67889-75-2

Usage

Uses

Used in Pharmaceutical Industry:
Cyclo(Pro-Trp) is used as a therapeutic substance for its potential applications in treating various diseases, such as cancer and neurodegenerative disorders. Its anti-inflammatory and antioxidant properties make it a valuable tool in combating oxidative stress and inflammation-related conditions.
Used in Research and Development:
Cyclo(Pro-Trp) is used as a drug candidate in research and development to further elucidate its mechanisms of action and therapeutic potential. Further studies are needed to explore its possible uses in clinical settings and to fully understand its impact on modulating immune responses and regulating cell growth.

Upstream product

• 43041-12-9 methyl (2R)-pyrrolidine-2-carboxylate 
• 34487-85-9 N-carboxy-DL-tryptophan anhydride 
• 38136-75-3 Tryptophyl-Proline 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 4299-70-1 D-Tryptophan methyl ester 
• 126689-19-8 4-(3-indolylmethyl)-2-trifluoromethyl-5(4H)-oxazolone 
• 153-94-6 D-tryptophan 
• 37784-17-1 N-(tert-butoxycarbonyl)-D-proline 
• 4299-70-1 L-tryptophan methyl ester 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 608146-30-1 N-tert-butyloxycarbonyl-L-prolyl-L-tryptophan methyl ester 
• 2133-40-6 D-proline methyl ester hydrochloride 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 79982-38-0 cyclic tautomer of cyclo-L-prolyl-L-tryptophyl 

Downstream Products

• 1454306-43-4 (3S,8aR)-3-((2-(4-(trifluoromethyl)phenyl)-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 34610-68-9 deoxybrevianamide E 
• 1429318-79-5 C₂₄H₂₀BrF₃N₄O₃ 
• 1429318-80-8 C₂₂H₂₁BrN₄O₂ 
• 1429318-62-6 C₂₂H₂₁N₃O₂ 
• 1454306-26-3 (3S,8aS)-3-((2-(p-tolyl)-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 1454306-27-4 (3S,8aS)-3-((2-(4-methoxyphenyl)-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 1454306-28-5 (3S,8aS)-3-((2-(4-(trifluoromethyl)phenyl)-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 1454306-29-6 (3S,8aS)-3-((2-(4-chlorophenyl)-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 1454306-30-9 methyl 4-(3-(((3S,8aS)-1,4-dioxooctahydropyrrolo[1,2-a]pyrazin-3-yl)methyl)-1H-indol-2-yl)benzoate 
• 1454306-31-0 (3S,8aS)-3-((2-(2-methoxyphenyl)-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 1454306-32-1 (3S,8aS)-3-((2-(2-(trifluoromethyl)phenyl)-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 1454306-33-2 (3S,8aS)-3-((2-(2-chlorophenyl)-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 1454306-34-3 (3S,8aS)-3-((2-(3-methoxyphenyl)-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 

Relevant academic research and scientific papers

A concise synthesis of (-)-dihydrospirotryprostatin B via tandem Michael addition

The asymmetric synthesis of (-)-dihydrospirotryprostatin B (3), a cytostatic spiro[pyrrolidine-3,3′-oxindole] alkaloid, has been accomplished in 8 longest linear steps (LLS) from commercially available amino acids. The key step of the synthetic approach consists of the tandem Michael addition of oxindole derived from dipeptide diketopiperazine to alkynone, leading to the rapid construction of the spiro[pyrrolidine-3,3′-oxindole] scaffold with the consecutive quaternary spiro carbon center and chiral tertiary amine being diastereoselectively established.

Studies towards the Total Synthesis of Drimentine C. Preparation of the AB and CDEF Ring Fragments

The drimentine family is a class of hybrid isoprenoids derived from actinomycete bacteria. Members of this family display weak antitumor and antibacterial activity. Herein we report our efforts toward the total synthesis of drimentine C using three distinct approaches incorporating palladium-catalyzed cyanoamidation, reductive cross-coupling, and photoredox-catalyzed α-alkylation of an aldehyde as key steps. Our synthetic efforts use a convergent synthesis to assemble the terpenoid and alkaloid portions of drimentine C from readily available l-tryptophan, l-proline, and (+)-sclareolide.

Beyond the Diketopiperazine Family with Alternatively Bridged Brevianamide F Analogues

A method for the preparation of 3,5-bridged piperazin-2-ones from a tryptophan-proline-based diketopiperazine is described using diphosgene to induce the ring closure. Density functional theory calculations were conducted to study the mechanism of this C-C bond formation. Several derivatives of the thus obtained α-chloroamine were synthesized by substitution of the chlorine atom using a range of O-, N-, S-, and C-nucleophiles. This novel class of brevianamide F analogues possess interesting breast cancer resistance protein inhibitory activity.

Total synthesis of (-)-aspergilazine A

The total synthesis of (-)-aspergilazine A, an alkaloid possessing a rare N1′ to C6 bisindole bond, is described. A palladium-catalyzed N-arylation was used to selectively install the N1′-C6 bond in the presence of three other possible arylation sites. The ligand XPhos displayed a unique capability to efficiently carry out the N-arylation while simultaneously suppressing epimerization of the sensitive C9 stereocenters. This total synthesis has confirmed that aspergilazine A is a dimer of brevianamide F.

Synthesis and biological evaluation of a post-synthetically modified Trp-based diketopiperazine

A series of C2-arylated analogues of the diketopiperazine brevianamide F has been synthesized using a mild Pd-catalyzed CH-activation procedure. Biological evaluation of the new derivatives in different cell lines shows that this modification is responsible for the remarkable change in activity, turning a mild antibiotic and antifungal natural product (brevianamide F) into novel antitumoral compounds. Furthermore, the approach stated represents a new straightforward and versatile methodology with promising applications in peptidomimetics and medicinal chemistry.

Copper-catalyzed diastereoselective arylation of tryptophan derivatives: Total synthesis of (+)-naseseazines A and B

A copper-catalyzed arylation of tryptophan derivatives is reported. The reaction proceeds with high site-and diastereoselectivity to provide aryl pyrroloindoline products in one step from simple starting materials. The utility of this transformation is highlighted in the five-step syntheses of the natural products (+)-naseseazine A and B.

AGRICULTURAL CHEMICAL CONTAINING 2,5-DIKETOPIPERAZINE DERIVATIVE AS ACTIVE INGREDIENT

Disclosed herein is an agricultural agent containing a 2,5-diketopiperazine derivative capable of controlling plant diseases and promoting plant growth or an agriculturally acceptable salt thereof as an active ingredient.

Side chain anchoring of tryptophan to solid supports using a dihydropyranyl handle: Synthesis of brevianamide F

The multifunctional character of tryptophan has made it a target for the development of new molecules with therapeutic applications. In this sense the design of alternative solid phase routes would allow the widening of synthetic possibilities to access these molecules through conventional or combinatorial strategies. The present work describes a new strategy for side-chain anchoring of tryptophan to dihydropyranyl-functionalized polystyrene resins and its application to the synthesis of the natural diketopiperazine Brevianamide F. For this study a new handle (4-[(3,4-dihydro-2H-pyran-2-yl)methoxy]benzoic acid) was prepared in order to functionalize aminomethyl or methylbenzhydrylamine resins. A preliminary study in solution using Fmoc-Trp-OR (R = Allyl or Me) and suitable resin models showed that the formation of an hemiaminal linkage with the indole system could be brought about by either conventional or microwave heating in 1,2-dichloroethane and in the presence of pyridine p-toluenesulfonate in yields of 70-95% practically without the formation of subproducts. On the other hand the amino acid could be liberated from the resin at room temperature in yields of up to 90% using trifluoroacetic acid in dichloromethane in the presence of 1,3-dimethoxybenzene as a cation scavenger. The conditions found in solution for the reversible formation of the hemiaminal were only reproducible in solid-phase work using conventional heating. These conditions were used in the synthesis of Brevianamide F, furnishing the diketopiperazine in an overall yield of 56%. These results demonstrate the potential of this strategy for the preparation of new molecules based upon tryptophan as a synthetic precursor. Springer Science+Business Media, LLC 2011.

Three types of induced tryptophan optical activity compared in model dipeptides: Theory and experiment

The tryptophan (Trp) aromatic residue in chiral matrices often exhibits a large optical activity and thus provides valuable structural information. However, it can also obscure spectral contributions from other peptide parts. To better understand the indu

Prenylation at the indole ring leads to a significant increase of cytotoxicity of tryptophan-containing cyclic dipeptides

Fourteen tryptophan-containing cyclic dipeptides 1a-14a, including all four stereoisomers of cyclo-Trp-Pro and cyclo-Trp-Ala, were converted to their C2-regularly prenylated derivatives 1b-14b in the presence of dimethylallyl diphosphate by using the purified recombinant FtmPT1 as catalyst. The enzyme products were isolated on HPLC in preparative scales and their structures were elucidated by NMR and MS analyses. The cytotoxic effects of the prenylated products and their substrates were tested with human leukemia K562 and ovarian cancer A2780 sens and A2780 CisR cell lines. Preliminary results have been clearly shown that prenylation at C2 led to a significant increase of the cytotoxicity of the tested cyclic dipeptides in all the 14 cases. The second amino acid and the stereochemistry of tryptophan moiety of the cyclic dipeptides showed less influence on the cytotoxicity of the tested compounds.