60197-58-2

Usage

InChI:InChI=1/C22H32N2/c1-13-11-15-12-14(2)22(4,24-6)18-8-7-17-20(19(15)18)16(13)9-10-21(17,3)23-5/h13-20H,7-12H2,1-4H3/t13-,14+,15-,16+,17-,18-,19+,20+,21-,22+/m0/s1

Upstream product

• 7677-24-9 trimethylsilyl cyanide 

Downstream Products

• 120591-16-4 1-(3-Chloro-phenyl)-3-{(1R,2R,3aS,5S,5aR,8S,8aS,10aS,10bS,10cS)-8-[3-(3-chloro-phenyl)-ureido]-1,2,5,8-tetramethyl-hexadecahydro-pyren-1-yl}-urea 
• 120591-17-5 N-{(1R,2R,3aS,5S,5aR,8S,8aS,10aS,10bS,10cS)-8-[3-(4-Bromo-phenyl)-thioureido]-1,2,5,8-tetramethyl-hexadecahydro-pyren-1-yl}-formamide 
• 120615-15-8 N-{(1R,2R,3aS,5S,5aR,8S,8aS,10aS,10bS,10cS)-8-[3-(3-Chloro-phenyl)-ureido]-1,2,5,8-tetramethyl-hexadecahydro-pyren-1-yl}-formamide 
• 120591-19-7 4-Bromo-N-((1S,3aR,4S,5aS,7R,8R,8aS,10aS,10bS,10cS)-8-formylamino-1,4,7,8-tetramethyl-hexadecahydro-pyren-1-yl)-benzamide 

Relevant academic research and scientific papers

Concise Synthesis of the Antiplasmodial Isocyanoterpene 7,20-Diisocyanoadociane

The flagship member of the antiplasmodial isocyanoterpenes, 7,20-diisocyanoadociane (DICA), was synthesized from dehydrocryptone in 10 steps, and in 13 steps from commercially available material. Our previous formal synthesis was reengineered, leveraging

Synthesis of (+)-7,20-Diisocyanoadociane and Liver-Stage Antiplasmodial Activity of the Isocyanoterpene Class

7,20-Diisocyanoadociane, a scarce marine metabolite with potent antimalarial activity, was synthesized as a single enantiomer in 13 steps from simple building blocks (17 linear steps). Chemical synthesis enabled identification of isocyanoterpene antiplasmodial activity against liver-stage parasites, which suggested that inhibition of heme detoxification does not exclusively underlie the mechanism of action of this class.