18542-45-5Relevant academic research and scientific papers
Synthesis, structure, and growth-promoting activity of 1-alkyl-4-(3- naphthyloxyprop-1-ynyl)piperidin-4-ols
Omirzak,Erkasov,Sukhov,Ganenko
, p. 2442 - 2444 (2013)
Alkylation of 1- and 2-naphthols with propargyl bromide in acetone in the presence of potassium carbonate led to prop-2-ynyloxynaphthalenes, which upon reaction with 1-alkyl-piperidin-4-ones under the Favorsky conditions afforded the corresponding tertiary alcohols. 1-Methyl-4-[3-(2-naphthyloxy)prop-1-ynyl] piperidin-4-ol hydrochloride was found to possess a high growth-promoting activity in the concentration of 0.001% upon the pre-sowing treatment of beetroot seeds and potatoes and increase their productivity by -20%.
Synthesis of functionalized β-cyclodextrins by "click chemistry"
Ke, Chenfeng,Yang, Cheng,Yang, Zixin,Wu, Weijia,Mori, Tadashi,Inoue, Yoshihisa,Liu, Yu
, p. 155 - 160 (2008)
Two new β-cyclodextrins (β-CDs) modified with chromophore were synthesized in high yields through Huisgen 1,3-dipolar cycloaddition. The amount of Cu catalyst was demonstrated to be a key factor that determines the yield of the 1,3-dipolar cycloaddition when applied to CD derivatization. While a catalytic amount of Cu-catalyst is commonly required in conventional click chemistry, more than a half equivalent of Cu catalyst was desirable for obtaining the modified CDs in satisfactory yields. The Japan Institute of Heterocyclic Chemistry.
Effect of quinoline based 1,2,3-Triazole and its structural analogues on growth and virulence attributes of Candida albicans
Irfan, Mohammad,Alam, Shadab,Manzoor, Nikhat,Abid, Mohammad
, (2017)
Candida albicans, along with some other non-Albicans Candida species, is a group of yeast, which causes serious infections in humans that can be both systemic and superficial. Despite the fact that extensive efforts have been put into the discovery of novel antifungal agents, the frequency of these fungal infections has increased drastically worldwide. In our quest for the discovery of novel antifungal compounds, we had previously synthesized and screened quinoline containing 1,2,3-Triazole (3a) as a potent Candida spp inhibitor. In the present study, two structural analogues of 3a (3b and 3c) have been synthesized to determine the role of quinoline and their anti-Candida activities have been evaluated. Preliminary results helped us to determine 3a and 3b as lead inhibitors. The IC50 values of compound 3a for C. albicans ATCC 90028 (standard) and C. albicans (fluconazole resistant) strains were 0.044 and 2.3 μg/ml, respectively while compound 3b gave 25.4 and 32.8 μg/ml values for the same strains. Disk diffusion, growth and time kill curve assays showed significant inhibition of C. albicans in the presence of compounds 3a and 3b. Moreover, 3a showed fungicidal nature while 3b was fungistatic. Both the test compounds significantly lower the secretion of proteinases and phospholipases. While, 3a inhibited proteinase secretion in C. albicans (resistant strain) by 45%, 3b reduced phospholipase secretion by 68% in C. albicans ATCC90028 at their respective MIC values. Proton extrusion and intracellular pH measurement studies suggested that both compounds potentially inhibit the activity of H+ ATPase, a membrane protein that is crucial for various cell functions. Similarly, 95±97% reduction in ergosterol content was measured in the presence of the test compounds at MIC and MIC/2. The study led to identification of two quinoline based potent inhibitors of C. albicans for further structural optimization and pharmacological investigation.
Molecular binding thermodynamics of spherical guests by β-cyclodextrins bearing aromatic substituents
Li, Nan,Chen, Yong,Zhang, Ying-Ming,Wang, Li-Hua,Mao, Wen-Zhao,Liu, Yu
, p. 18 - 26 (2014)
The molecular binding behaviors of two β-cyclodextrin (β-CD) derivatives bearing 1,2,3-triazole moieties, i.e. mono-6-deoxy-6-{4-(8- oxymethylquinolino)[1,2,3]triazolyl}-β-CD (1) and mono-6-deoxy-6-{4-(8- oxymethylnaphthol)[1,2,3]triazolyl}-β-CD (3), and their analogs without 1,2,3-triazole moieties, i.e. mono-6-deoxy-6-(8-oxymethylquinolino)-β-CD (2) and mono-6-deoxy-6-(8-oxymethylnaphthol)-β-CD (4) toward spherical guests (±)-borneol and (±)-camphor were investigated to elucidate how substituent moiety of host affects the binding abilities by 2D NMR as well as microcalorimetric titrations in aqueous phosphate buffer solution (pH 7.20) at 298.15 K. The binding modes of host-guest interactions obtained from 2D NMR displayed that host CDs without triazole moieties gave better induce-fit efficiency between hosts and guests, leading to stronger binding abilities. Thermodynamically, the inclusion complexation was driven by enthalpy with the stoichiometry of 1:1. Another factor contributed to the enhanced binding abilities was the enthalpy gain with the smaller entropy loss.
Synthesis and photophysical properties of 1, 4-disubstituted naphthyloxymethyl-N-alkyl naphthimido-1,2,3-triazole
Ramchander,Rameshwar,Reddy, T Sheshashena,Raju, Gajula,Reddy, A Ram
, p. 1063 - 1074 (2014)
Regioselective synthesis of a series of 1,4-disubstituted of naphthoxymethyl-N-alkyl naphthalimide-1,2,3-triazoles employing click reaction is presented. Highly selective and efficient copper(I)-catalysed 1,3-dipolar cyclo addition between 1-naphthylpropargylic ether and azido alkyl naphthalimides yielded the title compounds in 74% to 94%. The structure of all the new 1,2,3-triazoles was characterized by 1HNMR, 13C NMR, IR and Mass. The electronic absorption and emission studies revealed that the light absorbing and emitting chromophore is the naphthoxy moiety. There is no extensive delocalization of aromatic π-electrons in the active chromophore which exhibited lower quantum yields and lower Stokes shifts.
A Chemoenzymatic Cascade Combining a Hydration Catalyst with an Amine Dehydrogenase: Synthesis of Chiral Amines
Chang, Fengwei,Chen, Qipeng,Liu, Guohua,Wang, Chengyi,Zhang, Yongjin
supporting information, (2022/01/19)
The combination of biocatalysis and transition-metal catalysis can complement synthetic gaps only in a chemical or biological process. However, the intrinsic mutual deactivation between enzymatic and chemical species is a significant challenge in a single
A novel series of substituted 1,2,3-triazoles as cancer stem cell inhibitors: Synthesis and biological evaluation
Padhariya, Komal N.,Athavale, Maithili,Srivastava, Sangeeta,Kharkar, Prashant S.
, p. 68 - 85 (2020/08/14)
An alarming increase in global death toll resulting from cancer incidents, particularly due to multidrug resistance and reduced efficacy as a consequence of target mutations, has compelled us to look for novel anticancer agents. Cancer stem cells (CSCs),
Unusual absence of FRET in triazole bridged coumarin-hydroxyquinoline, an active sensor forHg2+detection
Chatterjee, Soumit,Dey, Swapan,Hira, Sumit K.,Mondal, Surajit,Nayek, Hari Pada,Patra, Niladri
, p. 1211 - 1221 (2020/10/02)
A triazole-bridged coumarin conjugated quinoline sensor has been ‘click’-synthesized by Cu(i) catalyzed Huisgen cycloaddition, and it exhibited high selectivity for toxicHg2+. Surprisingly, no evidence of energy transfer from the quinoline moiety to coumarin has been found, substantiated by time-resolved fluorescence study. The possible binding mode of this sensor toHg2+has been establishedviaNMR study, steady-state and time-resolved fluorescence spectroscopy, which is further supported by TDDFT calculations. The sensor has been found to be cell membrane permeable and non-toxic, and hence is suitable for intracellularHg2+detection.
Synthesis, antibacterial, and antioxidant activities of naphthyl-linked disubstituted 1,2,3-triazoles
Kaushik, Chander Prakash,Luxmi, Raj
, p. 2400 - 2409 (2020/03/16)
Here, click synthesis of 15 naphthyl-linked disubstituted 1,2,3-triazoles has been carried out by the reaction between 1-(prop-2-yn-1-yloxy)naphthalene and aromatic azides. The structure elucidation of the synthesized compounds was carried out by FTIR, s
Copper-Catalyzed Ring Opening of [1.1.1]Propellane with Alkynes: Synthesis of Exocyclic Allenic Cyclobutanes
Lasányi, Dániel,Tolnai, Gergely L.
supporting information, p. 10057 - 10062 (2019/12/24)
Despite the long history and interesting properties of propellanes, these compounds still have tremendous potential to be exploited in synthetic organic chemistry. Herein we disclose an experimentally simple procedure to achieve cyclobutane-containing allenes and alkynes through a copper-catalyzed ring opening of [1.1.1]propellane and subsequent reaction with ethynes.
