108455-80-7

Upstream product

• 112-80-1 cis-Octadecenoic acid 
• 79802-20-3 (S)-(+)-2-pyrrolidinemethanol hydrochloride 
• 59485-81-3 cis-1-chloro-9-octadecene 
• 498-63-5 2-hydroxymethylpyrrolidine 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 81480-40-2 N-hydroxysuccinimide ester of oleic acid 

Relevant academic research and scientific papers

Antiproliferative 3-deoxysphingomyelin analogs: Design, synthesis, biological evaluation and molecular docking of pyrrolidine-based 3-deoxysphingomyelin analogs as anticancer agents

Sphingomyelins and glycerophospholipids are structurally related phospholipids. Nevertheless, glycerophospholipids analogs are known as antitumor agents while sphingomyelin analogs were reported as cytoprotective agents. Herein, we have addressed the development of 3-deoxysphingomyelin analogs as cytotoxic agents possessing modified sphingobases. Thus, pyrrolidine-based 3-deoxysphingomyelin analogs were synthesized and evaluated against a panel of cell lines representing four major types of cancers. Compounds 3d, 4d and 6d elicited better GI50 values than the FDA approved drug miltefosine. Investigation of their impact on Akt phosphorylation as a possible mechanism for the antiproliferative activity of this class of compounds revealed that these compounds might elicit a concentration-dependent mechanism via inhibition of Akt phosphorylation at the lower concentration. Molecular docking predicted their binding modes to Akt to involve polar head binding to the Pleckstrin homology domain and hydrophobic tail extension into a hydrophobic pocket connecting the Pleckstrin homology domain and the kinase domain. As a whole, the described work suggests compounds 3d, 4d and 6d as promising pyrrolidine-based 3-deoxysphingomyelin analogs for development of novel cancer therapies.

Pyrrolidine-based 3-deoxysphingosylphosphorylcholine analogs as possible candidates against neglected tropical diseases (NTDs): identification of hit compounds towards development of potential treatment of Leishmania donovani

A rational-based process was adopted for repurposing pyrrolidine-based 3-deoxysphingosylphosphorylcholine analogs bearing variable acyl chains, different stereochemical configuration and/or positional relationships. Structural features were highly influential on activity. Amongst, enantiomer 1e having 1,2-vicinal relationship for the -CH2O- and the N-acyl moieties, a saturated palmitoyl chain and an opposite stereochemical configuration to natural sphingolipids was the most potent hit compound against promastigotes showing IC50 value of 28.32 μM. The corresponding enantiomer 1a was 2-fold less potent showing a eudismic ratio of 0.54 in promastigotes. Compounds 1a and 1e inhibited the growth of amastigotes more potently relative to promastigotes. Amongst, enantiomer 1a as the more selective and safer. In silico docking study using a homology model of Leishmania donovani inositol phosphoceramide synthase (IPCS) provided plausible reasoning for the molecular factors underlying the found activity. Collectively, this study suggests compounds 1a and 1e as potential hit compounds for further development of new antileishmanial agents.

COMPOUNDS AND METHODS OF TREATING OBESITY

The present invention relates to novel fatty acid derivatives, methods for their preparation, pharmaceutical compositions including such compounds, and methods of using these compounds and compositions, especially as agents for the treatment of obesity and related disorders, and for improving cognition.

The anandamide membrane transporter. Structurea€"activity relationships of anandamide and oleoylethanolamine analogs with phenyl rings in the polar head group region

A new series of arachidonic and oleic acids derivatives, most of which with aromatic moieties in the head group region, has been synthesized and evaluated as inhibitors of anandamide uptake. A new series of anandamide and N-oleoylethanolamine analogs, most of which with aromatic moieties in the head group region, has been synthesized and evaluated as inhibitors of anandamide uptake. Some of them efficaciously inhibit the uptake process with Ki values in the low micromolar range (2.4-21.2 μM). Strict structural requisites are needed to observe a significant inhibition and in no case inhibition of fatty acid amidohydrolase overlaps with inhibition of anandamide uptake.

Pantothenic acid derivatives

Compounds represented by general formula (I) below STR1 wherein R1 and R2, which are the same or different, each represent a hydrogen atom or a protective group for a hydroxyl group; R3 represents a saturated or unsaturated, linear, branched or cyclic, monovalent C5 ?C25 -aliphatic hydrocarbon group which may be substituted with an aromatic group, or a group of formula STR2 where R4 represents a saturated or unsaturated, linear, branched or cyclic, monovalent C5 ?C25 -aliphatic hydrocarbon group which may be substituted with an aromatic group, and R5 represents a hydrogen atom, or a saturated or unsaturated, linear, branched or cyclic, monovalent hydrovarbon group which may be substituted with an aromatic group; Q represents (a) a group of formula --X1 --A--Y1 --, where A represents a saturated or unsaturated, linear, branched or cyclic divalent C2 ?C16 -aliphatic hydrocarbon group which may be substituted with an aromativ group, a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group; one of X1 and Y1 represents STR3 and the other represents --O--, --S-- or STR4 in which R6 and R7 each represent a hydrogen atom or a lower alkyl group; (b) a group of formula --X2 --(CH2)l --Y2 --, where one of X2 and Y2 represents a group of formula STR5 and the other represents --O--, --S-- or STR6 in which STR7 represents a 4?7-membered, divalent nitrogen-containing aromatic heterocyclic group, and R6 has the same meaning as defined above, and l is 0, 1 or 2; or (c) a group of formula STR8 where m is 2 or 3; n is an integer of from 1 to 4. The compounds have excellent inhibitory activity against acyl Co A-cholesterol-acyltransferase.

Pantothenic acid derivatives

Compounds represented by general formula (I) below wherein R1 and R2, which are the same or different, each represent a hydrogen atom or a protective group for a hydroxyl group;, R3 represents a saturated or unsaturated, linear, branched or cyclic, monovalent C5～C25-aliphatic hydrocarbon group which may be substituted with an aro-matic group, or a group of formula where R4 represents a saturated or unsaturated, linear, branched or cyclic, monovalent C5～C25--aliphatic hydrocarbon group which may be sub-stituted with an aromatic group, and, R5 represents a hydrogen atom, or a saturated or unsaturated, linear, branched or cyclic, monovalent hydrocarbon group which may be substituted with an aromatic group; Q represents (a) a group of formula -X1-A-Y1-,where A represents a saturated or unsaturated, linear, branched or cyclic divalent C2～C16--aliphatic hydrocarbon group which may be sub-stituted with an aromatic group, a divalent aromatic hydrocarbon group or a divalent aro-matic heterocyclic group;, one of X1 and Y1 represents and the other represents -O-, -S- or in which R6 and R7 each represent a hydrogen atom or a lower alkyl group; (b) a group of formula -X2-(CH2)l-Y2-,where one of X2 and Y2 represents a group of formula and the other represents -O-, -S- or represents a 4～7--membered, divalent nitrogen-containing aromatic heterocyclic group, and R6 has the same meaning as defined above, and l is 0, 1 or 2; or (c) a group of formula where m is 2 or 3;, n is an integer of from 1 to 4. The compounds have excellent inhibitory activ-ity against acyl Co A-cholesterol-acyltransferase.