25784-91-2Relevant articles and documents
Metal-Free Oxidative Condensation of Catechols, Aldehydes and NH4OAc towards Benzoxazoles
Dong, Jianyu,Geng, Furong,Su, Lebin,Wu, Shaofeng,Yin, Shuang-Feng,Zhou, Dan,Zhou, Yongbo
supporting information, p. 3607 - 3614 (2021/07/28)
Benzoxazoles extensively exist in biologically active compounds, natural products, pharmaceuticals and functional materials. Thus, facile and green synthesis of such valuable compounds from easily available substrates will make a contribution to drug, material, and fine chemistry. A method for the synthesis of benzoxazoles from catechols, aldehydes and ammonium acetate is developed using NaIO4 as oxidant under metal- and additive-free conditions. A broad range of benzoxazoles including some fluorescent whitening agents, JTP-426467 and tafamidis analogues are synthesized in 56–95% yields with outstanding functional group tolerance. Mechanistic investigations suggest that an interesting o-iminocyclohexa-diene alcohol intermediate is involved in the reaction. These salient features of the protocol make it an alternative for the synthesis of benzoxazoles. (Figure presented.).
Synthesis and structure-activity relationship studies of n-monosubstituted aroylthioureas as urease inhibitors
Dawalamu,Fang, Hai-Lian,Fu, Zi-Juan,Li, Fang,Li, Ke,Li, Wei-Yi,Liu, Li,Ni, Wei-Wei,Ouyang, Hui,Xiao, Zhu-Ping,Ye, Ya-Xi,Zhu, Hai-Liang,Zhu, Wen-Yan,Zou, Xia
, p. 1046 - 1059 (2021/11/30)
Background: Thiourea is a classical urease inhibitor which is usually used as a positive control, and many N,N'-disubstituted thioureas have been determined as urease inhibitors. However, due to steric hindrance, N,N'-disubstituted thiourea motif could not bind urease as thiourea. On the contrary, N-monosubstituted thiourea with a tiny thiourea motif could theoretically bind into the active pocket as thiourea. Objective: A series of N-monosubstituted aroylthioureas were designed and synthesized for evaluation as urease inhibitors. Methods: Urease inhibition was determined by the indophenol method and IC50 values were calculated using computerized linear regression analysis of quantal log dose-probit functions. The kinetic parameters were estimated via surface plasmon resonance (SPR) and by nonlinear regression analysis based on the mixed type inhibition model derived from Michaelis-Menten kinetics. Results: Compounds b2, b11, and b19 reversibly inhibited urease with a mixed mechanism, and showed excellent potency against both cell-free urease and urease in the intact cell, with IC50 values being 90-to 450-fold and 5-to 50-fold lower than the positive control acetohydroxamic acid, respectively. The most potent compound b11 showed an IC50 value of 0.060 ± 0.004μM against cell-free urease, which bound to urea binding site with a very low KD value (0.420±0.003nM) and a very long residence time (6.7 min). Compound b11 was also demonstrated to have very low cytotoxicity to mammalian cells. Conclusion: The results revealed that N-monosubstituted aroylthioureas bound to the active site of urease as expected, and represent a new class of urease inhibitors for the development of potential therapeutics against infections caused by urease-containing pathogens.
2-Aminopyrazine-functionalized MCM-41 nanoporous silica as a new efficient heterogeneous ligand for Cu-catalyzed allylic C–H bonds oxidation of olefins
Samadi, Saadi,Ashouri, Akram,Kamangar, Shadi,Pourakbari, Fatemeh
, p. 557 - 569 (2019/11/03)
In spite of the importance of the application of allylic C–H bond oxidation of olefins in organic synthesis and existence of the numerous reports, lots of limitations such as large excess of the olefin respect to the oxidant, low chemical yield, long time of reaction and a large amount of the catalyst were reminded. We introduced a novel catalytic system using functionalized MCM-41 as catalyst support to promote efficiency of this reaction. The heterogeneous ligand Pyr-MCM-41 was prepared by substituted 2-aminopyrazine ligand on functionalized MCM-41 with 3-chloropropyltrimthoxysilane and characterized by FT-IR, XRD, SEM, EDX, BET, TGA, CHN techniques. In situ immobilized Pyr-MCM-41 by copper (I) trifluoromethanesulfonate (CuOTf) was applied in direct catalytic esterification of inert C–H bonds in olefins using various peresters at room temperature.
Synthesis and Antiproliferative Activities of Novel Substituted 5-Anilino-α-Glucofuranose Derivatives
Hou, Qiaoli,Li, Baolin,Li, Xiabing,Sun, Baoli,Wang, Lili,Wang, Wei,Zhang, Yaling
, (2020/05/05)
In order to find novel antitumor candidate agents with high efficiency and low toxicity, 14 novel substituted 5-anilino-α-glucofuranose derivatives have been designed, synthesized and evaluated for antiproliferative activities in vitro. Their structures were characterized by NMR (1H and 13C) and HR-MS, and configuration (R/S) at C(5) was identified by two-dimensional 1H,1H-NOESY-NMR spectrum. Their antiproliferative activities against human tumor cells were investigated by MTT assay. The results demonstrated that most of the synthesized compounds had antiproliferative effects comparable to the reference drugs gefitinib and lapatinib. In particular, (5R)-5-O-(3-chloro-4-{[5-(4-fluorophenyl)thiophen-2-yl]methyl}anilino)-5-deoxy-1,2-O-(1-methylethylidene)-α-glucofuranose (9da) showed the most potent antiproliferative effects against SW480, A431 and A549 cells, with IC50 values of 8.57, 5.15 and 15.24 μm, respectively. This work suggested 5-anilino-α-glucofuranose as an antitumor core structure that may open a new way to develop more potent anti-cancer agents.
Preparation method and application of antibacterial drugs
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Paragraph 0030-0034, (2020/05/02)
The invention provides phosphite ester compounds with an antibacterial effect and represented by a general formula I, a preparation method of the compounds, an application of the compounds in antibacterial drugs and pharmaceutical compositions containing the compounds. The ten synthesized compounds are novel in structure, the antibacterial activity of the compounds is equivalent to or even superior to that of positive control clindamycin and ciprofloxacin, the antibacterial spectrum is wide, and the compounds 5 and 10 are particularly expected to be further developed into antibacterial activedrugs.
Comprising benzimidazole structure of sulfonamide derivatives and its preparation and use
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Paragraph 0066-0068, (2019/07/04)
The invention belongs to the field of medical technology, discloses benzimidazole structure of sulfonamide derivatives and its preparation method and application. The derivatives of formula I as shown in the structural formula, in formula I, R1 , R2 , R3 , R4 , X such as the claim and the specification. The compounds of the invention has better anti-tumor activity, can be used as a therapeutic agent for the treatment of tumor, it is also SMO inhibitors. (Type I).
Novel quinazoline derivatives bearing various 6-benzamide moieties as highly selective and potent EGFR inhibitors
Hou, Weijie,Ren, Yan,Zhang, Zhenhua,Sun, Huan,Ma, Yongfen,Yan, Bo
, p. 1740 - 1750 (2018/03/12)
A series of novel quinazoline derivatives bearing various C-6 benzamide substituents were synthesized and evaluated as EGFR inhibitors, and most showed significant inhibitory potency against EGFR kinase. In particular, compound 6g possessed potent inhibitory activity against EGFR wild-type (IC50 = 5 nM), and strong antiproliferative activity against HCC827 and Ba/F3 (L858R) cell lines. Kinase profiling against a panel of 365 kinases showed that 6g was highly selective for EGFR. Furthermore, 6g showed desirable properties in assays of liver microsome metabolic stability and cytochromes P450 inhibition and preliminary pharmacokinetic study. The overall attractive profile of 6g made it an interesting compound for further development.
N - 3 - benzimidazole thiazole derivative and its preparation method and application
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Paragraph 0028; 0029-0031, (2018/06/04)
The invention discloses a new compound N-3-benzimidazole thiazole amine derivative and a preparation method and application thereof. A structural formula of the compound is shown as in figure I, and in the figure I, R1 is morpholinyl, piperidyl, N-methyl piperazinyl, N-arylpiperazine, diethylin, ethyoxyl, (dimethoxy)ethylamino, or R1 is one of mono-substituted or multi-substituted aniline on the following benzene ring: fluorine, chlorine, trifluoromethoxyl, methyl, methoxyl, hydroxyl group, nitryl, amino group, acetamido, trifluoromethyl and cyano group. The compound disclosed by the invention has better antineoplastic activity, and can be used as a therapeutic agent for treating a tumor in the field of antineoplastic drug preparation.
Nicotinamide derivative and preparation method and application thereof
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Paragraph 0060; 0062; 0064, (2018/07/30)
The invention discloses a novel compound N-3-(4-R2 substituted)-(1-R-substituted benzimidazole)-(1'-R3 substituted)-2'-oxa-nicotinamide derivative, and a preparation method and an application thereof.The structural formula of the compound is as shown in a formula I, in which R1, R2 and R3 are described in the claims and description. The compound has very good anti-diabetes activity, and can be used as therapeutic agent for treating diabetes in the field of preparing anti-diabetes drugs. The formula is as shown in the description.
Synthesis and antibacterial evaluation of 3,5-Diaryl-1,2,4-oxadiazole derivatives
Cunha, Felipe S.,Nogueira, Joseli M. R.,De Aguiar, Alcino P.
, p. 2405 - 2416 (2018/10/20)
This manuscript reports the synthesis of twenty 3,5-diaryl-1,2,4-oxadiazole derivatives, nine of which are novel compounds. The amidoxime reaction with acyl chlorides obtained from substituted benzoic acids was used. All compounds were tested against five standard (American Type Culture Collection (ATCC)) bacteria: Escherichia coli, Pseudomonas aeruginosa, Enterococcus faecalis, Proteus mirabilis and Staphylococcus aureus. Screening assays were carried out using agar-diffusion technique, in which 100 μM heterocyclic compounds solutions (20percent dimethylsulfoxide/water) were employed. The minimum inhibitory concentrations (MIC) of the active compounds were determined by serial dilutions at decreasing concentrations in microtiter plates. The nitrated derivatives gave the best test results, where MIC = 60 μM (E. coli) was the lowest value found for an ortho-nitrated derivative. The activity of these compounds possibly involves a mechanism via free radicals. S. aureus and P. aeruginosa were resistant to all compounds.