6344-18-9

Usage

Uses

Used in Pharmaceutical Applications:
1-(1,3-Benzothiazol-2(3H)-ylidene)naphthalen-2(1H)-one is used as a pharmaceutical compound for its potential biological activities. Its unique structure may contribute to the development of new drugs, particularly in the areas of medicinal chemistry and drug discovery.
Used in Agrochemical Applications:
In the agrochemical industry, 1-(1,3-benzothiazol-2(3H)-ylidene)naphthalen-2(1H)-one is used as a chemical intermediate for the synthesis of various agrochemical products. Its structural features make it a valuable component in the development of new pesticides, herbicides, and other agricultural chemicals.
Used in Material Science Applications:
1-(1,3-Benzothiazol-2(3H)-ylidene)naphthalen-2(1H)-one is used as a component in the field of material science, where its potential fluorescence and photochromism properties can be harnessed for the development of advanced materials with specific optical and electronic properties.
These applications highlight the versatility of 1-(1,3-benzothiazol-2(3H)-ylidene)naphthalen-2(1H)-one across different industries, showcasing its potential for further research and development to unlock its full range of uses.

Upstream product

• 137-07-5 2-amino-benzenethiol 
• 708-06-5 2-hydroxynaphthalene-1-carbaldehyde 
• 731-90-8 N-(2-hydroxy-1-naphthalidene)aniline 
• 70-18-8 GLUTATHIONE 
• 52-90-4 L-Cysteine 
• 6027-13-0 L-homocysteine 
• 95263-04-0 N-(2-hydroxy-1-naphthylidene)-2-mercaptoaniline 
• 56048-50-1 2-(1-naphthyl)benzothiazole 
• 66-77-3 1-naphthaldehyde 
• 135-19-3 β-naphthol 

Relevant academic research and scientific papers

A highly sensitive and selective turn-on fluorescent probe for hypochlorous acid monitoring

A novel turn-on fluorescent probe 3 for monitoring hypochlorous acid was investigated, which showed high selectivity and sensitivity to hypochlorous acid over other ROS and was loaded into cell media to image HClO.

Competitive intra- and inter-molecular proton transfer in hydroxynaphthyl benzothiazole: Selective ratiometric sensing of acetate

The receptor, naphthalene based benzothiazole (NHBT) shows acetate selectivity in its absorbance and emission behavior among the various interfering anions. Substantially red shifted absorption band and fluorescence emission of NHBT in pure acetonitrile media were developed which drastically got enhanced upon addition of tetrabutylammonium acetate. Excited-state intermolecular proton transfer in the sensor-anion hydrogen-bonding complex was suggested to be the signaling mechanism. NHBT, a good hydrogen-bonding donor, the ESIPT process is inhibited by the formation of a strong acetate-NHBT intermolecular hydrogen bond complex, and the inhibition mechanism consequently results in ratiometric response in absorption and emission spectroscopy, respectively.

ESIPT triggered swift determination of cysteine in HeLa cell line during redox imbalance

Detection of cysteine is crucial as its deviation from normal concentration leads to various diseases. In this work, benzothiazole based chemodosimeter was synthesized to discriminate cysteine rapidly in the presence of other competing interferences. The

Excited-state intramolecular proton transfer of naphthalene-fused 2-(2'-Hydroxyaryl)benzazole family

Intramolecularly hydrogen-bonded organic compounds often exhibit fluorescence emission at considerably longer wavelengths than typical fluorescence as a result of excited-state intramolecular proton transfer (ESIPT). The structure-property relationship of such ESIPT molecules, however, remains obscure. The present article reports the excited-state dynamics of a new family of ESIPT molecules, 2-(2'-hydroxynaphthyl)benzazoles 1-3, based on steady-state and time-resolved spectroscopy measurements. In comparison with the parent compound HBO, all three compounds 1-3 exhibited absorption bands at longer wavelengths and emitted fluorescence from the excited keto-tautomer K* at shorter wavelengths, indicating that the introduction of a naphthalene ring increases the energy gap between the ground and excited states for the keto-tautomer despite the expansion of the aromatic ring. Time-resolved fluorescence spectra revealed dual emission for compounds 1 and 3, consisting of two distinct fluorescence bands originating from K* and the excited rotamer E'*, whereas 2 exhibited fluorescence only from, the K* state. In the transient absorption spectra, both the T-T absorption band and the ground slate absorption band of the Z-keto tautomer were observed for 1, whereas only the T-T absorption band was observed for 2 and only the Z-keto tautomer band was observed for 3.

A new hydroxynaphthyl benzothiazole derived fluorescent probe for highly selective and sensitive Cu2?+ detection

A new reactive probe, 1-(benzo[d]thiazol-2-yl)naphthalen-2-yl-picolinate (BTNP), was designed and synthesized. BTNP acts as a highly selective probe to Cu2?+ in DMSO/H2O (7/3, v/v, Tris-HCl 10?mM, pH?=?7.4) solution based on Cu2?+ catalyzed hydrolysis of the picolinate ester moiety in BTNP, which leads to the formation of an ESIPT active product with dual wavelength emission enhancement. The probe also possesses the advantages of simple synthesis, rapid response and high sensitivity. The pseudo-first-order reaction rate constant was calculated to be 0.205?min??1. Moreover, application of BTNP to Cu2?+ detection in living cells and real water samples was also explored.

A colorimetric and ratiometric fluorescent turn-on fluoride chemodosimeter and application in live cell imaging: High selectivity via specific SiO cleavage in semi aqueous media and prompt recovery of ESIPT along with the X-ray structures

A ratiometric fluorescent turn-on probe for fluoride ion, based on modulation of the excited-state intramolecular proton transfer (ESIPT) process by chemodosimetric desilylation pathway is reported. The probe SNBT (silyl protected hydroxynaphthalene benzothiazole moiety) shows a significant increase of ratiometric absorption band at 440 nm and emission band at 477 nm by the deprotection of fluoride mediated silyl bond cleavage in CH3CN-H 2O (8/2, v/v, 25 °C). The test strips based on SNBT and F - are fabricated, which can act as a convenient and efficient F - test kits. Furthermore, the biological application shows that it can be very useful as a selective fluoride probe in the fluorescence imaging of living cells.

A fluorescent probe for discrimination of cysteine/homocysteine, glutathione and hydrogen polysulfides

Biothiols of cysteine (Cys), homocysteine (Hcy), glutathione (GSH) and hydrogen polysulfides (H2Sn, n > 1) play vital roles in physiological and pathological processes. In this manuscript, a fluorescent probe (compound 1) for simultaneous detection and discrimination of Cys/Hcy, GSH and H2Sn was developed, employing fluorophore of 1-(benzo[d]thiazol-2-yl)naphthalen-2-oxy linked with 7-nitrobenzo-2-oxa-1,3-diazole (NBD) as a response unit and a quencher. Compound 1 exhibited different ratiometric colorimetric responses toward GSH at 430?nm and 375?nm from Cys/Hcy at 480?nm and 375?nm, while it displayed a different colorimetric response at 561?nm toward H2Sn. Meanwhile it could act as a naked-eye probe toward GSH, Cys/Hcy and H2Sn with corresponding solution color of light yellow, orange and purple, respectively. Upon excitation at 370?nm, compound 1 responded to all these biothiols with 'turn-on' blue fluorescence, whereas upon excitation at 470?nm, it could respond to Cys/Hcy with 'turn-on' green fluorescence. Data of mass spectra, lifetimes and 1H NMR spectra interpreted the aromatic nucleophilic substitutions of compound 1 by GSH, Cys/Hcy and H2Sn to produce fluorophore1-(benzo[d]thiazol-2-yl)naphthalen-2-ol (compound 2) and corresponding NBD derivatives which could be discriminated through their absorption and fluorescence signals as well as solution colors. Furthermore, compound 1 was applied to image Cys/Hcy and H2Sn/GSH in 786-O cells.

Compound with aggregation-induced emission function and preparation method and application thereof

The invention relates to a compound with an aggregation-induced emission function, the chemical structure of the compound is shown as a general formula I, 2-hydroxy-1-naphthaldehyde and 2-aminothiophenol (or 2-aminophenol) react in organic solvents to obtain Schiff base structure intermediates; and recrystallizing and purifying are carried out to obtain the intermediate, and the intermediate is reacted with an oxidant in an organic solvent to obtain the compound with the aggregation-induced emission function. Further the compound is modified to obtain series of functionalized aggregation-induced emission compounds. The synthesis method of the compounds is simple, the reaction conditions are mild, the synthesis is easy, the post-treatment operation is convenient, the yield is high, and theheating reaction shortens the reaction time. The obtained aggregation-induced emission compound has an excited state intramolecular proton transfer effect. Intramolecular weak acting force hydrogen bonds exist between hydroxyl hydrogen atoms on a naphthalene ring and nitrogen atoms on an ortho-benzothiazole ring, an excited state intramolecular proton transfer effect is achieved, and large Stokesshift is shown.

Direct Oxygenation of C-H Bonds through Photoredox and Palladium Catalysis

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.

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

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.