67889-75-2

Basic information

• Product Name: Cyclo(Pro-Trp)
• Synonyms: Cyclo(Pro-Trp)
• CAS NO: 67889-75-2
• Molecular Formula: C₁₆H₁₇N₃O₂
• Molecular Weight: 283.32508
• Mol File: 67889-75-2.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 633.2±48.0 °C(Predicted)
• Appearance: /
• Density: 1.37±0.1 g/cm3(Predicted)
• PKA: 13.20±0.40(Predicted)
• CAS DataBase Reference: Cyclo(Pro-Trp)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclo(Pro-Trp)(67889-75-2)
• EPA Substance Registry System: Cyclo(Pro-Trp)(67889-75-2)

Safety Data

• Hazardous Substances Data: 67889-75-2(Hazardous Substances Data)

Usage

General Description

Cyclo(Pro-Trp) is a chemical compound composed of the cyclic dipeptide proline-tryptophan. Cyclo(Pro-Trp) has been identified as a promising new therapeutic substance with potential applications in the treatment of various diseases, including cancer and neurodegenerative disorders. Research has shown that Cyclo(Pro-Trp) exhibits anti-inflammatory and antioxidant properties that could make it a valuable tool in combating oxidative stress and inflammation-related conditions. Additionally, it has been suggested that Cyclo(Pro-Trp) may have the ability to modulate immune responses and regulate cell growth, further highlighting its potential as a versatile and impactful drug candidate. Further studies are needed to fully elucidate the mechanisms of action and therapeutic potential of Cyclo(Pro-Trp) and to explore its possible uses in clinical settings.

Upstream product

• 43041-12-9 methyl (2R)-pyrrolidine-2-carboxylate 
• 34487-85-9 N-carboxy-DL-tryptophan anhydride 
• 4299-70-1 D-Tryptophan methyl ester 
• 153-94-6 D-tryptophan 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 79982-38-0 cyclic tautomer of cyclo-L-prolyl-L-tryptophyl 
• 79982-39-1 C₁₆H₁₇N₃O₂ 
• 73-22-3 L-Tryptophan 
• 85416-63-3 N-tert-butyloxycarbonyl-L-tryptophan-L-proline methyl ester 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 608146-30-1 N-tert-butyloxycarbonyl-L-prolyl-L-tryptophan methyl ester 
• 813452-60-7 Fmoc-(S)-Trp-OAllyl 
• 2133-40-6 L-proline methyl ester monohydrochloride 

Downstream Products

• 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 
• 1454306-35-4 (3S,8aS)-3-((2-(3-(trifluoromethyl)phenyl)-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 

Relevant articles and documents

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.

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.

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.