- Decarboxylative Hydroxylation of Benzoic Acids
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Herein, we report the first decarboxylative hydroxylation to synthesize phenols from benzoic acids at 35 °C via photoinduced ligand-to-metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation. The aromatic decarboxylative hydroxylation is synthetically promising due to its mild conditions, broad substrate scope, and late-stage applications.
- Ritter, Tobias,Su, Wanqi,Xu, Peng
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p. 24012 - 24017
(2021/10/06)
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- ECTONUCLEOTIDE PYROPHOSPHATASE-PHOSPHODIESTERASE 1 (ENPP-1) INHIBITORS AND USES THEREOF
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Disclosed herein are methods and compounds of augmenting and enhancing the production of type I IFNs in vivo. In some embodiments, the compounds disclosed herein are ENPP-1 inhibitors, pharmaceutical compositions, and methods for the treatment of cancer or a viral infection.
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Paragraph 0588
(2019/03/17)
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- Method for catalytic synthesis of N-benzyl benzene sulfonamide compounds by boric acid/oxalic acid catalytic system under microwave radiation
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The invention discloses a method for catalytic synthesis of N-benzyl benzene sulfonamide compounds by a boric acid/oxalic acid catalytic system under microwave radiation. The method includes: adoptingbenzyl alcohol and derivatives thereof and benzene sulfonamide derivatives as raw materials, adopting the boric acid/oxalic acid system as a catalyst, and adopting fluorobenzene as a solvent; performing reaction in a microwave reactor under certain temperature and power conditions, performing vacuum concentration after reaction for a period of time, and subjecting a product to column chromatographic purification to realize efficient catalytic preparation of the N-benzyl benzene sulfonamide compounds. Compared with the prior art, the method has advantages of evidently higher reaction speed than that of conventional heating, mild reaction conditions, simplicity in operation, high yield, safety, low cost and environmental friendliness.
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Paragraph 0031; 0041
(2018/09/11)
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- Development of a novel sulfonate ester-based prodrug strategy
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A self-immolative γ-aminopropylsulfonate linker was investigated for use in the development of prodrugs that are reactive to various chemical or biological stimuli. To demonstrate their utility, a leucine-conjugated prodrug of 5-chloroquinolin-8-ol (5-Cl-8-HQ), which is a potent inhibitor against aminopeptidase from Aeromonas proteolytica (AAP), was synthesized. The sulfonate prodrug was considerably stable under physiological conditions, with only enzyme-mediated hydrolysis of leucine triggering the subsequent intramolecular cyclization to simultaneously release 5-Cl-8-HQ and form γ-sultam. It was also confirmed that this γ-aminopropylsulfonate linker was applicable for prodrugs of not only 8-HQ derivatives but also other drugs bearing a phenolic hydroxy group.
- Hanaya, Kengo,Yoshioka, Shohei,Ariyasu, Shinya,Aoki, Shin,Shoji, Mitsuru,Sugai, Takeshi
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supporting information
p. 545 - 550
(2016/01/09)
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- Radiosynthesis of 1-(4-(2-[18F] fluoroethoxy)benzenesulfonyl)-3-butyl urea: A potential β-cell imaging agent
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Tolbutamide (1) is a sulfonurea agent used to stimulate insulin secretion in type 2 diabetic patients. Its analogue 1-(4-(2-[18F]fluoroethoxy)benzenesulfonyl)-3-butyl urea (3) was synthesized in overall radiochemical yields of 45% as a potential β-cell imaging agent. Compound 3 was synthesized by 18F-fluoroalkylation of the corresponding hydroxy precursor (2) with 2-[18F]fluoroethyltosylate in DMF at 120°C for 10 min followed by purification with HPLC in a synthesis time of 50 min. Insulin secretion experiments of the authentic 19F-standard compound on rat islets showed that the compound has a similar stimulating effect on insulin secretion as that of tolbutamide (1). The partition coefficient of compound 3 between octanol/water was determined to be 1.3 × 0.3 (n = 5). Copyright
- Schirrmacher, Ralf,Weber, Michael,Schmitz, Alexander,Shiue, Chyng-Yann,Alavi, Abass A.,Feilen, Peter,Schneider, Stefan,Kann, Peter,Roesch, Frank
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p. 763 - 774
(2007/10/03)
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