89149-10-0

Usage

Uses

Used in Organ Transplantation:
(S)-15-Deoxyspergualin is used as an immunosuppressant for preventing organ rejection in transplant recipients. Its ability to inhibit T cell activation and proliferation makes it a valuable option for maintaining the viability of transplanted organs.
Used in Autoimmune Disease Treatment:
(S)-15-Deoxyspergualin is used as a therapeutic agent for the treatment of various autoimmune diseases. Its immunosuppressive properties help in managing the symptoms and progression of conditions such as rheumatoid arthritis, multiple sclerosis, and type 1 diabetes by modulating the immune system's response.
Used as an Alternative to Conventional Immunosuppressants:
(S)-15-Deoxyspergualin is considered as a possible alternative to conventional immunosuppressant drugs in certain clinical settings. Its unique mechanism of action and structural similarity to cyclosporine make it a promising candidate for patients who may not respond well to or cannot tolerate traditional immunosuppressive medications.

Upstream product

• 134067-90-6 sisylated bis(tert-butoxycarbonyl)guanidine methyl ester 
• 107819-91-0 7-heptanamide 
• 85503-20-4 N,N-bis(tert-butoxycarbonyl)spermidine 
• 98433-13-7 7-aminoheptanamide 
• 107819-93-2 pentakis(tert-butoxycarbonyl)-11-silyl-15-deoxyspergualin 

Relevant academic research and scientific papers

Crystalline deoxyspergualin, process for its preparation and suppository containing the same

The invention provides crystalline deoxyspergualin trihydrochloride, a process for the preparation of the same and a suppository composition containing the same. The compound and composition has antitumor and immunosuppressive activity.

Total Synthesis of (+/-)-15-Deoxyspergualin

The synthesis of (+/-)-7-N-butyl>amino>-1-hydroxy-2-oxoethyl>heptanamide trihydrochloride, (+/-)-15-deoxyspergualin, 2b, a potent antitumor and antibiotic spermidine alkaloid, is reported.The synthesis is predicated on the development of the protected spermidine N1,N4-bis(tert-butoxycarbonyl)spermidine (12) and guanidine reagent N,N'-bis(tert-butoxycarbonyl)-S-methylisothiourea (18).The sensitive alkanolamide moiety of (+/-)-15-deoxyspergualin ( C-11 in 2b ) is formed and then protected as its tert-butyldimethylsilyl ether in 21.The reactive ester group of 21 undergoes aminolysis with 12 to from protected deoxyspergualin 22.All of the protecting groups in 22 are removed by trifluoroacetic acid to furnish final product 2b.

Method for producing glyoxylylspermidine and the use thereof for the production of 15-deoxy spergualin-related compounds

Glyoxylylspermidine, an intermediate for 15-deoxyspergualin-related compounds, is prepared in an oxidative cleavage reaction.