38136-70-8Relevant academic research and scientific papers
Synthesis and evaluation of microtubule assembly inhibition and cytotoxicity of prenylated derivatives of cyclo-L-Trp-L-Pro
Sanz-Cervera, Juan F.,Stocking, Emily M.,Usui, Takeo,Osada, Hiroyuki,Williams, Robert M.
, p. 2407 - 2415 (2000)
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.
Hino, Tohru,Taniguchi, Mikio,Yamamoto, Ichiro,Yamaguchi, Keiichi,Nakagawa, Masako
, p. 2565 - 2568 (1981)
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
Song, Hengqian,Song, Jiacheng,Yan, Lihong,He, Weigang,Wang, Pengyan,Xu, Yuanzhen,Wei, Hongbo,Xie, Weiqing
, (2021/10/25)
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
Pound, Sarah M.,Underwood, Steven J.,Douglas, Christopher J.
supporting information, p. 2448 - 2453 (2020/04/27)
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
Wauters,Goossens,Delbeke,Muylaert,Roman,Van Hecke,Van Speybroeck,Stevens
, p. 8046 - 8054 (2015/09/02)
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
Boyd, Emily M.,Sperry, Jonathan
supporting information, p. 5056 - 5059 (2015/02/19)
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
Preciado, Sara,Mendive-Tapia, Lorena,Torres-Garcia, Carolina,Zamudio-Vazquez, Rubi,Soto-Cerrato, Vanessa,Perez-Tomas, Ricardo,Albericio, Fernando,Nicolas, Ernesto,Lavilla, Rodolfo
supporting information, p. 1171 - 1174 (2013/08/23)
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
-
Paragraph 0033, (2013/06/05)
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
Kieffer, Madeleine E.,Chuang, Kangway V.,Reisman, Sarah E.
supporting information, p. 5557 - 5560 (2013/05/22)
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.
Side chain anchoring of tryptophan to solid supports using a dihydropyranyl handle: Synthesis of brevianamide F
Torres-Garcia, Carolina,Diaz, Mireia,Blasi, Daniel,Farras, Immaculada,Fernandez, Irene,Ariza, Xavier,Farras, Jaume,Lloyd-Williams, Paul,Royo, Miriam,Nicolas, Ernesto
, p. 7 - 19 (2012/08/08)
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.
