103541-15-7

Usage

Uses

Used in Pharmaceutical Industry:
Clausenamide is used as a bioactive compound for its potential anti-inflammatory and antitumor properties. Its ability to inhibit the growth of cancer cells makes it a promising candidate for the development of novel medicinal drugs and natural therapeutic agents.
Used in Cancer Research:
Clausenamide is used as a research compound for studying its inhibitory effects on the growth of cancer cells. Further investigation and research are needed to explore its potential as a natural source of therapeutic compounds for cancer treatment.

InChI:InChI=1/C18H19NO3/c1-19-15(16(20)13-10-6-3-7-11-13)14(17(21)18(19)22)12-8-4-2-5-9-12/h2-11,14-17,20-21H,1H3/t14-,15-,16+,17+/m0/s1

Upstream product

• 109838-83-7 (+/-)-(4R^*,5R^*,7S^*)-5-(α-hydroxybenzyl)-1-methyl-4-phenylpyrrolidin-2-one 
• 109838-82-6 (+/-)-(4R^*,5R^*)-5-formyl-1-methyl-4-phenylpyrrolidin-2-one 
• 109838-81-5 (+/-)-(4R^*,5R^*)-5-(hydroxymethyl)-1-methyl-4-phenylpyrrolidin-2-one 
• 109838-79-1 (+/-)-(4R^*,5R^*)-5-(ethoxycarbonyl)-1-methyl-4-phenylpyrrolidin-2-one 
• 109838-83-7 (+/-)-(4R^*,5R^*,7R^*)-5-(α-hydroxybenzyl)-1-methyl-4-phenylpyrrolidin-2-one 
• 4192-77-2 ethyl cinnamate 
• 109838-77-9 5,5-Diethoxycarbonyl-1-methyl-4-phenyl-pyrrolidin-2-one 
• 109838-78-0 (2S,3R)-1-Methyl-5-oxo-3-phenyl-pyrrolidine-2,2-dicarboxylic acid ethyl ester 
• 109838-84-8 (+/-)-(4R^*,5R^*)-5-benzoyl-1-methyl-4-phenylpyrrolidin-2-one 
• 13992-75-1 5,5-Diethoxycarbonyl-4-phenylpyrrolidin-2-one 

Downstream Products

• 109905-95-5 (±)-(3R,4S,5S,6R)-clausenamide 

Relevant academic research and scientific papers

Highly efficient and concise synthesis of both antipodes of SB204900, clausenamide, neoclausenamide, homoclausenamide and ζ-clausenamide. Implication of biosynthetic pathways of clausena alkaloids

The synthesis of both antipodes of N-methyl-N-[(Z)-styryl]-3-phenyloxirane- 2-carboxamide (SB204900), clausenamide, neoclausenamide, homoclausenamide and ζ-clausenamide have been accomplished using (2S,3R)- and (2R,3S)-3-phenyloxirane-2-carboxamides as the starting materials, and SB204900 was found to be a common precursor to other N-heterocyclic clausena alkaloids. Mediated by Bronsted acids under different conditions, for example, SB204900 underwent efficient and diverse alkene-epoxide cyclization, enamide-epoxide cyclization and arene-epoxide cyclization reactions to produce the five-membered N-heterocyclic neoclausenamide, its 6-epimer, the six-membered N-heterocyclic homoclausenamide and the eight-membered N-heterocyclic ζ-clausenamide, respectively, in good to excellent yields. Regiospecific oxidation of neoclausenamide and its 6-epimer afforded neoclausenamidone. Enolization of neoclausenamidone in the presence of LiOH and the subsequent protonation under kinetic conditions at -78 °C led to the epimerization of neoclausenamidone into clausenamidone. Reduction of clausenamidone using NaBH4 furnished clausenamide in high yield. The Royal Society of Chemistry 2009.

Diastereoselective and Enantioselective Total Synthesis of the Hepatoprotective Agent Clausenamide

The diastereoselective total synthesis of the naturally ocurring hepatoprotective agent clausenamide (3-hydroxy-5-(α-hydroxybenzyl)-1-methyl-4-phenylpyrrolidin-2-one) is described, starting from ethyl cinnamate and diethyl acetamidomalonate.The enantioselective total synthesis of optically pure (+)-clausenamide is presented.The synthesis is based on a novel method for the preparation of optically pure (2S,3S)-3-phenylglutamic acid.