27007-78-9

Upstream product

• 111-64-8 n-octanoic acid chloride 
• 2345-51-9 3-butynoic acid 
• 638-45-9 1-Iodohexane 
• 150667-80-4 3-Decyn-1-yl tetrahydropyranyl ether 
• 51721-39-2 3-decyn-1-ol 

Downstream Products

• 15469-77-9 dec-3-enoic acid 

Relevant academic research and scientific papers

Metabolism of Deuterated threo-Dihydroxy Fatty Acids in Saccharomyces cerevisiae: Enantioselective Formation and Characterization of Hydroxylactones and γ-Lactones

Biotransformation of (±) -threo-7,8-dihydroxy(7,8-2H 2)tetradecanoic acids (threo-(7,8-2H2)-3) in Saccharomyces cerevisiae afforded 5,6-dihydroxy(5,6-2H 2)dodecanoic acids (threo-(5,6-2H2)-4), which were converted to (5S,6S)-6-hydroxy(5,6-2H 2)dodecano-5-lactone ((5S,6S)-(5,6-2H2)-7) with 80% e.e. and (5S,6S)-5-hydroxy(5,6-2H 2)dodecano-6-lactone ((5S-,6S)-5,6-2H2)-8). Further β-oxidation of threo-(5,6-2H2)-4 yielded 3,4-dihydroxy(3,4-2H2)decanoic acids (threo-(3,4- 2H2)-5), which were converted to (3R,4R)-3-hydroxy(3,4-2H2)decano-4-lactone ((3R,4R)-9) with 44% e.e. and converted to 2H-labeled decano-4-lactones ((4R)-(3-2H1)- and (4R)-(2,3-2H2)-6) with 96% e.e. These results were confirmed by experiments in which (±)-threo-3,4-dihydroxy(3,4-2H2)decanoic acids (threo-(3,4-2H2)-5) were incubated with yeast. From incubations of methyl (5S,6S)- and (5R,6R)-5,6-dihydroxy(5,6-2H 2)dodecanoates ((5S,6S)- and (5R,6R)-(5,6-2H 2)-4a), the (5S,6S)-enantiomer was identified as the precursor of (4R)-(3-2H1)- and (2,3-2H2)-6). Therefore, (4R)-6 is synthesized from (3S,4S)-5 by an oxidation/keto acid reduction pathway involving hydrogen transfer from C(4) to C(2). In an analogous experiment, methyl (9S, 10S)-9,10-dihydroxyoctadecanoate ((9S,10S)-10a) was metabolized to (3S,4S)-3,4-dihydroxydodecanoic acid ((3S,4S)-15) and converted to (4R)-dodecano-4-lactone ((4R)-18).

Acyl Histidines: New N-Acyl Amides from Legionella pneumophila

Legionella pneumophila, the causative agent of Legionnaires' disease, is a Gram-negative gammaproteobacterial pathogen that infects and intracellularly replicates in human macrophages and a variety of protozoa. L. pneumophila encodes an orphan biosynthetic gene cluster (BGC) that contains isocyanide-associated biosynthetic genes and is upregulated during infection. Because isocyanide-functionalized metabolites are known to harbor invertebrate innate immunosuppressive activities in bacterial pathogen–insect interactions, we used pathway-targeted molecular networking and tetrazine-based chemoseletive ligation chemistry to characterize the metabolites from the orphan pathway in L. pneumophila. We also assessed their intracellular growth contributions in an amoeba and in murine bone-marrow-derived macrophages. Unexpectedly, two distinct groups of aromatic amino acid-derived metabolites were identified from the pathway, including a known tyrosine-derived isocyanide and a family of new N-acyl-l-histidine metabolites.

CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF BACKGROUND

Disclosed herein are small molecule calpain modulators, pharmaceutical compositions, preparation methods and their use as therapeutic agents. The therapeutic agents can be used for treating fibrotic disease or a resulting secondary disease state or condition. The small molecules can inhibit calpain through contact with CAPN1, CAPN2, and/or CAPN9 enzymes.

Tandem Regioselective Hydroformylation-Hydrogenation of Internal Alkynes Using a Supramolecular Catalyst

New supramolecular ligands containing an acyl guanidine function were designed based on the strategy of increasing the π-acceptor ability of phosphine ligands by introducing electron-withdrawing groups. By applying this novel catalytic system, a general protocol for the Rh-catalysed hydroformylation-hydrogenation of unsymmetrical internal alkynes, functionalized with a carboxylic acid, was found to furnish aliphatic aldehydes in high regio- and chemoselectivities. Control experiments confirm the enzyme-like supramolecular catalyst mode of action.

Enantioselective Bronsted acid-catalyzed N-acyliminium cyclization cascades

(Chemical Equation Presented) An enantioselective Bronsted acid-catalyzed N-acyliminium cyclization cascade of tryptamines with enol lactones to form architecturally complex heterocycles in high enantiomeric excess has been developed. The reaction is technically simple to perform as well as atom-efficient and may be coupled to a gold(I)-catalyzed cycloisomerization of alkynoic acids whereby the key enol lactone reaction partner is generated in situ. Employing up to 10 mol % bulky chiral phosphoric acid catalysts in boiling toluene allowed the product materials to be generated in good overall yields (63-99%) and high enantioselectivities (72-99% ee). With doubly substituted enol lactones, high diastereo- and enantioselectivities were obtained, thus providing a new example of a dynamic kinetic asymmetric cyclization reaction.

Furyl, phenylene, and thienyl leukotriene B4 analogues

This invention relates to a compound of the formula: STR1 or a pharmaceutically acceptable salt thereof wherein X is oxygen, sulfur, or --CH=CH--; wherein Z is OR1 or --NR4 R5 ; wherein R1 is hydrogen, lower alkyl, or a pharmaceutically acceptable cation; wherein R2 is H, --CH3 or --C2 H5 ; wherein R3 is OH, H or =O; wherein R4 and R5 may independently be hydrogen, or lower alkyl having 1-6 carbon atoms, or R4 and R5 may act together with N to form a cyclic amide of the formula: STR2 wherein n is an integer from 4-5; and m is an integer from 0-4. More particularly, this invention relates to compounds of the above formula which have utility as LTB4 antagonists.