87-25-2Relevant academic research and scientific papers
Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions
Proietti, Giampiero,Prathap, Kaniraj Jeya,Ye, Xinchen,Olsson, Richard T.,Dinér, Peter
supporting information, p. 133 - 146 (2021/11/04)
Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.
Design, synthesis, in vitro and in vivo evaluation against MRSA and molecular docking studies of novel pleuromutilin derivatives bearing 1, 3, 4-oxadiazole linker
Liu, Jie,Zhang, Guang-Yu,Zhang, Zhe,Li, Bo,Chai, Fei,Wang, Qi,Zhou, Zi-Dan,Xu, Ling-Ling,Wang, Shou-Kai,Jin, Zhen,Tang, You-Zhi
, (2021/05/17)
A class of pleuromutilin derivatives containing 1, 3, 4-oxadiazole were designed and synthesized as potential antibacterial agents against Methicillin-resistant staphylococcus aureus (MRSA). The ultrasound-assisted reaction was proposed as a green chemistry method to synthesize 1, 3, 4-oxadiazole derivatives (intermediates 85–110). Among these pleuromutilin derivatives, compound 133 was found to be the strongest antibacterial derivative against MRSA (MIC = 0.125 μg/mL). Furthermore, the result of the time-kill curves displayed that compound 133 could inhibit the growth of MRSA in vitro quickly (- 4.36 log10 CFU/mL reduction). Then, compound 133 (- 1.82 log10 CFU/mL) displayed superior in vivo antibacterial efficacy than tiamulin (- 0.82 log10 CFU/mL) in reducing MRSA load in mice thigh model. Besides, compound 133 exhibited low cytotoxicity to RAW 264.7 cells. Molecular docking studies revealed that compound 133 was successfully localized in the binding pocket of 50S ribosomal subunit (ΔGb = -10.50 kcal/mol). The results indicated that these pleuromutilin derivatives containing 1, 3, 4-oxadiazole might be further developed into novel antibiotics against MRSA.
Tunable Electrosynthesis of Anthranilic Acid Derivatives via a C-C Bond Cleavage of Isatins
Qian, Peng,Liu, Jiaojiao,Zhang, Yan,Wang, Zhiyong
, p. 16008 - 16015 (2021/07/31)
A facile and direct electrocatalytic C-C bond cleavage/functionalization reaction of isatins was developed. With isatins as the amino-attached C1 sources, a variety of aminobenzoates, and aminobenzamides were synthesized in moderate to good yields under mild conditions.
Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids
Begam, Hasina Mamataj,Jana, Ranjan,Manna, Kartic,Samanta, Krishanu
supporting information, p. 7443 - 7449 (2020/10/09)
We report herein a Pd(II)/bis-sulfoxide-catalyzed intramolecular allylic C-H acetoxylation of aryl allyl ether, amine, and amino acids with the retention of a labile allyl moiety. Mechanistically, the reaction proceeds through a distinct double-bond isomerization from the allylic to the vinylic position followed by intramolecular carboxypalladation and the β-hydride elimination pathway. For the first time, C-H oxidation of N-allyl-protected amino acids to furnish five-membered heterocycles through 1,3-syn-addition is established with excellent diastereoselectivity.
PROCESS FOR THE PREPARATION OF QUINOLONE BASED COMPOUNDS
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Paragraph 0288; 0290-0291, (2019/12/06)
The present invention relates to an improved process for the preparation of quinolone based compounds of general formula (I) using intermediate compound of general formula (XII). Invention also provides an improved process for the preparation of compound of formula (I-a) using intermediate compound of formula (XII-a) and some novel impurities generated during process. Compounds prepared using this process can be used to treat anemia.
Halogen-substituted anthranilic acid derivatives provide a novel chemical platform for androgen receptor antagonists
Roell, Daniela,R?sler, Thomas W.,Hessenkemper, Wiebke,Kraft, Florian,Hauschild, Monique,Bartsch, Sophie,Abraham, Tsion E.,Houtsmuller, Adriaan B.,Matusch, Rudolf,van Royen, Martin E.,Baniahmad, Aria
, p. 59 - 70 (2019/02/01)
Androgen receptor (AR) antagonists are used for hormone therapy of prostate cancer (PCa). However resistance to the treatment occurs eventually. One possible reason is the occurrence of AR mutations that prevent inhibition of AR-mediated transactivation by antagonists. To offer in future more options to inhibit AR signaling, novel chemical lead structures for new AR antagonists would be beneficial. Here we analyzed structure-activity relationships of a battery of 36 non-steroidal structural variants of methyl anthranilate including 23 synthesized compounds. We identified structural requirements that lead to more potent AR antagonists. Specific compounds inhibit the transactivation of wild-type AR as well as AR mutants that render treatment resistance to hydroxyflutamide, bicalutamide and the second-generation AR antagonist enzalutamide. This suggests a distinct mode of inhibiting the AR compared to the clinically used compounds. Competition assays suggest binding of these compounds to the AR ligand binding domain and inhibit PCa cell proliferation. Moreover, active compounds induce cellular senescence despite inhibition of AR-mediated transactivation indicating a transactivation-independent AR-pathway. In line with this, fluorescence resonance after photobleaching (FRAP) - assays reveal higher mobility of the AR in the cell nuclei. Mechanistically, fluorescence resonance energy transfer (FRET) - assays indicate that the amino-carboxy (N/C)-interaction of the AR is not affected, which is in contrast to known AR-antagonists. This suggests a mechanistically novel mode of AR-antagonism. Together, these findings indicate the identification of a novel chemical platform as a new lead structure that extends the diversity of known AR antagonists and possesses a distinct mode of antagonizing AR-function.
Preparation method of ethyl o-aminobenzoate
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Paragraph 0024-0055, (2019/01/16)
The invention discloses a preparation method of ethyl o-aminobenzoate. The preparation method comprises the steps that 1, after phthalic anhydride and ammonium hydroxide are mixed, a mixture and a sodium hydroxide solution are mixed for first reaction to obtain first reaction liquid; 2, after the first reaction liquid and ethyl alcohol are mixed, second reaction is carried out to obtain second reaction liquid; 3, after the second reaction liquid and a sodium hypochlorite solution are mixed, third reaction is carried out to obtain third reaction liquid containing the ethyl o-aminobenzoate. Theraw materials used in the preparation method are low in price and easy to get, the preparation method is simple, easy and mild, the high-purity ethyl o-aminobenzoate can be prepared only through two steps, and a product is high in yield, high in purity and easy to separate.
Oxidative ring-opening of isatins for the synthesis of 2-aminobenzamides and 2-aminobenzoates
Wang, Yu-Wei,Zheng, Lei,Jia, Feng-Cheng,Chen, Yun-Feng,Wu, An-Xin
, p. 1497 - 1503 (2019/02/13)
An efficient and practical isatin-based oxidative domino protocol has been developed for the facile synthesis of 2-aminobenzamides and 2-aminobenzoates. The robust nature of this reaction system is reflected by accessible starting materials, room temperature and high-yield gram-scale synthesis.
Selective hydrogenation of nitroarenes using an electrogenerated polyoxometalate redox mediator
Macdonald, Lewis,Rausch, Benjamin,Symes, Mark D.,Cronin, Leroy
supporting information, p. 1093 - 1096 (2018/02/07)
The 2-electron reduced form of the polyoxometalate silicotungstic acid (H4[SiW12O4]) is shown to be an effective and selective hydrogenation agent for a range of nitroarenes without the need for any co-catalyst. The ease of generation of the active species and its recyclability suggest that a new approach to this important class of chemical conversions is possible.
2-[2-(2-methoxyl phenoxyl) ethylamino]-3-aryl-4-quinazolinones compound and application thereof
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Paragraph 0047; 0050, (2018/03/25)
The invention belongs to the technical field of medicines, and relates to a 2-[2-(2-methoxyl phenoxyl) ethylamino]-3-aryl-4-quinazolinones derivative and application thereof. The 2-[2-(2-methoxyl phenoxyl) ethylamino]-3-aryl-4-quinazolinones derivative comprises a stereisomer of the compound and pharmacologically applicable salt. The general structural formula is as follows: as shown in the description, wherein R is as described in claims and the description. The 2-[2-(2-methoxyl phenoxyl) ethylamino]-3-aryl-4-quinazolinones derivative and salt formed by addition of a pharmacologically applicable acid of the compound can be combined with an existing medicine or used independently to form an influenza virus inhibitor which is used for treating influenza and particularly has a relatively curative effect on various types of influenza A.
