85612-94-8Relevant academic research and scientific papers
Smooth muscle contractile activities of leukotriene analogues
Cho,Ueda,Funahashi,Koda
, p. 3326 - 3329 (1983)
Chemical modification in the hydrophilic and hydrophobic regions of leukotrienes was investigated in relation to their smooth muscle contractile activities. The conjugated diene or triene moeity in the hydrophobic region is crucial for potent contractile
Cellular uptake of a catechol iron chelator and chloroquine into Plasmodium falciparum infected erythrocytes
Hammadi, Akli,Ramiandrasoa, Florence,Sinou, Veronique,Rogier, Christophe,Fusai, Thierry,Le Bras, Jacques,Parzy, Daniel,Kunesch, Gerhard,Pradines, Bruno
, p. 1351 - 1360 (2003)
Our study demonstrates the capacity of FR160, a catechol iron chelator, to reach and accumulate into infected Plasmodium falciparum erythrocytes and parasites (cellular accumulation ratio between 12 and 43). Steady-state FR160 accumulation is obtained aft
Design, synthesis, and biological evaluation of N-Alkylated deoxynojirimycin (DNJ) derivatives for the treatment of dengue virus infection
Yu, Wenquan,Gill, Tina,Wang, Lijuan,Du, Yanming,Ye, Hong,Qu, Xiaowang,Guo, Ju-Tao,Cuconati, Andrea,Zhao, Kang,Block, Timothy M.,Xu, Xiaodong,Chang, Jinhong
supporting information; experimental part, p. 6061 - 6075 (2012/08/14)
We recently described the discovery of oxygenated N-alkyl deoxynojirimycin (DNJ) derivative 7 (CM-10-18) with antiviral activity against dengue virus (DENV) infection both in vitro and in vivo. This imino sugar was promising but had an EC50 against DENV in BHK cells of 6.5 μM, which limited its use in in vivo. Compound 7 presented structural opportunities for activity relationship analysis, which we exploited and report here. These structure-activity relationship studies led to analogues 2h, 2l, 3j, 3l, 3v, and 4b-4c with nanomolar antiviral activity (EC50 = 0.3-0.5 μM) against DENV infection, while maintaining low cytotoxicity (CC50 > 500 μM, SI > 1000). In male Sprague-Dawley rats, compound 3l was well tolerated at a dose up to 200 mg/kg and displayed desirable PK profiles, with significantly improved bioavailability (F = 92 α 4%).
Enantiospecific syntheses of leukotrienes C4, D4 and E4 and [14,15-3H2]leukotriene E4 dimethyl ester
Cohen,Banner,Lopresti,et al.
, p. 3661 - 3672 (2007/10/02)
A 'chiral-pool' approach was employed to synthesize various leukotrienes (slow-reacting substance of anaphylaxis, SRS-A) enantiospecifically. The pivotal (S,S)-trans-epoxy alcohol 9 was prepared by efficient and facile routes starting from erythorbic acid (D-araboascorbic acid, 13). This epoxide could also be produced starting from D-glucose. The epimeric (S,R)-cis-epoxide 38 was obtained utilizing L-tartaric acid as the chiral starting material. Elaboration of 9 into leukotriene A4 methyl ester (5) and the potassium salts of leukotrienes C4 (4a), D4 (4b), and E4 (4c) was accomplished by standard methods. These salts exhibited potent contractile activities in the in vitro guinea pig ileum assay. Reduction of 14,15-dehydroleukotriene A4 methyl ester (44) with tritium gas gave [14,15-3H2]-5 and subsequently the dimethyl ester of [14,15-3H2]leukotriene E4 having a high specific activity of 40 Ci/mmol.
