4568-88-1

Upstream product

• 7147-29-7 methyl ω-hydroxytridecanoate 
• 488117-68-6 (E)-14-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-tetradec-13-enoic acid methyl ester 
• 80982-86-1 methyl ω-bromotridecanoate 
• 65157-88-2 13-oxotridecanoic acid 
• 15462-16-5 13-bromotridecanoic acid 
• 7735-38-8 13-hydroxytridecanoic acid 
• 488117-69-7 (S)-14-(2,2-dimethyl-[1,3]dioxolan-4-yl)-tetradecanoic acid methyl ester 
• 112-86-7 cis-13-docosenoic acid 

Downstream Products

• 18270-60-5 15-hydroxy-pentadecanoic acid hydrazide 
• 76529-42-5 methyl 15-hydroxypentadecanoate 
• 4617-33-8 15-hydroxylpentadecanoic acid 
• 945226-22-2 C₄₇H₈₉N₃O₈ 

Relevant academic research and scientific papers

Annonaceous acetogenin mimics bearing a terminal lactam and their cytotoxicity against cancer cells

Annonaceous acetogenins are a large class of naturally occurring polyketides exhibiting potent anticancer activities. Based on our previous discovery of AA005, a multi-ether mimic of natural acetogenins having potent antitumor activities and significant selectivity between normal cells and cancer cells, a new series of mimics containing a terminal lactam were designed, synthesized and evaluated. Bioactivity study against cancer cells shows that the N-methylated lactam-containing compounds 3, 4, and 5 exhibit comparable potencies to that of AA005, as well as the similar selectivity to cancer cells. Hydrocarbon-length effects of N-alkyl were further explored through synthesizing derivatives 24-26, and application of this derivation protocol to the fluorescent labeling was also investigated.

Studies on mimicry of naturally occurring annonaceous acetogenins: Non-THF analogues leading to remarkable selective cytotoxicity against human tumor cells

A class of structurally simplified analogues of the naturally occurring annonaceous acetogenins were developed, amongst which some non-THF analogues showed remarkable cytotoxicities against tumor cell lines, as well as good selectivity between human tumor cells and normal cells. The synthetic routes were significantly shortened because of the removal of the chiral centers bearing the THF rings on the natural templates. This simplification also provides access to the parallel synthesis of these mimics by a combinatorial strategy. The remaining stereogenic centers at the positions α to the ethereal links were introduced by the Chiron approach from the easily accessible chiral building blocks 6a and/or 6b, made in turn from L-ascorbic acid or Dmannitol, while the one in the butenolide segment was taken from L-lactate. All four diastereomeric non-THF analogues 2a-2d showed remarkable activity against the HCT-8 cell line, and better differentiation was found when testing against the HT-29 cell line. It was also discovered that both the butenolide and ethylene glycol subunits play essential roles in the cytotoxicities against tumor cell lines, while the 10-substituted hydroxy group and the absolute configuration of methyl group at the butenolide moiety are less important for their activity.

Enantiopure simple analogues of annonaceous acetogenins with remarkable selective cytotoxicity towards tumor cell lines

Structure simplification with conservation of the essential functionalities for biological activity has been achieved with the design and synthesis of four analogues of annonaceous acetogenins. The compounds ((15 R/S, 24 R/S)-1) are easily synthesized wit