- Developing a novel ratiometric fluorescent probe based on ESIPT for the detection of pH changes in living cells
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As an important parameter of intracellular metabolism, pH plays important roles in maintaining normal physiological processes. The abnormal pH could cause disorder of cell function which may cause neurological diseases. Herein, we present two novel ratiometric fluorescent probes to detect pH changes. The probes employed 2-(2′-hydroxyphenyl)benzothiazole as fluorescent platform, and displayed desirable fluorescence response to pH on the basis of excited state intramolecular proton transfer (ESIPT) process. The probe BtyC-1 showed green fluorescence at 546 nm under acidic conditions, while it displayed strong blue fluorescence at 473 nm and weak green fluorescence at 546 nm under alkaline conditions. Biological experiments demonstrated that the probe BtyC-1 could be successfully applied for the ratiometric imaging of cellular pH and the NH4Cl-induced pH changes in living cells.
- Song, Wenhui,Dong, Baoli,Lu, Yaru,Lin, Weiying
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- An ESIPT-based highly selective and sensitive probe for the detection of hydrogen sulfide
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Abstract A new excited state intramolecular proton transfer dye with red keto emission (620 nm) and remarkably large Stokes shift (240 nm) was discovered. Based on its unique red emission and large Stokes shift, it was developed to a novel fluorescent probe which can highly selectively and sensitively detect hydrogen sulfide.
- Xu, Pengfei,Liu, Meihui,Gao, Tang,Zhang, Hailiang,Li, Ziwei,Huang, Xinyi,Zeng, Wenbin
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- Observation of the generation of peroxynitrite in mouse liver after acetaminophen overdose with a boronate-based ratiometric fluorescence probe
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A ratiometric fluorescent probe, BTPB, for the selective monitoring of hepatic peroxynitrite (ONOO-) in situ after acetaminophen (APAP) overdose has been developed. Our study provided direct evidence for supporting the generation of ONOO- in APAP-induced liver injury. This new probe will be a useful tool for studying the roles of ONOO-in vivo.
- Ma, Ying,Tian, Haigang,Jin, Zhengyu,Li, Xiaoyong,Li, Yiping
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- Benzothiazoline based chemodosimeters for fluorogenic detection of hypochlorous acid
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Two nonfluorescent and colorless chemodosimeters featuring benzothiazoline moiety were developed for chromo-fluorogenic detection of HOCl.
- Wu, Zhisheng,Wu, Xuanjun,Li, Zhu,Yang, Yuhui,Han, Jiahuai,Han, Shoufa
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- A water-soluble esipt fluorescent probe with high quantum yield and red emission for ratiometric detection of inorganic and organic palladium
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A novel fluorescent probe with a high quantum yield (0.41), large Stokes shifts (255 nm), and red emission (635 nm) was designed to detect all typical oxidation states of palladium species (0, +2, +4) by palladium-mediated terminal propargyl ethers cleavage reaction in water solution without any organic media. The probe showed a high selectivity and excellent sensitivity for palladium species, with a detection as low as 57 nM (6.2 μgL-1).
- Gao, Tang,Xu, Pengfei,Liu, Meihui,Bi, Anyao,Zeng, Wenbin,Hu, Pengzhi,Ye, Bin,Wang, Wei
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- Synthesis, Characterization, Properties and DFT Calculations of 2-(Benzo[b]thiophen-2-yl)pyridine-based Iridium(III) Complexes with Different Ancillary Ligands
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A series of new cyclometalated btp-based iridium(III) complexes with three different ancillary ligands, Ir(btp)2(bozp) (3a), Ir(btp)2(btzp) (3b) and Ir(btp)2(izp) (3c) (btp = 2-(benzo[b]thiophen-2-yl)pyridine, bozp =2-(benzo[d]oxazol-2-yl)phenol, btzp =2-(benzo[d]thiazol-2-yl)phenol, izp = 2-(2 H-indazol-2-yl)phenol), have been synthesized and fully characterized. The crystal structure of 3b has been determined by single crystal X-ray diffraction analysis. A comparative study has been carried out for complexes 3a - 3c by UV-vis absorption spectroscopy, photoluminescence spectroscopy, cyclic voltammetry and DFT calculations. This observation illustrates that the substitution of N or S in ancillary ligand can lead to a marked bathochromic shift of absorption and emission wavelengths. The spectroscopic characterisation of these complexes has been complemented by DFT and TD-DFT calculations, supporting the assignment of 3MLCT/3LC to the lowest energy excited state.
- Li, Gao-Nan,Zeng, Yong-Pi,Li, Kai-Xiu,Chen, Hao-Hua,Xie, Hui,Zhang, Fu-Lin,Chen, Guang-Ying,Niu, Zhi-Gang
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- Fluorometric determination of Au3+ via hydrolysis of thiocarbonate with bromide as a masking agent
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Gold ions are very important in chemistry and materials science owing to their various uses in chemical reactions as well as industrial and biological applications. In this study, we developed a novel reaction-based probe (GP), which is a thiocarbonate derivative of the 2-(2-hydroxyphenyl)benzothiazole dye, for the selective and sensitive determination of Au3+. The probe GP showed turn-on fluorescence signaling behavior toward Au3+ ions triggered by the metal-induced hydrolysis of the thiocarbonate group. Interference from other thiophilic ions, Ag+ and Hg2+, was effectively eliminated by using bromide ions as a masking agent. Prominent off–on type fluorescent sensing of Au3+ over other coexisting metal ions was possible with a detection limit of 4.8 × 10?8 M (9.5 ppb). Fluorescence sensing of Au3+ by GP was fast and applicable over a wide pH range between 4.0 and 10.5. Application of the probe to the analysis of Au3+ in synthetic wastewater was conducted using an easily accessible smartphone.
- Park, So Young,Choi, Myung Gil,Lim, Dae Sung,Chang, Suk-Kyu
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- A reversible, benzothiazole-based “Turn-on” fluorescence sensor for selective detection of Zn2+ ions in vitro
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Abstract: Temperature-driven, highly sensitive and selective “TURN-ON” fluorometric detection of Zn2+ by benzothiazole-based probes (L1 and L2) was reported in physiological pH in the present work. Iron(II) acted as the reversible switch or trigger for the reversible detection of Zn2+ ions by the probes resulting in “TURN-OFF” fluorescence at room temperature. However, selective detection of Zn2+ in the presence of Fe2+ was irreversible at 0–5 °C. Such temperature dependence on reversible fluorometric detection of Zn2+ in the presence of Fe2+ was explained from the thermodynamic perspective as well as DFT calculations in which the absolute enthalpy (H) and Gibbs free energy (G) of the resultant complexes and the fluorophores (L1 and L2) at different temperatures were determined. Enhanced fluorescence of the Zn2+ bound probes was due to the inhibition of excited-state intramolecular proton transfer (ESIPT). Effect of solvents, pH, and temperature on the fluorometric detection of Zn2+ was also probed in the present work. The results were translated into the visual detection of Zn2+ on paper-based fluorescence probe and later we demonstrated the sensing of mobile Zn2+ ions by the probes in living HeLa cells as the proof of concept of our present investigations. Graphic Abstract: A benzothiazole-based, “TURN-ON” fluorescent sensor was developed for selective and reversible detection of Zn2+in vitro, in which Fe2+ acted as the reversible switch. [Figure not available: see fulltext.].
- Musib, Dulal,Raza, Md Kausar,Devi, Salam Sujata,Roy, Mithun
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- A "turn-On" fluorescent probe for sensitive and selective detection of fluoride ions based on aggregation-induced emission
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Based on the fluorophore of 2-(2′-hydroxyphenyl)benzothiazole (HBT) with aggregation-induced emission (AIE) properties, a highly selective and sensitive fluorescent probe PBT towards F- was investigated. "Turn-On" fluorescence type signaling was realized by employing fluoride-selective cleavage of the latent thiophosphinated probe in mixed aqueous media. The probe is designed in such a way that the excited state intramolecular proton transfer (ESIPT) of the HBT moiety becomes blocked. The chemodosimetric approach of F- to the probe results in the recovery of the ESIPT by removal of a free AIE-active HBT moiety through a subsequent hydrolysis process. The F- detection limit of the probe was 3.8 nM in the dynamic range of 0.5 μM to 10 μM. In addition, the proposed probe has been used to detect F- in water samples and toothpaste samples with satisfying results.
- Du, Man,Huo, Baolong,Li, Mengwen,Shen, Ao,Bai, Xue,Lai, Yaru,Liu, Jiemin,Yang, Yunxu
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- A Turn on ESIPT Probe for Rapid and Ratiometric Fluorogenic Detection of Hg2+ and its Application in Live-Cell Imaging
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A probe based on 2-(2′-hydroxyphenyl) benzothiazole (HBT) and thiophosphate has been synthesized and used for the ratiometric detection of Hg2+. The probe was designed in such a way that the excited state intramolecular proton transfer (ESIPT) of the HBT moiety get blocked. The probe exhibited a strong fluorescence enhancement upon addition of Hg2+ while showing almost no response to other cations in CH3CN/HEPES buffer solution. The probe exhibited fast selectivity towards Hg2+ and could be completed in 1?min. Fluorescence imaging experiments of Hg2+ in living TE-1 cells demonstrated its value of practical applications in biological systems.
- Zhang, Di,Liu, Jihong,Yin, Haiyan,Wang, Hongqi,Li, Shufang,Wang, Min,Li, Man,Zhou, Ling,Zhang, Junfeng
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- Mn(I)-based photoCORMs for trackable, visible light-induced CO release and photocytotoxicity to cancer cells
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Four new Mn(I)–carbonyl complexes of general formula, [Mn(L)(CO)3] (1–4) where L = 2-(benzo[d]thiazol-2-yl)phenol (L1), 2-(benzo[d]thiazol-2-yl)-4,6-di-tert-butylphenol (L2), 2-(2-hydroxyphenyl)-3H-anthra[1,2-d]imidazole-6
- Musib, Dulal,Raza, Md Kausar,Martina, Kh.,Roy, Mithun
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- Synthesis, spectral, and magnetic studies of benzothiazolium tetrachlorocuprate salts: Crystal structure and semiconducting behavior of bis[2-(4-methoxyphenyl)benzothiazolium] tetrachlorocuprate(II)
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Reaction of Cu(NO3)2·3H2O with substituted 2-phenylbenzothiazoles and HCl in methanolic solution gave (2-PBZ)2[CuCl4], [2-PBZ = substituted 2-phenyl benzothiazolium]. Three such compounds, 2-(4-methox
- Sarau Devi,Ravindran, Reena,Fazil, Shiji,Minitha
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- Simpler molecular structure as selective & sensitive ESIPT-based fluorescent probe for cysteine and Homocysteine detection with DFT studies
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The undesired research results of triazole synthesis were successfully utilized as a simpler, sensitive and selective turn-on fluorescent probe 2 namely chloro-acetic acid 2-benzothiazol-2-yl-phenyl ester (HBT-AcCl) which was synthesized by simple chloroacylation of 2-hydroxyphenyl benzothiazole (HBT). Only one simple chloroacetate, a trigger unit as the reaction site of probe 2 makes it more simple, sensitive and selective for Cys and Hcy over other Amino Acids. The presented probe HBT-AcCl conserves simple structure, reduces the use of extra chloroacetate and improves %atom economy as compare to similar reported probes. Paper strip tests were carried out to explore the potential application for naked-eye detection of Cys under UV lamp. The selectivity of the HBT-AcCl probe for Cys and Hcy is supported by the results of absorbance and emission spectroscopy experiments and theoretical DFT calculations.
- Kaushik, Rahul,Nehra, Nidhi,Tittal, Ram Kumar,Vikas D, Ghule
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- Unique fluorogenic ratiometric fluorescent chemodosimeter for rapid sensing of CN- in water
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A new benzimidazole-spiropyran conjugate chemosensor molecule (BISP) has been synthesized and characterized by 1H NMR spectroscopy, mass spectrometry (ESI-MS), and elemental analysis. The two isomeric forms (BISPBIMC) were shown to be highly se
- Mahapatra, Ajit Kumar,Maiti, Kalipada,Manna, Saikat Kumar,Maji, Rajkishor,Mukhopadhyay, Chitrangada Das,Pakhira, Bholanath,Sarkar, Sabyasachi
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- Green synthesis of a benzothiazole based 'turn-on' type fluorimetric probe and its use for the selective detection of thiophenols in environmental samples and living cells
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We have developed an efficient turn-on type fluorescent chemodosimeter for the detection of aromatic thiols in aqueous media. The probe was successfully synthesized by condensation of 2-aminothiophenol with salicylaldehyde followed by SNAr with
- Khandare, Dipratn G.,Banerjee, Mainak,Gupta, Rishabh,Kumar, Nupur,Ganguly, Anasuya,Singh, Deepak,Chatterjee, Amrita
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- A Schiff base probe for competitively sensing Cu2+ and cysteine through hydrolysis, complexation, and cyclization
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The form of a single response to a single target analyte limits the development of fluorescent probes. Here, a probe (HBTA) based on HBT (2-(2-Hydroxyphenyl)-benzothiazole) was synthesized to achieve a concept about nested probe, completing continuous det
- Chen, Li,Chen, Liang,Jiang, Yingxia,Ma, Tengchuang,Sun, Xiaodong,Yan, Fanyong,Zhang, Yan
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- A Novel Turn-on Fluorescent Probe for Highly Selective Detection of Phosphate Ion in Living Cell
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A novel fluorescent probe was synthesized and studied. Fluorescent probe 1 undergoes a unique Pi induced hydrolytic reaction in DMSO- HEPES at physiological pH that produces a colorimetric change associated with a 76 nm red-shift in the UV-vis absorption maximum and up to a 210-fold enhancement in the fluorescence intensity. It has successfully been used to stain and record microscopy images of HeLa cells. Moreover, the mechanistic proposal that these spectroscopic changes are associated with the reaction of Pi and probe 1 to form 2-(2-hydroxyphenyl)benzothiazole gains support from the results of mass spectrometry studied.
- Zhang, Jin,Wang, Si,Liu, Changhui,He, Guowen,Peng, Tianying
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- Ruthenium silicate (RS-1) zeolite: novel heterogeneous efficient catalyst for synthesis of 2-arylbenzothiazole derivatives
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Abstract: Mesoporous silicate and transition metal (Ru+3) containing mesoporous silicate materials or ruthenium silicate Ru+3/Si+4 where synthesis by using hydrothermal process. Mesoporous ruthenium silicate (RS-1) and zeo
- Gadekar, Sachin P.,Lande, Machhindra K.
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p. 1253 - 1267
(2021/01/06)
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- A new ESIPT-based fluorescent probe for the highly sensitive detection of amine vapors
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Volatile amine vapors are toxic and corrosive irritants and can cause serious health problems. In addition, the biologically amine vapor produced by microorganisms is also an important indicator of food spoilage. Therefore, the development of simple, sensitive, and selective amine vapor detection methods is of great significance. A new ESIPT-based fluorescent probeHBTAchas been developed as a rapid, highly sensitive, and selective sensor for amine vapors in this work. TheHBTAcsensor exhibits an obvious fluorescence turn-on response at 514 nm toward amine vapors with a large Stokes shift (180 nm), and a low detection limit (12.7 ppm). Taking advantage of its portability and high sensitivity to amine vapors, theHBTAcsensor can be used for food spoilage monitoring by detecting volatile amines produced by microbial growth. Finally, agar gels based on theHBTAcprobe were fabricated, which could act as a solid optical sensor to conveniently and efficiently detect amine vapors.
- Bao, Cheng,Shao, Sufang,Zhou, Haifeng,Han, Yifeng
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p. 10735 - 10740
(2021/06/25)
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- Pentafluorophenylammonium Triflate: A Mild, Efficient and Reusable Catalyst for the Synthesis of 2-Arylbenzothiazole and 2-Arylbenzothiazoline Derivatives in a Green Chemical Approach
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In this work, one pot, simple and environmentally benign effective synthesis of 2-substituted benzothiazole and benzothiazoline derivatives are described in presence of PFPAT (pentafluorophenylammonium triflate) catalyst in water successfully. A series of benzothiazole derivative were synthesized by the reaction between 2-aminothiophenol and various aldehydes in good yields. Recyclability of the catalyst is observed for four times without loss of its activity in aqueous medium.
- Datta, Arup
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- Benzothiazole Synthesis: Mechanistic Investigation of an in Situ-Generated Photosensitizing Disulfide
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The use of a visible light absorbing intermediate as a photosensitizer makes a chemical process simple and sustainable, obviating the need for the use of chemical additives. Herein, the formation of a photosensitizing disulfide in benzothiazole synthesis from 2-Aminothiophenol and aldehydes was proposed and confirmed through in-depth mechanistic studies. A series of photophysical and electrochemical investigations revealed that an in situ-generated disulfide photosensitizes molecular oxygen to generate the key oxidants, singlet oxygen and superoxide anion, for the dehydrogenation step.
- Hwang, Ho Seong,Lee, Sumin,Han, Sung Su,Moon, Yu Kyung,You, Youngmin,Cho, Eun Jin
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p. 11835 - 11843
(2020/10/23)
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- Metal-organic framework mediated expeditious synthesis of benzimidazole and benzothiazole derivatives through an oxidative cyclization pathway
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Herein, we report the facile synthesis of various benzimidazoles and benzothiazoles by using the NH2-MIL-125(Ti) MOF as an efficient oxidant-free heterogeneous catalyst with good yield. Adsorption of the substrate on the NH2-MIL-125(Ti) MOF surface through electron deficient Ti4+ sites initiates the reaction. The broad substrate scope and high reusability of this catalyst are attractive for synthesis of a wide range of medicinally active benzimidazole and benzothiazole derivatives.
- Sankar, Velayudham,Karthik, Peramaiah,Neppolian, Bernaurdshaw,Sivakumar, Bitragunta
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p. 1021 - 1027
(2020/01/31)
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- Design, synthesis and evaluation of benzothiazole derivatives as multifunctional agents
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Oxidative stress is the product or aetiology of various multifactorial diseases; on the other hand, the development of multifunctional compounds is a recognized strategy for the control of complex diseases. To this end, a series of benzothiazole derivatives was synthesized and evaluated for their multifunctional effectiveness as antioxidant, sunscreen (filter), antifungal and antiproliferative agents. Compounds were easily synthesized via condensation reaction between 2-aminothiophenols and different benzaldehydes. SAR study, particularly in position 2 and 6 of benzothiazoles, led to the identification of 4g and 4k as very interesting potential compounds for the design of multifunctional drugs. In particular, compound 4g is the best blocker of hERG potassium channels expressed in HEK 293 cells exhibiting 60.32percent inhibition with IC50 = 4.79 μM.
- Andreotti, Elisa,Baldisserotto, Anna,Balzarini, Jan,Buzzi, Raissa,Dissette, Valeria,Djuidje, Ernestine Nicaise,Liekens, Sandra,Manfredini, Stefano,Sciabica, Sabrina,Serra, Elena,Vertuani, Silvia
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- Oxidative NHC catalysis for base-free synthesis of benzoxazinones and benzoazoles by thermal activated NHCs precursor ionic liquid catalyst using air as oxidant
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A reusable thermal activated NHC precursor ionic liquid catalyst ([BMIm]2[WO4]) has been prepared and developed for the synthesis of nitrogen-containing heterocycles such as benzoxazinones and benzoazoles through imines activation. [BMIm]2[WO4] exhibited the good activity for the base-free condensation and oxidative NHC catalysis tandem under air atmosphere. The catalyst can be recovered and reused for at least five runs in gram scale synthesis without any decrease in catalytic activity. Furthermore, the control experiments demonstrated that the reaction involved formation of aromatic aldimines, NHC-catalyzed oxidative formation of imidoyl azoliums and intramolecular cyclization to generate the product.
- Guan, Jiali,Liu, Wei,Liu, Yuchen,Song, Zhibin,Tao, Duan-Jian,Yan, Jieying,Yuan, Jian-Jun,Zhou, Youkang
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- Green synthesis and biological evaluation of 6-substituted-2-(2-hydroxy/methoxy phenyl)benzothiazole derivatives as potential antioxidant, antibacterial and antitumor agents
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We present a new efficient green synthetic protocol for introduction of substituents to the C-6 position of 2-arylbenzothiazole nuclei. Newly synthesized compounds were designed to study the influence of the hydroxy and methoxy groups on the 2-arylbenzothiazole scaffold, as well as the influence of the type of substituents placed on the C-6 position of benzothiazole moiety on biological activity, including antibacterial, antitumor and antioxidant activity. Modest activity was observed against the tested Gram-positive and Gram-negative bacterial strains for only amidino derivatives 5d and 6d. The tested compounds exhibited moderate to strong antiproliferative activity towards the tumor cell lines tested. The SAR study revealed that the introduction of substituents into the benzene ring of the benzothiazole nuclei is essential for antiproliferative activity, while introduction of the hydroxy group into the 2-aryl moiety of the 2-arybenzothiazole scaffold significantly improved selectivity against tumor cell lines. The observed results revealed several novel 6-substituted-2-arylbenzothiazole compounds, 5b, 5c, 5f and 6f, with strong and selective antiproliferative activity towards HeLa cells in micro and submicromolar concentrations, with the most selective compounds being 6-ammonium-2-(2-hydroxy/methoxyphenyl)benzothiazoles 5f and 6f. The compound 5f bearing the hydroxy group on the 2-arylbenzothiazole core showed the most promising antioxidative activity evaluated by DPPH, ABTS and FRAP in vitro assays. The presence of the amino protonated group attached at the benzothiazole moiety was essential for the antiproliferative and antioxidant activity observed, exerted through a change in the levels of the reactive oxygen species-modulated HIF-1 protein.
- Racané, Livio,Pti?ek, Lucija,Fajdeti?, Glorija,Trali?-Kulenovi?, Vesna,Klobu?ar, Marko,Kraljevi? Paveli?, Sandra,Peri?, Mihaela,Paljetak, Hana ?ip?i?,Verbanac, Donatella,Star?evi?, Kristina
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- Probe for detecting fluorine ions and preparation method thereof
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The invention discloses a probe for detecting fluorine ions and a preparation method thereof. The molecular structure of the probe is as shown in a formula (I) which is described in the specification.In the formula (I), R1 and R3 are respectively selected
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Paragraph 0034; 0041-0044; 0048-0051
(2020/07/13)
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- An Activity-Based Fluorogenic Probe Enables Cellular and in Vivo Profiling of Carboxylesterase Isozymes
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Carboxylesterases (CEs) exist as multiple types of isomers in humans, and two major types are CE1 and CE2. They are widely distributed in human tissues and well-known for their important roles in drug metabolism and pathology of various diseases. Thus, the detection of CEs in living systems could provide efficient proof in disease diagnostics, as well as important information regarding chemotherapeutic effects of antitumor drugs and prognosis. To develop a specific probe to discriminate CEs from other hydrolases, especially cholinesterases, is quite challenging due to their structural similarities and substrate specificity. To date, almost all of the fluorescent probes developed for CEs have been constructed with an acetyl group as the recognition unit. Herein we proposed a new design strategy of probe-cavity matching, which led to the identification of a new fluorogenic substrate (termed as HBT-CE) with high specificity toward both CE isomers and improved sensitivity, considering the higher binding affinity and catalysis efficiency. The promising capability of HBT-CE was further demonstrated for endogenous CEs imaging in living cells, zebrafish, and nude mice. In addition, HBT-CE was successfully applied in kinetically monitoring drug-induced CE regulation in cancer cells. All of these findings suggest that HBT-CE is a valuable tool for tracking and imaging endogenous CEs in complex biological systems.
- Li, Rong-Rong,Liu, Shi-Yu,Qu, Ren-Yu,Sun, Yao,Yan, Yao-Chao,Yang, Guang-Fu,Yang, Wen-Chao
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p. 9205 - 9213
(2020/08/14)
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- Direct Oxygenation of C-H Bonds through Photoredox and Palladium Catalysis
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This report presents the oxygenation of C-H bonds via the merger of photocatalysis and Pd catalysis. Herein, we describe the utilization of a photocatalyst to oxidize an organopalladium(II) intermediate to high-valent PdIII or PdIV intermediates, which promotes the formation of C-O bonds. The demonstrated method works efficiently with various directing groups, such as oxime ether and benzothiazole. The applicability of this direct C-O bond formation method is shown by synthesizing several metal complexes of 2-(benzo[d]thiazol-2-yl)phenol that can be used in organic light-emitting diodes and pharmaceuticals.
- Paul, Amrita,Shah, Sk. Sheriff,Shee, Maniklal,Singh, Amit Kumar,Singh, N. D. Pradeep
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p. 3426 - 3439
(2020/03/23)
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- Synthesis of Benzothiazoles via Photooxidative Decarboxylation of α-Keto Acids
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Herein, synthesis of benzothiazoles via decarboxylative cross-coupling between α-keto acids and 2-aminothiophenols under blue LED irradiation without using any photocatalyst or metal at room temperature is described. The formation of benzothiazole is driven by the EDA (electron donor-acceptor) complex formed between α-keto acid and 2-aminothiophenol. This methodology gives easy access to 2-substituted and -unsubstituted benzothiazoles in moderate to good yields. α-Keto acids and 2-aminothiophenols bearing different functional groups were easily transformed under the given conditions. (Figure presented.).
- Monga, Aparna,Bagchi, Sourav,Soni, Raj Kumar,Sharma, Anuj
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supporting information
p. 2232 - 2237
(2020/03/04)
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- Nanoporous Cu doped ZnS nanoparticles an efficient photo catalyst for the chemoselective synthesis of 2-substituted azoles via C-N arylation/ CSp3– H oxidation/ cyclization/dehydration sequence in visible light
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ZnS and Cu:ZnS nanoparticles were prepared by aqueous chemical method and characterized by several analytical tools. Nanoparticles have an average size of about ～ 18 nm and possess highly open mesopores, moderate surface area, and uniform morphology. UV–vis spectra designate that doping of Cu shifted the optical response of the ZnS nanoparticles in to a visible region. These Cu:ZnS nanoparticles were employed as a photocatalyst for chemoselective synthesis of 2-substituted azoles by the reaction of benzyl bromides and 1,2-Diaminobenzene or 2-Mercaptoaniline in visible light. Analogous experiments confirmed that the reaction were proceeds through one pot C–N arylation/ CSp3– H oxidation/ cyclization/dehydration sequence. The enhanced catalytic activity by doping could be attributed to the presence of trapping level generated by copper doping which augments the relaxation time of electron and holes so that they are easily available for the reaction. The method was also applicable for the synthesis of quinazolin-4(3H)-ones.
- Dandia, Anshu,Bansal, Sarika,Sharma, Ruchi,Kumar Mahawar, Dinesh,Rathore, Kuldeep S.,Lal Meena, Mohan,Parewa, Vijay
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- NCS/TBHP promoted C2 arylation of benzothiazoles with aldehydes in DMSO
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A N-chlorosuccinimide catalyzed oxidative synthesis of 2-aryl benzothiazole from benzothiazoles and aryl aldehydes using tert-butyl peroxybenzoate as an oxidant in dimethyl sulfoxide (DMSO) has been developed in moderate to good yields. Solvent DMSO as a strong Lewis base plays an efficient role in the reaction. Various substrates were tolerated under optimized conditions affording the arylated products in 12–94% yields for 28 examples. Additionally, acylated benzothiazoles were produced with 4 examples.
- Xu, Wen-Xiu,Ye, Fei-Xia,Liu, Xing-Hai,Weng, Jian-Quan
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- Preparation method of substituted benzothiazole C2 arylated derivative
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The invention discloses a substituted benzothiazole C2 arylated derivative and a preparation method thereof. The preparation method comprises the following steps: mixing substituted benzothiazole represented by a formula (II) and substituted benzaldehyde represented by a formula (III); adding a free radical initiator N-chlorosuccinimide (NCS) and an oxidant tert-butyl hydroperoxide (TBHP), carrying out a stirring reaction for about 12 h at 120 DEG C in a nitrogen atmosphere by using DMSO as a solvent, and after the reaction is finished, separating and purifying the reaction liquid to prepare the substituted benzothiazole C2 arylated derivative represented by a formula (I). The invention provides a new method for synthesizing a benzothiazole C2 arylated derivative by taking an NCS/TBHP double component as an oxidation system through a stirring and reaction for about 12 hours at 120 DEG C in a nitrogen atmosphere under the assistance of a strong Lewis base DMSO; and according to the method, an NCS/TBHP double-component oxidation system and an aprotic solvent are selected, and the method has the advantages of being simple in catalytic system, good in product yield and wide in substrate range.
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Paragraph 0047-0048
(2020/05/02)
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- Intracellular Reactions Promoted by Bis(histidine) Miniproteins Stapled Using Palladium(II) Complexes
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The generation of catalytically active metalloproteins inside living mammalian cells is a major research challenge at the interface between catalysis and cell biology. Herein we demonstrate that basic domains of bZIP transcription factors, mutated to include two histidine residues at i and i+4 positions, react with palladium(II) sources to generate catalytically active, stapled pallado-miniproteins. The resulting constrained peptides are efficiently internalized into living mammalian cells, where they perform palladium-promoted depropargylation reactions without cellular fixation. Control experiments confirm the requirement of the peptide scaffolding and the palladium staple for attaining the intracellular reactivity.
- Gutiérrez-González, Alejandro,Learte-Aymamí, Soraya,Mascare?as, José L.,Vidal, Cristian
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supporting information
p. 9149 - 9154
(2020/04/15)
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- Benzothiazole-based hydrogen sulfide fluorescent probe as well as preparation method and application thereof
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The invention discloses a benzothiazole-based hydrogen sulfide fluorescent probe as well as a preparation method and application thereof. The structural general formula of the fluorescent probe compound is shown as a formula (I). The compound is simple to synthesize, the fluorescence of the compound is remarkably enhanced after the compound reacts with hydrogen sulfide, and the compound shows goodselectivity on hydrogen sulfide, shows a very good linear relationship within a certain concentration range, and can be used as a fluorescent probe for qualitative and quantitative detection of hydrogen sulfide. In addition, raw materials for preparing the compound are cheap and easily available, the cost is low, the preparation process is simple, and the probe is suitable for large-scale industrial popularization and application.
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Paragraph 0023-0024; 0026
(2020/10/30)
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- Method for synthesizing benzothiazole by microwave radiation of benzothioamide compound in aqueous phase
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The invention discloses a method for synthesizing benzothiazole by microwave radiation of a benzothioamide compound in an aqueous phase. The method includes the steps: adding the benzothioamide compound into the aqueous phase under microwave conditions; performing cyclization under alkaline conditions to generate the benzothiazole. The method for preparing the benzothiazole is environmentally friendly, simple and convenient in operation, safe, cheap and efficient. Compared with the prior art, the method is applicable to a lot of functional groups, high in yield, few in by-products, simple in operation, safe, low in cost and environmentally friendly.
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Paragraph 0013; 0048
(2019/02/13)
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- Copper supported on functionalized MCM-41 as a novel and a powerful heterogeneous nanocatalyst for the synthesis of benzothiazoles
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A new functionalized mesoporous catalyst (Cu(II)-Glycerol/MCM-41) has been synthesized as a highly efficient heterogeneous nanocatalyst for the synthesis of benzothiazoles derivatives. Powder XRD, TGA, TEM, SEM, EDX, BET, FT-IR and ICP-OES techniques are
- Noroozi Pesyan, Nader,Batmani, Hana,Havasi, Forugh
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p. 248 - 254
(2018/11/26)
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- A novel ternary GO@SiO2-HPW nanocomposite as an efficient heterogeneous catalyst for the synthesis of benzazoles in aqueous media
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A new solid acid catalyst, consisting of 12-phosphotungstic heteropoly acid (HPW) supported on graphene oxide/silica nanocomposite (GO@SiO2), has been developed via immobilizing HPW onto an amine-functionalized GO/SiO2 surface through coordination interaction (GO@SiO2-HPW). The GO@SiO2-HPW nanocomposite was characterized by Fourier transform infrared (FT-IR) spectroscopy, thermogravimetric analysis (TGA), scanning electron microscopy (SEM), and powder X-ray diffraction (XRD). The prepared nanocomposite could be dispersed homogeneously in water and further used as a heterogeneous, reusable, and efficient catalyst for the synthesis of benzimidazoles and benzothiazoles by the reaction of 1,2-phenelynediamine or 2-aminothiophenol with different aldehydes.
- Habibzadeh, Setareh,Firouzzadeh Pasha, Ghasem,Tajbakhsh, Mahmood,Amiri Andi, Nasim,Alaee, Ehsan
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p. 934 - 944
(2019/06/13)
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- The effect of locking π-conjugation in organoboron moieties in the structures of luminescent tetracoordinate boron complexes
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A series of 8 luminescent borafluorene complexes were extensively studied both experimentally and theoretically in order to elucidate the effect of organoboron moiety rigidification on the physicochemical properties of these compounds. Due to the spiro ge
- Urban, Mateusz,Durka, Krzysztof,Górka, Patrycja,Wiosna-Sa?yga, Gabriela,Nawara, Krzysztof,Jankowski, Piotr,Luliński, Sergiusz
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supporting information
p. 8642 - 8663
(2019/06/24)
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- Photoactivated aggregation-inducing luminescent probe having in-situ generation capability and preparation and application thereof
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The invention belongs to the technical field of biological imaging, and discloses a photoactivated aggregation-inducing luminescent probe having in-situ generation capability and a preparation and application thereof. The preparation method comprises the following steps: reacting a bis(2-(2--hydroxybenzylidene)amino)aryldisulfide compound with a thiol to obtain the photoactivated aggregation-inducing luminescent probe, which has the structural formula III. The photoactivated aggregation-inducing luminescent probe is gathered in a specific organelle to produce a 2-(2-hydroxyphenyl)benzothiazolecompound having aggregation-inducing luminescent properties by photooxidation. The photoactivated aggregation-inducing luminescent probe having in-situ generation capability can effectively overcomethe defects of aggregation-induced quenching of traditional fluorescent dyes, and realize the organelle-targeting specific photo-activated fluorescence imaging in living cells, and has the advantagesof easy preparation, long-term storage, high light activation efficiency, large Stokes displacement, and strong ability to enter the cells.
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Paragraph 0108; 0110; 0112
(2018/09/11)
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- Highly efficient AgNO3-catalyzed approach to 2-(benzo[d]azol-2-yl)phenols from salicylaldehydes with 2-aminothiophenol, 2-aminophenol and benzene-1,2-diamine
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A new, convenient and efficient AgNO3-catalyzed strategy for the preparation of 2-(benzo[d]azol-2-yl)phenol derivatives in good to excellent yields (63–98%) is described. The reaction proceeds via condensation/intramolecular nucleophilic addition/oxidation process between substituted salicylaldehydes and 2-aminothiophenol, 2-aminophenol or benzene-1,2-diamine under mild reaction conditions. Notably, this reaction utilizes cheap AgNO3 as a readily available and low-cost benign oxidant at low catalyst loadings with excellent functional group tolerance.
- He, Xinwei,Wu, Yuhao,Jin, Wenjing,Wang, Xiaoshun,Wu, Cong,Shang, Yongjia
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- N-Heterocyclic Carbene (NHC)-Catalyzed One-Pot Aerobic Oxidative Synthesis of 2-Substituted Benzo[ d ]oxazoles, Benzo[ d ]thiazoles and 1,2-Disubstituted Benzo[ d ]imidazoles
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N-Heterocyclic carbene (NHC), generated in situ from easily available N-heterocyclic imidazolium salt with air as terminal oxidant, has successfully been utilized as a cheap and efficient catalyst for one-pot aerobic oxidative synthesis of 2-arylbenzo[ d ]oxazoles, 2-substituted benzo[ d ]thiazoles, and 1,2-disubstituted benzo[ d ]imidazoles.
- Zhou, Quan,Liu, Shu,Ma, Ming,Cui, He-Zhen,Hong, Xi,Huang, Shuang,Zhang, Jing-Fan,Hou, Xiu-Feng
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supporting information
p. 1315 - 1322
(2018/03/10)
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- Chitosan-SO3H: A green approach to 2-aryl/heteroaryl benzothiazoles under solvent-free conditions at room temperature
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An efficient green protocol have been developed for the synthesis of 2-aryl/heteroaryl benzothiazole derivatives by intramolecular cyclocondensation of 2-mercaptoaniline with various substituted aryl/heteroaryl aldehydes using chitosan-SO3H as an efficien
- Bathula, Surendra Bose,Khagga, Mukkanti,Venkatasubramanian, Hariharakrishnan
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p. 1512 - 1516
(2018/06/12)
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- Solid Acid Supported on Magnetic Nanoparticles as a Highly Efficient and Retrievable Catalyst for the Synthesis 2-Substituted Benzothiazoles
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The use of a recyclable heterogeneous nanomagnetic solid acid catalyst, [Fe3O4@SiO2@(CH2)3NPC–SO3H]Cl, in a simple and highly efficient synthesis of benzothiazole derivatives by the reactio
- Gorjizadeh,Sayyahi
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p. 1899 - 1903
(2018/11/24)
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- Metallaphotoredox-Mediated Csp2-H Hydroxylation of Arenes under Aerobic Conditions
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The direct hydroxylation of 2-arylpyridines and 2-arylbenzothiazoles via the merger of organic photoredox and metal catalysis is reported where 4CzIPN is used as the visible-light photocatalyst and Pd(OAc)2 as the metal catalyst. This method has been employed to synthesize organic molecules exhibiting excited-state intramolecular proton transfer properties for generating tunable luminescence responses.
- Shah, Sk. Sheriff,Paul, Amrita,Bera, Manoranjan,Venkatesh, Yarra,Singh, N. D. Pradeep
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p. 5533 - 5536
(2018/09/21)
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- N - hexyl carbazole substituted phenyl and [...] (III) complex and its preparation
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The invention discloses an N-hexyl carbazole substituted phenyl benzothiazole iridium (III) complex. The complex has a structure represented in a general structural formula (I). The complex emits organic yellow light, has double polarity and better solubility, and can be taken as a phosphorescent luminescence material for preparation of an organic light-emitting device with a wet method.
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Paragraph 0041; 0046-0049
(2020/02/07)
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- Synthesis, characterization and biological activities of mercury(II) ternary complexes of 2-substituted benzothiazoles derivatives
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Biological important ternary complexes of type [HgL(A-A)] [where L = 2-(2'-hydroxynaphthyl)benzothiazole (APBT), 2-(2'-hydroxyphenyl)benzothiazole (HPBT), 2-(2'-mercapto-phenyl)benzothiazole (MPBT)] (A = glycine or alanine) have been synthesized and characterized by m.w. determination, magnetic measurements, infrared and NMR studies. A tetrahedral geometry has been proposed for the present mercury(II) complexes. All the complexes are coloured, thermally stable, monomeric and non-electrolytic in nature. The ligands and their metal complexes showed biological activity against pathogenic fungi Aspergillus Niger and Fusarium oxysporum. The antifungal activity data revealed that mercury(II) complexes are found more fungi-toxic than the parent ligands.
- Chauhan, Manmohan Singh,Yadav, Mitlesh Kumari,Sharma, Aruna,Binani, Shradha,Lamba, Narendra Pal
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p. 1777 - 1780
(2018/07/10)
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- Synthesis of some benzothiazoles by developing a new protocol using urea nitrate as a catalyst and their antimicrobial activities
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The present communication demonstrates the development of urea nitrate as an effective and efficient catalyst for the synthesis of some 2-substituted benzothiazoles. Instant progress of reaction at room temperature under solvent-free condition, very high catalytic activity, inexpensive, clean reaction profile, operational simplicity, large-scale synthesis and appreciable yields are the main advantages of this protocol. These synthesized benzothiazoles have been evaluated for their antibacterial and antifungal activities against Gram-positive bacterium (Bacillus subtilis MTCC 121); two Gram-negative bacteria (Escherichia coli MTCC 1652 and Pseudomonas aeruginosa MTCC 741) and two fungi (Candida albicans MTCC 3017 and Saccharomyces cerevisiae MTCC 170). Compound 3n was found the most active against all the tested microbes.
- Kumar, Parvin,Bhatia, Rimpy,Khanna, Radhika,Dalal, Aarti,Kumar, Dinesh,Surain, Parveen,Kamboj, Ramesh C.
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p. 585 - 596
(2017/10/05)
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- Preparation method of 2-aryl benzoxazole and 2-aryl benzothiazole compounds
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The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 2-aryl benzoxazole and 2-aryl benzothiazole compounds. According to the invention, 2-aminophenol(2-aminothiophenol) and aromatic aldehydes are stirred at the temperature of 100 to 130 DEG C, imidazolium salt of which the molar equivalent amount is 10% to 20% and K2CO3 of which the molar equivalent amount is 25% to 50% are added, air is used as an oxidant, and then 2-aryl benzoxazole and 2-aryl benzothiazole compounds are synthesized by a reaction. According to the invention, the cheap and easily prepared imidazolium salt is taken as a catalyst and the cheap air is taken as the oxidant to synthesize target products in a high yield, so that the preparation method of the 2-aryl benzoxazole and 2-aryl benzothiazole compounds is greatly lowered in production cost and capable of adapting to the industrial application to a greater extent.
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Paragraph 0038; 0039
(2017/08/29)
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- Green and Highly Efficient Synthesis of Mono- and Bis-Benzothiazoles in the Presence of Fe(SD)3 under Ultrasound Irradiation
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A convenient, practical, green, and environmentally friendly method was developed for the synthesis of benzothiazoles from 2-aminothiophenol and various aldehydes. Bis-benzothiazoles were synthesized in high yield under mild reaction conditions. Products
- Pirbasti, Fateme Ghanbari,Mahmoodi, Nosrat Ollah
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- Visible-light-promoted synthesis of benzothiazoles from 2-aminothiophenols and aldehydes
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A visible-light-promoted synthesis of benzothiazoles from 2-aminothiophenols and aldehydes has been developed. A wide range of aromatic, heteroaromatic and aliphatic aldehydes were successfully applied. The benzothiazole products were prepared in good yields. The reaction was carried out in the absence of transition-metal catalysts and extra additives. A radical reaction pathway was proposed.
- Ye, Lin-miao,Chen, Jie,Mao, Peng,Mao, Zhi-feng,Zhang, Xue-jing,Yan, Ming
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supporting information
p. 874 - 876
(2017/02/18)
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- Aluminium complexes containing salicylbenzothiazole ligands and their application in the ring-opening polymerisation of rac-lactide and ?-caprolactone
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Two series of aluminium complexes bearing salicylbenzothiazole ligands, namely four-coordinate aluminium complexes (1a-7a) and five-coordinate aluminium complexes (1b-7b), were synthesized and characterized by NMR spectroscopy, elemental analysis and X-ra
- Nakonkhet, Chutikan,Nanok, Tanin,Wattanathana, Worawat,Chuawong, Pitak,Hormnirun, Pimpa
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p. 11013 - 11030
(2017/08/30)
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- Detecting peroxide nitroso fluorescence probe and its preparation and use
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The invention provides a fluorescent probe for detecting peroxynitrite. The probe has a general structure formula Ia or Ib. The probe is prepared by: (1) stirring R4-substituted o-aminothiophenol or R4-substituted o-aminophenol and R1/R2-substituted benza
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-
Paragraph 0044; 0045
(2017/08/24)
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- Elemental sulfur as a polyvalent reagent in redox condensation with: O -chloronitrobenzenes and benzaldehydes: Three-component access to 2-arylbenzothiazoles
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Sulfur was found to be a polyvalent reagent in the multicomponent redox condensation with o-chloronitrobenzenes and benzaldehydes. 2-Arylbenzothiazoles was obtained in moderate to good yields in a highly atom-economical pathway.
- Nguyen, Le Anh,Ngo, Quoc Anh,Retailleau, Pascal,Nguyen, Thanh Binh
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supporting information
p. 4289 - 4293
(2017/09/29)
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- A new ESIPT-based fluorescent probe for highly selective and sensitive detection of HClO in aqueous solution
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A new ESIPT-based fluorescent probe, PHC2, for the detection of hypochlorous acid has been rationally designed and developed. Endowed by the specific reaction between hypochlorous acid and phenyl azo group, PHC2 features high degree of selectivity and sensitivity for HClO with a low detection limit (13.2?nM) under physiological conditions in neutral aqueous solution.
- Pan, Yimin,huang, Jing,Han, Yifeng
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p. 1301 - 1304
(2017/03/10)
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- Direct arylation of benzoazoles with aldehydes utilizing metal-organic framework Fe3O(BDC)3 as a recyclable heterogeneous catalyst
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A metal-organic framework Fe3O(BDC)3 was synthesized and used as a recyclable heterogeneous catalyst for the direct arylation of azoles with benzaldehydes. Following this protocol, inexpensive and commercially available benzaldehydes could act as an aryl source for the transformation, replacing the aryl halides normally employed in the conventional cross-coupling reactions. The catalyst disclosed higher catalytic productivity for the formation of aryl-substituted azoles than various MOFs and diverse homogeneous iron catalysts. The conversion was considerably regulated by the solvent and the oxidant, and the combination of N-methyl-2-pyrrolidone with di-tert-butyl peroxide offered the best yield. Heterogeneous catalysis was verified for the reaction, and the production of aryl-substituted azoles was only feasible in the presence of the iron framework. It was possible to reuse the catalyst for the direct arylation of azoles with aldehydes while its catalytic activity was preserved for multiple cycles. To our best judgment, this direct arylation of azoles with aldehydes utilizing solid catalysts has not been previously reported.
- Doan, Son H.,Nguyen, Khoa D.,Nguyen, Tung T.,Phan, Nam T. S.
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p. 1423 - 1431
(2017/01/21)
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- An efficient green synthesis of 2-arylbenzothiazole analogues as potent antibacterial and anticancer agents
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We have demonstrated a novel and green approach for the synthesis of 2-substituted benzothiazole analogues. A number of 2-aryl and heteroaryl benzothiazole scaffolds were synthesized using Amberlite IR-120 resin under microwave irradiation. The catalytic
- Chhabra, Mohit,Sinha, Sohini,Banerjee, Swagata,Paira, Priyankar
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supporting information
p. 213 - 217
(2015/12/20)
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- Copper(II)-diaminosarcophagine-functionalized SBA-15: A heterogeneous nanocatalyst for the synthesis of benzimidazole, benzoxazole and benzothiazole derivatives under solvent-free conditions
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Solvent-free organic reactions were studied over periodic mesoporous silica (SBA-15) containing a Cu(II) organometallic complex. This heterogeneous catalyst was achieved by coordination of Cu(II) ions with the diaminosarcophagine ligand and then its grafting onto the surface of SBA-15. This catalyst displayed ordered mesoporous channels, which implies an extremely high dispersion of the Cu(II) complex and the convenient diffusion of reactant molecules into the pore channels. Therefore, this catalyst can offer high activity and also facile separation or recycling when compared with its homogeneous counterparts.
- Bardajee, Ghasem Rezanejade,Mohammadi, Marzieh,Kakavand, Nahale
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