5286-10-2

Usage

Uses

Used in Pharmaceutical Industry:
Cryogenine is used as an inhibitor of prostaglandin synthetase (IC50 = 469 μM) for its potential therapeutic applications in treating conditions related to prostaglandin synthesis, such as inflammation and pain.
Used in Chemical Research:
Cryogenine and its derivatives are used as research tools in the study of alkaloid chemistry, structural characterization, and the development of new compounds with potential applications in various fields.
Used in Drug Development:
The unique properties of cryogenine, such as its ability to inhibit prostaglandin synthetase, make it a valuable compound for the development of new drugs targeting prostaglandin-related conditions. Further research and development could lead to the creation of more effective and targeted therapies.

References

Blomster, Schwarting, Bobbitt., LZoydia, 27, 15 (1964) Douglas et aZ., ibid, 27, 25 (1964) Crystal structure: Zacharias et aZ., Experientia, 21, 247 (1965) Stereochemistry: Ferris, Boyce, Briner., J. Amer. Chern. Soc., 93,2942 (1971) Ferris etaZ., ibid, 93,2963 (1971)

Upstream product

• 1248344-23-1 4-(methoxymethoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde 
• 1214914-34-7 (S)-2-(2-oxo-propyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 1484-84-0 2(RS)-(2-hydroxyethyl)piperidine 
• 1202039-12-0 (+)-(2R)-(2-oxopropyl)piperidine-1-carbamic acid tert-butylester 
• 186581-53-3 diazomethane 
• 30356-01-5 Demethylvertine 
• 639458-43-8 (S)-2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 199942-74-0 (S)-2-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 121169-17-3 3-iodo-4-(methoxymethoxy)benzaldehyde 
• 60032-63-5 4-hydroxy-3-iodo-benzaldehyde 
• 1007600-14-7 N-acetyl-L-leucine (S)-2-piperidineethanol 
• 1393603-59-2 (4S,9aS)-hexahydro-4-(2-(2'-tert-butyldimethylsiloxy-5'-vinylphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2yl-acrylate 
• 1393603-58-1 (4S,9aS)-hexahydro-4-(2-(2'-tert-butyldimethylsiloxy-5'-carboxaldehyphenyl)-4,5dimethoxy-phenyl)-1H-quinolizin-2yl-acrylate 
• 1393603-56-9 (4S,9aS)-hexahydro-4-(2-(2'-hydroxy-5'-carboxaldehyphenyl)-4,5-dimethoxy-phenyl)-1H-quinolizin-2yl-acrylate 

Downstream Products

• 76193-27-6 12,13-dihydro-17,22,23-trimethoxy.13(S)-hydroxylythran-11-one 
• 76193-24-3 dihydro-13(S),17,22,23-tetramethoxylythran-11-one 
• 76193-25-4 12,13-dihydro-17-hydroxy-13(S),22,23-trimethoxylythran-11-one 
• 28457-84-3 17,22,23-trimethoxylythran-11-one 

Relevant academic research and scientific papers

Asymmetric Total Synthesis of Biphenylquinolizidine Alkaloids 4″- O-Demethyllythridine and 14- epi-4″- O-Demethyllythridine

The first asymmetric total synthesis of new biphenylquinolizidine alkaloids 4″-O-demethyllythridine and 14-epi-4″-O-demethyllythridine isolated from Heimia salicifolia was accomplished. The key steps in the synthesis were a copper(I)-catalyzed asymmetric intramolecular aza-Michael reaction to build a chiral 4-arylquinolizidine unit and an intramolecular Suzuki-Miyaura cross-coupling reaction to construct a macrolactone ring comprising a biphenyl moiety.

Asymmetric synthesis of (+)-vertine and (+)-lythrine

The total syntheses of the Lythracea alkaloids (+)-vertine and (+)-lythrine are described. Enantioenriched pelletierine is used as a chiral building block and engaged into a two step pelletierine condensation leading to two quinolizidin-2-one diastereomers in a 8:1 ratio. The major product is used in the synthesis of (+)-vertine via aryl-aryl coupling and ring closing metathesis to provide a Z-alkene α to the lactone carbonyl function. The same procedure was used for (+)-lythrine after base induced epimerization of the main quinolizidin-2-one diastereomer. Alternative classical ring closure strategies like macrolactonisation or aryl-aryl coupling failed.

ALKALOIDS OF HEIMIA MONTANA

The alkaloid composition of the little known Heimia species, H. montana has been determined.A new alkaloid, demethylvertine, has been isolated from this species and a close biogenetic correlation with other members of the genus has been established.Differences in alkaloid metabolism among the three species of Heimia have been demonstrated.