3281-08-1Relevant articles and documents
A Smart Molecule for Selective Sensing of Nitric Oxide: Conversion of NO to HSNO; Relevance of Biological HSNO Formation
Islam, Abu Saleh Musha,Bhowmick, Rahul,Pal, Kaberi,Katarkar, Atul,Chaudhuri, Keya,Ali, Mahammad
, p. 4324 - 4331 (2017)
A smart molecule, QT490, containing thiosemicarbazide moiety acts as a highly selective turn-on in vitro NO sensor through the unprecedented NO-induced transformation of thiosemicarbazide moiety to 1,3,4-oxadiazole heterocycle with the concomitant release of HSNO, thereby eliminating any interference from various endogenous biomolecules including dehydroascorbic acid, ascorbic acid, etc. The kinetic studies of the reactions between QT490 and NO provide a mechanistic insight into formation of HSNO/RSNO from the reaction between H2S/RSH and NO in the biological system. This novel probe is non-cytotoxic, cell permeable, water-soluble, and appropriate for intracellular cytoplasmic NO sensing with the possibilities of in vivo applications.
A novel ratiometric fluorescent probe for detection of Fe3+ by rhodamine-quinoline conjugate
Qin, Jing-Can,Yang, Zheng-Yin,Wang, Guan-Qun
, p. 122 - 127 (2015)
In this study, we have developed a novel ratiometric fluorescence probe (HL) which contains rhodamine and quinoline moiety. In the absence of Fe3+, the sensor displays fluorescence emission at 425 nm, in the presence of Fe3+, the sensor shows a large fluorescence enhancement at 550 nm in methanol. More importantly, the reversibility of the recognition process of HL is performed by adding a Fe3+ bonding agent Na2EDTA.
Both visual and ratiometric fluorescent sensor for Zn2+ based on spirobenzopyran platform
Zhu, Jian-Fa,Chan, Wing-Hong,Lee, Albert W.M.
, p. 2001 - 2004 (2012)
A ratiometric fluorescent Zn2+ chemosensor, SPQH, based on spirobenzopyran platform, was synthesized. In aqueous HEPES 7.4 buffer solution, upon chelation with Zn(II), SPQH demonstrates high selectivity and subnanomolar sensitivity for zinc ion with 36-fold enhancement in the NIR fluorescence output.
New N-(Aryl)-5-((quinolin-8-yloxy)methyl)-1,3,4-oxa/Thiadiazol-2-amines and 4-Aryl-5-((quinolin-8-yloxy)methyl)-2H-1,2,4-triazole-3(4H)-thiones, synthesis and characterization
Saeed, Aamer,Abbas, Naeem,Ibrar, Aliya,Bolte, Michael
, p. 1357 - 1362 (2015)
Figure presented In this study, methyl 2-(quinolin-8-yloxy) acetate (2) obtained by reaction of 8-hydroxyquinoline (1) with methyl chloroacetate was condensed with hydrazine hydrate to afford the carbohydrazide (3). Thio/semicarbazide derivatives (4a-g) w
Synthesis of some novel 3,4,5-trisubstituted triazole derivatives bearing quinoline ring and evaluation of their antimicrobial activity
Yurtta?, Leyla,Kubilay, Asl?han,Evren, Asaf Evrim,K?sac?k, ?pek,Karaca Gen?er, Hülya
, p. 767 - 773 (2020)
Some new 3,4,5-trisubstituted 1,2,4-triazole derivatives were synthesized and studied for their antimicrobial activity. The lead compounds were obtained starting from 8-hydroxyquinoline and ethyl 2-chloroacetate. The obtained ester compound (1) first reac
Synthesis, characterization and molecular docking of novel quinoline and pyridine derivatives
Saleh, Suheb,Al-Timari, Usama,Al-Fahdawi, Aeed,El-Khatatneh, Nasseem,Chandra,Mahendra,Al-Ghorbani6, Mohammed
, p. 2713 - 2719 (2017)
A new series of substituted quinoline and pyridine derivatives 6a-h are synthesized by the coupling of hydrazide derivatives 4a-b with substituted carboxylic acids 5a-c in the presence of N,N,N’,N’-tetramethyl-o-(benzotriazol-1-yl) uranium tetrafluoroborate TBTU as a coupling agent and lutidine as a base. The newly synthesized compounds 6a–l is characterized by analytical NMR and mass spectral data. The newly synthesized compounds were subjected to molecular docking studies for the inhibition of human Aurora A kinase target to evaluate their potential value for the treatment of cancers.
Nitric Oxide Sensing through 1,2,3,4-Oxatriazole Formation from Acylhydrazide: A Kinetic Study
Islam, Abu Saleh Musha,Bhowmick, Rahul,Chandra Garain, Bidhan,Katarkar, Atul,Ali, Mahammad
, p. 13287 - 13295 (2018)
A simple molecular probe displays highly selective turn-on response toward NO by the unprecedented NO-induced formation of a 1,2,3,4-oxatriazole ring exhibiting no interference from various endogenous biomolecules including DHA, AA, etc. Kinetics of the reactions between NO and the probe provide a mechanistic insight into the formation of 1,2,3,4-oxatriazole which showed that, though initially 1,2,3,4-oxatriazole is formed and extractable in solid form, it exists in equilibrium with the ring opened azide form which ultimately hydrolyzed and converted to carboxylic acid and nitrate. The reaction displays second-order dependence on [NO] and first-order on [Probe]. The probe is water-soluble, cell permeable, and noncytotoxic and appropriates for live cell imaging. This constitutes the first report where there is a direct evidence of NO-induced ring closing reaction of an acyl hydrazide moiety leading to the formation of 1,2,3,4-oxatriazole.
β-Hydroxy-α-naphthaldehyde [2-(quinolin-8′-yloxy) acetyl] hydrazone as an efficient fluorescent chemosensor for Mg2+
Qin, Jing-Can,Yang, Zheng-Yin,Fan, Long,Wang, Bao-Dui
, p. 21 - 26 (2015)
An efficient fluorescent sensor based on β-hydroxy-α-naphthaldehyde [2-(quinolin-8′-yloxy) acetyl] hydrazone (HL) for Mg2+ has been designed and synthesized. The receptor showed "off-on" fluorescent responses toward Mg2+ in acetonitrile. The reasons for this phenomenon is that the addition of Mg2+ to the solution of HL induce the formation of a 1:1 ligand-metal complex which inhibit excited-state intramolecular proton transfer (ESIPT).
Synthesis of indole–quinoline–oxadiazoles: their anticancer potential and computational tubulin binding studies
Kamath, Pooja R.,Sunil, Dhanya,Ajees, Abdul A.
, p. 5899 - 5914 (2016)
Abstract: Small hybrid molecules with two or more structural pharmacores having different biological functions and distinct activity have gained a significant role in cancer drug development to combat various types of malignancies. The present study describes an efficient, clean and strategic synthesis of 12 new substituted quinoline–indole–oxadiazole hybrids from substituted 2-(quinolin-8-yloxy)acetohydrazides and indole-3-carboxylic acids by employing T3P as a green catalyst. Structures of the newly synthesized compounds were established by IR, 1H NMR, 13C NMR, DEPT C-NMR and MS spectroscopic evidence, as well as CHN analysis data. All indole–quinoline–oxadiazoles were tested for their in vitro cytotoxic potential in breast adenocarcinoma (MCF7) and normal kidney (vero) cell lines using MTT assay. 8-((5-(3-(1H-indol-3-yl)propyl)-1,3,4-oxadiazol-2-yl)methoxy)quinoline (3d) exhibited a low IC50 value and a high selectivity index to MCF7 cells and also displayed a mitotic block in flow cytometric cell cycle progression analysis. Microtubule disruption can induce G2/M phase cell cycle arrest leading to abnormal mitotic spindle formation. Ligand 3d demonstrated its capability of being a probable tubulin inhibitor when docked in the colchicine domain of tubulin. Graphical Abstract: New series of 8-((5-((1H-indol-3-yl)methyl)-1,3,4-oxadiazol-2-yl)methoxy)quinolines were synthesized using T3P as a green catalyst and screened for their cytotoxic and antimitotic potential. The most active 8-((5-(3-(1H-indol-3-yl)propyl)-1,3,4-oxadiazol-2-yl)methoxy)quinoline?3d, displayed good binding interactions with the colchicine binding cavity of microtubule.[Figure not available: see fulltext.]
Novel Pyrazoline-based Organometallic Compounds Containing Ferrocenyl and Quinoline units: Synthesis, Characterization and Microbial susceptibilities
Parveen, Humaira,Alatawi, Raedah Aiyed Suliman,Alsharif, Meshari A.,Alahmdi, Mohammed Issa,Mukhtar, Sayeed,Khan, Salman Ahmad,Hasan, Sadaf,Khan, Asad U.
, (2018)
Some novel pyrazoline-based organometallic compounds were synthesized as new leads in antimicrobial chemotherapy. The structures of compounds were elucidated by different spectroscopic techniques and elemental analyses. All compounds were investigated for in vitro antimicrobial studies against fifteen ATTC bacterial and fungal strains. The microbial susceptibility of these compounds revealed that all the tested compounds gave good minimum inhibitory concentration (MIC) values against the tested organisms that are either similar or even better than the reference drugs amoxicillin and fluconazole, which gave MIC values 8-64?μg/ml against bacterial and 64?μg/ml against fungal strains, respectively. Among all compounds, compound (4d). 1-(5-(4-chlorophenyl)-3-ferrocenyl-4,5-dihydropyrazol-1-yl)-2-quinolin-8-yloxy) ethanone, emerged out the most promising antimicrobial organometallic derivative with MIC values against all the strains ranging from 8-32?μg/ml. Other compounds gave a range of MIC values between 16-64?μg/ml against S. bovis, 16-32?μg/ml against E. coli, and C. tropicalis except compound (4d) which gave MIC 8?μg/ml against S. bovis and E. coli, whereas 32?μg/ml against C. tropicalis. Collectively, these compounds gave a lower MIC value between 32-64?μg/ml against both of the biofilm forming strains namely, P. aeruginosa and S. mutans. The results of microbial susceptibility concluded that these novel organometallic compounds are new leads in antimicrobial chemotherapy and can be very useful for further optimization work on microbial chemotherapy.
