6952-34-7Relevant academic research and scientific papers
A new boronic acid based fluorescent reporter for catechol
Wu, Zhongyu,Li, Minyong,Fang, Hao,Wang, Binghe
, p. 7179 - 7182 (2012)
Catechol skeleton widely exists in natural products and bioactive substances. Fluorescent reporters which could recognize catechol are very promising for the construction of chemosensors to detect catechol and its derivatives in biological environment. Herein, we reported a novel catechol reporter, 2-(4-boronophenyl)quinoline-4-carboxylic acid, which exhibits significant fluorescent property changes upon binding catechol containing molecules in an aqueous solution.
Water-soluble diboronic acid-based fluorescent sensors recognizing d-sorbitol
Fang, Guiqian,Bian, Zhancun,Liu, Daili,Wu, Guiying,Wang, Hao,Wu, Zhongyu,Yao, Qingqiang
, p. 13802 - 13809 (2019)
Herein, several boronic acid-based sensors were reported selectively recognizing d-sorbitol in aqueous solution. The fluorescence of sensor 15c was enhanced by 1.5-fold when combined with a low concentration of d-sorbitol (8.88 μM), and the fluorescence enhanced by 0.6-fold after binding to d-fructose, while it did not change obviously when combined with other carbohydrates, including d-arabinose, d-galactose, d-mannose, d-ribose, d-maltose, d-xylose, d-glucose and d-glucosamine. Fluorescence tests were carried out in DMSO/PBS (pH 9, 0.1 M) solution (1:99, v/v), at room temperature, which indicated that the sensors are water-soluble. In addition, competition studies showed that sensor 15c works well as a d-sorbitol-specific fluorescence sensor in both the absence and presence of carbohydrate interferents. And sensor 15c has a high binding constant (10922 ± 776 M-1) and a low limit of detection (6.91 × 10-7 M) at pH 9 among the investigated sensors toward d-sorbitol. Furthermore, sensor 15c was applied to the analysis of real samples (d-sorbitol for oral administration). These studies indicated that sensor 15c may serve as a potential tool to detect the content of d-sorbitol in drugs and food products.
A highly selective and sensitive boronic acid-based sensor for detecting Pd2+ ion under mild conditions
Bian, Zhancun,Fang, Guiqian,Wang, Ran,Wu, Zhongyu,Yao, Qingqiang,Zhan, Dongxue,Zhang, Guimin
, (2020/07/20)
Herein, a boronic acid-based sensor was reported selectively to recognize Pd2+ ion. The fluorescence intensity increased 36-fold after sensor binding with 2.47 × 10?5 M of Pd2+ ion. It was carried out in the 99% aqueous so
A novel boronic acid-based fluorescent sensor for selectively recognizing Fe3+ ion in real time
Fang, Guiqian,Wang, Hao,Bian, Zhancun,Guo, Min,Wu, Zhongyu,Yao, Qingqiang
, p. 20306 - 20313 (2019/07/09)
Boronic acid provides faster fluorescence response to Fe3+ compared to other reported sensors, which is critical for continuous dynamic detection. Herein, we reported a novel boronic acid-based sensor 4 that could recognize Fe3+ ion in real time. After 10 equiv. of Fe3+ ion (1 mM) was added, the fluorescence of sensor 4 was immediately quenched by 96%. While other ions, including Ba2+, Ca2+, Cr2+, Cd2+, Co2+, Cs2+, Cu2+, Fe2+, K+, Li+, Mg2+, Mn2+, Na+, Ni2+ or Zn2+, respectively, did not change the fluorescence significantly. Further tests indicated that the high selectively sensing Fe3+ ion benefits from the two boronic acid functionalities in the structure. Moreover, interference experiments showed this sensor has an excellent anti-interference ability. In addition, we performed binding activity test in rabbit plasma and other real samples for practical applications, obtaining similar results. And the thin layer loading sensor 4 was also successfully applied to recognize Fe3+ ion among various ions. Therefore, 4 may serve as a potential sensor for continuous monitoring and detecting Fe3+ ion in real time.
Synthesis, characterization, and antileishmanial activity of certain quinoline-4-carboxylic acids
Abdelwahid, Mazin A. S.,Elsaman, Tilal,Mohamed, Malik S.,Latif, Sara A.,Mukhtar, Moawia M.,Mohamed, Magdi A.
, (2019/03/08)
Leishmaniasis is a fatal neglected parasitic disease caused by protozoa of the genus Leishmania and transmitted to humans by different species of phlebotomine sandflies. The disease incidence continues to increase due to lack of vaccines and prophylactic drugs. Drugs commonly used for the treatment are frequently toxic and highly expensive. The problem of these drugs is further complicated by the development of resistance. Thus, there is an urgent need to develop new antileishmanial drug candidates. The aim of this study was to synthesize certain quinoline-4-carboxylic acids, confirm their chemical structures, and evaluate their antileishmanial activity. Pfitzinger reaction was employed to synthesize fifteen quinoline-4-carboxylic acids (Q1-Q15) by reacting equimolar mixtures of isatin derivatives and appropriate α-methyl ketone. The products were purified, and their respective chemical structures were deduced using various spectral tools (IR, MS, 1H NMR, and 13C NMR). Then, they were investigated against L. donovani promastigote (clinical isolate) in different concentration levels (200 μg/mL to 1.56 μg/mL) against sodium stibogluconate and amphotericin B as positive controls. The IC50 for each compound was determined and manipulated statistically. Among these compounds, Q1 (2-methylquinoline-4-carboxylic acid) was found to be the most active in terms of IC50.
Phenylquinoline transient receptor potential vanilloid 1 antagonists for the treatment of pain: Discovery of 1-(2-phenylquinoline-4-carbonyl)-N-(4-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide
Liao, Chen,Liu, Yan,Liu, Chunxia,Zhou, Jiaqi,Li, Huilan,Wang, Nasi,Li, Jieming,Liu, Taiyu,Ghaleb, Hesham,Huang, Wenlong,Qian, Hai
, p. 845 - 854 (2018/01/10)
Reported herein is the design, synthesis, and pharmacologic characterization of a class of TRPV1 antagonists constructed on a phenylquinoline platform that evolved from Cinchophen lead. This design composes three sections: a phenylquinoline headgroup attached to an aliphatic carboxamides, which is tethered at a phenyl tail group. Optimization of this design led to the identification of 37, comprising a pyrrolidine linker and a trifluoromethyl–phenyl tail. In the TRPV1 functional assay, using cells expressed hTRPV1, 37 antagonized capsaicin-induced Ca2+ influx, with an IC50 value of 10.2 nM. In the complete mice analgesic model, 37 exhibited better antinociceptive activity than the positive control BCTC in diverse pain models. All of these results suggested that 37 could be considered as a lead candidate for the further development of antinociceptive drugs.
One-pot synthesis of quinoline-4-carboxylic acid derivatives in water: Ytterbium perfluorooctanoate catalyzed Doebner reaction
Wang, Li-Min,Hu, Liang,Chen, Hong-Juan,Sui, Yuan-Yuan,Shen, Wei
experimental part, p. 406 - 409 (2009/12/03)
Ytterbium perfluorooctanoate [Yb(PFO)3] has been proved to be an efficient catalyst for Doebner reaction of pyruvic acid, aldehydes and amines under mild conditions in water to afford quinoline-4-caboxylic acid derivatives with three component one-pot method in good yields. The process is operationally simple and environmentally benign and the catalyst has readily been recycled for several times with consistent activity. Furthermore, a plausible mechanism for this transformation is also presented.
Microwave-assisted Doebner synthesis of 2-phenylquinoline-4-carboxylic acids and their antiparasitic activities
Muscia, Gisela C.,Carnevale, Juan P.,Bollini, Mariela,Asis, Silvia E.
, p. 611 - 614 (2008/09/19)
(Chemical Equation Presented) A series of twelve substituted 2-phenylquinoline-4-carboxylic acids analogous to antimalarial and antileishmanial natural products was developed via the Doebner reaction employing microwave irradiation (MW). The products were obtained in moderate yields in 0.5-3 minutes and nine of them were evaluated in vitro against the parasites responsible for malaria, leishmaniasis and trypanosomiasis diseases (WHO, Switzerland). Four compounds exhibited activity against Trypanosoma cruzi and another two resulted active against Plasmodium falciparum and Leishmania infantum, respectively.
Discovery of a novel class of selective non-peptide antagonists for the human neurokinin-3 receptor. 1. Identification of the 4-quinolinecarboxamide framework
Giardina, Giuseppe A. M.,Sarau, Henry M.,Farina, Carlo,Medhurst, Andrew D.,Grugni, Mario,Raveglia, Luca F.,Schmidt, Dulcie B.,Rigolio, Roberto,Luttmann, Mark,Vecchietti, Vittorio,Hay, Douglas W. P.
, p. 1794 - 1807 (2007/10/03)
A novel class of potent and selective non-peptide neurokinin-3 (NK-3) receptor antagonists, featuring the 4-quinolinecarboxamide framework, has been designed based upon chemically diverse NK-1 receptor antagonists. The novel compounds 33-76, prompted by chemical modifications of the prototype 4, have been characterized by binding analysis using a membrane preparation of chinese hamster ovary (CHO) cells expressing the human neurokinin-3 receptors (hNK-3-CHO), and clear structure-activity relationships (SARs) have been established. From SARs, (R)-N-[α-(methoxycarbonyl)benzyl]-2- phenylquinoline-4-carboxamide (65, SB 218795, hNK-3-CHO binding K(i) = 13 nM) emerged as one of the most potent compounds of this novel class. Selectivity studies versus the other neurokinin receptors (hNK-2-CHO and hNK-1-CHO) revealed that 65 is about 90-fold selective for hNK-3 versus hNK-2 receptors (hNK-2-CHO binding K(i) = 1221 nM) and over 7000-fold selective versus hNK-1 receptors (hNK-1-CHO binding K(i) = >100 μM). In vitro functional studies in rabbit isolated iris sphincter muscle preparation demonstrated that 65 is a competitive antagonist of the contractile response induced by the potent and selective NK-3 receptor agonist senktide with a K(b) = 43 nM. Overall, the data indicate that 65 is a potent and selective hNK-3 receptor antagonist and a useful lead for further chemical optimization.
