37859-42-0Relevant articles and documents
A highly selective naked-eye and fluorescent probe for fluoride ion based on 1,8-naphalimide and benzothizazole
Chen, Xiaoxing,Leng, Taohua,Wang, Chengyun,Shen, Yongjia,Zhu, Weihong
, p. 299 - 305 (2017)
Based on benzothizazole and 1,8-naphalimide, a novel colorimetric and fluorescent probe (probe 1) for fluoride ion was synthesized by Schiff base reaction. The striking yellow-to-blue color change of the probe 1 in the CH3CN was observed with the naked eyes only in presence of F? among the eight anions (F?, Cl?, Br?, I?, NO3?, HSO4?, H2PO4?, AcO?). Besides that, upon addition of F?, both of the absorption and emission peaks shifted to near-infrared region (NIR) (>600?nm) in UV–vis and fluorescent spectra, and the detection limit reached as low as 0.41?μM. Furthermore, the 1H NMR titration and theoretical calculation based on TD-DFT indicated that the fluoride ion induced deprotonation of the probe 1 through hydrogen bonding interaction between amino group of probe 1 and fluoride ion.
A simple but sensitive and efficient fluorescent probe for “turn-on” sensing of ClO?
Cui, Chuanyang,Cui, Yu,Dong, Xiaoling,Huang, Xin,Li, Yexin,Shi, Wendi,Sun, Guoxin,Wang, Xue,Xie, Hangxin,Yan, Mei,Yang, Xiaofeng
, (2020)
A simple but sensitive and efficient fluorescent probe YXF for “turn-on” detecting ClO? had been developed. For compound YXF, the benzothiazole unit was the efficient fluorophore, and the C[dbnd]N unit was the recognition site for ClO?. It could detect ClO? with a high selectivity and sensitivity over other 29 kinds of common analytes including some reactive oxygen molecules. After addition of 30 equiv. NaClO to the solution of YXF, the fluorescent intensity at 452 nm enhanced with an approximately 37-fold within seconds. The fluorescence intensity of the reaction between YXF and NaClO showed a good linearity in the NaClO concentration range of 1–180 μM and YXF had a low detection limit of 1.8 × 10?8 M. In addition, NaClO-promoted oxidation cleavage of C[dbnd]N unit of probe YXF was verified by HR-MS and NMR spectrometry analysis. Moreover, probe YXF could be successfully applied for detection of ClO? concentration in several tap water and 84 disinfectant samples.
[1,3]-Claisen rearrangement via removable functional group mediated radical stabilization
Alam, Md Nirshad,Dash, Soumya Ranjan,Mukherjee, Anirban,Pandole, Satish,Marelli, Udaya Kiran,Vanka, Kumar,Maity, Pradip
, p. 890 - 895 (2021/02/01)
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.
Discovery of anti-cell migration activity of an anti-HIV heterocyclic compound by identification of its binding protein hnRNP M
Kamo, Masahiro,Ito, Miu,Toma, Tsugumasa,Gotoh, Haruna,Shimozono, Rie,Nakagawa, Riko,Koga, Ryoko,Monde, Kazuaki,Tateishi, Hiroshi,Misumi, Shogo,Otsuka, Masami,Fujita, Mikako
supporting information, (2021/02/05)
One compound sometimes shows two biological functions, becoming important aspect of recent drug discovery. This study began with an attempt to confirm the previously reported molecular mechanism of the anti-human immunodeficiency virus (HIV) heterocyclic compound BMMP [2-(benzothiazol-2-ylmethylthio)-4-methylpyrimidine], i.e., induction of abnormal uncoating of the viral core at the post-entry step. Our mechanistic study gave results consistent with this mechanism. We further attempted to find out the molecular target of BMMP by a pulldown approach using previously synthesized biotinylated BMMP (Biotin-BMMP) and successfully identified heterogenous nuclear ribonucleoprotein M (hnRNP M) as a BMMP-binding protein. This protein was found not to be accountable for the anti-HIV activity of BMMP. As hnRNP M has been reported to promote cancer metastasis, we tested this mechanism and found that BMMP suppressed migration of the human lung carcinoma cell line A549 stimulated with transforming growth factor-β (TGF-β). Mechanistic study showed that BMMP suppressed the expression of CD44 mRNA via the regulation of hnRNP M. Furthermore, six new derivatives of BMMP were synthesized, and the patterns of their activities against HIV-1 and cell migration were not uniform, suggesting that the anti-HIV mechanism and the anti-cell migration mechanism of BMMP are independent. Taken together, the anti-cell migration activity of the anti-HIV heterocyclic compound BMMP was newly discovered by identification of its binding protein hnRNP M using a chemical biology approach.
Biocatalytic reduction of α,β-unsaturated carboxylic acids to allylic alcohols
Aleku, Godwin A.,Leys, David,Roberts, George W.
, p. 3927 - 3939 (2020/07/09)
We have developed robust in vivo and in vitro biocatalytic systems that enable reduction of α,β-unsaturated carboxylic acids to allylic alcohols and their saturated analogues. These compounds are prevalent scaffolds in many industrial chemicals and pharmaceuticals. A substrate profiling study of a carboxylic acid reductase (CAR) investigating unexplored substrate space, such as benzo-fused (hetero)aromatic carboxylic acids and α,β-unsaturated carboxylic acids, revealed broad substrate tolerance and provided information on the reactivity patterns of these substrates. E. coli cells expressing a heterologous CAR were employed as a multi-step hydrogenation catalyst to convert a variety of α,β-unsaturated carboxylic acids to the corresponding saturated primary alcohols, affording up to >99percent conversion. This was supported by the broad substrate scope of E. coli endogenous alcohol dehydrogenase (ADH), as well as the unexpected CC bond reducing activity of E. coli cells. In addition, a broad range of benzofused (hetero)aromatic carboxylic acids were converted to the corresponding primary alcohols by the recombinant E. coli cells. An alternative one-pot in vitro two-enzyme system, consisting of CAR and glucose dehydrogenase (GDH), demonstrates promiscuous carbonyl reductase activity of GDH towards a wide range of unsaturated aldehydes. Hence, coupling CAR with a GDH-driven NADP(H) recycling system provides access to a variety of (hetero)aromatic primary alcohols and allylic alcohols from the parent carboxylates, in up to >99percent conversion. To demonstrate the applicability of these systems in preparative synthesis, we performed 100 mg scale biotransformations for the preparation of indole-3-aldehyde and 3-(naphthalen-1-yl)propan-1-ol using the whole-cell system, and cinnamyl alcohol using the in vitro system, affording up to 85percent isolated yield.
Visible light-induced hydroxyalkylation of 2H-benzothiazoles with alcohols via selectfluor oxidation
Kong, Yaolei,Xu, Wenxiu,Liu, Xinghai,Weng, Jianquan
supporting information, p. 3245 - 3249 (2020/06/21)
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.
TRANSGLUTAMINASE 2 (TG2) INHIBITORS
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Paragraph 00778, (2020/03/02)
Described herein are compounds and pharmaceutical compositions containing such compounds which inhibit transglutaminase 2 (TG2). Also described herein are methods for using such TG2 inhibitors, alone or in combination with other compounds, for treating diseases or conditions that would benefit from TG2 inhibition.
Application of substituted benzothiazole C2 hydroxyl alkylated derivative as bactericide
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Paragraph 0027-0030, (2019/11/12)
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
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Paragraph 0016-0017, (2019/11/29)
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.
SNAr catalysis enhanced by an aromatic donor-acceptor interaction; Facile access to chlorinated polyfluoroarenes
Senaweera, Sameera,Weaver, Jimmie D.
, p. 7545 - 7548 (2017/07/12)
Selective catalytic SNAr reaction of polyfluoroaryl C-F bonds with chloride is shown. Stoichiometric TMSCl makes the reaction exergonic and allows catalysis, which involves ground state elevation of chloride, aromatic donor-acceptor interactions, and stabilization of the Meisenheimer complex. Traditional cross-coupling of the products is now possible and demonstrates the utility.
