21979-59-9Relevant academic research and scientific papers
A Concave Fluorescent Sensor for Anions Based on 6-Methoxy-1-methylquinolinium
Amendola, Valeria,Fabbrizzi, Luigi,Monzanita, Enrico
, p. 76 - 82 (2004)
The ligand 2, in which three fluorogenic 6-methoxy-1-methylquinolinium fragments are appended to a mesityl platform, in MeCN forms 1:1 adducts with halides and other inorganic anions. 1H NMR studies and molecular modelling indicate that 2 provides a cavity for anion inclusion and establishes electrostatic interactions with the guest. Anion inclusion induces quenching of the fluorogenic fragments with an efficiency decreasing along the series Br - ? I- > NCS- ? Cl- > NO3- > > HSO4-. The fluorimetric response of 2 to anions is orders of magnitude more sensitive than that of just 6-methoxy-1-methylquinolinium, ligand 1.
Iodination/Amidation of the N-Alkyl (Iso)quinolinium Salts
Tang, Juan,Chen, Xue,Zhao, Chao-Qun,Li, Wen-Jing,Li, Shun,Zheng, Xue-Li,Yuan, Mao-Lin,Fu, Hai-Yan,Li, Rui-Xiang,Chen, Hua
supporting information, p. 716 - 730 (2020/12/22)
The NaIO4-mediated sequential iodination/amidation reaction of N-alkyl quinolinium iodide salts has been first developed. This cascade process provides an efficient way to rapidly synthesize 3-iodo-N-alkyl quinolinones with high regioselectivity and good functional group tolerance. This protocol was also amenable to the isoquinolinium salts, thus providing a complementary method for preparing the 4-iodo-N-alkyl isoquinolinones.
Design, Synthesis, and Antifungal Evaluation of Neocryptolepine Derivatives against Phytopathogenic Fungi
Gao, Jian-Mei,Lawoe, Raymond Kobla,Liu, Ying-Qian,Shang, Xiao-Fei,Sun, Yu,Yang, Cheng-Jie,Yin, Xiao-Dan,Zhao, Zhong-Min,Zhou, Rui,Zhu, Jia-Kai
, p. 2306 - 2315 (2020/03/10)
Neocryptolepine is an alkaloid isolated from traditional African herbal medicine Cryptolepis sanguinolenta, and its broad spectrum of biological activities has been illuminated in past decades. In this study, neocryptolepine and its derivatives (1-49) were designed and synthesized from economical and readily available starting materials. Their structures were confirmed by proton nuclear magnetic resonance, carbon nuclear magnetic resonance, and mass spectrometry. The synthesized compounds were screened for their antifungal profile against six agriculturally important fungi Rhizoctonia solani, Botrytis cinerea (B. cinerea), Fusarium graminearum, Mycosphaerella melonis, Sclerotinia sclerotiorum, and Magnaporthe oryzae. The results of in vitro assay revealed that compounds 5, 21, 24, 35, 40, 45, and 47 presented remarkable antifungal activity against the fungi tested with EC50 values lower than 1 μg/mL. Significantly, compound 24 displayed the most effective inhibitory potency against B. cinerea (EC50 = 0.07 μg/mL), and the data from in vivo experiments revealed that compound 24 demonstrated comparable protective activity with the positive control boscalid. Preliminary mechanism studies indicated that compound 24 showed impressive spore germination inhibitory effectiveness and lower cytotoxicity than azoxystrobin, imparted on normal function of the cell membrane and cell wall, and arrested the normal function of the nucleus. Besides the excellent inhibitory activity against agriculturally important phytopathogenic fungi tested, the designed assemblage possesses several benefits with a high profile of variation in synthesized molecules, the ease of synthesis, and good cost-effectiveness of commercially available synthetic reagents, all of these have highlighted the potential worth of compound 24 as a new and highly efficient agricultural fungicide.
Diastereoselective Synthesis of Novel Pyrrolidine or Pyrrolizine-Fused Benzo-δ-sultams via 1,3-Dipolar Cycloadditions
Ghandi, Mehdi,Kia, Maryam Asle,Sadeghzadegh, Masoud,Bozcheloei, Abolfazl Hasani,Kubicki, Maciej
, p. 1646 - 1653 (2015/02/19)
The synthesis of novel pyrrolidine or pyrrolizine-fused benzosultams is described. A number of (E)-N-(2-formylphenyl)-N-alkyl-2-phenylethenesulfonamides derivatives were synthesized and subjected to intramolecular [3+2] cycloaddition with azomethine ylides derived in situ from the reaction with sarcosine, phenylglycine, and L-proline.
Synthesis of novel tetra- and pentacyclic benzosultam scaffolds via domino Knoevenagel hetero-Diels-Alder reactions in water
Ghandi, Mehdi,Sheibani, Shahab,Sadeghzadeh, Masoud,Daha, Fariba Johari,Kubicki, MacIej
, p. 1057 - 1065 (2013/11/06)
An efficient catalyst-free and diastereoselective synthesis of novel dihydropyrano[2,3-d]pyrimidine and dihydropyrano[3,2-c]chromen-annulated benzosultams is described. A number of (E)-N-(2-formylphenyl)-N-methyl-2- phenylethenesulfonamides were synthesized and underwent a one-pot domino Knoevenagel hetero-Diels-Alder reaction, respectively, with N,N- dimethylbarbituric acid and 4-hydroxycoumarin in water, giving the desired products, in moderate to excellent yields.
Facile synthesis of 1-Methyl-1 H -benzo[ b ]azepines from 1-methylquinolinium iodides and diazo(trimethylsilyl)methylmagnesium bromide
Morita, Mikio,Hari, Yoshiyuki,Aoyama, Toyohiko
experimental part, p. 4221 - 4227 (2011/02/22)
The reaction of diazo(trimethylsilyl)methylmagnesium bromide, TMSC(MgBr)N2, with 1-methylquinolinium iodides followed by sequential ring expansion using copper(I) chloride gives 1-methyl-3-(trimethylsilyl)-1H- benzo[b]azepines in moderate to go
Synthesis of tetrahydroquinolines, hexahydrobenzoindolizines and an aryl phosphonate linker for the generation of catalytic antibodies
Gonzalez-Bello, Concepcion,Abell, Chris,Leeper, Finian J.
, p. 1017 - 1024 (2007/10/03)
Syntheses of 6-methoxy-1-methyl-1,2,3,4-tetrahydroquinoline-3-methanol 10 and 1,2,3,5,6,10b-hexahydrobenzo[g]indolizine-6-methanol 34 are described. The aryl phosphonic acid 14, which can be used as a linker to a protein, is synthesised and coupled to the above alcohols. These haptens, when linked to a protein, are intended to generate antibodies able to catalyse cationic cyclisation reactions.
