38136-70-8

Usage

Uses

1. Used in Pharmaceutical Industry:
Cyclo(L-Pro-L-Trp-) is used as a bioactive natural product for the preparation, reactions, and medicinal and chemical properties of diketopiperazines. It acts as a reagent in the total synthesis and antitumor activity in vitro of glioperazine C and its derivatives, as well as in the synthesis and biological evaluation of a post-synthetically Trp-based diketopiperazine and its antitumor structure-activity relationship.
2. Used in Antimicrobial Applications:
Cyclo(L-Pro-L-Trp-) is used as an antimicrobial agent, inhibiting the growth of M. luteus and S. aureus in an inhibitory disc assay when used at a concentration of 30 μg/disc. It also shows activity against the Bacille Calmette-Guerin M. bovis strain with a minimum inhibitory concentration (MIC) of 12.5 μg/ml.
3. Used in Antifouling Applications:
In the marine industry, Cyclo(L-Pro-L-Trp-) is used as an antifouling agent, inhibiting the attachment of B. neritina larvae to PVC plates without inducing lethality. It has an effective concentration (EC50) of 6.35 μg/ml and a lethal concentration (LC50) of greater than 200 μg/ml in paint used to coat PVC plates.

InChI:InChI=1/C16H17N3O2/c20-15-14-6-3-7-19(14)16(21)13(18-15)8-10-9-17-12-5-2-1-4-11(10)12/h1-2,4-5,9,13-14,17H,3,6-8H2,(H,18,20)/t13-,14-/m0/s1

Upstream product

• 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 
• 79982-39-1 C₁₆H₁₇N₃O₂ 
• 236123-12-9 N-(t-Boc)-L-Trp-L-ProNH₂ 
• 13139-14-5 Boc-Trp-OH 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 85416-63-3 N-tert-butyloxycarbonyl-L-tryptophan-L-proline methyl ester 
• 207349-25-5 (S)-2-((R)-2-tert-Butoxycarbonylamino-propionylamino)-3-(1H-indol-3-yl)-propionic acid methyl ester 
• 204980-52-9 D-alanyl-L-tryptophan methyl ester 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 1228076-72-9 N-Fmoc-L-Pro-L-Trp-OMe 
• 92178-03-5 L-tryptophan allyl ester 
• 55782-87-1 N-carbobenzyloxy-L-tryptophanyl-L-proline methyl ester 

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

Synthesis and evaluation of microtubule assembly inhibition and cytotoxicity of prenylated derivatives of cyclo-L-Trp-L-Pro

The synthesis of three isoprenylated derivatives of cyclo-L-Trp-L-Pro is described. These substances have been evaluated for cytotoxic activity in rat normal fibroblast 3Y1 cells and have also been evaluated in vitro for the inhibition of microtubule assembly. Copyright (C) 2000 Elsevier Science Ltd.

CYCLIC TAUTOMERS OF TRYPTAMINES AND TRYPTOPHANS. V1. FORMATION AND REACTIONS OF CYCLIC TAUTOMERS OF CYCLO-L-TRYPTOPHANYL-L-PROLINE.

Two stereoisomeric cyclic tautomers (5 and 6) of cyclo-L-tryptophanyl-L-proline whose stereochemistry was established by x-ray analysis, gave 5- and 6-hydroxytryptophanyl derivatives (10, 11 and 19) on the hydroxylation with lead tetraacetate in trifluoroacetic acid.

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.

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.

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.

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.