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.
New coordination architectures of dithioether ligand with silver salts: Effect of anions on complex structures
Xie, Ya-Bo,Li, Jian-Rong,Bu, Xian-He
, p. 34 - 39 (2006)
Reactions of a flexible dithioether ligand, 2,3-bis(5-methyl-1,3,4- thiadiazole-2-thiomethyl)quinoxaline (L), with AgX (X = ClO4 - or PF6-) lead to the formation of two new one-dimensional (1D) silver(I) complexes: {[AgL](ClO4)} ∞ 1 and {[Ag2L(CH3OH)](PF 6)2(CH3OH)}∞ 2, which have been characterized by elemental analysis, IR spectroscopy, and X-ray crystallography. Although 1 and 2 are synthesized under the same conditions, they take different structures due to the difference in anions in the silver salts. In 1, each ligand supplies three N-donors to bridge two silver atoms to result in a chain structure, and all silver atoms in the chain possess the same coordination geometry. In 2, each ligand gives six N-donors to coordinate to two silver atoms of different geometries, forming a ID chain. The changes in counteranions affect the coordination mode of the ligand and the geometry of the Ag(1) centre, and consequently give rise to complexes with different structures. The coordination features of the ligand have also been primarily investigated through density functional theory calculations. CSIRO 2006.
NHC metal (silver, mercury, and nickel) complexes based on quinoxaline-dibenzimidazolium salts: Synthesis, structural studies, and fluorescent chemosensors for Cu2+ by charge transfer
Liu, Qing-Xiang,Yao, Zhao-Quan,Zhao, Xiao-Jun,Zhao, Zhi-Xiang,Wang, Xiu-Guang
, p. 3493 - 3501 (2013)
The two dibenzimidazolium salts 2,3-bis[(1-nPr- benzimidazoliumyl)methyl]quinoxaline hexafluorophosphate (H2-1a) and 2,3-bis[(1-Pi-benzimidazoliumyl)methyl]quinoxaline hexafluorophosphate (H 2-1b) (nPr = n-propyl and Pi = picolyl) and their four NHC metal complexes [Ag2(1a)2](PF6)2 (2a), [Hg(1a)(OAc)(H2O)]2(PF6)2 (2b), [Ag2(1b)2](PF6)2 (2c) and [Ni(1b)](NiCl4) (2d) have been synthesized and characterized. Each cation in 2a,c possesses a boxlike structure with different sizes. In 2b, one 18-membered macrometallacycle is formed by two bidentate NHC ligands and two mercury(II) atoms, in which an inversion center is observed. In 2d, one nickel(II) atom is surrounded by two carbene carbon atoms and two nitrogen atoms from two pyridine rings to adopt a square geometry. The recognition of Cu 2+ using 2a,c as chemosensors by charge transfer was investigated on the basis of fluorescence and UV/vis spectroscopic titrations. The results show that complexes 2a,c are effective chemosensors for Cu2+.
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.
Synthesis and photo physical properties of carbazole based quinoxaline conjugated polymer for fluorescent detection of Ni2+
Upadhyay, Anjali,Karpagam
, p. 50 - 64 (2017)
A new series of donor-acceptor (P1-P3) conjugated polymers containing carbazole and quinoxaline units have been synthesized through multistep reactions. In the final step, the polymerization was carried out using Wittig reaction. The optical and potential charge –transporting properties of the polymers has been carefully investigated by UV-Vis, fluorescence emission spectroscopy and cyclic voltammetry. Solvent effects on absorption and emission spectra of these polymers have also been studied. Compared with optical spectra of the polymers in solution and in solid state, the solid state of the polymers was significantly red shifted. Cyclic voltammetry experiments showed that these polymers have high lying HOMO energy levels ranging from ?5.57 to ?5.49 eV and low-lying LUMO energy levels ranging from 3.24 to 3.30 eV. The electrochemical band gap was good agreement with the optical band gap. Results of TGA and AFM analysis demonstrated that the compounds exhibited good thermal stabilities and smooth roughness. Furthermore, the molecular interactions of polymers with electron donor (N, N'-dimethylaniline) and electron acceptor (dimethyl terephthalate) were also investigated. In addition, the sensing behaviour was observed with various metal ions such as Li+, Na+, K+, Mg2+, Ca2+, Mn2+, Ni2+, Cd2+, Cu2+, Zn2+, Fe2+ and Hg2+. The synthesized polymers were shown excellent sensing behaviour towards Ni2+ ions. Excellent metal ion sensing and luminescence of our polymer will move towards to the application of chemical and bio sensor field.
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.
Cu(ii), Ir(i) and CuO nanocatalyzed mild synthesis of luminescent symmetrical and unsymmetrical bis(triazolylmethyl)quinoxalines: Biocompatibility, cytotoxicity, live cell imaging and biomolecular interaction
Maiti, Santanu,Roy, Nilmadhab,Babu, Lavanya Thilak,Moharana, Prithvi,Athira,Darsana Sreedhar,De, Sourav,Ashok Kumar,Paira, Priyankar
, p. 920 - 931 (2020)
Quinoxaline derivatives play versatile roles in various fields of science. Thus different types of scaffolds have been designed with these quinoxaline moieties to make them more efficient for preparation of various biologically active materials in the pharmaceutical industry. The ability of quinoxaline moieties has been reinforced by introducing triazole rings into them with the aid of a "click reaction" following environmentally friendly green techniques in the presence of a Cu(ii) catalyst as well as in the presence of a CuO nanomaterial under microwave irradiation. The novelty of our work is being highly focussed on the introduction of unsymmetrical triazole rings with the isolation of mono triazolyl quinoxaline derivatives using an Ir(i) catalyst in aqueous medium and on the capability of the CuO nanomaterial in catalyzing a "click reaction" in various biological media. The role of our synthsized bis(trizolylmethyl)quinoxaline compounds as cytotoxic agents has been confirmed with clear evidence from a DNA and BSA binding study, stability study, viscosity study and MTT assay. Due to the detecting ability of live cancer cells, high cellular uptake, biocompatibility and high cytoselectivity of these scaffolds, ultimately compound 6g has been established as a cancer theranostic drug.
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.
Mitochondria-Targeting Click-Derived Pyridinyltriazolylmethylquinoxaline-Based Y-Shaped Binuclear Luminescent Ruthenium(II) and Iridium(III) Complexes as Cancer Theranostic Agents
Roy, Nilmadhab,Sen, Utsav,Madaan, Yukti,Muthukumar, Venkatesan,Varddhan, Seshu,Sahoo, Suban K.,Panda, Debashis,Bose, Bipasha,Paira, Priyankar
, p. 17689 - 17711 (2020)
Due to several negative issues, market available drugs have been gradually losing their importance in the treatment of cancer. With a view to discover suitable drugs capable of diagnosing as well as inhibiting the growth of cancer cells, we have aspired to develop a group of theranostic metal complexes which will be (i) target specific, (ii) cytoselective, thus rendering the normal cell unaffected, (iii) water-soluble, (iv) cancer cell permeable, and (v) luminescent, being beneficial for healing the cancer eternally. Therefore, to reach our goal, we have prepared novel Ru(II)- and Ir(III)-based bimetallic and hetero bimetallic scaffolds using click-derived pyridinyltriazolylmethylquinoxaline ligands followed by metal coordination. Most of the compounds have displayed significant cytoselectivity against colorectal adenocarcinoma (Caco-2) and epithiloid cervical carcinoma (HeLa) cells with respect to normal human embryonic kidney cells (HEK-293) compared to cisplatin [cis-diamminedichloroplatinum(II)] along with excellent binding efficacy with DNA as well as serum albumin. Complex [(η6-p-cymene)(η5-Cp*)RuIIIrIIICl2(K2-N,N-L)](PF6)2 [RuIrL] exhibited the best cytoselectivity against all the human cancer cells and was identified as the most significant cancer theranostic agent in terms of potency, selectivity, and fluorescence quantum yield. Investigation of the localization of complex [Ir2L] and [RuIrL] in the more aggressive colorectal adenocarcinoma cell HT-29 indicates that mitochondria are the key cellular target for destroying cancer cells. Mitochondrial dysfunction and G2/M phase cell cycle arrest in HT-29 cell were found to be involved in the apoptotic cell death pathway induced by the test complexes [Ir2L] and [RuIrL]. These results validate the concept that these types of complexes will be reasonably able to exert great potential for tumor diagnosis as well as therapy in the near future.
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.
