34610-68-9 Usage
Description
(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 a complex organic compound with a unique molecular structure. It is an alkaloidal diketopiperazine derived from tryptophan and proline, which is a cyclic dipeptide. (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 characterized by the presence of a 1,1-dimethylallyl group substitution at position 2 on the indole ring. It has been isolated from various sources, including Aspergillus and Penicillium species, and is known to be a precursor in the biosynthesis of notoamides.
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, this compound 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.
Check Digit Verification of cas no
The CAS Registry Mumber 34610-68-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,4,6,1 and 0 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 34610-68:
(7*3)+(6*4)+(5*6)+(4*1)+(3*0)+(2*6)+(1*8)=99
99 % 10 = 9
So 34610-68-9 is a valid CAS Registry Number.
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
34610-68-9Relevant articles and documents
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Ritchie,Saxton
, p. 611 (1975)
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Reverse prenyl transferases exhibit poor facial discrimination in the biosynthesis of paraherquamide A, brevianamide A, and austamide
Stocking, Emily M.,Williams, Robert M.,Sanz-Cervera, Juan F.
, p. 9089 - 9098 (2000)
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.
Total synthesis of gypsetin, deoxybrevianamide E, brevianamide E, and tryprostatin B: Novel constructions of 2,3-disubstituted indoles
Schkeryantz, Jeffrey M.,Woo, Jonathan C. G.,Siliphaivanh, Phieng,Depew, Kristopher M.,Danishefsky, Samuel J.
, p. 11964 - 11975 (2007/10/03)
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.
