162465-74-9

Upstream product

• 50-00-0 formaldehyd 
• 162465-72-7 (-)-dihydroverbacine 
• 162465-73-8 (+)-(S)-2-phenyl-9-[(E)-phenylprop-2-enoyl]-1,5,9,14-tetraazabicyclo[12.3.1]octadecan-4-one 
• 162709-45-7 (+)-(S)-isoverbamethine 
• 164230-52-8 (-)-(S)-8-phenyl-1-[(E)-phenylprop-2-enoyl]-1,5,9,13-tetraazacycloheptadecan-6-one 
• 164176-10-7 (-)-verballocine 

Downstream Products

• 216855-93-5 (S)-3-(3-{4-[(3-Amino-propyl)-(3-phenyl-propionyl)-amino]-butylamino}-propylamino)-3-phenyl-propionic acid 
• 216856-02-9 (3S)-8-acetyl-N-butyl-18-oxo-3-phenyl-13-(3-phenylpropanoyl)-4,8,13,17-tetraazanonadecanamide 
• 216855-99-1 methyl (3S)-8-acetyl-18-oxo-3-phenyl-13-(3-phenylpropanoyl)-4,8,13-triazanonadecanoate 
• 216855-96-8 (S)-3-(3-{4-[(3-Amino-propyl)-(3-phenyl-propionyl)-amino]-butylamino}-propylamino)-3-phenyl-propionic acid methyl ester 

Relevant academic research and scientific papers

Chiroptical Properties of the Protoverbine Class of Macrocyclic Spermine Alkaloids

The chiroptical properties (circular dichroism, CD) of the 17-membered macrocyclic spermine lactam alkaloids (-)-protoverbine (16), its N,N′-methylene-bridged natural analogue (+)-protomethine (17), their natural derivatives (-)-verbacine (1), (-)-verballocine (2), (-)-verbascenine (3), (-)-verballoscenine (4), (+)-verbamethine (5), (+)-incasine C (6), (+)-verdoline (incasine B′, 30), (+)-incasine B (31), and some of their isosteric analogues were studied. By chemical and chiroptical correlation, it was confirmed that an amidically bonded (S)-β-phenyl-β-alanine fragment forms the chiral moiety in all of these natural compounds. The signs of the registered Cotton effects (CEs) are interpreted in terms of the Smith's quadrant rule for the 1Lb CEs of chiral α-substituted benzylamines and the Ogura's sign rule for n→π* CEs of lactams. Some of the conclusions regarding configuration are supported for the rigid bicyclic compound (-)-(9S)-9-phenyl-1,6-diazabicyclo[4.3.1]decan-7-one (15) by the X-ray crystal structure of the racemate.

Verbacine and Verballocine, Novel Macrocyclic Spermine Alkaloids from Verbascum pseudonobile Stoj. et Stef. (Scrophulariaceae)

The isolation and structural elucidation of the novel 17-membered lactam alkaloids verbacine (1) and verballocine (2) containing spermine, E- (or Z-)cinnamoyl and phenylpropionyl precursory units, is reported.Evidence for the artificial origin of the prev