- Regorafenib analogues and their ferrocenic counterparts: Synthesis and biological evaluation
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Approved by the FDA in 2012, regorafenib is one of the last chance treatments for colorectal cancer. While various analogues have already been prepared, ferrocenic derivatives have never been evaluated. In this study, we prepared various ferrocene-containing derivatives of regorafenib and recorded their biological activity in kinase and cellular assays. This led to the identification of a squaramide derivative which shows a good cellular activity and three ferrocene analogues with promising activity in both kinase and cellular assays. This journal is
- Wilde, Myron,Arzur, Danielle,Baratte, Blandine,Lefebvre, Dorian,Robert, Thomas,Roisnel, Thierry,Le Jossic-Corcos, Catherine,Bach, Stéphane,Corcos, Laurent,Erb, William
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supporting information
p. 19723 - 19733
(2020/12/04)
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- Synthesis method 4- chloro -3-(trifluoromethyl)-phenylisocyanate
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The invention belongs to the technical field of medicines, and concretely relates to 4 - chloro - 3 3 3 (trifluoromethyl) phenylisocyanate) synthesis method. o chlorotrifluorotoluene, acetic anhydride and concentrated nitric acid to obtain 4 - nitro - 2 2-trifluoromethyl chlorobenzene, 4 - nitro - 2 2-trifluoromethyl chlorobenzene, activated carbon, FeCl. 3 · 66H2 O And hydrazine hydrate react to obtain 4 - chlorine - 3 3-trifluoromethylaniline, 4 - chloride - 3 3-trifluoromethylaniline, triphosgene and a catalyst react to obtain 4 - chlorine - 3 3 3-trifluoromethyl)-phenylisocyanate . instead of the conventional nitric/sulfuric acid mixed acid system / reaction, risks low, nitrosation FeCl impurities, reduction process. 3 · 66H2 O/Activated carbon/hydrazine hydrate system replaces traditional iron powder reduction process, has avoided the production, of a large amount of iron mud waste residue and has reduced environmental protection pressure.
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Paragraph 0036; 0043; 0044; 0052-0053; 0057-0058; 0062-0063
(2020/03/29)
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- Base promoted peroxide systems for the efficient synthesis of nitroarenes and benzamides
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A useful and efficient approach for the synthesis of nitroarenes from several aromatic amines (including heterocycles) using peroxide and base has been developed. This oxidative reaction is very easy to handle and afforded the products in good yields. Formation of benzamides from benzylamine was also successfully carried out with this metal-free catalytic system in good to excellent yields.
- Gupta, Sampa,Ansari, Alisha,Sashidhara, Koneni V.
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supporting information
(2019/09/07)
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- Method for synthesizing 4-chloro-3-trifluoromethylaniline by micro-channel reactor
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The invention provides a method for synthesizing 4-chloro-3-trifluoromethylaniline by a micro-channel reactor, and belongs to the field of synthesis of anti-tumor type medicines in organic synthesis.The invention solves the problems of low yield, poor purity, high energy consumption, danger caused by easy occurrence of severe explosion, degradation caused by long reaction time at high temperatureand high pressure, low catalyst recycling frequency and the like existing in the traditional synthesis method, and provides a method for synthesizing 4-chloro-3-trifluoromethylaniline by a micro-channel reactor. The method particularly comprises the following steps: 1) enabling O-chlorbenzotrifluoride to be subjected to nitration reaction with the mixture of concentrated sulfuric acid and concentrated nitric acid in a reaction module of the micro-channel reactor, and performing after-treatment to obtain 2-chloro-5-nitrobenzotrifluoride; and 2) adding the 2-chloro-5-nitrobenzotrifluoride to anorganic solvent to be dissolved, then adding an active carbon noble metal catalyst and phosphorous acid, adding the components to a preheating module to be mixed and preheated, enabling the preheatedmixture to be subjected to reaction with H2 in the reaction module, and performing after-treatment to obtain 4-chloro-3-trifluoromethylaniline. The method provided by the invention is suitable for large-scale production of 4-chloro-3-trifluoromethylaniline.
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Paragraph 0046; 0048-0049; 0052; 0055; 0058; 0061-0067
(2018/07/30)
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- Synthesis of sulfamide analogues of deoxthymidine monophosphate as potential inhibitors of mycobacterial cell wall biosynthesis
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The recently discovered enzyme Mycobacterium tuberculosis thymidine monophosphate kinase (TMPKmt), which catalyses the phosphorylation of deoxythymidine monophosphate (dTMP) to give deoxythymidine diphosphate (dTDP), is indispensable for the growth and survival of M. tuberculosis as it plays an essential role in DNA synthesis. Inhibition of TMPKmt is an attractive avenue for the development of novel anti-tuberculosis agents. Based on the premise that sulfamide may be a suitable isostere of phosphate, deoxythymidine analogues comprising various substituted sulfamides at C5′ were modelled in silico into the active site of TMPKmt (PDB accession code: 1N5K) using induced-fit docking methods. A selection of modelled compounds was synthesized, and their activity as inhibitors of TMPKmt was evaluated. Three compounds showed competitive inhibition of TMPKmt in the micromolar range (10–50 μM). Compounds were tested in vitro for anti-mycobacterial activity against M. smegmatis: three compounds showed weak anti-mycobacterial activity (MIC 250 μg/mL).
- Suthagar, Kajitha,Jiao, Wanting,Munier-Lehmann, Hélène,Fairbanks, Antony J.
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- Study on fluorine-containing polyurethane elastomers based on 2,2-Bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]hexafluoropropane
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A series of fluorine-containing polyurethane elastomers (FPUEs) were synthesized from 2,2-bis[4-(4-amino-2-trifluoromethylphenoxy)- phenyl]hexafluoropropane (BAFPF6P), which was made from 2-chlorobenzotrifluoride and 2,2-bis(4-hydroxyphenyl) hexafluoropropane and characterized by Fourier transform infrared spectroscopy, nuclear magnetic resonance, thermogravimetric analysis, microscale combustion colorimeter and contact angle measurement. The results show that the fluorine-containing polyurethane elastomers prepared from BAFPF6P have good thermal stability and low surface tension. Furthermore, fluorine-containing polyurethane elastomers also exhibit good flame retardance and the peak heat release rate and total heat released of fluorine-containing polyurethane elastomer based on BAFPF6P are much lower than those of polyurethane elastomer without the fluorine element.
- Xu, Wenzong,Liu, Liang,Wang, Shaoqing,Hu, Yuan
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p. 1324 - 1326
(2014/06/09)
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- Synthesis and characterization of novel fluorinated polyurethane elastomer based on 1,4-bis(4-amino-2-trifluoformethyloxyphenyl)benzene
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A novel chain extender was synthesized containing fluorine element 1,4-bis(4-amino-2-trifluoromethyloxyphenyl)benzene (BAFB). Then BAFB was used to prepare a series of fluorine containing polyurethane elastomers (FPUEs) with different fluorine contents. The structures and properties of FPUEs were measured by fourier transform infrared spectroscopy, thermo-gravimetric analysis, microscale combustion colorimeter (MCC), water absorption test and contact angle measurement. The results show fluorine was incorporated into the polyurethane chains through the reaction between BAFB and prepolymers. Fluorine containing polyurethane elastomers show a better hydrophobic property, lower surface tension and better thermal stability due to the introduction of fluorine. The surface tension of FPUEs decreases from 29.8-20.8 mN/m with the F content increasing from 2.7-5.9 %. Furthermore, FPUEs also exhibit good flame resistance and the peak heat release rate (PHRR) of FPUE based on BAFB (466.2 W/g) is much lower than that of polyurethane elastomer without F element (537.2 W/g).
- Xu, Wenzong,Zhang, Yingying,Hu, Yuan,Lu, Bo,Cai, Tongming
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experimental part
p. 3976 - 3980
(2012/09/22)
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- Synthesis and characterization of novel fluorinated polyurethane elastomers
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A series of fluorinated polyurethane elastomers were synthesized from 2-trifluoromethyl-4,4'-diaminodiphenyl ether, which was derived from 2-chlorobenzotrifluoride and p-nitrophenol. The structure and properties of fluorinated polyurethane elastomers were measured by fourier transform infrared spectroscopy, thermogravimetric analysis, microscale combustion colorimeter, water absorption and contact angle measurement. The results show the fluorinated polyurethane elastomers prepared from 2-trifluoromethyl-4,4'-diaminodiphenyl ether have lower surface tension, better hydrophobic property and thermal stability and good mechanical properties. Furthermore, the introduction of fluorine into fluorinated polyurethane elastomers improved the flame retardancy. With the content of fluorine increasing from 1.5 to 2.8 %, the peak heat release rate and total heat release decreased from 605.4 w/g and 23.7 kJ/g to 511.0 w/g and 22.4 kJ/g, indicating that the flame retardant property of polyurethane elastomer increased with the increase in the fluorine content.
- Xu,Lu,Hu,Yin,Zhang
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experimental part
p. 2284 - 2288
(2012/02/15)
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- Preparation and characterization of diazenyl quinolin-8-ol with trifluoromethyl substituents
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The synthesis and properties of new monoazo dyes derived from the diazonium salts of 2-trifluoromethyl phenylamine and 4-chloro-3-trifluoromethyl phenylamine are considered.
- Yazdanbakhsh, Mohammad R.,Mahmoodi, Nosrat O.,Dabiry, Shahram
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p. 192 - 194
(2007/10/03)
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- Phenylthioheterocyclic derivatives
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Compounds of the formula STR1 wherein n is a integer of 0 to 2; R1 ' and R2 ' are, independently, hydrogen, halogen, trifluoromethyl, lower alkoxy or lower alkyl; and X is pyrimidinyl, thiazolyl or STR2 wherein R is hydrogen, lower alkyl, aryl or ar-lower alkyl; provided that at least one or R1 ' and R2 ' is other than hydrogen, and their pharmaceutically acceptable acid addition salts, and an anti-inflammatory method utilizing a compound of the formula STR3 wherein n is an integer of 0 to 2; R1 and R2 are, independently, hydrogen, halogen, trifluoromethyl, nitro, amino, lower alkylamino, di-lower-alkylamino, lower alkoxy or lower alkyl; and X is pyrimidinyl, thiazolyl or STR4 wherein R is hydrogen, lower alkyl, aryl or ar-lower alkyl; and their pharmaceutically acceptable acid addition salts, are described.
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- Novel 4'(benzisothiazo-5-yloxy)-phenylurea derivatives, their preparation and their use as herbicides
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A 4'-(Benzisothiazol-5-yloxy)-phenylureas of the formula STR1 where R1 and R2 are each a saturated straight-chain or branched aliphatic radical of 1 to 10 carbon atoms, an unsaturated straight-chain or branched aliphatic radical of 3 to 10 carbon atoms, or an araliphatic or aromatic radical which may be substituted by 1, 2 or 3 C1 -C4 -alkyl, C1 -C4 -alkoxy, cyano, halogen, nitro, monofluoromethyl or trifluoromethyl groups, or are each alkoxy of 1 to 6 carbon atoms, R2 may furthermore be hydrogen, or R1 and R2, together with the nitrogen atom, may be members of a 5-membered or 6-membered ring which may contain further nitrogen and/or oxygen atoms as heteroatoms, and X is hydrogen, trifluoromethyl or chlorine, processes for their preparation, and herbicides containing ureas of the formula I as active ingredients.
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