64947-43-9

Usage

Uses

Used in Pharmaceutical Applications:
[10b,10'b-Bi-10bH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole]-1,1',4,4'-tetrone,2,2',3,3',5a,5'a,6,6',11,11',11a,11'a-dodecahydro-2,2'-dimethyl-3,3'-bis(phenylmethyl)-,(3S,3'S,5aS,5'aS,10bS,10'bS,11aS,11'aS)may be used as a pharmaceutical compound for [application reason] due to its complex structure and potential interactions with biological systems.
Used in Materials Science Applications:
In the field of materials science, [10b,10'b-Bi-10bH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole]-1,1',4,4'-tetrone,2,2',3,3',5a,5'a,6,6',11,11',11a,11'a-dodecahydro-2,2'-dimethyl-3,3'-bis(phenylmethyl)-,(3S,3'S,5aS,5'aS,10bS,10'bS,11aS,11'aS)could be utilized as a component in the development of new materials with specific properties, such as [application type] for [application reason], based on its unique structural features.

Upstream product

• 7479-05-2 L-tryptophan ethyl ester 
• 2899-07-2 (S)-N-benzyloxycarbonyl-N-methyl-phenyl alanine 
• 1629094-37-6 dimethyl (-)-(2S,2'S,3aS,3'aS,8aR,8'aR)-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-3a,3'a-bipyrrolo[2,3-b]indole-2,2'-dicarboxylate 
• 1629094-38-7 dimethyl (-)-(2S,2'S,3aS,3'aS,8aS,8'aS)-1,1'-bis{(S)-2-[tert-butoxycarbonyl(methyl)amino]-3-phenylpropanoyl}-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-3a,3'a-bipyrrolo[2,3-b]indole-2,2-dicarboxylate 
• 96238-68-5 tert-butyl (+)-(S)-3-[2-(tert-butoxycarbonylamino)-3-methoxy-3-oxopropyl]-1H-indole-1-carboxylate 
• 37553-65-4 Boc-N-Me-Phe-OH 
• 1064604-21-2 methyl (2S,3aR,8aR)-[3a-bromo-(1,2,3,3a,8,8a)-hexahydropyrrolo[2,3-b]indole-1,8-di-tertbutoxycarbonyl]-2-carboxylate 
• 4299-70-1 L-tryptophan methyl ester 
• 73-22-3 L-Tryptophan 
• 1020064-59-8 C₅₄H₄₈N₆O₈S₂ 
• 132294-79-2 (3S,6S)-6-Benzyl-3-(1H-indol-3-ylmethyl)-1-methyl-piperazine-2,5-dione 
• 64-18-6 formic acid 

Downstream Products

• 159355-77-8 (-)-1'-(2-phenylethylene)-ditryptophenaline 
• 1020064-60-1 C₅₈H₅₂N₆O₄ 

Relevant academic research and scientific papers

Total Synthesis of Homo-and Heterodimeric Bispyrrolidinoindoline Dioxopiperazine Natural Products

Total synthesis and structural confirmation of homo-and heterodimeric bispyrrolidinoindoline dioxopiperazine alkaloids isolated from fungi and bacteria, namely, ditryptoleucine A, ditryptoleucine B (11), the N,N′-bis-demethylated analogue (+)-12, (-)-dibrevianamide F (13), (-)-SF-5280-451 (14), tetratryptomycin A (15), (-)-Tryprophenaline (17), and (-)-SF-5280-415 (18), has been carried out starting from the corresponding bispyrrolidinoindolines derived from tryptophan. Our efforts to synthesize all possible diastereomers of the natural ditryptoleucine isolates uncovered structural factors that determine the rate and efficiency of dioxopiperazine ring formation, leading in some cases to mixtures of diastereomers by concomitant epimerization, to the formation of their putative monomeric dioxopiperazine dipeptide biogenetic precursors, and to the alternative formation of a dimer with a fused 1,3,5-Triazepan-6-one heterocycle.

Collective synthesis and biological evaluation of tryptophan-based dimeric diketopiperazine alkaloids

A concise two one-pot synthesis of WIN 64821, eurocristatine, 15,15′-bis-epi-eurocristatine, ditryptophenaline, ditryptoleucine A, WIN 64745, cristatumin C, asperdimin, naseseazine A, and naseseazine B is detailed, based on a unique bioinspired dimerization reaction of tryptophan derivatives in aqueous acidic solution and a one-pot procedure for the construction of diketopiperazine rings. Total yields of these alkaloid syntheses were from 10 up to 27 %. In addition, 1′-(2-phenylethylene)-ditryptophenaline was synthesized by using three one-pot operations. The studies detailed herein provided synthesized natural products for inhibitory activities of ubiquitin-specific protease 7 (USP7) and foam cell formation in macrophages. The newly listed biological evaluation for tryptophan-based dimeric diketopiperazine alkaloids discovered 15,15′-bis-epi-eurocristatine, 1′-(2-phenylethylene)-ditryptophenaline, and WIN 64745 as new drug candidates. All in one: A concise synthesis of tryptophan-based dimeric diketopiperazine alkaloids (see scheme) is detailed based on a unique bioinspired dimerization reaction of tryptophan derivatives and a one-pot procedure for construction of diketopiperazine rings. Some of the synthetic alkaloids were discovered as new drug candidates for cancer or atherosclerosis therapy.

Copper-mediated dimerization to access 3a,3a′-bispyrrolidinoindoline: Diastereoselective synthesis of (+)-WIN 64821 and (-)-ditryptophenaline

A copper-mediated cyclization and dimerization of tryptamine or tryptophan was developed to generate a C2-symmetry C3(sp3)-C3(sp3) bridge with two contiguous stereogenic quaternary carbons in one step. Impressively, the ratio between exo and endo cyclization products varies when different protecting groups of Nb are utilized. This dimerization reaction could be conducted in gram scale. With this dimerization method, both endocyclotryptophan (+)-WIN 64821 and exocyclotryptophan (-)-ditryptophenaline were synthesized in 5 steps.

Unified synthesis of (-)-folicanthine and (-)-ditryptophenaline enabled by a room temperature nickel-mediated reductive dimerization

A Ni·Phen-mediated reductive homocoupling of an optically active tertiary bromide has been efficiently achieved after the systematic screen of reaction conditions including ligands. This key step establishes sterically hindered vicinal quaternary stereocenters embedded in natural bispyrrolo[2,3-b]indoline alkaloids, thus enabling to realize the first asymmetric total synthesis of (-)-folicanthine via the detailed investigation of a challenging double decarboxylation. Notably, the concise synthesis of diketopiperazine alkaloid (-)-ditryptophenaline was also completed from the common dimeric intermediate. Georg Thieme Verlag Stuttgart New York.

Bio-inspired dimerization reaction of tryptophan derivatives in aqueous acidic media: Three-step syntheses of (+)-WIN 64821, (-)-ditryptophenaline, and (+)-naseseazine B

Doubling up: The direct bio-inspired dimerization of commercially available amine-free tryptophan derivatives in aqueous acidic media provides C 2-symmetrical and nonsymmetrical dimeric compounds. Further processing completes the concise synthe

Concise total synthesis of (+)-WIN 64821 and (-)-ditryptophenaline

(Chemical Equation Presented) On a fast track: The secondary metabolites (+)-WIN 64821 and (-)-ditryptophenaline have been synthesized in six and seven steps, respectively, from amino acid derivatives in a concise and enantioselective manner. The gram-scale synthesis of key intermediates and the simultaneous introduction of vicinal quaternary stereocenters are described. The synthesis and structural confirmation of (-)-1′-(2-phenylethylene) ditryptophenaline is also reported.

OXIDATIVE DIMERIZATION OF Nb-ACYLTRYPTOPHANES TOTAL SYNTHESIS AND ABSOLUTE CONFIGURATION OF DITRYPTOPHENALINE

First total synthesis of ditryptophenaline 1 is described and the absolute configuration was determined.