36341-25-0

Usage

Uses

Used in UV-Absorbing Materials:
2-(4-Hydroxy-3-methoxyphenyl)benzothiazole is used as a UV-absorbing agent in various materials to protect against the harmful effects of ultraviolet radiation. Its ability to absorb and convert UV light into less damaging forms makes it a valuable ingredient in sunscreens and other protective coatings.
Used in Optical Brightening Agents for Textiles and Paper:
In the textile and paper industries, 2-(4-Hydroxy-3-methoxyphenyl)benzothiazole is used as an optical brightening agent. Its fluorescent properties enhance the appearance of these materials, making them brighter and more visually appealing.
Used in Pharmaceutical Synthesis:
2-(4-Hydroxy-3-methoxyphenyl)benzothiazole serves as a potential intermediate in the synthesis of pharmaceuticals. Its unique structure and properties make it a valuable component in the development of new drugs with various therapeutic applications.
Used in Agrochemical Synthesis:
Similarly, in the agrochemical industry, 2-(4-Hydroxy-3-methoxyphenyl)benzothiazole is used as an intermediate in the synthesis of agrochemicals. Its properties contribute to the development of effective and innovative products for agricultural applications.
Used in Fluorescent Dyes and Materials:
The fluorescent properties of 2-(4-Hydroxy-3-methoxyphenyl)benzothiazole make it useful in the development of fluorescent dyes and materials for various applications, such as in research, diagnostics, and imaging technologies.

InChI:InChI=1/C14H11NO2S/c1-17-12-8-9(6-7-11(12)16)14-15-10-4-2-3-5-13(10)18-14/h2-8,16H,1H3

Upstream product

• 121-33-5 vanillin 
• 137-07-5 2-amino-benzenethiol 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 1173707-00-0 C₁₄H₁₂INO₃ 
• 1141-88-4 2-Aminophenyl disulfide 
• 95-16-9 1,3-Benzothiazole 
• 98370-54-8 zinc 2-aminobenzenethiolate 
• 3292-42-0 2-aminobenzenethiol hydrochloride 

Downstream Products

• 1049018-55-4 (2S)-N-{4-(N-[4-(1,3-benzothiazol-2-yl)-2-methoxyphenoxy]pentyl)oxy-5-methoxy-2-nitrobenzoyl}-pyrrolidine-2-carboxaldehyde diethylthioacetal 
• 1061691-99-3 2-[4-(4-bromobutyloxy)-3-methoxyphenyl]-1,3-benzothiazole 
• 1061692-01-0 2-[4-(5-bromopentyloxy)-3-methoxyphenyl]-1,3-benzothiazole 
• 1280220-13-4 C₂₉H₂₃N₃O₈S 
• 1280220-14-5 C₂₉H₂₇N₃O₄S 
• 96460-77-4 4-(1,3-benzothiazol-2-yl)-1,2-benzenediol 
• 1417793-30-6 C₃₄H₃₂N₂O₆S₂ 
• 1061691-98-2 2-[4-(3-bromopropoxy)-3-methoxyphenyl]-1,3-benzothiazole 
• 723298-40-6 ethyl 2-(4-(benzo[d]thiazol-2-yl)-2-methoxyphenoxy)acetate 

Relevant academic research and scientific papers

New multitarget hybrids bearing tacrine and phenylbenzothiazole motifs as potential drug candidates for Alzheimer’s disease

Research on neurodegenerative brain disorders, namely the age-dependent Alzheimer’s disease (AD), has been intensified in the last decade due to the absence of a cure and the recognized increasing of life expectancy for populations. To address the multifa

Quantitative structure activity relationship studies of novel hydrazone derivatives as α-amylase inhibitors with index of ideality of correlation

The present manuscript describes the synthesis, α-amylase inhibition, in silico studies and in-depth quantitative structure–activity relationship (QSAR) of a library of aroyl hydrazones based on benzothiazole skeleton. All the compounds of the developed l

Amyloid β-Binding Bifunctional Chelators with Favorable Lipophilicity for 64Cu Positron Emission Tomography Imaging in Alzheimer's Disease

Herein, we report a new series of bifunctional chelators (BFCs) with a high affinity for amyloid aggregates, a strong binding affinity toward Cu(II), and favorable lipophilicity for potential blood-brain barrier penetration. The alkyl carboxylate ester pendant arms offer up to 3 orders of magnitude higher binding affinity toward Cu(II) and enable the BFCs to form stable 64Cu-radiolabeled complexes. Among the five compounds tested, the 64Cu-YW-7 and 64Cu-YW-10 complexes exhibit strong and specific staining of amyloid plaques in ex vivo autoradiography studies. Importantly, these BFCs have promising partition coefficient (log Doct) values of 0.91-1.26 and show some brain uptake in biodistribution studies using CD-1 mice. Overall, these BFCs could serve as lead compounds for the development of positron emission tomography imaging agents for AD diagnosis.

Synthesis, XRD single crystal structure analysis, vibrational spectral analysis, molecular dynamics and molecular docking studies of 2-(3-methoxy-4-hydroxyphenyl) benzothiazole

The vibrational spectra and corresponding vibrational assignments of 2-(3-methoxy-4-hydroxyphenyl)benzothiazole is reported. Single crystal XRD data of the title compound is reported and the orientation of methoxy group is cis to nitrogen atom of the thiazole ring. The phenyl ring breathing modes of the title compound are assigned at 1042 and 731 cm?1 theoretically. The charge transfer within the molecule is studied using frontier molecular orbital analysis. The chemical reactivity descriptors are calculated theoretically. The NMR spectral data predicted theoretically are in good agreement with the experimental data. The strong negative region spread over the phenyl rings, nitrogen atom and oxygen atom of the hydroxyl group in the MEP plot is due to the immense conjugative and hyper conjugative resonance charge delocalization of π-electrons. Molecule sites prone to electrophilic attacks have been determined by analysis of ALIE surfaces, while Fukui functions provided further insight into the local reactivity properties of title molecule. Autoxidation properties have been investigated by calculation of bond dissociation energies (BDEs) of hydrogen abstraction, while BDEs of the rest of the single acyclic bonds were valuable for the further investigation of degradation properties. Calculation of radial distribution functions was performed in order to determine which atoms of the title molecule have pronounced interactions with water molecules. The title compound forms a stable complex with aryl hydrocarbon receptor and can be a lead compound for developing new anti-tumor drug. Antimicrobial properties of the title compound was screened against one bacterial culture Escherchia coli and four fungal cultures viz., Aspergillus niger, Pencillum chrysogenum, Saccharomyces cerevisiae and Rhyzopus stolonifer.

Novel 2-arylbenzothiazole DNA gyrase inhibitors: Synthesis, antimicrobial evaluation, QSAR and molecular docking studies

A series of new 2-arylbenzothiazole derivatives (4, 5, 6a-j, 7a-i and 8a,b) was synthesized and tested for their antimicrobial activity against different Gram-positive, Gram-negative bacteria and yeast using ciprofloxacin and fluconazole as positive contr

A fluorescence turn-on probe for the recognition of Al3+ and its application in cell image

An easy prepared benzothiazole-based probe (E)-5-(benzo[d]thiazol-2-yl)-2-hydroxy-3- methoxybenzaldehyde benzoyl hydrazone (BHMBH) was designed and synthesized, which displayed a significant fluorescence enhancement (over 500-fold) and obvious color changes in the recognition of Al3+. The binding ratio of probe BHMBH to Al3+ was determined as 1:1 according to Job's plot. The binding mechanism was fully clarified by the experiments such as FT-IR spectrum, ESI-MS analysis, and 1H NMR titration. The limit of detection (LOD) for Al3+ was determined as low as 0.232 μM based on the fluorescence titration of BHMBH. Moreover, the results of real sample experiments including real water sample, test papers, and cell image were all well demonstrated that BHMBH was capable of sensing Al3+ in environmental and biological system as well.

Synthesis, anticancer evaluation and molecular docking of new benzothiazole scaffolds targeting FGFR-1

This work deals with the design and synthesis of a series of new substituted 2-arylbenzothiazole compounds attached to 4-oxothiazolidin-2-ylidene ring 2–12 and chain elongation with different amino acids and their corresponding ester derivatives 13–18. All prepared derivatives were screened for their in vitro cytotoxicity activities against two cancer cell lines (HepG-2 and MCF-7) in comparison with doxorubicin; in addition to their safety towards thenormal cell line. Furthermore, all compounds 2–18 were evaluated as FGFR-1 inhibitors using AZD4547 as a reference. The 4-oxothiazolidin-2-ylidene derivatives 3 and 8 exhibited the highest cytotoxic activity (IC50 HepG-2 = 2.06, 2.21 μM and IC50 MCF-7 = 0.73, 0.77 μM, respectively) through their promising FGFR-1 suppression effects (IC50 = 16.31 and 18.08 nM, respectively) in comparison to AZD4547 (IC50 = 21.45 nM). Cell cycle and apoptosis analysis indicated that compounds 3 and 8 induce pronounced increase in the cell percentages at pre-G1 and G2/M phase compared to the untreated MCF-7 cancer cells, in addition to their up regulation of caspase-3/7/9. The molecular docking simulation was created to elucidate the binding modes of benzothiazole derivatives 1–18 bearing various scaffolds within the ATP-binding pocket of FGFR-1 enzyme compared with AZD4547.

2-(4-Hydroxyphenyl)benzothiazole dicarboxylate ester TACN chelators for64Cu PET imaging in Alzheimer's disease

Herein we report a new series of bifunctional chelators (BFCs) with high affinity for amyloid β aggregates, strong binding affinity towards Cu(ii), and favorable lipophilicity for potential blood–brain barrier (BBB) penetration. The alkyl carboxylate ester pendant arms show high binding affinity towards Cu(ii). The BFCs form stable 64Cu-radiolabeled complexes and exhibit favorable partition coefficient (log?D) values of 0.75–0.95. Among the five compounds tested, 64Cu-YW-1 and 64Cu-YW-13 complexes exhibit significant staining of amyloid plaques in ex vivo autoradiography studies.

Recyclable copper-catalyzed cyclization of o-haloanilides and metal sulfides: An efficient and practical access to substituted benzothiazoles

An efficient heterogeneous copper-catalyzed cyclization of o-haloanilides and metal sulfides has been achieved via the C–S coupling in DMF at 80 or 140 °C in the existence of an MCM-41-bound NHC-Cu(I) catalyst and then intramolecular condensation, delivering a wide range of substituted benzothiazoles in mostly good to high yields. This new MCM-41-NHC-CuI complex can facilely be obtained by a two-step procedure starting from easily accessible and inexpensive reagents and reused more than seven times without any significant loss of its catalytic efficiency. The present protocol has been successfully applied to the gram-scale synthesis of two antitumor agents 5F203 and PMX 610.

Pentafluorophenylammonium Triflate: A Mild, Efficient and Reusable Catalyst for the Synthesis of 2-Arylbenzothiazole and 2-Arylbenzothiazoline Derivatives in a Green Chemical Approach

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.