6265-56-1

Usage

Uses

Used in Pharmaceutical Industry:
(4E)-4-(1,3-benzothiazol-2(3H)-ylidene)-3-hydroxycyclohexa-2,5-dien-1-one is used as a potential pharmaceutical agent for its unique structure and functional groups, which may contribute to the development of new drugs or therapeutic agents. Further research and testing are required to fully understand its properties and potential uses in this field.
Used in Materials Science:
In the materials science field, (4E)-4-(1,3-benzothiazol-2(3H)-ylidene)-3-hydroxycyclohexa-2,5-dien-1-one may be utilized for the development of new materials or the improvement of existing ones, thanks to its distinctive molecular structure. Its potential applications could range from enhancing material properties to creating novel materials with specific functions.
Used in Organic Synthesis:
(4E)-4-(1,3-benzothiazol-2(3H)-ylidene)-3-hydroxycyclohexa-2,5-dien-1-one can be employed as a key intermediate or building block in organic synthesis, allowing for the creation of a variety of complex organic compounds. Its unique structure and functional groups make it a valuable component in the synthesis of new organic molecules with potential applications in various industries.

Upstream product

• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 108-46-3 recorcinol 
• 98370-54-8 zinc 2-aminobenzenethiolate 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 137-07-5 2-amino-benzenethiol 
• 89-86-1 4-hydroxysalicylic acid 

Downstream Products

• 1435485-97-4 C₃₁H₂₄N₂O₄S 
• 1470370-35-4 2',7'-di(1H-benzo[d]thiazol-2-yl)-3',6'-dihydroxy-3H-spiro[isobenzofuran-1-9'-xanthen]-3-one 

Relevant academic research and scientific papers

A simple and readily available fluorescent turn-on probe for cysteine detection and bioimaging in living cells

A new simple and readily available fluorescent probe for cysteine (Cys) was reported. This probe is based on an excited-state intramolecular proton transfer (ESIPT) dye and uses two acrylate moieties as the Cys reaction sites to promote signal changes. Im

Optimization of an analytical method for the spectrophotometric determination of copper in tea and water samples after ultrasonic assisted cloud point extraction using a benzothiazole fluorescein derivative complexing agent

In this work, 2′,7′-di(2-benzothiazolyl)-fluorescein (BTF) was synthesized by using 2-(2′,4′-dihydroxyphenyl) benzothiazole (BT) and phthalic anhydride. BTF is colorful and its absorption maximum occurs at 559 nm. Interestingly, the introduction of Cu2+ affords a dramatic decrease of the absorbance at 559 nm, which is due to the spirolactonization of BTF induced by Cu2+. BTF shows high selectivity toward Cu2+ over other common metal ions in real samples, such as K+, Mg2+, Ca2+, Na+, Fe3+, Cd2+, Al3+, Co2+, Cr3+, Mn2+, Ni2+, La3+ and Zn2+. On this basis, a cloud point extraction (CPE) was developed for copper determination by a UV-vis method. The BTF-Cu2+ complex was explored for pre-concentration, and dissolved in a micellar phase composed by octylphenoxypolyethoxyethanol (Triton X-114). Under optimal experimental conditions, the decrease of the absorbance value (ΔA) at 559 nm is linear with Cu2+ concentration in the range from 0.03 to 2 μmol L-1 (1.90-127 μg L-1) with a limit of detection of 7.48 nmol L-1 (3σ). The method has been successfully applied for the determination of copper in tea and water samples.

A reversible vapor-responsive fluorochromic molecular platform based on coupled AIE–ESIPT mechanisms and its applications in anti-counterfeiting measures

In this work, a series of 2-(2-hydroxyphenyl)benzothiazole (HBT) derivatives with an aggregation-induced emission–excited state intramolecular proton transfer (AIE-ESIPT) dual mechanism was synthesized. We systematically investigated their optical properties in solution, aqueous suspension, and the solid state. The fluorescence properties of these five compounds were highly dependent on the solvent environment. Particularly, DMSO and DMF were found to significantly promote deprotonation of the phenolic hydroxyl and favor fluorescence emission from the phenolic anion. The Keto or Enol forms generally could be transformed to phenolic anions with the aid of base in solution. The results from aggregation-induced emission enhancement (AIEE) and red-shifted AIE clearly illustrated the evolution process of the fluorescence spectra, indicating that the three luminescent species in the solution were transformable. The systematic investigation demonstrated that the desired fluorescence could be generated for HBT derivatives by varying the solvents or adding additives, such as base or water, to the solution. Because of the synergistic effect of AIE and ESIPT, these fluorophores exhibited high solid-state quantum yields and large Stokes shifts. These dyes also featured high photostability and tunable emission spectra covering most of the visible light region. Single crystal studies and theoretical calculations elucidated the luminescent properties. When loaded on filter paper, the HBT-based dyes exhibited high-efficiency fluorescence visualization and reversible solid-state luminescence switching under alternating amine and acid vapor treatments. These dyes were used on banknotes for anti-counterfeiting measures, demonstrating the practical applications of these molecules as security inks.

A ratiometric fluorescence mitochondrial-targeted probe for imaging HOCl in vitro and in vivo

HOCl, as one of reactive oxygen species, could cause tissue damage and induce various disease when it is at abnormal level or improper location. To monitor HOCl, we developed a near infrared ratiometric fluorescence probe C3H, which is capable to detect HOCl in real time. This probe gives two emission signals with no cross-talk in the process of monitoring HOCl, accompanied by a considerable variation (up to 348-fold) in its fluorescence intensity ratio (F480 nm/F750 nm). Additionally, probe C3H exhibited excellent properties such as fast response (? in vivo.

Novelmeta-benzothiazole and benzimidazole functionalised POCOP-Ni(ii) pincer complexes as efficient catalysts in the production of diarylketones

The synthesis of four novel non-symmetric Ni(ii)-POCOP pincer complexesmeta-functionalized with either benzothiazole or benzimidazole at the central aryl ring is described. All complexes were fully characterised in solution by various analytical techniques and the molecular structures in the solid state of complexes1b,2aand2bwere unequivocally determined by single crystal X-ray diffraction analysis. In addition, the Ni(ii)-POCOP pincer complexes were efficiently used as catalysts in the synthesis of diarylketones by cross-coupling reactions of functionalized benzaldehydes and boronic acid derivatives under relatively mild conditions. An important aspect of this transformation is the dependence on the steric properties of the donor groups (OPR2) of the pincer ligands, the more active compounds having the phosphinitos bearing isopropyl groups (1aand2a) than those containingtert-butyl substituents (1band2b).

Ratiometric fluorescence imaging of Cu2+ based on spirolactamized benzothiazole-substituted N,N-diethylrhodol probe

A novel ratiometric chemosensor BSRH based on spirolactamized benzothiazole-substituted N,N-diethylrhodol was developed for recognizing Cu2+. In sensing process of BSRH, The Cu2+ was detected by the inhibition of ESIPT and formation of the delocalized xanthene with high sensitivity and selectivity. The Cu2+-induced emission intensity/absorbance showed linearly proportional to the Cu2+concentration (0.0–10.0 μM) with the low detection limit of 0.11 μM / 0.18 μM. Moreover, the probe was further successfully applied to test Cu2+ in real water samples and living Hela imaging. This work provides a promising and useful tool to determine Cu2+ in biological and environmental samples.

Stress response decay with aging visualized using a dual-channel logic-based fluorescent probe

Diagnosing aging for preventative intervention generally relies on the tracking of aging biomarkers in the resting state. However, the static marker levels are insufficient to fully evaluate aging, particularly given that the stress response capacity (SRC) decay is currently viewed as a critical feature of aging. Therefore, we have developed a dual-channel fluorescent probe ROKS capable of the logic-based visualization of thiophenol (stressor) and HOCl (thiophenol-activated stress response product) in vivo, which provides a new strategy from the time dimension to precisely assess the SRC of individuals under stress using the dual-channel fluorescence ratio. Using ROKS we observed that the SRC of live cells decayed with senescence, and that a higher SRC was found for young vs. aged Caenorhabditis elegans. As such, our study offers a promising strategy for the fluorescence-guided diagnosis of aging and paves the way for accurate evaluation of the efficacy of anti-aging drugs.

Rhodol-HBT derivative and preparation method and application thereof

The invention discloses a Rhodol derivative as shown in a structural general formula (I). According to the invention, benzothiazole is introduced into a Rhodol structure, a novel Rhodol-HBT dye is developed, the dye has multiple excellent properties of two fluorophores Rhodol and HBT, and two active sites which are easy to modify are provided. The compound can be used as a fluorescent probe for logic detection of thiophenol and hypochlorous acid, visual imaging of the oxidative stress process in cells, zebra fishes and nematodes is successfully achieved by means of a fluorescence confocal microscope, and dynamic evaluation of aging of the cells and the nematodes is further achieved by means of the probe.

Design, synthesis and evaluation of benzothiazole derivatives as multifunctional agents

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.

ESIPT-rhodol derivatives with enhanced Stokes shift: Synthesis, photophysical properties, viscosity sensitivity and DFT studies

Three rhodol derivatives, namely spirolactamized phenanthrene-imidazole, diphenyl-imidazole and benzothiazole substituted N, N-diethylamine rhodols were designed, synthesized and characterized. Their photophysical properties were studied in spirocyclic and open form from non-polar to polar solvents. The spirocyclic form exhibited larger Stokes shifts (50–260 nm) due to presence of ESIPT process whereas, open form showed small Stokes shift (10–40 nm) due to the lack of protons. Positive solvatochromism was observed for both the spirocyclic and open forms which is well supported by the linear (Lippert-Mataga and Mac-Rae) and multi-linear (Kamlet-Taft and Catalan parameters) analysis. Solvent polarizability (dSP) is the major factor responsible for red shift in absorption/emission and larger Stokes shift for spirocyclic form. Polarity graphs and charge transfer descriptors are in good relation with Generalized Mulliken-Hush (GMH) parameters. From the solvatochromic data we observed that open forms show good TICT characteristics as compared to their respective spirocyclic forms. Open form is highly sensitive to viscosity as compared to spirocyclic form in a mixture of polar-protic solvents (EtOH:PEG 400). The experimental results are well correlated theoretically using Density Functional Theory (DFT) computations.