403-14-5Relevant academic research and scientific papers
Development of pH-activatable fluorescent probes for rapid visualization of metastatic tumours and fluorescence-guided surgeryviatopical spraying
Cao, Wenwen,Li, Xiaoxin,Wu, Peng,Xiong, Hu
supporting information, p. 10636 - 10639 (2021/10/19)
A series of pH-activatable aza-BODIPY-based fluorescent probes were developed for rapid cancer visualization and real-time fluorescence-guided surgery by harnessing topical spraying. These probes exhibited good water-solubility, a tunable pKafrom 5.0 to 7.9, and stable intense NIR emission at ～725 nm under acidic conditions.AzaB5with a pKavalue of 6.7 was able to rapidly and clearly visualize pulmonary and abdominal metastatic tumours including tiny metastases less than 2 mmviatopical spraying, further improving intraoperative fluorescence-guided resection. We believe thatAzaB5is promising as a powerful tool to rapidly delineate a broad range of malignancies and assist surgical tumour resection.
Phenol compound ortho-position direct fluorination method
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Paragraph 0070-0072, (2020/04/17)
The invention relates to a phenol compound ortho-position direct fluorination method which comprises the following steps: reacting a phenol compound shown in a formula (1A) with a fluorination reagentin a solvent under the action of a photocatalyst and a light source at room temperature, and separating and purifying a reaction mixture after the reaction to obtain a fluorinated phenol compound shown in a formula (2A). The advantages are as follows: the method for directly fluorinating phenol by organic photocatalysis is simple in operation process; raw materials are commercialized and easy toobtain; the photocatalyst is low in price, easy to obtain and environmentally friendly; the reaction condition is mild; the site selectivity is high; the reaction is efficient; and a fluorinated phenol derivative can be prepared only through one step.
Synthesis of 2 - fluoro phenol compounds
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, (2017/04/21)
The present invention provides a method for synthetizing a 2-fluoro phenol compound shown in a formula IV. The phenol compound shown in the formula I is prepared into a 2-pyridine oxygroup arene compound shown in a formula II through an Ullmann reaction, the 2-pyridine oxygroup arene compound shown in the formula II is mixed with a palladium catalyst, a fluorinating reagent, an additive and an organic solvent, the mixture is stirred under the temperature of 30-160 DEG C to perform a fluorination reaction to obtain an ortho-position fluoridated 2-pyridine oxygroup arene compound shown in a formula III, and the ortho-position fluoridated 2-pyridine oxygroup arene compound shown in the formula III is prepared into the 2-fluoro phenol compound shown in the formula IV through the action of alkali. The method provided by the present invention has the advantages of mild reaction conditions, simplicity in operations, good substrate adaptability, high fluorination selectivity and the like. The 2-fluoro phenol compound is shown in the figure below.
Synthesis and biological evaluation of phenoxyacetic acid derivatives as novel free fatty acid receptor 1 agonists
Wang, Xuekun,Zhao, Tianxiao,Yang, Baowei,Li, Zheng,Cui, Jian,Dai, Yuxuan,Qiu, Qianqian,Qiang, Hao,Huang, Wenlong,Qian, Hai
, p. 132 - 140 (2015/02/18)
Free fatty acid receptor 1 (FFA1) is a new potential drug target for the treatment of type 2 diabetes because of its role in amplifying glucose-stimulated insulin secretion in pancreatic β-cell. In the present studies, we identified phenoxyacetic acid derivative (18b) as a potent FFA1 agonist (EC50 = 62.3 nM) based on the structure of phenylpropanoic acid derivative 4p. Moreover, compound 18b could significantly improve oral glucose tolerance in ICR mice and dose-dependently reduced glucose levels in type 2 diabetic C57BL/6 mice without observation of hypoglycemic side effect. Additionally, compound 18b exhibited acceptable PK profiles. In summary, compound 18b with ideal PK profiles exhibited good activity in vitro and in vivo, and might be a promising drug candidate for the treatment of diabetes mellitus.
Fries rearrangement: Scalable synthesis of key fluoro building blocks 3-fluoro-4-methoxybenzoyl chloride and 1,2-diethoxy-3-fluorobenzene
Yerande, Swapnil G.,Shendage, Deepak M.,Wakchaure, Prasad B.,Phadtare, Ganesh R.,Bhoite, Madhavrao Y.,Gangopadhyay, Ashok Kumar,Nagarajan, Kuppuswamy,Rupp, Richard Helmut
supporting information, p. 2426 - 2429 (2014/05/06)
Lewis acid catalyzed Fries rearrangement of 2-fluorophenyl acetate (3) was performed on kg scale. The ortho 5 and para 4 isomers obtained were separated in an industrially feasible way. Compound 4 was then converted into fluorinated building block 3-fluoro-4-methoxybenzoyl chloride (1) while compound 5 was converted into 1,2-diethoxy-3-fluorobenzene (2) in high yields.
Antibacterial chalcones - Bioisosteric replacement of the 4′-hydroxy group
Nielsen, Simon Feldbaek,Boesen, Thomas,Larsen, Mogens,Schonning, Kristian,Kromann, Hasse
, p. 3047 - 3054 (2007/10/03)
Hydroxy chalcones, for example, Licochalcone A, has for several years been known to be antibacterial. The low aqueous solubility and the medium antibacterial potency have limited the usefulness of the compounds. We describe the bioisosteric replacement of
HETEROCYCLIC BETA-3 ADRENERGIC RECEPTOR AGONISTS
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, (2008/06/13)
This invention provides compounds of Formula I having the structure U, V, W, X, and Y are as defined hereinbefore, or a pharmaceutically acceptable salt thereof, which are useful in treating or inhibiting metabolic disorders related to insulin resistance or hyperglycemia (typically associated with obesity or glucose intolerance), atherosclerosis, gastrointestinal disorders, neurogenetic inflammation, glaucoma, ocular hypertension and frequent urination; and are particularly useful in the treatment or inhibition of type II diabetes.
Solvent directing immediate fluorination of aromatic ketones using 1- fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)
Stavber, Stojan,Jereb, Marjan,Zupan, Marko
, p. 1323 - 1324 (2007/10/03)
Reactions of aryl alkyl ketones with 1-fluoro-4-hydroxy1,4- diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Accufluor(TM) NFTh) in methanol result in selective and almost quantitative formation of the corresponding α-fluoroketones, while in acetonitrile exclusive fluorofunctionalisation of the activated aromatic ring take place.
Elemental fluorine Part 12. Fluorination of 1,4-disubstituted aromatic compounds
Chambers, Richard D.,Hutchinson, John,Sparrowhawk, Matthew E.,Sandford, Graham,Moilliet, John S.,Thomson, Julie
, p. 169 - 173 (2007/10/03)
Direct fluorination of a series of 1,4-disubstituted benzene derivatives in acid reaction media at convenient temperature leads, in many cases, to selectively fluorinated aromatic products in preparatively useful conversions and yields.
