- The Condensation of Isatin with o-Phenylenediamine
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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.
- Niume, Kazuma,Kurosawa, Shigeru,Toda, Fujio,Hasegawa, Masaki,Iwakura, Yoshio
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Read Online
- Self-assembled quinoxaline derivative: Insight into disaggregation induced selective detection of nitro-aromatics in aqueous medium and live cell imaging
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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.
- Basak, Megha,Bhattacharjee, Basu,Das, Gopal,Ramesh, Aiyagari
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- β-cyclodextrin mediated synthesis of indole derivatives: reactions of isatins with 2-amino(or 2-thiole)anilines by supramolecular catalysis in water
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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.
- Shivhare, Km Neha,Siddiqui
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Read Online
- Cu doped CdS nanoparticles: A versatile and recoverable catalyst for chemoselective synthesis of indolo[2,3-b]quinoxaline derivatives under microwave irradiation
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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
- Dandia, Anshu,Parewa, Vijay,Maheshwari, Shuchi,Rathore, Kuldeep S.
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- Preparation and structure of tetrakis(indolo[2,3-b]quinoxalinato)dinickel(II)
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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.
- Takekuma, Shin-Ichi,Katayama, Satoshi,Takekuma, Hideko
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Read Online
- 3-Oxo 3H-Indole from Dioxygen Copper-Catalyzed Oxidation of Indole: One-Flask Synthesis of 2-Dialkylamino 3-Oxo 3H-Indoles.
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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.
- Capdevielle, Patrice,Maumy, Michel
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Read Online
- Indoloquinoxaline derivatives as promising multi-functional anti-Alzheimer agents
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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.
- 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
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p. 2498 - 2515
(2020/11/02)
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- Propargylamines in Pd/Cu-catalyzed tandem coupling-cyclization-N-deprotection in a single pot: Construction of N-unsubstituted vs N-sulfonyl indole ring
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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
- Sujeevan Reddy, Gangireddy,Sandeep Kumar, Jetta,Thirupataiah,Amirul Hossain, Kazi,Babu Nallapati, Suresh,Bhat Giliyaru, Varadaraj,Chandrashekhar Hariharapura, Raghu,Gautham Shenoy,Pal, Manojit
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supporting information
(2021/06/18)
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- Br?nsted acid hydrotrope combined catalysis in water: a green approach for the synthesis of indoloquinoxalines and bis-tetronic acids
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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
- Kumbhar, Arjun,Kanase, Dhanaji,Mohite, Suhas,Salunkhe, Rajshri,Lohar, Trushant
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p. 2263 - 2278
(2021/03/31)
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- Activities of quinoxaline, nitroquinoxaline, and [1,2,4]triazolo [4,3-a]quinoxaline analogs of mmv007204 against schistosoma mansoni
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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.
- Debbert, Stefan L.,Hintz, Mikaela J.,Bell, Christian J.,Earl, Kenya R.,Forsythe, Grant E.,H?berli, Cécile,Keiser, Jennifer
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supporting information
(2021/03/04)
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- Synthesis of New 2-(6H-Indolo[2,3-b]quinoxalin-6-yl)-1-phenylethane-1-ones
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Abstract: A series of new 2-(6H-indolo[2,3-b]quinoxalin-6-yl)-1-phenylethan-1-ones was synthesized by the reaction of various 6H-indolo[2,3-b]quinoxalines with 4-substituted 2-bromophenylethan-1-ones in a DMSO–K2CO3 system.
- Grekhneva, E. V.,Kudryavcev, T. A.,Kudryavtseva, T. N.,Lamanov, A. Y.,Melnichenko, V. E.
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p. 2114 - 2117
(2021/11/13)
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- One-Pot Construction of Indolo[2,3- b]quinoxalines through Ruthenium-Catalyzed Ortho C-H Bond Functionalization of 2-Arylquinoxalines with Sulfonyl Azides
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The synthesis of N-substituted indolo[2,3-b]quinoxalines has been developed through a Ru(II)-catalyzed ortho C-H functionalization of 2-arylquinoxalines with sulfonyl azides and further oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in one pot. This double C-N bond formation strategy provides a new efficient route for the preparation of a series of biologically relevant 6H-indolo[2,3-b]quinoxaline derivatives in up to 94% yield, suggesting a broad substrate scope applicability. The preliminary mechanistic studies reveal that the sequential C-N bond formations proceed through the formation of a five-membered ruthenacyclic intermediate in the first step and a radical mechanism in the second step.
- Laru, Sudip,Bhattacharjee, Suvam,Ghosh, Sumit,Hajra, Alakananda
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p. 7624 - 7629
(2021/10/12)
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- Synthesis and Some Reactions of 6H-Indolo[2,3-b]quinoxalines
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Abstract: 6H-Indolo[2,3-b]quinoxalines were synthesized by condensation of isatin and 5-nitroisatin with o-phenylenediamine. The alkylation of the title compounds with dimethyl sulfate gave the corresponding quaternary salts which were converted to perchlorates and oxidized with potassium hexacyanoferrate(III) to previously unknown 5-methyl-6H-indolo[2,3-b]quinoxalin-3-one and its 9-nitro derivative. Treatment of 6H-indolo[2,3-b]quinoxalin-3-ones with dimethyl sulfate afforded 3-methoxyindoloquinoxalinium salts which were demethylated by the action of hydrobromic acid at 130–140°C. The structure of the isolated compounds was confirmed by IR and NMR spectra and elemental analyses.
- Shulga,Shulga
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p. 2104 - 2108
(2021/02/09)
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- Electron transporting and hole blocking organic material and application thereof in thin-film light-emitting diode
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The invention provides an electron transporting and hole blocking material with an A-D-A link structure as a core. The material is applied to a thin-film semiconductor light-emitting diode, for example, an organic light-emitting diode and a quantum dot thin-film light-emitting diode; and the molecule of the material takes bipolar carbazole and a derivative group thereof as electron donating centers, so a relatively high triplet state energy level can be maintained to ensure exciton blocking capability.
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Paragraph 0005
(2020/11/02)
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- NON-PEPTIDIC GLUCAGON-LIKE PEPTIDE-1 RECEPTOR AGONISTS AND METHOD OF PREPARATION THEREOF
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The present invention provides novel compounds, which specifically bind with GLP-1R and which have beneficial effects as therapeutics for diabetes and other metabolic diseases. The present invention also describes the process of synthesis of said novel co
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Page/Page column 9; 12; 34
(2020/06/19)
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- Design, Synthesis, Molecular Docking, and ADME Studies of Some New 2-Substituted 1-(6H-indolo[2,3-b]quinoxalin-6-yl)ethan-1-ones as Antitubercular Agents
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A new series of 2-substituted 1-(6H-indolo[2,3-b]quinoxalin-6-yl)ethan-1-ones (4a-l) was synthesized and evaluated for antitubercular activity against Mycobacterium tuberculosis H37 Rv strains (ATCC27294) by Microplate Alamar blue assay method using isoniazid and rifampicin as reference drugs. The structures of all synthesized compounds 4a-l were confirmed by spectroscopic (infrared, 1H NMR, 13C NMR, and mass) and elemental analysis data. The synthesized compounds were also screened for their binding analysis and pharmacokinetic properties using glide and QikProp tool of Maestro. Among all the compounds, compound 4e and 4g exhibited excellent antitubercular activity against M. tuberculosis H37 Rv strains. All tested compounds showed excellent binding affinity towards target protein.
- Kumar, Neeraj,Sharma, Chandra S.,Pandiya, Harshda,Mishra, Shashank Shekhar
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p. 473 - 481
(2021/02/02)
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- An environmentally benign attribute for the expeditious synthesis of quinoxaline and its derivatives
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A simple, efficient, and environmentally friendly ionic liquid mediated protocol for the synthesis of quinoxaline derivatives using carbonyl substrate and phenylenediamines has been described. A range of ionic liquids were synthesized, characterized via IR, 1H and 13C NMR and used as a solvent as well as catalyst for above protocol. The catalytic activities of ILs were evaluated and the relationship between the catalytic activity and acidity was discussed. It was also found that among the all ILs, [Bmim]CF3SO3 was the most effective, eco-friendly and less expensive solvent and catalyst for the above etiquette. This method is of significant value due to the eco-friendly nature of ionic liquid and non usage of separate catalyst to drive the reaction forward. The protocol proves to be efficient and environmentally benign in terms of good to excellent yields, low reaction times, simple work-up, ease of recovery, and reusability of ionic liquid for six times.
- Bhargava, Sangeeta,Soni,Rathore, Deepti
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- 6H-indolo[2,3-b]quinoxaline derivative, and preparation method and application thereof
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The invention provides a 6H-indolo[2,3-b]quinoxaline derivative, and a preparation method and application thereof. The general formula is as shown in the specification. The preparation method comprises a step of preparing the 6H-indolo[2,3-b]quinoxaline derivative by taking o-phenylenediamine, indoldione, dihaloalkane and amine compounds as raw materials. The compounds provided by the invention show good antitumor activity.
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Paragraph 0027; 0028
(2019/12/25)
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- Synthesis, cytotoxic evaluation and DNA binding study of 9-fluoro-6: H -indolo[2,3- b] quinoxaline derivatives
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A series of novel 9-fluoro-6H-indolo[2,3-b]quinoxaline derivatives as antitumor agents were synthesized and studied. The designed compounds feature positive charges both at the 11-N position of the aromatic scaffold and the side-chain alkylamino group. The corresponding in vitro antitumor activities were evaluated against MCF-7, HeLa and A549 cancer cell lines and the DNA binding properties of these compounds were characterized by UV-vis, fluorescence, and circular dichroism (CD) spectroscopy as well as thermal denaturation. The obtained results indicate that the dicationic quaternary ammonium salt derivatives of 9-fluoro-6H-indolo[2,3-b]quinoxaline may serve as intercalators with increased DNA binding affinity. Furthermore, both the incorporation of fluorine, and alkyl amino side chains and the introduction of a positive charge at the 11-N position of the aromatic scaffold was shown to be responsible for their antitumor activity and improved DNA binding ability. Taken in concert, these findings may be valuable in the understanding of the antitumor effect of these compounds and may further provide important information for the future optimization of the DNA binding properties of this drug type.
- Gu, Zhenyu,Li, Yanci,Ma, Songliang,Li, Shenghui,Zhou, Guoqiang,Ding, Shan,Zhang, Jinchao,Wang, Shuxiang,Zhou, Chuanqi
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p. 41869 - 41879
(2017/09/08)
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- Microwave-assisted Synthesis of 6-{(5-Aryl-1,3,4-oxadiazol-2-yl)methyl}-6H-indolo[2,3-b]quinoxalines
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An efficient and convenient synthesis of a new series of 2-{(6H-indolo[2,3-b]quinoxalin-6-yl)methyl}-5-aryl-1,3,4-oxadiazoles from readily available 1,2-diaminobenzene and isatins under microwave irradiation conditions was disclosed. The 6-{(5-aryl-1,3,4-
- Avula, Sreenivas,Komsani, Jayaram Reddy,Koppireddi, Satish,Yadla, Rambabu
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p. 1737 - 1742
(2015/11/09)
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- An efficient synthesis of quinoxaline derivatives using zeolite y as a catalyst
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A convenient and simple procedure for the synthesis of some quinoxaline derivatives was developed via a reaction of oaryldiamines and 1,2-dicarbonyl compounds in the presence of Zeolite NaY as an efficient catalyst. The reactions were carried out at room
- Bodaghifard, Mohammad Ali,Mobinikhaledi, Akbar,Zendehdel, Mojgan,Ayalvar, Zeinab
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p. 345 - 348
(2015/09/07)
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- Cerium oxide nanoparticle-catalyzed three-component protocol for the synthesis of highly substituted novel quinoxalin-2-amine derivatives and 3,4-dihydroquinoxalin-2-amines in water
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The syntheses of novel quinoxalin-2-amine derivatives were conducted in water using CeO2 nanoparticle catalyzed three-component reactions of 1,2-diamines with aldehydes and isocyanides. A variety of 3,4-dihydroquinoxalin- 2-amine derivatives we
- Edayadulla, Naushad,Lee, Yong Rok
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p. 11459 - 11468
(2014/03/21)
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- Sulfamic acid: A mild, efficient, and cost-effective catalyst for synthesis of indoloquinoxalines at ambient temperature
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A simple, cost-effective method for synthesis of indoloquinoxalines from isatin and o-phenylenediamine employing a catalytic amount of sulfamic acid at ambient temperature is reported. Moreover, the method is applicable for a variety of isatins, ninhydrin, 4-hydroxynaphthaquinone, and 1,2-diketones. The key features of the protocol include rapid reactions with good yields, simple workup procedure, and easy isolation of products.
- Hegade, Pravin G.,Mane, Mansing M.,Patil, Jayavant D.,Pore, Dattaprasad M.
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supporting information
p. 3384 - 3391
(2014/12/11)
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- Friedl?nder reaction/quinoxalinone-benzimidazole rearrangement sequence: Expeditious entry to diverse quinoline derivatives with the benzimidazole moieties
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A protocol has been developed for the efficient synthesis of structurally diverse 4-(benzimidazol-2-yl)quinolines via reactions of 3-(2-aminophenyl)quinoxalin-2(1H)-ones and ketones, including acetone, acetophenones, 1,3-pentanedione and ethyl acetoacetat
- Mamedov, Vakhid A.,Kadyrova, Saniya F.,Zhukova, Nataliya A.,Galimullina, Venera R.,Polyancev, Fedor M.,Latypov, Shamil K.
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p. 5934 - 5946
(2015/03/30)
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- Quinoxalinone-benzimidazole rearrangement: An efficient strategy for the synthesis of structurally diverse quinoline derivatives with benzimidazole moieties Dedicated to the 80th anniversary of Academician Oleg Nikolaevich Chupakhin
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A novel and efficient procedure for the synthesis of structurally diverse benzimidazolylquinolines has been realized through a new acid-catalyzed quinoxalinone-benzimidazole rearrangement of the spiro-quinoxalinone derivatives formed in situ from the reaction of 3-(2-aminophenyl)quinoxalin-2(1H)-ones and different ketones.
- Mamedov, Vakhid A.,Galimullina, Venera R.,Zhukova, Nataliya A.,Kadyrova, Saniya F.,Mironova, Ekaterina V.,Rizvanov, Il'Dar Kh.,Latypov, Shamil K.
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p. 4319 - 4324
(2014/07/22)
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- Synthesis and cytotoxicity of novel 6H-indolo[2,3-b]quinoxaline derivatives
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A series of new 6-[(N 1-aryl-1H-1,2,3-triazol-4-yl)methyl]-6H- indolo[2,3-b]quinoxa-line derivatives 7a i-ix and 7b i-vi is synthesized by a simple multi-step protocol starting from isatin 1a or 5-fluoroisatin 1b. These co
- Avula, Sreenivas,Komsani, Jayaram Reddy,Koppireddi, Satish,Yadla, Rambabu,Kanugula, Anantha Koteswararao,Kotamraju, Srigiridhar
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p. 3712 - 3718
(2013/07/26)
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- A greener, facile and scalable synthesis of indole derivatives in water: Reactions of indole-2,3-diones with 1,2-difunctionalized benzene
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An efficient, facile and greener protocol for the synthesis of indole derivatives viz., 3'H-spiro[indole- 3,2'-[1,3]benzothiazole]-2(1H)-ones, 6H-indolo[2,3-b]quinoxalines and 3-(2-hydroxy-phenylimino)- 1,3-dihydro-indol-2- ones, by the reactions of indol
- Jain, Renuka,Sharma, Kanti,Kumar, Deepak
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p. 6236 - 6240,5
(2012/12/11)
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- A novel one-pot synthesis of quinoxaline derivatives in fluorinated alcohols
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Hexafluoroisopropanol (HFIP) is explored as an effective medium for the synthesis of quinoxaline derivatives in high yields at room temperature. The solvent (HFIP) can be readily separated from reaction products and recovered in excellent purity for direc
- Khaksar, Samad,Rostamnezhad, Fariba
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p. 2581 - 2584
(2012/10/29)
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- 2-quinoxalinylnitrenes and 4-quinazolinylnitrenes: Rearrangement to cyclic and acyclic carbodiimides and ring-opening to nitrile ylides
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This work was undertaken with the aim to obtain direct evidence for the interrelationships between hetarylnitrenes, their ring-expanded cyclic carbodiimide isomers, and ring-opened nitrile ylides. Tetrazolo[1,5-a] quinoxaline 11T and tetrazolo[5.1-c]quina
- Kvaskoff, David,Vosswinkel, Michael,Wentrup, Curt
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scheme or table
p. 5413 - 5424
(2011/06/21)
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- Polyethylene glycol in water: A simple, efficient and green protocol for the synthesis of quinoxalines
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A variety of biologically important quinoxaline derivatives has been efficiently synthesized in excellent yields under extremely mild conditions using PEG-600 and water. This inexpensive, non-toxic, ecofriendly and readily available system efficiently condensed several aromatic as well as aliphatic 1,2-diketones with aromatic and aliphatic 1,2-diamines to afford the products in excellent yield. Polyethylene glycol (PEG) can be recovered and recycled. Indian Academy of Sciences.
- Chavan, Hemant V.,Adsul, Laxman K.,Bandgar, Babasaheb P.
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experimental part
p. 477 - 483
(2012/03/26)
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- Impact of substituents on the isatin ring on the reaction between isatins with ortho-phenylenediamine
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The reaction of different substituted isatins with ortho-phenylenediamine in acetic acid has been investigated. While electron-donor substituents on isatin shift the reaction toward classical 6H-indolo[2,3-b]quinoxaline ring closure, electron-withdrawing
- Dowlatabadi, Reza,Khalaj, Ali,Rahimian, Sima,Montazeri, Maedeh,Amini, Mohsen,Shahverdi, Ahmadreza,Mahjub, Elham
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experimental part
p. 1650 - 1658
(2011/06/22)
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- Synthesis of substituted pyrazino[5,6-b]pyrimidine and some indole derivatives
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Refluxing dimethyl acetylenedicarboxylate (DMAD) or 1,2-dibenzoylacetylene with isatin-3-thiosemicarbazone or isatin-3-thiocarbohydrazone in methanol produced 3-substituted oxindoles in good yields. Reaction of equimolecular amounts of 5,6-diamino-urasil-
- Nami, Navabeh,Hosseinzadeh, Masoumeh,Nami, Nasrin,Haghdadi, Mina
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body text
p. 2846 - 2855
(2010/04/05)
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- Microwave assisted synthesis of new indophenazine 1,3,5-trisubstruted pyrazoline derivatives of benzofuran and their antimicrobial activity
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2-[1-(5,8-Dihydro quinoxalino[2,3-b]indoloacetyl)-3-(1-benzofuran-2-yl)-4,5-dihydro-1H-pyr azol-5-yl] phenyl derivatives were synthesized from 2-(5,8-dihydro quinoxalino[2,3-b]indol-5-yl) acetohydrazide and (2E)-1-(1-benzofuran-2-yl)-4-phenylbut-2-en-1-on
- Manna, Kuntal,Agrawal, Yadvendra K.
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supporting information; experimental part
p. 2688 - 2692
(2010/03/24)
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- Bismuth(III)-catalyzed rapid synthesis of 2,3-disubstituted quinoxalines in water
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A variety of 2,3-disubstituted quinoxalines are readily prepared in high yields under extremely mild conditions by cyclocondensation of arene-1,2-diamines with 1,2-dicarbonyls using a catalytic amount of bismuth(III) triflate. The reactions of 2,3-diamino
- Yadav, Jhillu S.,Subba Reddy, Basi V.,Premalatha, Kokku,Shankar, Kattela Shiva
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experimental part
p. 3787 - 3792
(2009/06/17)
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- Interactions of antiviral indolo[2,3-b]quinoxaline derivatives with DNA
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Here, we present the synthesis of five novel indoloquinoxaline derivatives and investigate the DNA binding properties of these monomeric as well as dimeric compounds using absorption, fluorescence, and linear dichroism. Several of the mono- and dicationic derivatives presented have previously demonstrated an excellent antiviral effect that is higher than already acknowledged agents against human cytomegalovirus (CMV), herpes simplex virus type 1 (HSV-1), and varicella-zoster virus (VZV). We find that the DNA binding constants of the monomeric and dimeric derivatives are high (~106) and very high (~109), respectively. Results from the spectroscopic measurements show that the planar aromatic indoloquinoxaline moieties upon interaction with DNA intercalate between the nucleobases. Furthermore, we use poly(dAdT) 2 and calf thymus DNA in a competitive binding experiment to show that all our derivatives have an AT-region preference. The findings are important in the understanding of the antiviral effect of these derivatives and give invaluable information for the future optimization of the DNA binding properties of this kind of drugs.
- Wilhelmsson, L. Marcus,Kingi, Ngarita,Bergman, Jan
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experimental part
p. 7744 - 7750
(2009/12/07)
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- Microwave irradiation for enhancing the regioselective synthesis of 6H-indolo[2,3-b]quinoxalines
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Microwave irradiation (MWI) promotes the regioselective synthesis of 6H-indolo[2,3-b]quinoxaline (5) by condensation of isatin (1) with o-phenylenediamine. Ethyl indolo[2,3-b]quinoxaline-6-acetate (8) was prepared via the carbethoxymethylation of 5, or fr
- El Ashry, El Sayed H.,Ramadan, El Sayed,Hamid, Hamida Abdel,Hagar, Mohamed
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p. 229 - 232
(2007/10/03)
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- A novel route to anticonvulsant imesatins and an approach to cryptolepine, the alkaloid from Cryptolepis Sp.
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Interesting products having anticonvulsant properties are synthesized from solution phase dielectric heating of isatin and aromatic amines and diamines without any catalyst and an approach to cryptolepine skeleton is made from one of them. In addition, th
- Banerji,Lai,Basak,Neuman,Prange,Chatterjee
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p. 426 - 429
(2007/10/03)
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- A straightforward synthesis of pyridopyrazino[2,3-b]indoles and indolo [2,3-b]-quinoxaline
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1,2-Diamines (ethylenediamine, o-phenylenediamine, 2,3-diamino-pyridine, 3,4-diaminopyridine) were reacted with 1-acetyl-2-bromo-3-indolinone to afford 5H-pyrazino[2,3-b]indoles, indolo[2,3-b]quinoxaline and pyridopyrazino[2,3-b]indole in good yields. Alkylation of the indolic nitrogen atom of these indolic derivatives with 2-chloroethylmorpholine, 2-chloroethyl-dimethylamine and allyl bromide was carried out in order to obtain the corresponding N-alkylated derivatives.
- Alphonse, France-Aimée,Routier, Sylvain,Coudert, Gérard,Mérour, Jean-Yves
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p. 925 - 940
(2007/10/03)
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- Reactions of 3-([(trifiuoromethyl)sulfonyl]oxy)-1H-indole derivatives with diamines and carbon nucleophiles. Synthesis of 6H-indolo[2,3- b]quinoxaline derivatives
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Indolic triflate reacted with 1,2-diamines to afford pyrazino[2,3- b]indole or indolo[2,3-b] quinoxaline. Carbon nucleophiles such as malonate derivatives also reacted with indolic triflate in absence of palladium catalyst to afford 2-(3-oxo-2,3-dihydro-1
- Malapel-Andrieu, Beatrice,Merour, Jean-Yves
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p. 11095 - 11110
(2007/10/03)
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- Synthesis of quinoxalines under focussed microwave irradiation
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Quinoxalines were obtained by the condensation of α-diones with o-diaminobenzenes without solvent under focussed microwave irradiation.
- Villemin,Martin
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p. 2319 - 2326
(2007/10/02)
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- A new Route for the Synthesis of Phenazine Di-N-Oxides
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Several phenazine 5,10-dioxides (7a-d) were prepared by the reaction of 2-methyl-3-acetylquinoxaline 1,4-dioxide (2) with different aromatic aldehydes or by direct cyclization of the quinoxaline cinnamoyl derivatives 3 in basic medium.In addition, the phe
- El-Halim, M. S. Abd,El-Ahl, A. S.,Etman, H. A.,Ali, M. M.,Fouda, A.,Fadda, A. A.
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p. 1217 - 1224
(2007/10/03)
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- Substituted indoloquinoxalines
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Substituted indoloquinoxalines of the general formula I STR1 wherein R1 represents one of several, preferably 1 to 4, similar or different substituents in the positions 1-4 and/or 7-10, selected from halogen, prefrably Br, lower alkyl/alkoxy group having not more than 4 carbon atoms, trifluoromethyl group, trichloromethyl group; X is a group --(CH2)n--R2 wherein R2 represents a nitrogen containing basic residue such as NH2, NHR4 or NR5 R6 wherein R4, R5 and R6 independently are lower alkyl or cykloalkyl and n is an integer of from 1 to 4 and R3 represents hydrogen, lower alkyl/cykloalkyl group having not more than 4 carbon atoms, and the physiologically acceptable addition products of the compounds with acids and halogen adducts, preferably adducts with iodine, iodine monochloride or iodine monobromide. Also methods for preparing said compounds by reacting a compound of the formula II STR2 with a reactive compound containing the residue --CHR3 R7 or by rearranging a compound the formula III by heating are described. The novel indoloquinoxalines have antiviral effect and have effect against cancer.
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- Formation of N-N Bonds by Thermolysis of 5-(2-Dimethylaminoethyl)-5H-indoloquinoxaline
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Alkylation of the anion of indoloquinoxaline with 2-(N,N-dimethylamino)ethyl chloride gave a mixture of 6- and 5-isomers.Thermolysis of the 5-isomer resulted in the formation of 6-dimethylamino-6H-indoloquinoxaline and ethylene rather than isomerization.
- Bergman, Jan
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p. 1837 - 1840
(2007/10/02)
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- REACTION OF o-PHENYLENEDIAMINE WITH ISATINS
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It is shown that the reaction of o-phenylenediamine with isatins in the general case leads to mixtures of indoloquinoxalines, 3-(2'-aminophenyl)-2(1H)-quinoxalinones, and spiro.Spiro2H-benzimidazole-2,3'-in
- Ivashchenko, A. V.,Drushlyak, A. G.,Titov, V. V.
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p. 537 - 542
(2007/10/02)
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