7521-41-7Relevant academic research and scientific papers
Synthesis, characterization, biological screening and molecular docking studies of 2-aminonicotinaldehyde (ANA) and its metal complexes
Konakanchi, Ramaiah,Mallela, Ramachary,Guda, Ramu,Kotha, Laxma Reddy
, p. 27 - 53 (2018)
The biological and optical importance of the o-aminoaldehyde family of ligands inspired us to evaluate the coordination properties and biological activities of 2-aminonicotinaldehyde (ANA). Here, we report the synthesis, characterization, biological screening and molecular docking studies of ANA and its metal complexes of Ni(II), Pd(II), Co(II) and Cu(II) using various analytical and spectroscopic techniques. The single crystal X-ray diffraction studies of ANA explain the solid-state assembly and an interesting supramolecular herring bone stacking pattern by classical N–HO/N intra/inter molecular and non-classical C–HO/N intermolecular H-bonding. ANA and its metal complexes were screened for in vitro anticancer, antimicrobial and anti-oxidant activities. Anticancer activity was tested against HeLa, MCF-7 and HEK293 human cancer cell lines. The [Ni(ANA)2Cl2] complex showed good activity against HeLa and MCF-7, the [Pd(ANA)2Cl2] and [Cu(ANA)2Cl2] complexes against HeLa, and the [Co(ANA)2Cl2] complex against MCF-7. In antimicrobial screening, the [Co(ANA)2Cl2] and [Cu(ANA)2Cl2] complexes were proved to be potent antibacterial and antifungal agents. The anti-oxidant activity of these complexes was investigated through DPPH radical assay, and it was found that all the complexes have good radical scavenging capability. Molecular docking studies were also carried for all the metal complexes against EGFR as a target protein by using Autodock, and the results strongly correlated with the anticancer activity.
Highly efficient synthesis of 2-amino-3-pyridinecarboxaldehyde
Rivera,Hsiao,Cowen,McWilliams,Armstrong,Yasuda,Hughes
, p. 1573 - 1579 (2001)
2-Amino-3-pyridinecarboxaldehyde is synthesized in a highly efficient process via ortho-lithiation of 2-(pivaloyl-amino)pyridine and reaction with DMF, followed by acid hydrolysis. Major impurities were identified and were cleanly eliminated through careful choice of base and solvent.
A 1,8-naphthyridine-based fluorescent chemodosimeter for the rapid detection of Zn2+ and Cu2+
Yu, Ming-Ming,Li, Zhan-Xian,Wei, Liu-He,Wei, Dong-Hui,Tang, Ming-Sheng
, p. 5115 - 5118 (2008)
(Figure Presented) A novel fluorescent chemodosimeter based on 1,8-naphthyridine exhibits high selectivity to Zn2+ and Cu 2+. When 1-(7-acetamino-1,8-naphthyridyl)-2-(6-diacetaminopyridyl) ethene was mixed with CuCl2, hydrolysis of the acetamino group catalyzed by Cu2+ complex was first observed. Resulting from coordination and hydrolysis catalyzed by the corresponding complex of Zn 2+ or Cu2+, the highly effective fluorescent detection of Zn2+ and Cu2+ is realized with Zn2+-selective dual-emission and Cu2+-selective ON-OFF behavior.
A dual-model and on-off fluorescent Al3+/Cu2+- chemosensor and the detection of F-/Al3+ with 'in situ' prepared Al3+/Cu2+ complexes
Li, Xiaoya,Yu, Mingming,Yang, Faliu,Liu, Xingjiang,Wei, Liuhe,Li, Zhanxian
, p. 2257 - 2260 (2013)
A multifunctional fluorescent chemosensor for Al3+ and Cu 2+ has been developed, which displays a dual-model and on-off fluorescence response upon addition of Al3+ and Cu2+ respectively. The fluorescence signals of the chemosensor can be restored with F- and ethylenediaminetetraacetic acid (EDTA) disodium for Al 3+ and Cu2+, showing that the binding of the chemosensor and Al3+/Cu2+ is chemically reversible. The 'in situ' prepared Al3+ complex (1·Al) showed high selectivity toward F-, which can be applied to distinguish F- from Cl -, Br- and I-. Moreover, the fluorescence emission intensity of the 'in situ' prepared Cu2+ complex (1·Cu) is increased with the addition of Al3+, demonstrating that 1·Cu could be a good off-on Al3+ sensor candidate.
Non-alkylator anti-glioblastoma agents induced cell cycle G2/M arrest and apoptosis: Design, in silico physicochemical and SAR studies of 2-aminoquinoline-3-carboxamides
Gu, Xiangyu,Liu, Jianwen,Ni, Xintong,Qi, Yingxue,Qian, Xuhong,Shao, Xusheng,Xu, Xiaoyong,Yuan, Pengtao
, (2021/09/22)
Malignant gliomas are the most common brain tumors, with generally dismal prognosis, early clinical deterioration and high mortality. Recently, 2-aminoquinoline scaffold derivatives have shown pronounced activity in central nervous system disorders. We herein reported a series of 2-aminoquinoline-3-carboxamides as novel non-alkylator anti-glioblastoma agents. The synthesized compounds showed comparable activity to cisplatin against glioblastoma cell line U87 MG in vitro. Among them, we found that 6a displayed good inhibitory activity against A172 and U118 MG glioblastoma cell lines and induced cell cycle arrest in the G2/M phase and apoptosis in U87 MG by flow cytometry analysis. Additionally, 6a displayed low cytotoxicity to several normal human cell lines. In silico study showed 6a had promising physicochemical properties and was predicted to cross the blood–brain barrier. Moreover, preliminary structure–activity relationships are also investigated, shedding light on further modifications towards more potent agents on this series of compounds. Our results suggest this compound has a promising potential as an anti-glioblastoma agent with a differential effect between tumor and non-malignant cells.
Diruthenium complexes with a 1,8-Naphthyridine-based Bis(silyl) supporting ligand: Synthesis and structures of complexes containing RuII2(μ-H)2 and RuI2 cores
Kusuma, Indra,Komuro, Takashi,Tobita, Hiromi
, p. 400 - 403 (2018/03/27)
We designed a novel naphthyridine-based supporting ligand involving two silyl coordinating moieties at 2,7-positions, t-BuNBSi, for the synthesis of dinuclear metal complexes. Reaction of a ligand precursor t-BuNBSi(H)2 (1) with Ru3(CO)12 gave a di-μ-hydridodiruthenium(II,II) complex (t-BuNBSi)Ru2(μ-H)2(CO)4 (2). Photoirradiation to 2 resulted in the formation of a diruthenium(I,I) complex (t-BuNBSi)Ru2(CO)6 (3). The SiRuRuSi linkage of 2 takes a zigzag arrangement, whereas that of 3 adopts a roughly linear one.
Ugi three-component reaction of alcohols, amines and isocyanides: A new approach to the synthesis of cyclic amidines
Dev, Kapil,Ramakrishna,Maurya, Saransh Wales,Siddiqui, Ibadur Rahman,Kant, Ruchir,Maurya, Rakesh
supporting information, p. 1202 - 1206 (2017/03/02)
We have developed a novel, simple, efficient and one pot synthetic protocol for the synthesis of cyclic amidines via Ugi three-component reaction of alcohols, amines, and isocyanides.
A silicon-containing organic electroluminescent material and its application and its manufacturing device
-
, (2016/12/01)
The invention relates to a silicon-containing organic electroluminescent material and an application thereof as well as a device manufactured by using the silicon-containing organic electroluminescent material. The silicon-containing organic electroluminescent material is a compound which is formed by centering on naphthyridine substituted tetraphenyl-silicon and introducing substituent groups with relatively good electronic transmission performance into benzene rings. The silicon-containing organic electroluminescent material can serve as an electron transport layer of an organic electroluminescent device. The material provided by the invention has relatively good thin-film stability, appropriate energy level and wide application prospect in the organic electroluminescent device, can serve as an electron transport material to be applied to the organic electroluminescent device and is capable of remarkably improving the color purity of blue light devices.
A formaldehyde fast detection reagent and its preparation method and application
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, (2017/07/04)
The invention discloses a formaldehyde quick detection reagent, a preparation method and an application thereof. A chemical name of the formaldehyde quick detection reagent is 2-amino-3-(3-amino-1H-benzo[d]imidazole)-pyridine of which a chemical structure formula is represented as the formula I. The preparation method comprises following steps: (1) carrying out a reaction to a mixture consisting of nicotinamide and ammonium sulfamate in oil bath at 200 DEG C for 6 hours to obtain an intermediate 3; (2) performing temperature-increasing reflux to the intermediate 3 in an acid environment for 4 hours, cooling the intermediate 3 to room temperature and adjusting the pH value to 7-8 to obtain an intermediate 2; and (3) carrying out a reaction to the intermediate 2 with 1,2,4-triaminobenzene to obtain a target product. The reagent prepared according to the method hereinbefore can quite easily detect the concentration of formaldehyde. The formaldehyde quick detection reagent is simple in synthetic route, is low in cost, is convenient to use, is suitable for actual production application, is high in probe responding speed and is high in sensitivity. The reagent can achieve quick detection quantitatively and high-sensitively of the formaldehyde in environment and foods.
Piperazine analogs of naphthyridine-3-carboxamides and indole-2-carboxamides: Novel 5-HT3 receptor antagonists with antidepressant-like activity
Dhar, Arghya K.,Mahesh, Radhakrishnan,Jindal, Ankur,Bhatt, Shvetank
, p. 34 - 45 (2015/03/03)
Series of piperazine analogs of naphthyridine-3-carboxamides and indole-2-carboxamides were designed using a ligand-based approach with consideration of the pharmacophoric requirements for 5-HT3 receptor antagonists. The title carboxamides were synthesized using appropriate synthetic routes. Initially, the 5-HT3 receptor antagonistic activity of all the compounds was determined on isolated guinea pig ileum tissue against the 5-HT3 agonist, 2-methyl-5-hydroxytryptamine, which was denoted in the form of pA2 values. The structure-activity relationship regarding the influence of the aromatic part and basic moiety as features in the 5-HT3 pharmacophore was derived. Among all the compounds screened, the piperazine derivatives of indole-2-carboxamide 13i and naphthyridine-3-carboxamide 8h exhibited prominent 5-HT3 receptor antagonism with pA2 values of 7.5 and 7.3, respectively. Subsequent investigation of the antidepressant activities of selected compounds in the mouse forced swim test (FST) led to the identification of the piperazine analogs of indole-2-carboxamide 13i and naphthyridine-3-carboxamide 8h as the most promising compounds. Both 13i and 8h demonstrated significant reduction in the duration of immobility as compared to the control. Importantly, none of the tested compounds affected the baseline locomotion of mice at the tested dose levels.
