- Synthesis, characterization, biological screening and molecular docking studies of 2-aminonicotinaldehyde (ANA) and its metal complexes
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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.
- Konakanchi, Ramaiah,Mallela, Ramachary,Guda, Ramu,Kotha, Laxma Reddy
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- Highly efficient synthesis of 2-amino-3-pyridinecarboxaldehyde
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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.
- Rivera,Hsiao,Cowen,McWilliams,Armstrong,Yasuda,Hughes
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- A 1,8-naphthyridine-based fluorescent chemodosimeter for the rapid detection of Zn2+ and Cu2+
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(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.
- Yu, Ming-Ming,Li, Zhan-Xian,Wei, Liu-He,Wei, Dong-Hui,Tang, Ming-Sheng
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- A dual-model and on-off fluorescent Al3+/Cu2+- chemosensor and the detection of F-/Al3+ with 'in situ' prepared Al3+/Cu2+ complexes
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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.
- Li, Xiaoya,Yu, Mingming,Yang, Faliu,Liu, Xingjiang,Wei, Liuhe,Li, Zhanxian
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- 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
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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.
- Gu, Xiangyu,Liu, Jianwen,Ni, Xintong,Qi, Yingxue,Qian, Xuhong,Shao, Xusheng,Xu, Xiaoyong,Yuan, Pengtao
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- 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
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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.
- Kusuma, Indra,Komuro, Takashi,Tobita, Hiromi
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p. 400 - 403
(2018/03/27)
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- Ugi three-component reaction of alcohols, amines and isocyanides: A new approach to the synthesis of cyclic amidines
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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.
- Dev, Kapil,Ramakrishna,Maurya, Saransh Wales,Siddiqui, Ibadur Rahman,Kant, Ruchir,Maurya, Rakesh
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supporting information
p. 1202 - 1206
(2017/03/02)
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- A silicon-containing organic electroluminescent material and its application and its manufacturing device
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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.
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- A formaldehyde fast detection reagent and its preparation method and application
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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.
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- Piperazine analogs of naphthyridine-3-carboxamides and indole-2-carboxamides: Novel 5-HT3 receptor antagonists with antidepressant-like activity
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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.
- Dhar, Arghya K.,Mahesh, Radhakrishnan,Jindal, Ankur,Bhatt, Shvetank
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- Design, Synthesis, and Pharmacological Evaluation of Novel 2-(4-substituted piperazin-1-yl)1, 8 Naphthyridine 3-Carboxylic Acids as 5-HT3 Receptor Antagonists for the Management of Depression
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1, 8-naphthyridine-3-carboxylic acid analogs were synthesized and found to possess potential 5-HT3 receptor antagonism as well as antidepressant-like activity. Initially, 5-HT3 receptor antagonism of all the compounds was determined in the form of pA2 value against agonist 2-methyl 5-HT in longitudinal muscle-myenteric plexus preparation from Guinea-pig ileum. Among all the compounds tested, compound 7a demonstrated most promising pA2 value of 7.6. Subsequently, all the compounds were evaluated for antidepressant activity using forced swim test and tail suspension test in mice. Compounds 7a, 7d, 7f, 7h, and 7i exhibited significant (p 0.05) antidepressant-like activity as compound to vehicle-treated group. Importantly, none of the tested compound affected locomotor activity of mice at tested dose levels.
- Dhar, Arghya K.,Mahesh, Radhakrishnan,Jindal, Ankur,Devadoss, Thangaraj,Bhatt, Shvetank
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p. 721 - 731
(2015/08/25)
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- Highly efficient electron-transporting/injecting and thermally stable naphthyridines for organic electrophosphorescent devices
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A series of 1,8-naphthyridine derivatives is synthesized and their electron-transporting/injecting (ET/EI) properties are investigated via a multilayered electrophosphorescent organic light-emitting device (OLED) using fac-tris(2-phenylpyridine)iridium [Ir(ppy)3] as a green phosphorescent emitter doped into a 4,4′-N,N′-dicarbazolebiphenyl (CBP) host with 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (a-NPD) as the hole-transporting layer, and poly(arylene ether sulfone) containing tetraphenylbenzidine (TPDPES) doped with tris(4-bromophenyl)ammonium hexachloroantimonate (TBPAH) as the hole-injecting layer. The turn-on voltage of the device is 2.5 V using 2,7-bis[3-(2-phenyl)-1,8-naphthyridinyl]-9,9- dimethylfluorene (DNPF), lower than that of 3.0 V for the device using a conventional ET material. The maximum current efficiency (CE) and power efficiency (PE) of the DNPF device are much higher than those of a conventional device. With the aid of a hole-blocking (HB) and exciton-blocking layer of bathocuproine (BCP), 13.2-13.7% of the maximum external quantum efficiency (EQE) and a maximum PE of 50.2-54.5 lm W-1 are obtained using the naphthyridine derivatives; these values are comparable with or even higher than the 13.6% for conventional ET material. The naphthyridine derivatives show high thermal stabilities, glass-transition temperatures much higher than that of aluminum(III) bis(2-methyl-8-quinolinato)-4-phenylphenolate (BAlq), and decomposition temperatures of 510-518 °C, comparable to or even higher than those of Alq3. A series of 1,8-naphthyridine derivatives with high thermal stabilities are synthesized and their electron-transporting properties for green electrophosphorescence are investigated via a multilayered organic light-emitting device using fac-tris(2-phenylpyridine)iridium [Ir(ppy) 3] as the phosphorescent emitter. A maximum external quantum efficiency of 13.2-13.7% and a maximum power efficiency of 50.2-54.5 lm W -1 are obtained using the naphthyridine derivatives. Copyright
- Xiao, Lixin,Xing, Xing,Chen, Zhijian,Qu, Bo,Lan, Hsinglin,Gong, Qihuang,Kido, Junji
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p. 1323 - 1330
(2013/05/21)
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- Cyanoacetamides (IV): Versatile one-pot route to 2-quinoline-3-carboxamides
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Cyanoacetic acid derivatives are the starting materials for a plethora of multicomponent reaction (MCR) scaffolds. Herein, we describe scope of a valuable general protocol for the synthesis of arrays of 2-aminoquinoline-3-carboxamides from cyanoacetamides and 2-aminobenzaldehydes or heterocyclic derivatives via a Friedlaender reaction variation. In many cases, the reactions involve a very convenient work up by simple precipitation and filtration. More than 40 new products are described. We foresee our protocol and the resulting derivatives becoming very valuable to greatly expanding the scaffold space of cyanoacetamide derivatives.
- Wang, Kan,Herdtweck, Eberhardt,Doemling, Alexander
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scheme or table
p. 316 - 322
(2012/06/18)
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- Silver and gold complexes with a new 1,10-phenanthroline analogue n-heterocyclic carbene: A combined structural, theoretical, and photophysical study
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Unusual coordination for gold: An imidazolium salt was synthesized and used as a precursor for an N-heterocyclic carbene, which can be considered as the carbene analogue of 1,10-phenanthroline. Like the diimine congener, this ligand gives luminescent metal complexes. Remarkably, the AuIII complex features a gold atom in an unusual environment: it is surrounded by six donor atoms, two of which interact electrostatically with the Au atom (see figure).
- Kriechbaum, Margit,List, Manuela,Berger, Raphael J.F.,Patzschke, Michael,Monkowius, Uwe
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body text
p. 5506 - 5509
(2012/06/01)
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- An efficient synthesis of 2-amino-5-chloro-3-pyridinecarbox-aldehyde and 5-amino-2-chloro-4-pyridinecarboxaldehyde
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Efficient synthetic routes to the title compounds 2-amino-5-chloro-3- pyridinecarboxaldehyde (1a) and 5-amino-2-chloro-4-pyridinecarboxaldehyde (1b) are reported. Both compounds are important substrates in the synthesis of naph-thyridine derivatives. Copyright by Walter de Gruyter Berlin Boston.
- Hou, Chuan-Jin,Guo, Wei-Lei,Liu, Xiao-Ning,Yang, Da-Wei
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experimental part
p. 21 - 23
(2011/10/02)
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- NOVEL ANTIMALARIA AGENT CONTAINING HETEROCYCLIC COMPOUND
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Disclosed is an antimalarial agent containing a compound represented by the formula: [wherein A1 represents a 3-pyridyl group that may have a substituent, a 6-quinolyl group that may have a substituent, or the like; X1 represents a group represented by the formula -C(=O)-NH- or the like; E represents a furyl group, a thienyl group or a phenyl group; with the proviso that A1 may have one to three substituents, and E has one of two substituents] or a salt thereof or hydrates thereof.
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Page/Page column 59
(2008/06/13)
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- NOVEL ANTIFUNGAL AGENT COMPRISING HETEROCYCLIC COMPOUND
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The present invention provides an antifungal agent represented by the formula: [wherein A1 represents a 3-pyridyl group which may have a substituent, a quinolyl group which may have a substituent, or the like; X1 represents a group represented by the formula -NH-C(=O)-, a group represented by the formula -C(=O)-NH-, or the like; E represents a furyl group, a thienyl group, a pyrrolyl group, a phenyl group, a pyridyl group, a tetrazolyl group, a thiazolyl group or a pyrazolyl group; with the proviso that A1 may have 1 to 3 substituents, and E has one or two substituents].
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(2010/11/08)
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- Non-peptidic αvβ3 antagonists containing indol-1-yl propionic acids
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We describe the synthesis and structure/activity relationship of RGD mimetics that are potent inhibitors of the integrin αvβ 3. Indol-1-yl propionic acids containing a variety of basic moieties at the 5-position, as well as substitutions alpha and beta to the carboxy terminus were synthesized and evaluated. Novel compounds with improved potency have been identified.
- Leonard, Kristi,Pan, Wenxi,Anaclerio, Beth,Gushue, Joan M.,Guo, Zihong,DesJarlais, Renee L.,Chaikin, Marge A.,Lattanze, Jennifer,Crysler, Carl,Manthey, Carl L.,Tomczuk, Bruce E.,Marugan, Juan Jose
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p. 2679 - 2684
(2007/10/03)
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- Cycloalkyl alkanoic acids as integrin receptor antagonists derivatives
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The present invention relates to a class of compounds represented by the Formula I or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of the Formula I, and methods of selectively inhibiting or antagonizing the αvβ3 and/or αvβ5 integrin.
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- VITRONECTIN RECEPTOR ANTAGONISTS
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Compounds of formula (I) are disclosed which are vitronectin receptor antagonists and are useful in the treatment of osteoporosis wherein R is Het- or Ar; R is formula (a) or formula (b); or a pharmaceutically acceptable salt thereof.
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- Cycloalkyl alkanoic acids as integrin receptor antagonists derivatives
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The present invention relates to a class of compounds represented by the Formula I or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of the Formula I, and methods of selectively inhibiting or antagonizing the αvβ3 and/or αvβ5 integrin.
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- A new quadruply bound heterodimer DDAD·AADA and investigations into the association process
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DDAD·AADA heterodimers based on the structures 8 and 9 have been synthesised and characterised. Solubility problems have been overcome through the introduction of a 2,6-dimethylphenyl substituent (8c), and association constants Kass have been determined by 1H NMR titrations. The Kass values obtained could be confirmed by osmometry, as could the association constants for other heterodimers. The Kass value increases when the acidity of participating N-H hydrogen atoms is enhanced. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
- Brammer, Stefan,Luening, Ulrich,Kuehl, Christine
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p. 4054 - 4062
(2007/10/03)
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- Bicyclic alphavbeta3 antagonists
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The present invention relates to a class of compounds represented by the Formula I or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of the Formula I, and methods of selectively inhibiting or antagonizing the αvβ3 and/or αvβ5 integrin.
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- Cycloalkyl alkanoic acids as integrin receptor antagonists
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The present invention relates to a class of compounds represented by the Formula I or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of the Formula I, and methods of selectively inhibiting or antagonizing the αVβ3 and/or αVβ5 integrin.
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- SYNTHESIS OF PYRROLOQUINOLINE AND PYRROLONAPHTHYRIDINE BY AN INTRAMOLECULAR CYCLISATION REACTION
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4-methylthiopyrrolonaphthyridine and pyrroloquinoline were prepared by an intramolecular cyclisation in acidic media of 1-methylsulfinyl-1-methylthio-2-ethylene.
- Cardinaud, Isabelle,Gueiffier, Alain,Debouzy, Jean-Claude,Milhavet, Jean-Claude,Chapat, Jean-Pierre
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p. 2513 - 2522
(2007/10/02)
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- A FACILE SYNTHESIS OF 2-AMINONICOTINALDEHYDE
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A synthesis of 2-aminonicotinaldehyde (1) which does not require chromatography and is easily scaled up has been developed.Bromination of 2-amino-3-picoline, protected as a phthalimide (4), produced the gem-dibromide (5), which was reacted with NH4OH.The imine intermediate (7) was hydrolyzed with acid, producing (1) in a 56percent conversion from 4.
- Moormann, Alan E.,Yen, Chung H.,Yu, Stella
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p. 1695 - 1700
(2007/10/02)
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- Ring Opening and Transamination of Pyridinium Salts
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N-Alkyl-3-cyanopyridinium iodides (Ia-c) undergo ring opening and recyclization when heated with aq. alkyl amine to give 2-alkylamino-3-formylpyridines (IIa-c) and 3-cyanopyridine (III).However, when compounds Ia-c are treated with alkyl amines in which t
- Fadda, A. A.,Abdelrazek, F. M.,El-Habbal, M. M.
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p. 194 - 195
(2007/10/02)
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- Regiospecific Electrophilic Substitution of Aminopyridines: Ortho Lithiation of 2-, 3-, and 4-(Pivaloylamino)pyridines
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2- and 4-(pivaloylamino)pyridines have been shown to undergo metalation exclusively at C-3 and these smoothly react with a variety of electrophiles to produce 2,3- and 3,4-disubstituted pyridines, respectively.Removal of the pivaloyl protecting group results in overall electrophilic substitution of an aminopyridine.Utilization of this method is exemplified by efficient syntheses of 2- and 4-aminonicotinaldehydes.Minor modifications of the reaction conditions permitted exclusive ortho metalation of 2-(pivaloylamino)pyridines additionally functionalized by chloro, fluoro, or methyl groups.Although the major product from reaction of 3-(pivaloylamino)pyridine by this method was metalation at C-4, the reaction was complicated by substantial quantities of product derived from nucleophilic attack by n-butyllithium on the pyridine nucleus.
- Turner, James A.
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p. 3401 - 3408
(2007/10/02)
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