31823-43-5Relevant articles and documents
[6, 7, 10, 11-13C4]-labelled leukotriene B4 synthesis: Standard for mass spectrometry determination and metabolic studies
Treilhou, Michel,Couderc, Francois
, p. 737 - 745 (2001)
The mass spectrometry quantification and metabolic studies of leukotriene B4 (LTB4) in biological fluids require standards labelled with stable isotopes. This paper describes the synthesis of LTB4 labelled with 13C in positions 6, 7, 10 and 11 (1). These labelled carbons come from 13C2-acetylene. A labelled LTB4 is obtained with an isotopic enrichment of 99%. Copyright
A new efficient synthesis of (58,12S)-DiHETE
Chemin,Alami,Linstrumelle
, p. 2681 - 2684 (1992)
An efficient synthesis of (5S,12S)-diHETE was realized by a Pd-Cu catalysed coupling of the chiral synthons 3 and 4 which were easily obtained by the kinetic resolution of the corresponding racemates using the Sharpless reagent.
A convergent strategy toward linear Cis-skipped polyenes
Sandri, Jacqueline,Soto, Thierry,Gras, Jean-Louis,Viala, Jacques
, p. 6611 - 6612 (1997)
An easy preparation of symmetric Cis-skipped polyenic hydrocarbons 1 to 5 combining the controlled classical Wittig reaction or the oxidative dimerization of phosphoranes is described.
An Efficient Stereocontrolled Synthesis of 12(R)-HETE and 12(S)-HETE
Chemin, Denis,Gueugnot, Sylvie,Linstrumelle, Gerard
, p. 4369 - 4378 (1992)
An efficient synthesis of 12(R) and 12(S) HETEs was realized by assembly of the easily obtainable synthons: optically pure iodo-alcohols 3(R) and 3(S) with the ester 4, followed by reduction with activated zinc.
Synthesis of 7-thiaarachidonic acid as a mechanistic probe of prostaglandin H synthase-2
McGinley, Chris M.,Jacquot, Cyril,van der Donk, Wilfred A.
, p. 4049 - 4052 (2007)
The mechanism by which prostaglandin synthase converts arachidonic acid to prostaglandin G2, creating five new chiral centers in the process, is still incompletely understood. The first radical intermediate has been characterized by EPR spectroscopy but subsequent proposed intermediates have not succumbed to detection. We report the synthesis of 7-thiaarachidonic acid designed to stabilize one of the proposed radical intermediates, which may allow its detection.
Catalytic asymmetric synthesis of Leukotriene B4
Yang, Pengfei,Zhong, Jiangchun,Ji, Kaijie,Yin, Jingwei,Li, Shuoning,Wei, Siyuan,Zhou, Yun,Wang, Lifeng,Wang, Min,Bian, Qinghua
, p. 1596 - 1601 (2017/10/20)
Leukotriene B4 1 was prepared from two chiral synthons 8 and 14. The chiral secondary alcohols of 8 and 14 were constructed by BINOL/Ti(OiPr)4 catalyzed enantioselective alkynylzinc addition to aldehydes.
3-Aminoazetidin-2-one derivatives as N-acylethanolamine acid amidase (NAAA) inhibitors suitable for systemic administration
Fiasella, Annalisa,Nuzzi, Andrea,Summa, Maria,Armirotti, Andrea,Tarozzo, Glauco,Tarzia, Giorgio,Mor, Marco,Bertozzi, Fabio,Bandiera, Tiziano,Piomelli, Daniele
supporting information, p. 1602 - 1614 (2014/07/21)
N-Acylethanolamine acid amidase (NAAA) is a cysteine hydrolase that catalyzes the hydrolysis of endogenous lipid mediators such as palmitoylethanolamide (PEA). PEA has been shown to exert anti-inflammatory and antinociceptive effects in animals by engaging peroxisome proliferator-activated receptor α (PPAR-α). Thus, preventing PEA degradation by inhibiting NAAA may provide a novel approach for the treatment of pain and inflammatory states. Recently, 3-aminooxetan-2-one compounds were identified as a class of highly potent NAAA inhibitors. The utility of these compounds is limited, however, by their low chemical and plasma stabilities. In the present study, we synthesized and tested a series of N-(2-oxoazetidin-3-yl)amides as a novel class of NAAA inhibitors with good potency and improved physicochemical properties, suitable for systemic administration. Moreover, we elucidated the main structural features of 3-aminoazetidin-2-one derivatives that are critical for NAAA inhibition. Stability is the key: α-Amino-β-lactams were synthesized as amide derivatives, and the effect of the azetidin-2-one ring, the stereochemistry at the α-position, and the functionalization of the α-amino group were studied with regard to N-acylethanolamine acid amidase inhibitory potency and hydrolytic and plasma stability.
