- Domino multicomponent approach for the synthesis of functionalized spiro-indeno[1,2-b]quinoxaline heterocyclic hybrids and their antimicrobial activity, synergistic effect and molecular docking simulation
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An expedient synthesis of hitherto unexplored novel hybrid heterocycles comprising dispiropyrrolidine, N-styrylpiperidone and indeno[1,2-b]quinoxaline units has been developed via domino multicomponent 1,3-dipolar cycloaddition strategy employing a new cl
- Almansour, Abdulrahman I.,Arumugam, Natarajan,Kumar, Raju Suresh,Al-Thamili, Dhaifallah M.,Periyasami, Govindasami,Ponmurugan, Karuppiah,Al-Dhabi, Naif Abdullah,Perumal, Karthikeyan,Premnath, Dhanaraj
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- Expeditious construction of spiro-pyrrolidines by an autocatalytic one-pot, five-component, 1,3-dipolar cycloaddition of in situ generated azomethine ylides and olefinic dipolarophiles
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Two series of previously unknown spiro-pyrrolidine derivatives were prepared by a five-component reaction that employed ninhydrin, 1,2-phenylenediamine, sarcosine, aldehydes, and malononitrile or cyanoacetic ester in a solvothermal synthesis. This is the first report of an autocatalytic five-component reaction involving a classical Huisgen reaction, in which the dipole - an azomethine ylide - and the dipolarophile were simultaneously generated in situ. The 1,3-dipolar cycloaddition reaction was found to proceed in a highly regio- and diastereoselective manner. The methodology for the preparation of the spiro-pyrrolidines could be an ideal tool for green chemistry and the synthesis of alkaloids. The highly regio- and stereoselective synthesis of new spiro-pyrrolodines by a combination of a five-component tandemKnoevenagel reaction with a [3+2] dipolarcycloaddition is described, for which azomethine ylides and olefinic dipolarophiles are generated in situ. Copyright
- Li, Ming,Gong, Fu-Meng,Wen, Li-Rong,Li, Zhao-Rui
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- Synthesis of new spiro compounds proceeding from 11H-Indeno[1,2-b]quinoxalin-2-one
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Reaction of 11H-indeno[1,2-b]quinoxalin-2-one with semi(thiosemi)carbazides in ethanol resulted in semi(thiosemi)carbazones which at boiling in acetic anhydride underwent cylization yielding N-{3′-acetyl-3′H-spiro[indeno[1,2-b]quinoxalin-11,2′-[1,3,4]oxa(
- Velikorodov,Stepkina,Shustova,Ionova
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- A sequential multicomponent reaction (SMCR) strategy: Synthesis of novel pyrazolo-1,4-dioxaspiro[4,5]decane grafted spiro-indenoquinoxaline pyrrolidine heterocycles
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A facile and expedient one-pot sequential five-component synthesis of highly substituted trispiro-pyrrolidine heterocycles is described. The key step involves [3 + 2]-cycloaddition of azomethine ylide. This multicomponent reaction (MCR) strategy provides a mild reaction condition, high yield of the products, high regioselectivity, and operational simplicity to assemble complex structural entity in a single operation. The structure of product was confirmed by IR, 1H-NMR, 13C-NMR, and high-resolution mass spectroscopic analysis. A theoretical insight is provided through MM2 calculation for the formation of the observed products.
- Deivasigamani, Gavaskar,Adukamparai Rajukrishnan, Suresh Babu
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- One-pot three-component synthesis of novel spiroindenoquinoxalines
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Numerous new spiroindenoquinoxalines containing pyrano groups were synthesized via a one-pot, three-component reaction of indenoquinoxaline, malononitrile with various α-methylenecarbonyl compounds (β-diketones, pyrazolones) catalyzed by triethylamine.
- Chen, Feiran,Zheng, Jia,Huang, Mingming,Li, Yiqun
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- An expedient ultrasonic assisted one-pot four component synthesis of novel ferrocene grafted pyrrolidine heterocycles via [3 + 2]-cycloaddition of azomethine ylides
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An expedient one-pot four component ultrasonic assisted synthesis of novel ferrocene grafted spiro-pyrrolidine heterocycles via [3 + 2]-cycloaddition of azomethine ylides is described. The protocol provides a mild reaction conditions, high yield of product in short reaction time, high regioselectivity, operational simplicity and applicable to a wide variety of ferrocene derived dipolarophiles for the efficient synthesis of ferrocene appended heterocycles. The structures of cycloadducts were confirmed by spectroscopic analysis. X-ray analysis of the products adds conclusive support to the proposed structure.
- Suresh Babu,Gavaskar,Raghunathan
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- Synthesis of new functionally substituted hetarylcarbamates from methyl {4-[(2E)-3-(4-methoxyphenyl)-prop-2-enoyl]phenyl}carbamate
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Three-component condensation of methyl {4-[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]phenyl}- carbamate with ninhydrin and L-proline in methanol–water (10: 1) afforded methyl {4-[1,3-dioxo-1′- (4-methoxyphenyl)-1,1′,2′,3,5′,6′,7′,7a′-octahydrospiro[indene-2,3′
- Velikorodov,Stepkina
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- Metal-free regioselective construction of diazabenzo[e]acephenanthrylene-1,2-dicarboxylates via a phosphine-mediated cycloadditon
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A number of new diazabenzo[e]acephenanthrylene-1,2-dicarboxylate derivatives have been prepared regiospecifically in moderate to good yields from the triphenylphosphine-mediated cyclocondensation reaction of dialkyl acetylenedicarboxylates with 1-(4-aryl)-2-(11H-indeno[1,2-b]quinoxalin-11-ylidene)ethanones, derived from reaction of ninhydrin, o-phenylenediamine, and 1-aryl-2-(triphenylphosphoranylidene)ethanones.
- Alizadeh, Abdolali,Mohammadi, Reza,Bayat, Fahimeh,Zhu, Long-Guan
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- A synthesis of spirofuran-indenoquinoxalines via isocyanid-based one-pot four-component reaction
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A simple and versatile procedure for the combinatorial synthesis of (Z)-dialkyl-5-(alkylimino)-5H-spiro[furan-2,11′-indeno[1,2-b]quinoxaline]-3,4-dicarboxylates via the catalyst-free one-pot four-component reaction of ninhydrin, benzene-1,2-diamines, dial
- Sabouri, Nahid,Mahdavinia, Gholam Hossein,Notash, Behrouz
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- A synthetic route to 11-(1H-pyrrol-1-yl)-11H-indeno[1,2-b]quinoxaline derivatives exploiting a three-component coupling strategy under microwave irradiation
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11H-Indeno[1,2-b]quinoxalin-11-ones generated in situ from ninhydrin and various 1,2-phenylenediamines, catalysed by montmorillonite K10 under microwave irradiation, condense with 4-hydroxyproline to produce 11-(1H-pyrrol-1-yl)-11H- indeno[1,2-b]quinoxaline derivatives in good yields.
- Azizian, Javad,Karimi, Ali Reza,Kazemizadeh, Zahra,Mohammadi, Ali A.,Mohammadizadeh, Mohammad R.
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- Dispiropyrrolidinyl-piperidone embedded indeno[1,2-b]quinoxaline heterocyclic hybrids: Synthesis, cholinesterase inhibitory activity and their molecular docking simulation
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A small library of new class of dispiropyrrolidinyl-piperidone tethered indono[1,2-b]quinoxaline heterocyclic hybrids 7a–j were synthesized employing multicomponent 1,3-dipolar cycloaddition strategy in [bmim]Br. The azomethine ylide employed is first of
- Arumugam, Natarajan,Almansour, Abdulrahman I.,Kumar, Raju Suresh,Kotresha,Saiswaroop,Venketesh
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- NIR sensing of Zn(II) and subsequent dihydrogen phosphate detection by a benzothiazole functionalized ninhydrin based receptor
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A benzothiazole functionalized ninhydrin based chemosensor (L1), exhibits selective naked eye detection of biologically important zinc ions (from light yellow to orange) accompanied by a 'turn-on' fluorescence emission response in the near infra-red (NIR) region. Most importantly, Zn2+ ion induced 'turn-on' fluorescence emission is also preserved in the presence of Cd2+ and most of the other competing metal ions which clearly suggests the high sensitivity of the chemosensor towards Zn2+. The Job's plot suggests 1:1 binding of the L1 with the Zn2+ ion with a detection limit of 6 nM. Detailed 1H NMR titrations were also conducted to understand the binding behaviour of L1 towards the Zn2+ ion. The 'L1-Zn2+ ensemble' further shows a ratiometric response to H2PO4- among other competitive anions and nucleotides in the same experimental conditions.
- Gogoi, Abhijit,Das, Gopal
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- Domino synthesis of quinoxaline derivatives using SBA-Pr-NH2 as a nanoreactor and their spectrophotometric complexation studies with some metals ions
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Abstract: Amino-functionalized SBA-15 (SBA-Pr-NH2) with a pore size of 6?nm has been used as a basic nanocatalyst in the domino one-pot synthesis of quinoxaline derivatives via the four-component reaction of ninhydrin, 1,2-aryl-diamines, malono derivatives, and α-methylenecarbonyl compound using microwave irradiation. The solid basic catalyst plays a significant role in catalysis, and enhancing the rate and yield of the reaction, it can be easily handled and removed from the reaction mixture by simple filtration and also reused several times without substantial loss of reactivity. Moreover, the complexation reaction between quinoxaline as a model ligand and some metal ions including Cd2+, Co2+, Cu2+, Fe3+, Hg2+, Ni2+, Pb2+, and Zn2+ ions was examined spectrophotometrically in DMF solution at 25?°C. The formation constants of the resulting complexes were calculated from the computer fitting of the molar absorbance measurements in different mole ratios. The obtained data indicated that the stability constant of the resulting complexes varied in the following order Pb2+>?Hg2+>?Cd2+>?Ni2+>?Cu2+>?Fe3+>?Zn2+>?Co2+.
- Ahmadi, Tahereh,Mohammadi Ziarani, Ghodsi,Bahar, Shahriyar,Badiei, Alireza
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- Synthesis and characterization of N′-(11H-indeno[1,2-b]quinoxalin-11-ylidene)benzohydrazonamides as potential antimicrobial agents
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A series of new N′-(11H-indeno[1,2-b]quinoxalin-11-ylidene)benzohydrazonamides 3a–3j was synthesized in excellent yields from the reaction of N3-substituted benzohydrazonamides 1 and 2-(11H-indeno[1,2-b]quinoxalin-11-ylidene)malononitrile 2 in
- Gomaa, Mohsen A.-M.,El-Katatny, Momein H.,Ali, Huda A.
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- TiO2-mediated, one-pot, four-component 1,3-dipolar cycloaddition reaction: A facile synthesis of dispiro-pyrrolidine ring systems
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An expedient regioselective synthesis of dispiroindenoquinoxaline pyrrolidine derivatives mediated by TiO2 in a one-pot, four-component 1,3-dipolar cycloaddition reaction is described. Copyright Taylor & Francis Group, LLC.
- Suresh Babu,Raghunathan
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- Upregulation of BAX and caspase-3, as well as downregulation of Bcl-2 during treatment with indeno[1,2-b]quinoxalin derivatives, mediated apoptosis in human cancer cells
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Cancer is the world's foremost cause of death. There are over 100 different forms of cancer. Cancers are frequently named after the organs or tissues in which they develop. As a part of our aim to develop promising anticancer agents, a series of new indeno[1,2-b]quinoxaline derivatives were synthesized. All of the synthesized compounds were tested for anticancer activity in vitro in three human cancer cell lines: the HCT-116 colon cancer cell line, the HepG-2 liver cancer cell line, and the MCF-7 breast cancer cell line. Among the tested derivatives, 2, 3, 5, 12, 21, and 22 showed exceptional antiproliferative activities against the three tested cell lines compared to the reference standard imatinib. These compounds were, therefore, selected for further investigations. Evaluation of their cytotoxicity against a normal human cell line (WI-38) was performed, to ensure their safety and selectivity (IC50 > 92 μM). Then, induction of apoptosis by the most active compounds was found to be accomplished by downregulation of Bcl-2 and upregulation of BAX and caspase-3. After that, the most promising apoptotic compound that increases the caspase-3 and BAX expression and downregulates Bcl-2 activity (3) was assessed for its impact on the cell cycle distribution in HepG-2 cells: The most potent derivative (3) induced cell cycle arrest at the G2/M phase. Finally, in silico evaluation of the ADME properties indicated that compound 3 is orally bioavailable and can be readily synthesized on a large scale.
- Ammar, Yousry A.,Farrag, Amel M.,Fayed, Eman A.,Gohar, Nirvana A.
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- DNA interaction, anticancer, antibacterial, ROS and lipid peroxidation studies of quinoxaline based organometallic Re(I) carbonyls
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Hetero mononuclear rhenium(I) complexes (I-V) using ligands (L1-L5) [L1-L5 = 11-((2-chlorobenzylidene)hydrazono)-11H-indeno[1,2-b]quinoxaline (L1), 8-methyl-11-((4-methyl-benzylidene)hydrazono)-11H-indeno[1,2-b]quinoxaline (L2), 11-((4-bromobenzylidene) hydrazono)-8-nitro-11H-indeno[1,2-b]quinoxaline (L3), 11-((4-bromobenzylidene) hydrazono)-8-chloro-11H-indeno[1,2-b]quinoxaline (L4), 8-bromo-11-((4-fluorobenzylidene) hydrazono)-11H-indeno[1,2-b]quinoxaline (L5)] were synthesized and characterized by spectroscopic method. All the synthesized compounds have biological importance. DNA interaction studies gave information about the modes of binding and the nucleolytic efficiency of compounds. The binding of the rhenium complexes to Herring sperm DNA (HS DNA) was monitored by UV–visible spectroscopy, viscosity measurements, and molecular docking studies; groove binding was suggested as the most possible mode. The DNA-complexes binding strength was measured in terms of intrinsic binding constants. In vivo and In vitro cytotoxicity against the eukaryotic and prokaryotic cells gave the toxic nature of the synthesized compounds. An antimicrobial study was carried out by estimating MIC (Minimum Inhibitory Concentration) against two Gram-positive (S. aureus, B. subtilis) and three Gram-negative (S. marcescens, P. aeruginosa, E. coli) bacteria. All synthesized complexes are biologically more active than the corresponding ligands. Complexes were having higher MDA and H2O2 production than ligands.
- Varma, Reena R.,Pandya, Juhee G.,Vaidya, Foram U.,Pathak, Chandramani,Dabhi, Ravi A.,Dhaduk, Milan P.,Bhatt, Bhupesh S.,Patel, Mohan N.
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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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- Ultrasound-Promoted Synthesis of Spirocyclopropanes from Switchable Starting Materials via Azomethine Ylide [3+2]-Cycloaddition
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An ultrasound-promoted green protocol to access a new series of spirocyclopropanes from indeno[1,2- b ]quinoxaline derivatives and azomethine ylides, generated in situ from the iodine-catalyzed reaction of acetophenones as well as of 2-methylquinoline with pyridine in the presence of a base, is described. These transformations proceed via a spirocyclopropanation reaction followed by elimination of pyridine. Clear evidence for the structure of a spirocyclopropane-linked indenoquinoxaline derivative was obtained from single-crystal X-ray analysis. The most important feature of this reaction is the fact it forms three stereogenic centers, one of which is quaternary, with excellent selectivity.
- Yavari, Issa,Sheikhi, Sara,Sheykhahmadi, Jamil,Taheri, Zohreh,Halvagar, Mohammad Reza
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p. 2057 - 2066
(2021/02/26)
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- Synthesis, characterization, theoretical, and antimicrobial studies of indenoquinoxalin-based ligands and their reactions with CuBr(PPh3)3
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A series of three ligands were derived from the condensation of indeno[1,2-b]quinoxalin-11-one and hydrazines (L1 from hydrazine, L2 from phenylhydrazine and L3 from thiosemicarbazide). The three ligands were stirred with CuBr(PPh3)3 in dichloromethane; no reaction was observed except in the case of L3, providing a complex with the formula CuBr(PPh3)2(κS-L3) (Cu-L3). Crystal structure of the complex revealed that the central copper atom in the molecule is coordinated to two triphenylphosphine groups, a bromine atom and to the indeno[1,2-b]quinoxalin-11-ylidenecarbothioamidohydrazide (L3) ligand via S atom; forming a distorted tetrahedral geometry around it. In general, Cu-L3 complex has shorter Cu-P bond lengths compared to the parent complex which suggest less steric hindrance in Cu-L3. None of the three ligands were able to use the nitrogen atoms as donating atoms due to their highly engagement in hydrogen-bonding as observed in the crystal structure of Cu-L3 as well as the theoretical calculations. Moreover, theoretical calculation indicated that Cu-N interactions were weak with long distances beyond the typical bonding distances. Antimicrobial screening against a range of strains showed selective inhabitations of indeno[1,2-b]quinoxalin-11-one, L1 and L3 against S. aureus strain. Moreover, the introduction of the copper fragment to L3 did not cause any significant improvements to the antimicrobial properties of L3.
- Babgi, Bandar A.,Bawazeer, Musab,Alzaidi, Najah A.,Arshad, Muhammad N.,Jedidi, Abdesslem,Bataweel, Noor M.,Al-Hejin, Ahmed M.,Hussien, Mostafa A.
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- Synthesis and evaluation of tryptanthrins as antitumor agents
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Here, an efficient and convenient method has been developed for the rapid preparation of N-substituted tryptanthrin analogues through the reaction of tryptanthrins and secondary amines under mild reaction conditions. All compounds were tested for their anti-tumor activity in cancer cell lines by MTT assay. The results showed that some of them exhibited anti-tumor activity against human tumor cell lines A549, HCT116, MDA-MB-231 with IC50 mean values at a low micromolar level. In particular, compound 3b induced G2/S cell cycle arrest and apoptosis in A549 cells dose-dependently.
- Hou, Baolong,Zhou, Ying,Li, Wenyu,Liu, Jianli,Wang, Cuiling
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supporting information
(2021/10/01)
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- Synthesis, characterization of some pyrazine derivatives as anti-cancer agents: In vitro and in Silico approaches
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In continuation of our interest on the synthesis of fused quinoxalines and pyrazines derivatives and due to the resultant pharmacological interest in compounds which belong to these heterocyclic derivatives. In this manuscript, we direct for preparation of some indenoquinoxaline and pyrazine derivatives, with spectral characterization using different spectral techniques including IR, NMR, together with elemental analyses. The newly synthesized derivatives were subjected to cytotoxic screening using the MTT assay against MCF-7 and A549 cell lines. Compounds 6, 8a, 9, 10, and 11 exhibited a potent cytotoxic activity, especially compound 11 with IC50 values 5.4 and 4.3 μM against MCF-7 and A549, respectively. Molecular docking calculations of the tested derivatives exhibited a good binding affinity towards EGFR receptor binding site, which might explain their proposed mode of action.
- Abd Alla, Mohamed M.,Amer, Atef M.,Mohamed, Enaiat K.,Nafie, Mohamed S.,Tantawy, Eman S.
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- Discovery of Tryptanthrins as Novel Antiviral and Anti-Phytopathogenic-Fungus Agents
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Plant diseases seriously affect the yield and quality of crops and are difficult to control. Tryptanthrin and its derivatives (tryptanthrins) were synthesized and evaluated for their antiviral activities and fungicidal activities. We found that tryptanthrins have good antiviral activities against tobacco mosaic virus (TMV) for the first time. Most of the tryptanthrins showed higher anti-TMV activities than that of ribavirin (inhibitory rates of 40, 37, and 38% at 500 μg/mL for inactivation, curative, and protection activities in vivo, respectively). Compound 3n (inhibitory rates of 52, 49, and 54% at 500 μg/mL for inactivation, curative, and protection activities in vivo, respectively) and compound 14 (inhibitory rates of 51, 48, and 53% at 500 μg/mL for inactivation, curative, and protection activities in vivo, respectively) emerged as new antiviral lead compounds with excellent antiviral activities. Compound 16 was selected for further antiviral mechanism research, which revealed that compound 16 could inhibit virus assembly by decomposing 20S coat protein (CP) disk. Molecular docking results showed that compounds 3n and 14, which have higher antiviral activities in vivo than that of compound 16, do show stronger interaction with TMV CP. Further fungicidal activity tests showed that tryptanthrins displayed broad-spectrum fungicidal activities, especially for compound 16. These compounds showed good selectivity to Physalospora piricola. In the current study, a small molecular library of tryptanthrin was constructed and the bioactivity spectrum of these compounds was broadened, which lays a foundation for their application in plant protection.
- Guo, Jincheng,Hao, Yanan,Li, Yongqiang,Liu, Yuxiu,Ma, Dejun,Wang, Qingmin,Wang, Ziwen
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p. 5586 - 5595
(2020/06/27)
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- Synthesis of spirohydantoins and schiff bases of indenoquinoxalinones and indenopyridopyrazinones
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The main structure of many compounds containing spirohydantoin and Schiff bases of indenoquinoxalines and indenopyridopyrazinones expose valuable pharmacological properties. Herein, an effective synthesis and stereochemistry of indenoquinoxalinones (2a, 2
- Song,Bae,Shin,Jung,Cho
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p. 1925 - 1930
(2020/09/02)
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- Design and synthesis of novel spirooxindole–indenoquinoxaline derivatives as novel tryptophanyl-tRNA synthetase inhibitors
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Abstract: In the current study, we used an integrated approach combining bioinformatics, rational drug design, one-pot synthesis, and biological experiments in vitro for the potential discovery of novel tryptophanyl-tRNA synthetase (TrpRS) inhibitors. Atom economic and diastereoselective syntheses were used to generate several Spirooxindole–indenoquinoxaline derivatives in situ from isatin and amino acids viz. proline, phenylglycine, and sarcosine through targeting the 1,3-dipolar cycloaddition of azomethine ylides. These compounds were assayed by biochemical TrpRS inhibition, using in vitro experiments to test against various gram-positive and gram-negative strains, and using diffuse large B cell lymphoma (DLBCL) cell lines. Compound 6e was found to be the most active in vitro with IC50 values of 225 and 74?nM for tests against hmTrpRS and ecTrpRS, respectively. We also found a MIC90 value of 4?μg/mL for tests against S. aureus and IC50 values which ranged from 2.9 to 4.8?μM for tests against proliferation of DLBCL cell lines. Moreover, compound 6e was remarkably good at inducing bacterial autolysis in MRSA strains. Our results suggested that such an integrated approach could be an attractive and viable strategy for the discovery of novel TrpRS inhibitors as potential lead compounds for antibiotics and as novel anticancer agents. Graphic abstract: Discovery of novel spirooxindole-indenoquinoxaline TrpRS inhibitors as potential lead compounds with antibacterial and antitumor activities.[Figure not available: see fulltext.].
- Ren, Wen,Zhao, Qian,Yu, Meng,Guo, Li,Chang, Hongmei,Jiang, Xian,Luo, Youfu,Huang, Wei,He, Gu
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p. 1043 - 1063
(2019/12/24)
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- Synthesis and Biological Activities of Some Novel Spiro Heterocyclic Pyrrolizidine Derivatives of 11H-indeno[1,2-b]quinoxaline through 1,3-Dipolar Cycloaddition
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The synthesis of spiropyrrolidines by the Knoevenagel condensation has been reported as highly bioactive natural and synthetic organic products. The synthesis was initiated by Knoevenagel condensation of indole-2-one with an appropriate benzaldehyde in pr
- Kumar, Nakul,Lal, Chhagan,Singh, Bijendra,Patel, Angik K.
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p. 1255 - 1258
(2020/06/09)
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- Regio- And Diastereoselective Synthesis of Novel Polycyclic Pyrrolo[2,1- a ]isoquinolines Bearing Indeno[1,2- b ]quinoxaline Moieties by a Three-Component [3+2]-Cycloaddition Reaction
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A regio- and diastereoselective synthesis of 2,3-dihydro-10b′ H -spiro[indeno[1,2- b ]quinoxaline-11,1′-pyrrolo[2,1- a ]isoquinoline]-2′,3′-diylbis(phenylmethanone) derivatives containing four contiguous chiral stereocenters was achieved through 1,3-dipolar cycloaddition of isoquinolinium N -ylides in a one-pot three-component reaction. The desired products were obtained in short reaction times and in moderate to high yields (up to 92percent) under relatively mild reaction conditions. The structure and relative stereochemistry of the desired product was confirmed by X-ray diffraction analysis.
- Jafari, Behzad,Langer, Peter,Moafi, Atiyeh,Moghaddam, Firouz Matloubi,Vilinger, Alexander
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supporting information
p. 267 - 271
(2020/02/18)
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- Discovery of Nonquinone Substrates for NAD(P)H: Quinone Oxidoreductase 1 (NQO1) as Effective Intracellular ROS Generators for the Treatment of Drug-Resistant Non-Small-Cell Lung Cancer
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The elevation of oxidative stress preferentially in cancer cells by efficient NQO1 substrates, which promote ROS generation through redox cycling, has emerged as an effective strategy for cancer therapy, even for treating drug-resistant cancers. Here, we described the identification and structural optimization studies of the hit compound 1, a new chemotype of nonquinone substrate for NQO1 as an efficient ROS generator. Further structure-activity relationship studies resulted in the most active compound 20k, a tricyclic 2,3-dicyano indenopyrazinone, which selectively inhibited the proliferation of NQO1-overexpressing A549 and A549/Taxol cancer cells. Furthermore, 20k dramatically elevated the intracellular ROS levels through NQO1-catalyzed redox cycling and induced PARP-1-mediated cell apoptosis in A549/Taxol cells. In addition, 20k significantly suppressed the growth of A549/Taxol xenograft tumors in mice with no apparent toxicity observed in vivo. Together, 20k acts as an efficient NQO1 substrate and may be a new option for the treatment of NQO1-overexpresssing drug-resistant NSCLC.
- Wu, Xingsen,Li, Xiang,Li, Zhihong,Yu, Yancheng,You, Qidong,Zhang, Xiaojin
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p. 11280 - 11297
(2019/01/04)
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- Isobutyl Nitrite-Mediated Synthesis of Quinoxalines through Double C?H Bond Amination of N-Aryl Enamines
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An efficient and metal-free double C?H bond amination of N-aryl enamines using isobutyl nitrite (IBN) has been developed. This method enables the preparation of functionalized quinoxalines in good to excellent yields and tolerates a variety of N-aryl enamines with diverse functional substituents. Mechanistic studies revealed the presence of a key β-imino oxime ester intermediate. A quinoxaline derivative could be prepared from β-carbonyl ester in one-pot sequence on a gram scale. Finally, two important quinoxaline scaffolds were easily prepared in moderate yields over two steps. (Figure presented.).
- Jiao, Yan-Xiao,Wei, Lin-Su,Zhao, Chun-Yang,Wei, Kai,Mo, Dong-Liang,Pan, Cheng-Xue,Su, Gui-Fa
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p. 4446 - 4451
(2018/10/20)
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- Synthesis of some novel indeno[1,2-b]quinoxalin spiro-β-lactam conjugates
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This article reports the synthesis of some new spiro-β-lactams bearing an indeno[1,2-b]quinoxaline ring system, prepared by a [2?+?2] cycloaddition of ketenes with imines derived from 11-H-indeno[1,2-b]quinoxalin-11-one. The structures of newly synthesized spiro-β-lactams 2a–i and 3a-i were characterized by FT-IR,1H NMR,13C NMR, mass spectrometry and elemental analyses. The relative stereochemistry of spiro-β-lactams 2a and 3a was determined unequivocally by X-ray crystallographic studies.
- Ameri Rad, Javad,Jarrahpour, Aliasghar,Ersanl?, Cem Cüneyt,Atio?lu, Zeliha,Akkurt, Mehmet,Turos, Edward
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p. 1135 - 1142
(2017/02/05)
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- Green synthesis of novel spiro-indenoquinoxaline derivatives and their cholinesterases inhibition activity
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A convenient synthesis of substituted spiroindenoquinoxalines at mild and green conditions was developed. Multicomponent reaction of substituted phenylene diamines, ninhydrin, malononitrile and N,N′-substituted-2-nitroethene-1,1-diamines produced the targ
- Maryamabadi, Ammar,Hasaninejad, Alireza,Nowrouzi, Najmeh,Mohebbi, Gholamhossein
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p. 2057 - 2064
(2017/03/23)
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- Theophylline as a new and green catalyst for the one-pot synthesis of spiro[benzo[a]pyrano[2,3-c]phenazine] and benzo[a]pyrano[2,3-c]phenazine derivatives under solvent-free conditions
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A green, convenient, high yielding and one-pot procedure for the synthesis of novel spiro[benzo[a]pyrano[2,3-c]phenazine] derivatives by domino multi-component condensation reaction between 2-hydroxynaphthalene-1,4-dione, benzene-1,2-diamines, ninhydrine,
- Yazdani-Elah-Abadi, Afshin,Maghsoodlou, Malek-Taher,Mohebat, Razieh,Heydari, Reza
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p. 446 - 452
(2017/01/28)
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- Imidazolium-based ionic liquid promoted facile and efficient one-pot four-component synthesis of spiro[furan-2,11'-indeno[1,2-b]quinoxaline]s under ambient conditions
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Spiro compounds are one of the most important organic molecules. Spiro rings such as spiroketals are present in numerous natural products; simple spiroketals are known insect pheromones. A small number of spiro containing drugs has been investigated durin
- Zarei-Haji-abadi, Morteza,Mohebat, Razieh,Mosslemin, Mohammad Hossein
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- Nanomagnetically modified thioglycolic acid (γ-Fe2O3@SiO2-SCH2CO2H): Efficient and reusable green catalyst for the one-pot domino synthesis of spiro[benzo[a]benzo[6,7]chromeno[2,3-c]phenazine] and benzo[a]benzo[6,7]chromeno[2,3-c]phenazines
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Superparamagnetic nanoparticles of modified thioglycolic acid (γ-Fe2O3@SiO2-SCH2CO2H) represent a new, efficient and green catalyst for the one-pot synthesis of novel spiro[benzo[a]benzo[6,7]chromeno[2,3-c]phenazine] derivatives via domino Knoevenagel–Michael–cyclization reaction of 2-hydroxynaphthalene-1,4-dione, benzene-1,2-diamines, ninhydrin and isatin. This novel magnetic organocatalyst was easily isolated from the reaction mixture by magnetic decantation using an external magnet and reused at least six times without significant loss in its activity. The catalyst was fully characterized using various techniques. This procedure was also applied successfully for the synthesis of benzo[a]benzo[6,7]chromeno[2,3-c]phenazines.
- Abbasi Pour, Sajjad,Yazdani-Elah-Abadi, Afshin,Afradi, Mojgan
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- An efficient domino one-pot synthesis of novel spirofuran-indenoquinoxalines by vinyltriphenylphosphonium salts
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Abstract: A simple and convenient multi-component domino reaction has been described for the synthesis of novel spirofuran-indenoquinoxaline derivatives. Products were obtained by a three-component condensation reaction between ninhydrin, aromatic 1,2-diamines and dialkyl ethynedicarboxylates in the presence of a catalytic amount of triphenylphosphine in CH 2Cl 2 at ambient temperature in excellent yields. This one-pot process produces biologically and pharmacologically significant heterocycles with the formation of five new bonds (one C–C, two C=N and two C–O) and two new rings in a single operation. Graphical Abstract: [Figure not available: see fulltext.].
- Yazdani-Elah-Abadi, Afshin,Maghsoodlou, Malek-Taher,Mohebat, Razieh,Heydari, Reza
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p. 691 - 698
(2017/06/29)
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- Ultrasound-assisted rapid and efficient one-pot synthesis of furanyl spirooxindolo and spiroquinoxalinopyrrolizidines by 1,3-dipolar cycloaddition: a green protocol
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Efficient synthesis of novel spirooxindolo and spiroquinoxalinopyrrolizidine derivatives was expediently accomplished with regioselectivity via one-pot, three-component 1,3-dipolar cycloaddition using ultrasonication. Chalcones derived from both heteroaryl methyl ketones and furfural were used as dipolarophiles in these reactions. The synthesized compounds were analyzed by 1H and 13C nuclear magnetic resonance (NMR), mass spectrometry, and elemental (CHN) analysis. Single-crystal X-ray diffraction studies of one of the compounds (11d) proved the structure and regiochemistry of the cycloaddition. The ultrasound methodology is clearly advantageous, and the desired products were obtained in moderate to good yield in shorter reaction time compared with conventional heating and fusion methods.
- Nishtala, Venkata Bharat,Nanubolu, Jagadeesh Babu,Basavoju, Srinivas
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p. 1365 - 1381
(2017/02/15)
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- Discovery of indeno[1,2-b]quinoxaline derivatives as potential anticancer agents
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We have synthesized certain indeno[1,2-b]quinoxaline derivatives for antiproliferative evaluation. Among them, 11-{[3-(dimethylamino)propoxy]imino}-N-[3-(dimethylamino) propyl]-11H-indeno[1,2-b]quinoxaline-6-carboxamide (10a) was active against the growth of MDA-MB231, PC-3, and Huh-7 with IC50 values of 0.87 (selectivity index, SI = 36.22), 0.82 (SI = 38.43), and 0.64 μM (SI = 49.23) respectively. Compound 10a was inactive against the growth of normal human fetal lung fibroblast cell line (MRC-5) with an IC50 value of 31.51 μM. Its analogs, 10b and 10c, were also active against the growth of MB231, PC-3, and Huh-7 with IC50 values of 1.0 μM in each case. Our results have also indicated compounds 10a-10c exhibited comparable inhibitory activities against topo I and topo II with the positive compound 2 at a concentration of 10 μM. Mechanism studies indicated that compound 10a induced cell cycle arrest at S phase via activation of caspase-3, -7 and an increase in the protein expression of Bad and Bax but a decrease in expression of Bcl-2 and PARP, which consequently cause cell death. In addition, compound 10a attenuated the levels of phosphorylated Src, Akt-1, and Akt-2 protein levels but did not affect the total protein expression of Akt. We have also implanted human hepatocellular carcinoma cells into the yolk sac of zebrafish larvae and incubated larvae with various concentrations of 10a. Our results of the zebrafish xenograft assay confirmed the anti-tumor effect of 10a in vivo.
- Tseng, Chih-Hua,Chen, You-Ren,Tzeng, Cherng-Chyi,Liu, Wangta,Chou, Chon-Kit,Chiu, Chien-Chih,Chen, Yeh-Long
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p. 258 - 273
(2015/12/18)
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- Synthesis and characterization of acetic acid functionalized poly (4-vinylpyridinium) salt as new catalyst for the synthesis of spiropyran derivatives and their biological activity
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Acetic acid functionalized poly(4-vinylpyridinium) bromide (APVPB), as a new and heterogeneous catalyst, was designed and successfully tested on the synthesis of 2-aminospiro[indoline-3,4?pyran]-2-one and spiro[indeno[1,2-b]quinoxaline-11,4-pyran]-2?-amine derivatives. Also, infrared spectroscopy (FT-IR), thermal gravimetric analysis (TGA), differential thermal gravimetric (DTG), scanning electron microscope (SEM), X-ray diffraction analysis (XRD) and energy dispersive X-ray analysis (EDX) of the catalyst has been studied in the presented work. The prepared spiro-pyrans were solved in DMSO and subjected to antioxidant activity screening by DPPH free radical scavenging assay and antifungal activity against Fusarium oxysporum. Results showed that the synthesized spiro-pyran possess strong antioxidant activity (IC50; 0.161 ± 0.009 to 1.509 ± 0.007 mg/ml) and also good inhibition activity against Fusarium oxysporum (65.8 ± 1.4% to 88.3 ± 2.2% at 500 ppm concentration and 89.2 ± 3.2% to 100 ± 0.0% at 1000 ppm concentration). For their biological activities, the prepared spiro-pyran compounds may be suggested to apply as alternative systems in medicine and agriculture.
- Moosavi-Zare, Ahmad Reza,Zolfigol, Mohammad Ali,Noroozizadeh, Ehsan,Zarei, Mahmoud,Karamian, Roya,Asadbegy, Mostafa
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p. 217 - 228
(2016/10/30)
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- Propylsulfonic acid functionalized nanozeolite clinoptilolite as heterogeneous catalyst for the synthesis of quinoxaline derivatives
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In this work, the natural nanozeolite clinoptilolite (Nano CP) was successfully functionalized by propylsulfonic acid and applied as efficient heterogeneous catalyst for the synthesis of quinoxaline derivatives in aqueous media. The nanocatalyst was chara
- Baghbanian, Seyed Meysam
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p. 1113 - 1116
(2015/09/01)
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- Design, synthesis and antitumor activity of non-camptothecin topoisomerase i inhibitors
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Three groups of non-camptothecin compounds with four to five fused rings have been designed and synthesized. Their in vitro anti-proliferative activity has been evaluated with five different cancer cell lines (HCT116, PC3, U87MG, HepG2, SK-OV-3). Compound
- Zhang, Chao,Li, Shasha,Ji, Liyan,Liu, Shan,Li, Zhongjun,Li, Shuchun,Meng, Xiangbao
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supporting information
p. 4693 - 4696
(2015/10/12)
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- Synthesis and biological evaluation of phaitanthrin congeners as anti-mycobacterial agents
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Abstract Natural alkaloid, tryptanthrin (indolo[2,1-b]quinazoline-6,12-dione) and its analogues are found to exhibit potent anti-tubercular activity against MDR-TB. A novel class of indolo[2,1-b]quinazolinones have been synthesized to evaluate their anti-
- Kamal, Ahmed,Reddy, B.V. Subba,Sridevi,Ravikumar,Venkateswarlu,Sravanthi,Sridevi, J. Padma,Yogeeswari,Sriram
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p. 3867 - 3872
(2015/08/24)
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- Asymmetric synthesis approach of enantiomerically pure spiro-indenoquinoxaline pyrrolidines and spiro-indenoquinoxaline pyrrolizidines
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An efficient, one-pot, four-component procedure for the synthesis of a small library of novel chiral spiro-indenoquinoxaline pyrrolidines and chiral spiro-indenoquinoxaline pyrrolizidines with high regio-, diastereo- (up to 96 dr), and enantioselectivity (up to 99% ee), through a 1,3-dipolar cycloaddition reaction of azomethine ylides and an optically active cinnamoyl-crotonoyl oxazolidinone is described. This methodology was very simple and was utilized to construct complex products from simple starting materials. The process was carried out in aqueous ethanol as an eco-friendly solvent and in the absence of any Lewis acids catalysts. The oxazolidinone chiral auxiliary was removed through a non-destructive protocol. The reaction mechanism is discussed on the basis of the assignment of the absolute configuration of the cycloadducts and using quantum mechanical calculations. The regio- and stereoselectivity were described on the basis of transition states' stabilities and global and local reactivity indices of the reactants. The results of the theoretical calculations are in agreement with the experimental outcomes.
- Shahrestani, Naeimeh,Salahi, Farbod,Tavakoli, Niloofar,Jadidi, Khosrow,Hamzehloueian, Mahshid,Notash, Behrouz
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p. 1117 - 1129
(2015/10/28)
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- On the reactivity of benzo[a]phenazine-5,6-dione 7-oxides with methanolic alkali and pyrrolidine
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[MediaObject not available: see fulltext.]When treated with methanolic alkali, benzo[a]phenazine-5,6-dione 7-oxides convert into 11H-indeno[1,2-b]quinoxalin-11-ones, whereas 11-hydroxy-11-(pyrrolidine-1-carbonyl)-11H-indeno[1,2-b]quinoxaline 10-oxides form upon treatment with pyrrolidine.
- Gornostaev, Leonid M.,Rukovets, Tatyana A.,Arnold, Elena V.,Lavrikova, Tatyana I.,Khalyavina, Juliya G.,Kryukovskaya, Irina S.
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p. 166 - 169
(2016/01/12)
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- Highly efficient one-pot four-component Kabachnik-Fields synthesis of novel α-amino phosphonates under solvent-free and catalyst-free conditions
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In the present study, a simple and highly efficient protocol for the preparation of novel α-amino phosphonates is achieved based on the one-pot reaction of ninhydrin, 1,2-phenylenediamines, aniline derivatives, and dialkyl or diaryl phosphites, without using any catalyst under solvent-free conditions. The main advantages of the reaction are short reaction time, high yields, simple workup, and no need for further purification.
- Rashid, Zahra,Naeimi, Hossein,Ghahremanzadeh, Ramin
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p. 99148 - 99152
(2015/12/04)
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- Synthesis of bisindolylindeno[1,2-b]quinoxaline and bisindolylindeno[3,4-b] pyrazine with poly(N,N ′-dibromo-N-ethylnaphthyl-2,7-disulfonamide)
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Poly(N,N′-dibromo-N-ethylnaphthyl-2,7-disulfonamide) (PBNS) as novel reagent was synthesized. Bisindolylindeno[1,2-b]quinoxaline and bisindolylindeno[3,4-b]pyrazine derivatives were synthesized in a simple and efficient method from the three-component condensation reaction of indole, indane-1,2,3-trione, and diamine aromatic compounds by PBNS under solvent-free conditions at 80 °C in good to excellent yields, short reaction times, and a simple procedure for new derivatives. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.] Copyright
- Khazaei, Ardeshir,Massoudi, Abdolhossien,Chegeni, Mahdieh
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p. 633 - 639
(2014/01/17)
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- Synthesis of novel indenoquinoxaline derivatives as potent α-glucosidase inhibitors
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A series of new N-(11H-Indeno[1,2-b]quinoxalin-11-ylidene)benzohydrazide derivatives (3a-3p) were synthesized and evaluated for their α-glucosidase inhibitory activity The synthesized compounds 3d, 3f, 3g, 3k, 3n, 3p and 4 showed significant α-glucosidase
- Khan, Madiha Sahar,Munawar, Munawar Ali,Ashraf, Mohammad,Alam, Umber,Ata, Athar,Asiri, Abdullah Mohamed,Kousar, Samina,Khan, Misbahul Ain
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p. 1195 - 1200
(2014/02/14)
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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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- Ninhydrin as a building block in scaffold-linked chromophoric dyad construction
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The reaction of ninhydrin with ester-activated cyclobutene epoxide (CE-1) containing the fused 1,4-dimethoxynaphthalene (DMN) chromophore, gave adducts formed by 1,3-dipolar cycloaddition at the central (C2)-CO (major) and the outer (C1,3
- Margetic, Davor,Mann, David A.,Warrener, Ronald N.
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p. 210 - 224
(2014/10/16)
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- A one-pot three-component reactions for the synthesis of fully substituted spiro indeno[1,2-b]quinoxaline derivatives
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An efficient and simple approach of the synthesis of some spiro indeno[1,2-b]quinoxalines via a one-pot three-component reaction of 11H-indeno[1,2-b]quinoxalin-11-one, pyrazolone, and malononitrile in the presence of Na2CO3 at 70 C is reported. This reaction has shown to have high atom economy.
- Soleimani, Ebrahim,Hariri, Mina,Saei, Parisa
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p. 773 - 777
(2013/09/02)
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- An efficient multicomponent and stereoselective synthesis of new spiro[indeno[1,2-b]quinoxaline-11,2′-pyrrolidine] derivatives
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New spiro[indeno[1,2-b]quinoxaline-11,2′-pyrrolidine] derivatives were prepared in high yield stereoselectively from an efficient multicomponent 1,3-dipolar cycloaddition reaction between ninhydrin, phenylenediamine, sarcosine, and chalcones. The regiochemistry and stereochemistry of resultant cycloadducts have been determined by several 2D NMR spectroscopic techniques and X-ray single crystal diffraction..
- Moemeni, Mehdi,Arvinnezhad, Hamid,Samadi, Saadi,Tajbakhsh, Mahmood,Jadidi, Khosrow,Khavasi, Hamid Reza
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experimental part
p. 190 - 194
(2012/04/17)
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- Et3N-catalyzed oxidative dehydrogenative coupling of α-unsubstituted aldehydes and ketones with aryl diamines leading to quinoxalines using molecular oxygen as oxidant
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A novel Et3N-catalyzed oxidative dehydrogenative coupling of α-unsubstituted carbonyl compounds with aryl diamines leading to quinoxaline derivatives using molecular oxygen as oxidant has been developed. Six hydrogen dissociations involving 2 sp3 C-H bonds activation are realized under mild conditions in this approach. Plausible mechanism is proposed for this novel Et3N-catalyzed transformation on the basis of the aboratively designed mechanistic studies including the radical detection by EPR. 2012 Elsevier Science. All rights reserved.
- Zhang, Chun,Xu, Zejun,Zhang, Liangren,Jiao, Ning
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supporting information; experimental part
p. 5258 - 5262
(2012/08/08)
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