- A highly selective naked-eye and fluorescent probe for fluoride ion based on 1,8-naphalimide and benzothizazole
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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.
- Chen, Xiaoxing,Leng, Taohua,Wang, Chengyun,Shen, Yongjia,Zhu, Weihong
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Read Online
- A simple but sensitive and efficient fluorescent probe for “turn-on” sensing of ClO?
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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.
- Cui, Chuanyang,Cui, Yu,Dong, Xiaoling,Huang, Xin,Li, Yexin,Shi, Wendi,Sun, Guoxin,Wang, Xue,Xie, Hangxin,Yan, Mei,Yang, Xiaofeng
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Read Online
- Discovery of anti-cell migration activity of an anti-HIV heterocyclic compound by identification of its binding protein hnRNP M
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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.
- Kamo, Masahiro,Ito, Miu,Toma, Tsugumasa,Gotoh, Haruna,Shimozono, Rie,Nakagawa, Riko,Koga, Ryoko,Monde, Kazuaki,Tateishi, Hiroshi,Misumi, Shogo,Otsuka, Masami,Fujita, Mikako
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supporting information
(2021/02/05)
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- [1,3]-Claisen rearrangement via removable functional group mediated radical stabilization
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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.
- Alam, Md Nirshad,Dash, Soumya Ranjan,Mukherjee, Anirban,Pandole, Satish,Marelli, Udaya Kiran,Vanka, Kumar,Maity, Pradip
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supporting information
p. 890 - 895
(2021/02/01)
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- Biocatalytic reduction of α,β-unsaturated carboxylic acids to allylic alcohols
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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.
- Aleku, Godwin A.,Leys, David,Roberts, George W.
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p. 3927 - 3939
(2020/07/09)
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- Visible light-induced hydroxyalkylation of 2H-benzothiazoles with alcohols via selectfluor oxidation
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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.
- Kong, Yaolei,Xu, Wenxiu,Liu, Xinghai,Weng, Jianquan
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supporting information
p. 3245 - 3249
(2020/06/21)
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- TRANSGLUTAMINASE 2 (TG2) INHIBITORS
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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.
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Paragraph 00778
(2020/03/02)
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- Application of substituted benzothiazole C2 hydroxyl alkylated derivative as bactericide
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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.
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Paragraph 0027-0030
(2019/11/12)
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- Mild preparation method of substituted benzothiazole C2 hydroxyalkylated derivative
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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.
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Paragraph 0016-0017
(2019/11/29)
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- SNAr catalysis enhanced by an aromatic donor-acceptor interaction; Facile access to chlorinated polyfluoroarenes
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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.
- Senaweera, Sameera,Weaver, Jimmie D.
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supporting information
p. 7545 - 7548
(2017/07/12)
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- Synthesis of novel 3-(benzothiazol-2-ylmethylene)indolin-2-ones
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A mild method for the synthesis of 3-(benzothiazol-2-ylmethylene)indolin-2-ones via the aldol condensation of substituted indolin-2-ones and benzothiazole-2-carbaldehyde is described. This new procedure has significant advantages, such as mild conditions, high yields and simple work-up.
- Zhang, Chao,Xu, Juan,Zhao, Xinyu,Kang, Congmin
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p. 537 - 540
(2017/10/03)
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- Synthesis of the biotinylated anti-HIV compound BMMP and the target identification study
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BMMP [2-(benzothiazol-2-ylmethylthio)-4-methylpyrimidine], an inhibitor of HIV-1 replication, was linked to biotin to study the interaction with the presumed target, HIV-1 Pr55Gag or CA, by means of surface plasmon resonance. The synthesized Bi
- Kamo, Masahiro,Tateishi, Hiroshi,Koga, Ryoko,Okamoto, Yoshinari,Otsuka, Masami,Fujita, Mikako
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supporting information
p. 43 - 45
(2015/12/18)
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- Catalytic Aerobic Photo-oxidation of a Methyl Group on a Heterocycle to Produce an Aldehyde via Homolytic C-I Bond Cleavage caused by Irradiation with Visible Light
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A new catalytic method was developed for photo-oxidizing the methyl group on aromatic heterocycles such as benzothiazole, benzoxazole, and quinoline to produce the corresponding aldehyde. This is the first report of the metal-free catalytic synthesis of benzothiazole-2-carboxaldehydes using molecular oxygen as the terminal oxidant.
- Nagasawa,Tachikawa,Yamaguchi,Tada,Miura,Itoh
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supporting information
p. 178 - 182
(2016/02/14)
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- Structure-Activity Relationship and Pharmacokinetic Studies of 1,5-Diheteroarylpenta-1,4-dien-3-ones: A Class of Promising Curcumin-Based Anticancer Agents
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Forty-three 1,5-diheteroaryl-1,4-pentadien-3-ones were designed as potential curcumin mimics, structurally featuring a central five-carbon dienone linker and two identical nitrogen-containing aromatic rings. They were synthesized using a Horner-Wadsworth-Emmons reaction as the critical step and evaluated for their cytotoxicity and antiproliferative activities toward both androgen-insensitive and androgen-sensitive prostate cancer cell lines and an aggressive cervical cancer cell line. Most of the synthesized compounds showed distinctly better in vitro potency than curcumin in the four cancer cell lines. The structure-activity data acquired from the study validated (1E,4E)-1,5-dihereroaryl-1,4-pentadien-3-ones as an excellent scaffold for in-depth development for clinical treatment of prostate and cervical cancers. 1-Alkyl-1H-imidazol-2-yl, ortho pyridyl, 1-alkyl-1H-benzo[d]imidazole-2-yl, 4-bromo-1-methyl-1H-pyrazol-3-yl, thiazol-2-yl, and 2-methyl-4-(trifluoromethyl)thiazol-5-yl were identified as optimal heteroaromatic rings for the promising in vitro potency. (1E,4E)-1,5-Bis(2-methyl-4-(trifluoromethyl)thiazol-5-yl)penta-1,4-dien-3-one, featuring thiazole rings and trifluoromethyl groups, was established as the optimal lead compound because of its good in vitro potency and attractive in vivo pharmacokinetic profiles. (Chemical Equation Presented).
- Wang, Rubing,Chen, Chengsheng,Zhang, Xiaojie,Zhang, Changde,Zhong, Qiu,Chen, Guanglin,Zhang, Qiang,Zheng, Shilong,Wang, Guangdi,Chen, Qiao-Hong
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p. 4713 - 4726
(2015/06/25)
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- Hydrogenation of esters to alcohols with a well-defined iron complex
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We present the first base-free Fe-catalyzed ester reduction applying molecular hydrogen. Without any additives, a variety of carboxylic acid esters and lactones were hydrogenated with high efficiency. Computations reveal an outer-sphere mechanism involving simultaneous hydrogen transfer from the iron center and the ligand. This assumption is supported by NMR experiments.
- Werkmeister, Svenja,Junge, Kathrin,Wendt, Bianca,Alberico, Elisabetta,Jiao, Haijun,Baumann, Wolfgang,Junge, Henrik,Gallou, Fabrice,Beller, Matthias
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supporting information
p. 8722 - 8726
(2014/08/18)
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- Direct C2-alkylation of azoles with alcohols and ethers through dehydrogenative cross-coupling under metal-free conditions
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A metal-free novel, simple, and highly efficient method for the direct C2-alkylation of azoles with alcohols and ethers has been developed on the basis of an oxidative C-H activation process. The dehydrogenative C-C cross-coupling reactions of R-position
- He, Tao,Yu, Lin,Zhang, Lei,Wang, Lei,Wang, Min
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supporting information; experimental part
p. 5016 - 5019
(2011/11/12)
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- ARYL SUBSTITUTED OLEFINIC COMPOUNDS AS PDE10A INHIBITORS
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The present invention provides aryl substituted olefinic compounds as Phosphodiesterase 1 0A (PDE 1 0A) inhibitors. In particular, compounds described herein are useful for treating or preventing diseases, conditions and/or disorders by inhibiting Phospho
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Page/Page column 50
(2011/11/30)
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- Practical access to metallo thiophenes: Regioselective synthesis of 2,4-disubstituted thiophenes
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This report describes a protocol for functionalization of thiophenes, utilizing a regioselective magnesiation mediated by commercial Grignard reagents and catalytic 2,2,6,6-tetramethylpiperidine. This metalation provides practical access to metallo thiophenes, avoiding cryogenic conditions, prolonged reaction times, and prohibitively expensive reagents. Application to a target thiophene-phthalazinone 6 was accomplished by addition of 2-magnesio-4- methylthiophene to phthalic anhydride, providing the product with >40:1 regioselectivity. This also solved a chemoselectivity issue encountered with analogous lithio-thiophene reagents and cyclic anhydrides, or with magnesio-thiophene generated by simultaneous lithium-to-magnesium transmetalation/anhydride acylation. These alternative in situ transmetalation sequences were plagued by an age effect dictated by the kinetic solubility of MgCl2/THF complexes.
- Asselin, Sylvie M.,Bio, Matthew M.,Langille, Neil F.,Ngai, Ka Yi
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supporting information; experimental part
p. 1427 - 1431
(2011/09/20)
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- Ag-TiO2/clay composite photocatalyst for the oxidation-cyclization of 1,2-diamine compounds with propylene glycol or alcohols
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Silver-loaded TiO2 (Ag-TiO2) and acidic clay (K10 montmorillonite) composite photocatalyst has been successfully applied for the light-induced conversion of o-phenylenediamine (OPD) and its derivatives to substituted benzimidazoles with various alcohols in acetonitrile using UV-A and solar light. The influence of the various photocatalysts, solvents, and substituents on the yield and selectivity of the products has been investigated. The mechanism of photocatalysis is proposed. Loading silver on TiO2 enhances product yield and selectivity both in UV and solar light. In the presence of primary alcohols, 2-aminothiophenol forms only disulfide and hence Ag-TiO2/ clay can be used as a green catalyst for the synthesis of disulfides.
- Selvam, Kaliyamoorthy,Annadhasan, Mari,Velmurugan, Rengasamy,Swaminathan, Meenakshisundaram
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experimental part
p. 831 - 837
(2010/09/06)
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- OXAZOLIDONE DERIVATIVE
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An oxazolidone derivative represented by formula (I) which has a monoamine oxidase inhibition effect:{wherein A and B each represents a nitrogen atom, a sulfur atom or an oxygen atom, with the proviso than at least one of A and B must be a nitrogen atom, R1 represents a group of the formula: (in which n and m each represents 0 or an integer of 1 to 4, and R3 and R4 each represents a hydrogen atom, a hydroxyl group, a lower alkyl group, etc.), a group represented by the formula: (in which p and q each represents 0 or an integer of 1 to 4 and X represents an oxygen atom, sulfur atom, etc.) and a group represented by the formula: R2 represents a hydrogen atom or a lower alkyl group}
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- THIAZOLYLMETHYLENETRIPHENYLPHOSPHORANE AND ITS BENZO DERIVATIVE: STABLE AND PRACTICAL WITTIG REAGENTS FOR THE SYNTHESIS OF VINYLTHIAZOLES AND VINYLBENZOTHIAZOLES. TWO-CARBON HOMOLOGATION OF ALDEHYDES.
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The title thiazolyl phosphorane is a stable yet quite reactive Wittig-type reagent which uppon reaction with various aldehydes affords vinylthiazoles, mainly or exclusively as E-isomers, in very good yields.Also the benzothiazolyl phosphorane derivative, unlike a literature report, prove to react with aldehydes.Vinylthyazoles subjected to formyl deblocking from thiazole nucleous afford two-carbon homologated satured aldehydes.As an example, one of these vinylthiazoles, viz. the β-phenyl derivative 8f, proves to add n-butyl lithium cuprate to give after the formyl deblocking 3-phenylheptanal.
- Dondoni, Alessandro,Fantin, Giancarlo,Fogagnolo, Marco,Medici, Alessandro,Pedrini, Paola
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p. 2021 - 2032
(2007/10/02)
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