34610-68-9

Usage

Uses

1. Pharmaceutical Industry:
(3S,8aα)-3β-[[2-(1,1-Dimethyl-2-propenyl)-1H-indol-3-yl]methyl]-1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine-1,4-dione is used as a pharmaceutical compound for its potential therapeutic applications. (3S,8aα)-3β-[[2-(1,1-Dimethyl-2-propenyl)-1H-indol-3-yl]methyl]-1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine-1,4-dione's unique structure and properties make it a promising candidate for the development of new drugs, particularly in the areas of cancer treatment and other diseases where its specific molecular interactions could be exploited.
2. Research and Development:
In the field of research and development, (3S,8aα)-3β-[[2-(1,1-Dimethyl-2-propenyl)-1H-indol-3-yl]methyl]-1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine-1,4-dione serves as a valuable tool for studying the structure-activity relationships of alkaloidal diketopiperazines and their potential applications in various therapeutic areas. It can also be used to investigate the biosynthesis of notoamides and other related compounds, contributing to the understanding of their biological activities and potential uses.
3. Drug Delivery Systems:
Similar to gallotannin, (3S,8aα)-3β-[[2-(1,1-Dimethyl-2-propenyl)-1H-indol-3-yl]methyl]-1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine-1,4-dione could potentially be used in drug delivery systems. By employing various organic and metallic nanoparticles as carriers, the compound's delivery, bioavailability, and therapeutic outcomes could be improved, enhancing its efficacy against specific targets, such as cancer cells.
4. Chemical Synthesis:
(3S,8aα)-3β-[[2-(1,1-Dimethyl-2-propenyl)-1H-indol-3-yl]methyl]-1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine-1,4-dione's unique structure also makes it an interesting subject for chemical synthesis research. Scientists can explore various synthetic routes to produce this complex molecule, potentially leading to the development of more efficient and cost-effective methods for its synthesis.

InChI:InChI=1/C21H25N3O2/c1-4-21(2,3)18-14(13-8-5-6-9-15(13)22-18)12-16-20(26)24-11-7-10-17(24)19(25)23-16/h4-6,8-9,16-17,22H,1,7,10-12H2,2-3H3,(H,23,25)/t16-,17-/m0/s1

Upstream product

• 75526-77-1 (S)-3-[2-(1,1-Dimethyl-allyl)-1H-indol-3-ylmethyl]-1,4-dioxo-octahydro-pyrrolo[1,2-a]pyrazine-3-carboxylic acid 
• 358-72-5 dimethylallyl diphosphate 
• 38136-70-8 brevianamide F 
• 82255-21-8 (S)-2-{1-Carboxy-2-[2-(1,1-dimethyl-allyl)-1H-indol-3-yl]-ethylcarbamoyl}-pyrrolidine-1-carboxylic acid benzyl ester 
• 67099-44-9 diethyl N-benzyloxycarbonyl-L-prolylaminomalonate 
• 22102-56-3 3-dimethylaminomethyl-2-(1',1'-dimethylallyl)indole 
• 57767-77-8 3-<2-(N-benzyloxycarbonyl-L-prolylamido)-2,2-diethoxycarbonylethyl>-2-(1,1-dimethylallyl)-indole 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 75526-74-8 dimethyl N-benzyloxycarbonyl-L-prolylaminomalonate 
• 75535-72-7 2-[((S)-Pyrrolidine-2-carbonyl)-amino]-malonic acid dimethyl ester 
• 205875-04-3 methyl 1,4-dioxoperhydropyrrolo[1,2-a]pyrazine-3-carboxylate 
• 61350-60-5 (S)-benzyloxycarbonyl-proline acid chloride 
• 55454-18-7 9-(3-methylbut-2-enyl)-9-borabicyclo[3.3.1.]nonane 
• 259674-17-4 2-{2-[2-(1,1-dimethyl-allyl)-1H-indol-3-yl]-1-methoxycarbonyl-ethylcarbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 75557-86-7 C₂₁H₂₅N₃O₃ 
• 23454-27-5 brevianamide E 

Relevant academic research and scientific papers

Genome-based characterization of two prenylation steps in the assembly of the stephacidin and notoamide anticancer agents in a marine-derived aspergillus sp.

Stephacidin and notoamide natural products belong to a group of prenylated indole alkaloids containing a core bicyclo[2.2.2]diazaoctane ring system. These bioactive fungal secondary metabolites have a range of unusual structural and stereochemical features but their biosynthesis has remained uncharacterized. Herein, we report the first biosynthetic gene cluster for this class of fungal alkaloids based on whole genome sequencing of a marine-derived Aspergillus sp. Two central pathway enzymes catalyzing both normal and reverse prenyltransfer reactions were characterized in detail. Our results establish the early steps for creation of the prenylated indole alkaloid structure and suggest a scheme for the biosynthesis of stephacidin and notoamide metabolites. The work provides the first genetic and biochemical insights for understanding the structural diversity of this important family of fungal alkaloids.

Reverse prenyl transferases exhibit poor facial discrimination in the biosynthesis of paraherquamide A, brevianamide A, and austamide

The mode of attachment of dimethylallyl pyrophosphate (DMAPP) in the biosynthesis of the indole alkaloids paraherquamide A, austamide, and brevianamide A has been studied. Feeding experiments on Penicillium fellutanum, Penicillium brevicompactum, and Aspergillus ustus using [13C2]-acetate showed isotopic scrambling of the geminal methyl groups originating from C-2 of the indole ring precursors in paraherquamide A, brevianamide A, and austamide biosynthesis. The labeling patterns suggest that the methyl groups of dimethylallyl pyrophosphate become equivalent during the biosyntheses; a non-face-selective S(N)' mechanism has been invoked to account for these observations.

Complete Decoration of the Indolyl Residue in cyclo- l -Trp- l -Trp with Geranyl Moieties by Using Engineered Dimethylallyl Transferases

Mutation of the gatekeeping residues for prenyl donor selectivity in six dimethylallyl transferases significantly increased their activities toward geranyl diphosphate. Forty-two geranylated derivatives were obtained from 15 cyclic dipeptides by using the engineered enzymes. Taking cyclo-l-Trp-l-Trp as an example, the geranyl moiety can be attached to all seven possible positions of the indole nucleus. This study demonstrates a convenient way to increase the structural diversity of geranylated products by structure-based engineering of the available dimethylallyl transferases.

Total synthesis of gypsetin, deoxybrevianamide E, brevianamide E, and tryprostatin B: Novel constructions of 2,3-disubstituted indoles

A concise and efficient total synthesis of the acyl-CoA:cholesterol acyltransferase inhibitor gypsetin (1) is described. The route features a straightforward method for the introduction of a reverse prenyl group into the C2-position of an N-phthaloyl-protected tryptophan (11). The total synthesis of gypsetin was completed by the dimethyldioxirane-promoted double- oxidative cyclization of a prefashioned diketopiperazine (19). Total syntheses of deoxybrevianamide E (24) and brevianamide E (25) following similar procedures are also described. The reaction of nucleophiles with in situ-generated 3-chloroindolenines provides a route to 2,3-disubstituted indoles from 3-substituted precursors. Indications of the scope and limitations of such reactions are provided. A total synthesis of tryprostatin B (41), a diketopiperazine derived from an L-tryptophan derivative (bearing a prenyl group at the α position of the indole) and L-proline, was accomplished. The key step involved the introduction of the prenyl function onto a protected tryptophan congener (11). A route for the prenylation of ketones with virtually no competitive reverse prenylation is also provided.

STUDIES ON INDOLIC MOULD METABOLITES. TOTAL SYNTHESIS OF L-PROLYL-2-METHYLTRYPTOPHAN ANHYDRIDE AND DEOXYBREVIANAMIDE E

Syntheses of L-prolyl-2-methyl-L-tryptophan anhydride, L-prolyl-2-methyl-D-tryptophan anhydride, deoxybrevianamide E, and L-prolyl-2-(1,1-dimethylallyl)-D-tryptophan anhydride are described.A route for the conversion of deoxybrevianamide E into brevianami

Studies on the Syntheses of Heterocyclic Compounds. Part 876. The Chiral Total Synthesis of Brevianamide E and Deoxybrevianamide E

The chiral total synthesis of brevianamide E (1) and deoxybrevianamide E (2) starting from L-proline is described.Condensation of 2-(1,1,dimethylallyl)-3-dimethylaminomethylindole (3) and (-)-methyl 1,4-dioxoperhydropyrrolopyrazine-3-carboxylate (7