3138-86-1Relevant articles and documents
Luminescent bis(benzo[: D] thiazolyl)quinoxaline: Facile synthesis, nucleic acid and protein BSA interaction, live-cell imaging, biopharmaceutical research and cancer theranostic application
Babu, Lavanya Thilak,Jadhav, Gajanan Raosaheb,Paira, Priyankar
, p. 8748 - 8752 (2019)
A series of quinoxaline-2-hydroxyphenylbenzothiazole scaffolds were synthesized and characterized using NMR, UV, fluorescence spectroscopy and LCMS. These newly synthesized compounds were found to be cytotoxic in human epithelioid cervix carcinoma (HeLa) and human colon cancer cell lines (Caco-2). Selectivity of the compounds 7e and 7g are more than 9 fold higher in Caco-2 cells with respect to the normal cell line HEK-293. The most fluorescent compound 7e has displayed high cytoselectivity, significant cellular uptake in HeLa cells and strong binding efficacy with DNA and BSA. The most potent compound 7g has primarily classified as BCS class 4 and BDDCS class 4.
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Bennett,Willis
, p. 1709 (1930)
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Synthesis and structure of a silver(I) complex {[Ag5(L) 2(NO3)4](NO3)(CHCl3) 2}n [L = 2,3-bis(pyrimidine-2-thiomethyl)quinoxaline]
Zhang, Chao-Yan,Gao, Qian,Xie, Ya-Bo,Feng, Jian-Bo
, p. 749 - 753 (2008)
The reaction of the dithioether ligand, 2,3-bis(pyrimidine-2-thiomethyl) quinoxaline (L) with AgNO3, leads to the formation of a novel complex {[Ag5(L)2(NO3)4](NO 3)(CHCl3)2}n 1, which has been characterized by single-crystal X-ray diffraction analysis: monoclinic, space group C2/c, with a = 34.741(7), b = 9.930(2), c = 17.004(4) A, β = 106.497(6)° and V = 5625(2) A3. Complex 1 consists of 2D {[Ag 5(L)2(NO3)4]+}n cations, uncoordinated NO3- anions and CHCl3 solvent molecules. In 1, there exist three crystallographic independent AgI centers, which adopt different coordination geometries. There exist π-π stacking interactions in the complex and these weak interactions further stabilize the crystal structure in the solid state. The coordination feature of the ligand has been investigated by DFT calculations.
Facile synthesis of 6,6,8,6,6-ring fused pentacyclic heterocycles: annelation of quinolines to quinoxalines under PTC condition
Paira, Priyankar,Paira, Rupankar,Hazra, Abhijit,Naskar, Subhendu,Sahu, Krishnendu B.,Saha, Pritam,Mondal, Shyamal,Maity, Arindam,Banerjee, Sukdeb,Mondal, Nirup B.
, p. 4619 - 4623 (2009)
An efficient and simple synthesis of pentacyclic quinolonoquinoxalinooxazocines in a one-pot sequence has been performed by unique application of phase transfer catalysis. Preparative simplicity and conceptual novelty of the methodology offer an attractive general application for the synthesis of novel quinoline antibiotics.
Synthesis and crystal structure of a silver(I) complex with dithioether ligand
Xie, Ya-Bo,Li, Jian-Rong,Bu, Xian-He
, p. 211 - 215 (2006)
The reaction of the dithioether ligand, 2,3-bis(5-methyl-1,3,4-thiadiazole- 2-thiomethyl) quinoxaline (L) with AgBF4, leads to the formation of a novel complex {[AgL](BF4)}∞ 1, which has been characterized by single-crystal X-ray diffraction analysis: monoclinic, space group C2/c, with a = 20.316(7) A, b = 12.401(4) A, c = 18.039(6) A, β = 108.404(6)° and V = 4312(3) A3. The crystal structure of the complex consists of 1D {[AgL]+} ∞ cation chain and BF4 - anions. In 1, the coordination geometry of AgI center can be best described as trigonal planar coordinated by three N from two distinct L ligands. The ligand is polydentate with one end adopting a bidentate conformation to chelate an AgI atom and the other end monodentate to bridge another Ag I resulting in an infinite chain along b axis. There exist Ag...N weak coordination, π-π stacking and F...S weak interactions in the complex, and these weak interactions link the 1D complex into 3D supramolecular structure and further stabilize the crystal structure in the solid state.
Versatile Heteroleptic Cu(I) Complexes Based on Quino(xa)-line-Triazole Ligands: from Visible-Light Absorption and Cooperativity to Luminescence and Photoredox Catalysis
Bruschi, Cecilia,Gui, Xin,Salaeh-arae, Nasrin,Barchi, Tobia,Fuhr, Olaf,Lebedkin, Sergei,Klopper, Wim,Bizzarri, Claudia
, p. 4074 - 4084 (2021/08/27)
Four new heteroleptic Cu(I) complexes based on 1, 2, 3-triazolyl-quinoline or quinoxaline and a chelating diphosphine were prepared and fully characterised. The mononuclear derivatives absorb in the visible region, up to 600 nm, while the dinuclear complex has a long-tail absorption up to 800 nm, showing an additional electronic state corroborated by theoretical calculations. Although a methylene group between the triazole and the quino(xa)line moiety increases the bite angle and decreases the luminescence in solution, all complexes emit brightly in the solid-state. Their redox properties in the excited state were determined, proving their ability in serving as photoredox catalysts in atom transfer radical addition successfully.
Pharmacological investigation of quinoxaline-bisthiazoles as multitarget-directed ligands for the treatment of Alzheimer's disease
Sagar, Sneha R.,Singh, Devendra Pratap,Das, Rajesh D.,Panchal, Nirupa B.,Sudarsanam, Vasudevan,Nivsarkar, Manish,Vasu, Kamala K.
, (2019/06/08)
Alzheimer's disease (AD) is the most prevalent disease of old age leading to dementia. Complex AD pathogenesis involves multiple factors viz. amyloid plaque formation, neurofibrillary tangles and inflammation. Herein we report of a new series of quinoxaline-bisthiazoles as multitarget-directed ligands (MTDLs) targeting BACE-1 and inflammation concurrently. Virtual screening of a library of novel quinoxaline-bisthiazoles was performed by docking studies. The most active molecules from the docking library were taken up for synthesis and characterized by spectral data. Compounds 8a-8n showed BACE-1 inhibition in micro molar range. One of the compounds, 8n showed BACE-1 inhibition at IC50 of 3 ± 0.07 μM. Rat paw edema inhibition in acute and chronic models of inflammation were obtained at 69 ± 0.45% and 55 ± 0.7%, respectively. Compound 8n also showed noteworthy results in AlCl3 induced AD model. The treated rats exhibited excellent antiamnesic, antiamyloid, antioxidant, and neuroprotective properties. Behavioural parameters suggested improved cognitive functions which further validates the testimony of present study. Moreover, compound 8n was found to have inherent gastrointestinal safety. This new string of quinoxaline-bisthiazoles were identified as effective lead for the generation of potent MTDLs and compound 8n was found to showcase qualities to tackle AD pathogenesis.
