4996-33-2

Upstream product

• 5264-35-7 2-methoxy-1-pyrroline 
• 5661-55-2 4-phenylazetidin-2-one 
• 616-45-5 2-pyrrolidinon 
• 1022958-12-8 C₉H₈ClNO₂S 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 76528-86-4 1-(4,5-Dihydro-3H-pyrrol-2-yl)-4-phenyl-azetidin-2-one 

Downstream Products

• 76528-87-5 4-phenyl-1,5-diazacyclononan-2-one 
• 73465-24-4 (+/-)-celacinnine 
• 141991-06-2 1-(3-aminopropyl)-4-phenyl-1,5-diazacyclononan-2-one 
• 76528-88-6 4-phenyl-N-(3-phthalimidopropyl)-1,5-diazacyclononan-2-one 
• 73397-35-0 2-phenyl-1,5,9-triazacyclotridecan-4-one 

Relevant academic research and scientific papers

Synthesis and structure-activity relationships of vasicine analogues as bronchodilatory agents

The series of vasicine (1) analogues, an alkaloid from Adhatoda vasica Nees., were synthesized with changes in A, B or C rings. Compounds 3-19 were evaluated for in vitro bronchodilatory activity using isolated guinea pig tracheal chain. Compounds 3-8 were also synthesized in good yields using microwave-mediated synthesis under solvent free conditions. Compounds 5 and 8 with seven-member C ring were more active than etofylline and caused 100% relaxation of both the histamine and acetylcholine pre-contracted guinea pig tracheal chain. The structure-activity relationship studies showed that the quinazoline and oxo functionalities were essential for activity. The compounds without C ring and instead having aliphatic and phenyl substitutions in B ring showed relaxation against histamine pre-contracted tracheal chain only, 2-methyl substituted analogues, 12 and 13, being most active with 100% relaxation effect. Birkhaeuser Boston 2006.

NEW APPROACHES TO THE SYNTHESIS OF SPERMINE AND SPERMIDINE ALKALOIDS

New approaches to the formation of macrocyclic lactams are described involving successive ring expansion of 8-lactams and other heterocyclic systems.These methods have been used in the synthesis of a number of spermine and spermidine alkaloids including homaline, celacinnine, dihydroperiphylline, chaenorhine and verbascenine.

TRANSAMIDATION REACTIONS IN THE FORMATION OF MACROCYCLIC LACTAMS. A TOTAL SYNTHESIS OF CELLACINNINE.

The macrocyclic spermidine alkaloid, cellacinnine, has been synthetized by methods involving successive ring expansion reactions.One route starts with 4-phenyl-2-azetidinone; another, with piperidazine.