69218-46-8Relevant academic research and scientific papers
Synthesis, local anesthetic activity and QSAR studies for a set of N-[2-(alkylamino)ethyl]benzotriazol-x-yl acetamides
Caliendo,Di Carlo,Greco,Grieco,Meli,Novellino,Perissutti,Santagada
, p. 603 - 608 (1995)
A set of N-[2-(alkylamino)ethyl]benzotriazol-x-yl acetamides were synthesized and tested for local anesthetic activity. The compounds were designed by varying independently the hydrophobicity and size of the side chains. Anesthetic activity was assessed by different tests using lidocaine as a reference: rabbit corneal and mouse tail anesthesia. These two anesthetic activities were correlated with calculated log P values and significant linear dependences were observed. The three most potent compounds of the series were evaluated in the rat sciatic nerve block assay and their acute toxicity in mice was also assessed. Compound 4b(N-[2-(diethylamino)ethyl]benzotriazol-2-yl acetamide), which has an anesthetic activity comparable to that of lidocaine, was also characterized by a more favorable therapeutic index.
A “turn-on” small molecule fluorescent sensor for the determination of Al3+ion in real samples: theoretical calculations, and photophysical and electrochemical properties
?enocak, Ahmet,Mermer, Arif,Tümay, Süreyya O?uz
, p. 18400 - 18411 (2021/10/19)
Aluminum, one of the most plentiful metal ions on Earth, demonstrates toxic effects after excessive accumulation in the environment and human bodies because it is a non-essential element for living organisms. Therefore, strict limits on Al3+intake by humans have been proposed by the EPA and WHO. In the current study, ultrasound sonication was used for the green synthesis of the naphthalene-based acetohydrazide derivative (3), and it was used as a fluorescent sensor in order to determine the levels of Al3+ions in real samples. Theoretical calculations were carried out and the photophysical and electrochemical properties of3were deeply investigatedviaDFT; steady-state fluorescence, UV-vis absorption, time-resolved fluorescence, and 3D-fluorescence spectroscopy; excitation-emission matrix (EEM) analysis; and CV and SWV measurements. The fluorescent sensor investigations demonstrated that3can sensitively and selectively detect Al3+ionsviaa “turn-on” fluorescence response, which is based on the inhibition of PET and ESIPT processes with a synergistic effect from CHEF. The optimal conditions with regards to the initial sensor concentration, pH, selectivity, and interaction time were determined for the detection of Al3+ions. The linear working range and detection limit for Al3+ions were calculated to be 1.00-20.00 μmol L?1and 0.34 μmol L?1, respectively. Method validation was examinedviathe analysis of a certified reference material (CRM-TMDW-500), and spike/recovery testing and spectrofluorimetric analysis of Al3+ions in drinking water, seawater, and urine samples were successfully carried out using3. Importantly,3-capped paper-based test strips were developed for the practical analysis and monitoring of Al3+ions in the field. According to the obtained results, the presented detection technique, which is based on a “turn-on” fluorescence response change of3, can be applied to the highly sensitive, facile, reliable, and fast determination of Al3+ions in real samples.
B(C6F5)3-Catalyzed site-selective N1-alkylation of benzotriazoles with diazoalkanes
Guo, Jing,Mandal, Dipendu,Stephan, Douglas W.,Wu, Yile,Zhao, Yunbo
supporting information, p. 7758 - 7761 (2021/08/13)
Alkylation of benzotriazoles is synthetically challenging, often leading to mixtures of N1 and N2 alkylation. Herein, metal-free catalytic site-selective N1-alkylation of benzotriazoles with diazoalkanes is described in the presence of 10 mol% of B(C6F5)3. These reactions provide N1-alkylated benzotriazoles in good to excellent yields and this protocol is successfully adapted to gram-scale syntheses as well as a derivative with antimicrobial activity.
Visible-Light-Promoted Site-Selective N1-Alkylation of Benzotriazoles with α-Diazoacetates
Duan, Jiaokui,Ma, Ben,Wang, Ganggang,Wu, Chengqi,Xiao, Jianliang,Yang, Jingya,Zhou, Hongyan
supporting information, p. 7284 - 7289 (2020/10/12)
A visible-light-promoted highly site-selective N1-alkylation of benzotriazoles with diazo compounds has been achieved under mild and metal-free conditions. Using cheap, readily available p-benzoquinone (PBQ) as a catalyst, a wide range of benzotriazoles and diazo compounds are reacted, providing N1-alkylated benzotriazoles in moderate to excellent yields with excellent N1-selectivities. Preliminary mechanistic studies suggest that a radical process accounts for the exclusive site-selectivity of this transformation.
Synthesis and characterization of ethyl benzotriazolyl acrylate-based D-π-A fluorophores for live cell-based imaging applications
Ortega-Villarreal, Ana Sofia,Hernández-Fernández, Eugenio,Jensen, Christopher,Valdivia-Berroeta, Gabriel A.,Garrard, Samuel,López, Israel,Smith, Stacey J.,Christensen, Kenneth A.,Reyes-González, Miguel A.,Michaelis, David J.
, p. 8759 - 8767 (2019/03/28)
A series of eight new ethyl (Z)-benzotriazolyl acrylates 6a-d and 7a-d have been synthesized by conventional heating and microwave irradiation from ethyl benzotriazolyl acetates 3 and 4 with the corresponding aromatic aldehydes. This work reports the synthetic approach and spectroscopic characterization (1H, 13C-NMR, HRMS) of all the synthesized compounds. X-ray diffraction analyses were performed for molecules 6a, 7a and 7d. Photophysical properties of compounds were evaluated. Finally, compound 6a was tested in a human cell line and showed low to no cytotoxicity at relevant concentrations. Initial testing demonstrates its potential use as a fluid-phase fluorescent marker for live cell imaging.
Enhanced proton conductivity of Nafion-azolebisphosphonate membranes for PEM fuel cells
Teixeira, Fátima C.,De Sá, Ana I.,Teixeira, António P. S.,Rangel
, p. 15249 - 15257 (2019/10/08)
Fuel cells are among the cleaner alternatives of sustainable energy technologies, where their proton exchange membranes continue to be a key component with many challenges and opportunities ahead. In this study, different indazole-and benzotriazolebisphosphonic acids were prepared and incorporated into new Nafion-doped membranes up to a 5 wt% loading. The new membranes were characterised, and their proton conductivities were evaluated using electrochemical impedance spectroscopy. Membranes with a 1 wt% loading showed better proton conductivities than Nafion N-115 at all temperature and under relative humidity conditions studied. In these conditions, the best value was observed for the membrane doped with [hydroxy(1H-indazol-3-yl)methanediyl]bis(phosphonic acid) (BP2), with a proton conductivity of 98 mS cm-1. Activation energy (Ea) values suggests that both Grotthuss and vehicular mechanisms are involved in the proton conduction across the membrane.
Synthesis and antimicrobial and antioxidant activities of hybrid molecules containing benzotriazole and 1,2,4-triazole
Chand, Mahesh,Kaushik, Reena,Chand Jain, Subhash
, p. 1663 - 1677 (2019/01/03)
Eleven novel 1,2,4-triazolylbenzotriazoles have been prepared using 1-(hydrazinylcarbonylmethyl)-1 H -benzotriazole (3) as a potent intermediate. Compound 3, however, was obtained from benzotriazole in two steps. All synthesized compounds were characteriz
Synthesis of coumarin-benzotriazole hybrids and evaluation of their anti-tubercular activity
Ambekar, Sachin P.,Mohan, Chakrabhavi Dhananjaya,Shirahatti, Arunkumar,Kumar, Mahesh K.,Rangappa, Shobith,Mohan, Surender,Basappa,Kotresh, Obelannavar,Rangappa, Kanchugarakoppal S.
, p. 25 - 31 (2018/03/06)
Background: Tuberculosis is one of the top ranked airborne infectious diseases caused by the bacillus Mycobacterium tuberculosis with high mortality rate from a single infectious agent. In the present article, we aimed to synthesize oxadiazole-coumarin-triazole based small molecules and evaluate for their possible anti-mycobacterial activity. Method: Herein, we describe the facile synthesis of 5-((1H-benzo[d][1, 2, 3]triazol-1-yl)methyl)-1, 3, 4- oxadiazole-2-thiol-tethered substituted 4-(bromomethyl)-7-methyl-2H-chromen-2-one derivatives and evaluated for their anti-mycobacterial activity against H37Rv strain of M. tuberculosis. We also evaluated the cytotoxic effect of new compounds on normal cells. Results: Among the 14 novel oxadiazole-coumarin-triazole derivatives, 4-((5-((1H-benzo[d][1, 2, 3]triazol-1- yl)methyl)-1, 3, 4-oxadiazol-2-ylthio)methyl)-6-methoxy-2H-chromen-2-one (5f) displayed good antimycobacterial activity towards M. tuberculosis with an MIC value of 15.5 μM. Pyrazinamide was used as reference drug. Our investigation also revealed that, 5f is not cytotoxic to normal cells. Conclusion: In summary, the findings suggested that novel 1, 3, 4-oxadiazole coumarin-triazole hybrids are promising antimycobacterial agents against M. tuberculosis.
Novel benzotriazole N-acylarylhydrazone hybrids: Design, synthesis, anticancer activity, effects on cell cycle profile, caspase-3 mediated apoptosis and FAK inhibition
Kassab, Asmaa E.,Hassan, Rasha A.
, p. 531 - 544 (2018/07/25)
A series of novel benzotriazole N-acylarylhydrazone hybrids was synthesized according fragment-based design strategy. All the synthesized compounds were evaluated for their anticancer activity against 60 human tumor cell lines by NCI (USA). Five compounds: 3d, 3e, 3f, 3o and 3q exhibited significant to potent anticancer activity at low concentrations. Compound 3q showed the most prominent broad-spectrum anticancer activity against 34 tumor cell lines, with mean growth inhibition percent of 45.80%. It exerted the highest potency against colon HT-29 cell line, with cell growth inhibition 86.86%. All leukemia cell lines were highly sensitive to compound 3q. Additionally, compound 3q demonstrated lethal activity to MDA-MB-435 belonging melanoma. Compound 3e exhibited the highest anticancer activity against leukemic CCRF-CEM and HL-60(TB) cell lines, with cell growth inhibition 86.69% and 86.42%, respectively. Moreover, it exerted marked potency against ovarian OVCAR-3 cancer cell line, with cell growth inhibition 78.24%. Four compounds: 3d, 3e, 3f and 3q were further studied through determination of IC50 values against the most sensitive cancer cell lines. The four compounds exhibited highly potent anticancer activity against ovarian cancer OVCAR-3 and leukemia HL-60 (TB) cell lines, with IC50 values in nano-molar range between 25 and 130 nM. They showed 18–2.3 folds more potent anticancer activity than doxorubicin. The most prominent compound was 3e, (IC50 values 29 and 25 nM against OVCAR-3 and HL-60 (TB) cell lines, respectively), representing 10 and 18 folds more potency than doxorubicin. The anti-proliferative activity of these four compounds appeared to correlate well with their ability to inhibit FAK at nano-molar range between 44.6 and 80.75 nM. Compound 3e was a potent, inhibitor of FAK and Pyk2 activity with IC50 values of 44.6 and 70.19 nM, respectively. It was 1.6 fold less potent for Pyk2 than FAK. Additionally, it displayed inhibition in cell based assay measuring phosphorylated-FAK (IC50 = 32.72 nM). Inhibition of FAK enzyme led to a significant increase in the level of active caspase-3, compared to control (11.35 folds), accumulation of cells in pre-G1 phase and annexin-V and propidium iodide staining in addition to cell cycle arrest at G2/M phase indicating that cell death proceeded through an apoptotic mechanism.
Stereoselective synthesis and spectral studies of some benzotriazolylacetyl hydrazones of 3–alkyl–2,6–diarylpiperidin–4–ones
Pillai, M. Velayutham,Rajeswari,Kumar, C. Udhaya,Krishnan, K. Gokula,Mahendran,Ramalingan,Nagarajan,Vidhyasagar
, p. 558 - 565 (2017/09/19)
An effort to include biologically potent benzotriazole nucleus into piperidine ring is achieved through hydrazone formation. The characterization of the synthesized compounds was carried out using FT-IR, 1H &13C NMR, 1H–1H COSY, 1H–13C COSY, NOESY spectral techniques and GC-Mass spectrum. The spectral assignments were done without ambiguity using 2D-NMR techniques. The conformational preference of the piperidine ring deduced from the spectral studies is ‘chair’. The diastereotopic nature of the methylene protons/methyl groups present in the molecules is revealed clearly in their spectral pattern observed.
