of the compounds of the series also displayed moderate anti-oxidant activity. To perceive a putative binding mode of the compound 9f, molecular docking studies were carried out, and the results pointed out significant interactions of compound 9f with the enzymes in the binding sites of cholinesterases as well as Aβ1-42. Additionally, compound 9f exhibited favorable in silico ADMET properties. Put together these findings project compound 9f as a potential multitarget-directed ligand in the direction of developing novel anti-AD drugs. Communicated by Ramaswamy H. Sarma.
Propargylamines in Pd/Cu-catalyzed tandem coupling-cyclization-N-deprotection in a single pot: Construction of N-unsubstituted vs N-sulfonyl indole ring
Sujeevan Reddy, Gangireddy,Sandeep Kumar, Jetta,Thirupataiah,Amirul Hossain, Kazi,Babu Nallapati, Suresh,Bhat Giliyaru, Varadaraj,Chandrashekhar Hariharapura, Raghu,Gautham Shenoy,Pal, Manojit
supporting information, (2021/06/18)
The Pd/Cu-catalyzed tandem coupling–cyclization-N-deprotection in a single pot (Method a) vs sequential coupling–cyclization under similar conditions (Method b) has been studied using propargylamine as a terminal alkyne under environmentally friendly cond
Br?nsted acid hydrotrope combined catalysis in water: a green approach for the synthesis of indoloquinoxalines and bis-tetronic acids
Kumbhar, Arjun,Kanase, Dhanaji,Mohite, Suhas,Salunkhe, Rajshri,Lohar, Trushant
, p. 2263 - 2278 (2021/03/31)
The present work describes the applications of Br?nsted acid hydrotrope combined catalyst (BAHC) as a mild, efficient and reusable catalyst for synthesis of indoloquinoxalines and bis-tetronic acids in water. Using BAHC, we synthesized many indoloquinoxal
Activities of quinoxaline, nitroquinoxaline, and [1,2,4]triazolo [4,3-a]quinoxaline analogs of mmv007204 against schistosoma mansoni
Debbert, Stefan L.,Hintz, Mikaela J.,Bell, Christian J.,Earl, Kenya R.,Forsythe, Grant E.,H?berli, Cécile,Keiser, Jennifer
supporting information, (2021/03/04)
The reliance on one drug, praziquantel, to treat the parasitic disease schistosomiasis in millions of people a year shows the need to further develop a pipeline of new drugs to treat this disease. Recently, an antimalarial quinoxaline derivative (MMV007204) from the Medicines for Malaria Venture (MMV) Malaria Box demonstrated promise against Schistosoma mansoni. In this study, 47 synthesized compounds containing quinoxaline moieties were first assayed against the larval stage of this parasite, newly transformed schistosomula (NTS); of these, 16 killed over 70% NTS at 10mM. Further testing against NTS and adult S. mansoni yielded three compounds with 50% inhibitory concentrations (IC50s) of#0.31mM against adult S. mansoni and selectivity indices of$8.9. Administration of these compounds as a single oral dose of 400mg/kg of body weight to S. mansoni-infected mice yielded only moderate worm burden reduction (WBR) (9.3% to 46.3%). The discrepancy between these compounds' good in vitro activities and their poor in vivo activities indicates that optimization of their pharmacokinetic properties may yield compounds with greater bioavailabilities and better antischistosomiasis activities in vivo.
