17147-80-7

Usage

InChI:InChI=1/C9H9NOS/c1-6(11)9-10-7-4-2-3-5-8(7)12-9/h2-6,11H,1H3

Upstream product

• 95-16-9 1,3-Benzothiazole 
• 64-17-5 ethanol 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 1629-78-3 2-acetylbenzothiazole 
• 75-07-0 acetaldehyde 
• 849585-22-4 LACTIC ACID 
• 137-07-5 2-amino-benzenethiol 

Downstream Products

• 1629-78-3 2-acetylbenzothiazole 
• 110704-27-3 2-(1-chloroethyl)benzothiazole 
• 1059697-82-3 (S)-1-(benzo[d]thiazol-2-yl)ethan-1-ol 
• 1059698-08-6 (R)-1-(benzo[d]thiazol-2-yl)ethanol 
• 1315309-23-9 C₂₃H₁₉NO₂S 
• 453558-32-2 1-(benzo[d]thiazol-2-yl)-2-chloroethanone 
• 54469-55-5 4-(benzo[d]thiazol-2-yl)-N-phenylthiazol-2-amine 
• 29947-33-9 2-(2-benzyl-thiazol-4-yl)-benzothiazole 
• 29947-34-0 2-(2-m-tolyl-thiazol-4-yl)-benzothiazole 
• 29947-32-8 2-(2-phenylthiazol-4-yl)benzo[d]thiazole 
• 29947-31-7 2-(4-Thiazolyl)-benzothiazol 
• 54223-20-0 1-(benzo[d]thiazol-2-yl)-2-bromoethanone 
• 29942-03-8 2-[2-(4-methoxy-phenyl)-thiazol-4-yl]-benzothiazole 

Relevant academic research and scientific papers

Lipase-catalyzed kinetic resolution of racemic 1-heteroarylethanols-experimental and QM/MM study

The kinetic resolution of racemic 1-(benzothiazol-2-yl)ethanol rac-2a, 1-(benzo[b]thiophen-2-yl)ethanol rac-2b, 1-(benzo[b]furan-3-yl)ethanol rac-2c and 1-(benzo[b]thiophen-3-yl)ethanol rac-2d was studied by enantiomer selective acylation catalyzed by a selection of commercially available and in house produced lipases. Alcoholysis of the corresponding racemic acetates rac-3a-d catalyzed by Candida antarctica lipase B (CaLB) was also investigated. Two racemic 1-heteroarylethanols rac-2a,b were prepared by addition of the corresponding lithiated heteroarylic compounds 1a,b to acetaldehyde, whereas two others, rac-2c,d were synthesized by the addition of MeMgI onto the corresponding heteroaryl-carbaldehydes 1c,d. The high enantiomer selectivities of CaLB in the acylation of racemic 1-heteroarylethanols rac-2a-d allowed the determination of the enantiomeric preference of these enzymatic acetylation reactions by QM/MM [pm3/uff or hf(3-21+g**)/uff] calculations. For acetylation of each of the racemic alcohols rac-2a-d, four possible tetrahedral intermediate states were compared and analyzed.

[1,3]-Claisen rearrangement via removable functional group mediated radical stabilization

A thermal O-to-C [1,3]-rearrangement of α-hydroxy acid derived enol ethers was achieved under mild conditions. The 2-aminothiophenol protection of carboxylic acids facilitates formation of the [1,3] precursor and its thermal rearrangement via stabilization of a radical intermediate. Experimental and theoretical evidence for dissociative radical pair formation, its captodative stability via aminothiophenol, and a unique solvent effect are presented. The aminothiophenol was deprotected from rearrangement products as well as after derivatization to useful synthons.

Neutral analogs of the heat shock protein 70 (Hsp70) inhibitor, JG-98

The heat shock protein 70 (Hsp70) family of molecular chaperones are highly expressed in tumors. Inhibitors containing a pyridinium-modified benzothiazole, such as JG-98, bind to a conserved, allosteric site in Hsp70, showing promising anti-proliferative activity in cancer cells. When bound to Hsp70, the charged pyridinium makes favorable contacts; however, this moiety also increases the inhibitor's fluorescence, giving rise to undesirable interference in biochemical and cell-based assays. Here, we explore whether the pyridinium can be replaced with a neutral pyridine. We report that pyridine-modified benzothiazoles, such as compound 17h (JG2-38), have reduced fluorescence, yet retain promising anti-proliferative activity (EC50 values ~0.1 to 0.07 μM) in breast and prostate cancer cell lines. These chemical probes are expected to be useful in exploring the roles of Hsp70s in tumorigenesis and cell survival.

Direct α-Arylation of Alcohols with Aryl Halides through a Radical Chain Mechanism

Alcohols were found to be arylated directly at their α-C?H bond with aryl halides in the presence of a base and a substoichiometric amount of t-BuOOt-Bu through a homolytic aromatic substitution mechanism. (Figure presented.).

Preparation method of C2-substituted 2H-benzothiazole hydroxyalkylated derivative

The invention discloses a preparation method of a C2-substituted 2H-benzothiazole hydroxyalkylated derivative. The preparation method comprises the following steps: mixing substituted 2H-benzothiazolewith fatty alcohol, taking an organic dye photosensitizer as a catalyst, carrying out a normal-temperature stirring reaction in a solvent under the protection of nitrogen and the irradiation of an LED white light lamp, carrying out TLC monitoring until the reaction is finished, and carrying out separation and purification on a reaction solution to obtain the C2-substituted 2H-benzothiazole hydroxyalkylated derivative. By adopting the technology, a cheap and readily available organic dye is used as the catalyst, the new method for synthesizing the 2H-benzothiazole C2 hydroxyalkylated derivative through visible light induction is simple in catalytic system, mild in reaction condition, cheap and readily available in catalyst and good in yield.

Photocatalytic synthesis method of C2 substituted 2H-benzothiazole hydroxyalkylated derivative

The invention discloses a photocatalytic synthesis method of a C2 substituted 2H-benzothiazole hydroxyl alkylation derivative. The method comprises the following steps of: mixing substituted 2H-benzothiazole shown as a formula (II) with fatty alcohol shown as a formula (III), adding an oxidizing agent Selectfluor, an additive trifluoroacetic acid and a solvent acetonitrile, and carrying out a normal temperature stirring reaction under the protection of nitrogen and the irradiation of an LED blue light lamp; carrying out TLC monitoring until the reaction is finished, and carrying out separationand purification on the reaction liquid to obtain the C2-substituted 2H-benzothiazole hydroxyalkylated derivative represented by formula (I). The invention provides a new method for synthesizing the2H-benzothiazole C2 hydroxyalkylated derivative through visible light induction by taking Selectfluor as an oxidizing agent, trifluoroacetic acid as an additive and acetonitrile as a solvent. The method is simple in catalytic system, mild in reaction condition and wide in substrate range.

Visible light-induced hydroxyalkylation of 2H-benzothiazoles with alcohols via selectfluor oxidation

A visible-light induced metal-free approach was described for the hydroxyalkylation of 2H-benzothiazoles with alcohols by using selectfluor as the oxidant. A variety of 2H-benzothiazoles and alcohols could be tolerated, providing a mild and simple method for the synthesis of C2-hydroxyalkylated 2H-benzothiazoles in moderate to good yields. Besides, ethers were also compatible in this reaction, leading to corresponding C2 ether-substituted 2H-benzothiazoles with high regioselectivity.

Asymmetric Hydroboration of Heteroaryl Ketones by Aluminum Catalysis

A series of methyl aluminum complexes bearing chiral biphenol-type ligands were found to be highly active catalysts in the asymmetric reduction of heterocyclic ketones (S/C = 100-500, ee up to 99%). The protocol is suitable for a wide range of substrates and has a high tolerance to functional groups. The formed 2-heterocyclic-alcohols are valuable building blocks in drug discovery or can be used as ligands in asymmetric catalysis. Isolation and comprehensive characterization of the reaction intermediates support a catalysis cycle proposed by DFT calculations.

Application of substituted benzothiazole C2 hydroxyl alkylated derivative as bactericide

The invention discloses application of a substituted benzothiazole C2 hydroxyl alkylated derivative as a bactericide. The structural formula of the substituted benzothiazole C2 hydroxyl alkylated derivative is shown in the formula (I)(please see the specification for the formula); in the formula (I), R1 and R2 are independently selected from hydrogen or C1-C5 alkyl: H on a benzothiazole ring is mono substituted, multi substituted or not substituted by substituent R, and the C2 position of the benzothiazole ring is not substituted by R; n is an integer from 0-4, wherein the n represents numberof the R on the benzothiazole ring: when the n is equal to 0, the H on the benzothiazole ring is not substituted; when the n is equal to 1, the H on the benzothiazole ring is mono substituted by the R; when the n is equal to 2-4, the H on the benzothiazole ring is multi substituted by the R, and the substituent R on the different substituted positions is the same or different; and the substituentR is the hydrogen, the C1-C5 alkyl, C1-C2 alkoxy or halogen. According to the substituted benzothiazole C2 hydroxyl alkylated derivative, particular good inhibitory activity against wheat scab germs,corn southern leaf blight germs, cucumber anthracnose germs, rice sheath blight disease germs and other germs is provided.

Mild preparation method of substituted benzothiazole C2 hydroxyalkylated derivative

The invention discloses a mild preparation method of a substituted benzothiazole C2 hydroxyalkylated derivative. The preparation method comprises: mixing substituted benzothiazole represented by a formula (II) and a fatty alcohol represented by a formula (III), adding an oxidant K2S208 and water, carrying out a room temperature stirring reaction under the illumination of a LED white light lamp, monitoring by TLC until the reaction is completed, and separating and purifying the reaction solution to obtain the substituted benzothiazole C2 hydroxyalkylated derivative represented a formula (I). According to the present invention, the new method for synthesizing a substituted benzothiazole C2 hydroxyalkylated derivative in a water-containing system by using an inorganic peroxide K2S2O8 as an oxidant under the inducing with visible light is provided, and has advantages of high atomic economy, simple catalytic system, good product yield, wide substrate range and short reaction time.