94313-60-7

Usage

InChI:InChI=1/C22H45NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23-22(26)27-20-21(25)19-24/h21,24-25H,2-20H2,1H3,(H,23,26)

Upstream product

• 112-96-9 octadecyl isocyanate 

Downstream Products

• 126272-33-1 1-octadecylcarbamoyloxy-3-trityloxypropan-2-ol 
• 126271-36-1 2-methylcarbamoyloxy-1-octadecylcarbamoyloxy-3-trityloxypropane 
• 111325-15-6 1-O-(octadecylcarbamoyl)-2-O-acetyl-3-O-tritylglycerol 

Relevant academic research and scientific papers

A novel class of platelet activating factor (PAF) antagonists. II. Modification of the 2-position of the glycerol backbone of PAF-sulfonamide isosteres

In a continuing effort to obtain more potent platelet activating factor (PAF) antagonists, we tried to synthesize a series of PAF-sulfonamide isosteres in which the substituent at the 2-position was modified to an acetoxy equivalent other than the methoxy group. These modifications produced highly active PAF antagonists. Compound 3-[2-(5-methyl-2H-tetrazol-2-yl)-3-(octadecylcarbamoyloxy)propylaminosu lfonyl]propylquinolinium iodide (52) showed the most potent activity in the in vitro inhibitory effect on PAF-induced platelet aggregation in rabbit platelet-rich plasma (IC50 = 125 nm) and also in the in vivo protective effect on PAF-induced lethality in mice, with prolonged duration of action. Optically active enantiomers of this compound were synthesized and the (S)-(-)-isomer (IC50 = 87 nM) was found to be three times more potent that the (R)-(+)-isomer (IC50 = 289nM), clearly exemplifying the enantioselectivity in the PAF-antagonist action of this novel compound.

Structure-Activity Relationship in PAF-acether. 4. Synthesis and Biological Activities of Carboxylate Isosteres

The synthesis and biological characterization of some 3-carboxylate isosteres of PAF-acether structurally modified in positions 1 (ether, carbamate), 2 (acetoyl, ethoxy), and 3 (chain length and polar head group) are reported.All derivatives present antagonist activities against PAF-acether-induced effects in vitro (platelet aggregation) and in vivo (bronchoconstriction and thrombocytopenia in guinea pig and, to a lesser extent, hypotension in rat).The functional modifications presented here do not modify dramatically the potency of antagonist activities, and there is no enantioselectivity.All of the isosteres are specific PAF-acether...