16750-42-8Relevant articles and documents
Metabolism of the Insecticide Phoxim in Plants and Cell Suspension Cultures of Soybean
Hoehl, Hans-Ulrich,Barz, Wolfgang
, p. 1052 - 1056 (1995)
The metabolism of phoxim (Z-α-imino>phenylacetonitrile), Volaton, was investigated using heterotrophic cell suspension cultures of soybean (Glycine max L.) and isolated organs (roots, stems, cotyledons, and leaves) of aseptically grown soybean plants.In both systems phoxim was first hydrolyzed to the corresponding oxime, which was then reduced to a primary nitrile amine.The primary amino group was N-malonylated as the terminal step of the catabolic sequence.The structure of this terminal metabolite was elucidated by spectroscopic (UV, IR, NMR, and MS) methods and chemical synthesis.In the plant no organ-specific differences in phoxim metabolism were observed.In the cell culture system phoxim was quantitatively converted to the N-malonate within 18-20 h, whereas in plant organs such extensive conversion could not be observed even within incubation times of about 5 days.The N-malonate was found to be excreted from the cultured cells into the medium; this effect could not be shown for the plant tissues.Keywords: Organothiophosphate metabolism; soybean plants and cell suspension cultures; conjugation reactions; N-malonylation; O-glucoside formation
Discovery of N-Cyano-sulfoximineurea Derivatives as Potent and Orally Bioavailable NLRP3 Inflammasome Inhibitors
Agarwal, Sameer,Sasane, Santosh,Shah, Hardik A.,Pethani, Jignesh P.,Deshmukh, Prashant,Vyas, Vismit,Iyer, Pravin,Bhavsar, Harsh,Viswanathan, Kasinath,Bandyopadhyay, Debdutta,Giri, Poonam,Mahapatra, Jogeswar,Chatterjee, Abhijit,Jain, Mukul R.,Sharma, Rajiv
supporting information, p. 414 - 418 (2020/03/13)
NLRP3 inflammasome mediated release of interleukin-1β (IL-1β) has been implicated in various diseases. In this study, rationally designed mimics of sulfonylurea moiety were investigated as NLRP3 inhibitors. Our results culminated into discovery of series of unprecedented N-cyano sulfoximineurea derivatives as potent NLRP3 inflammasome inhibitors. Compound 15 (IC50 = 7 nM) and analogues were found to be highly potent and selective NLRP3 inflammasome inhibitor with good pharmacokinetic profile. These effects translate in vivo, as 15, 29, and 34 significantly inhibit NLRP3 dependent IL-1β secretion in mice.
Titanium-Catalyzed Cyano-Borrowing Reaction for the Direct Amination of Cyanohydrins with Ammonia
Li, Qing-Hua,Li, Zhao-Feng,Tao, Jing,Li, Wan-Fang,Ren, Li-Qing,Li, Qian,Peng, Yun-Gui,Liu, Tang-Lin
supporting information, p. 8429 - 8433 (2019/10/14)
α-Aminonitrile was an important building block in natural products and key intermedia in organic chemistry. Herein, the direct amination of cyanohydrins with the partner of ammonia to synthesis N-unprotected α-aminonitriles is developed. The reaction proceeds via titanium-catalyzed cyano-borrowing reaction, which features high atom economy and simple operation. A broad range of ketone or aldehyde cyanohydrins was tolerated with ammonia, and the N-unprotected α-aminonitriles were synthesis with moderate to high yields under mild reaction conditions.