Efficient synthesis of 2,5-diketopiperazines using microwave assisted heating

Tullberg, Marcus; Grøtli, Morten; Luthman, Kristina

doi:10.1016/j.tet.2006.05.010

Cited by 83 publications

(42 citation statements)

References 51 publications

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“…m / z 334.1548 [M + H] + (calcd. for C 20 H 20 N 3 O 2 , 334.1550); 1 H NMR data were fully consistent with those reported in literature …”

Section: Methodssupporting

confidence: 88%

“…S3). All of the known compounds ( 2–4 ) were identified by comparison of their 1 H NMR, 13 C NMR, and/or MS data with literature values …”

Section: Methodsmentioning

confidence: 99%

“…The extracts from solid‐substrate fermentation cultures exhibited cytotoxic activity against MDA‐MB‐435 (human melanoma) cells and were therefore pursued for further analysis. Chemical separation of the CH 3 CN/CH 3 OH extract afforded a new diketopiperazine dimer ( 1 ) in addition to three known compounds including cyclo‐( L ‐phenylalaninyl‐ L ‐tryptophanyl), S ‐sydonic acid ( 3 ), and S ‐sydonol ( 4 ) (Fig. ) …”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

New diketopiperazine dimer from a filamentous fungal isolate of Aspergillus sydowii

Kaur

Raja

Darveaux

et al. 2015

Magnetic Reson in Chemistry

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“…m / z 334.1548 [M + H] + (calcd. for C 20 H 20 N 3 O 2 , 334.1550); 1 H NMR data were fully consistent with those reported in literature …”

Section: Methodssupporting

confidence: 88%

“…S3). All of the known compounds ( 2–4 ) were identified by comparison of their 1 H NMR, 13 C NMR, and/or MS data with literature values …”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

New diketopiperazine dimer from a filamentous fungal isolate of Aspergillus sydowii

Kaur

Raja

Darveaux

et al. 2015

Magnetic Reson in Chemistry

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“…In 2006, Tullberg et al reported the solution-phase cyclization of 11 dipeptide methyl esters in various solvents and performed a systematic comparison of the yields obtained with conventional vs MW heating [63]. Their synthetic method differed from those previously discussed (Figs.…”

Section: Solution-phase Mw-assisted Dkp Routesmentioning

confidence: 99%

Solid-Phase and Microwave-Assisted Syntheses of 2,5-Diketopiperazines:Small Molecules with Great Potential

O’Neill¹,

Blackwell²

2007

CCHTS

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Diketopiperazines (DKPs) are a well-known class of heterocycles that have recently emerged as a promising biologically active scaffold. Solid-phase organic synthesis has become an important tool in the combinatorial exploration of these privileged structures, expediting the synthesis and, therefore, the discovery of active compounds. To date, certain DKPs have shown potent activities against a range of diseases and biological phenomena, including bacterial infections, various cancers, asthma, infertility, premature labor, and HIV. Recent applications of solid-phase DKP synthesis, with a particular focus on cyclative cleavage and microwave-assisted reactions, are highlighted herein.

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“…26,27 Notable epimerization, side reactions and low yields were often reported. [28][29][30][31][32][33][34] Tetra-and pentapeptides do cyclize under sequence-specific conditions (see above) and classical peptide coupling conditions. 21 Hexapeptides were usually reported to cyclize without any particular problem.…”

mentioning

confidence: 99%

Efficient Synthesis of 2,5-Diketopiperazines by Staudinger-Mediated Cyclization

Beagle

Hansen

Monbaliu

et al. 2012

Synlett

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Solution-and solid-phase Staudinger-mediated cyclizations were assessed to efficiently prepare hetero-2,5-diketopiperazines from their protected azido dipeptide thioesters under microwave irradiation. Short reaction time, good yields and ease of purification are the main assets of this methodology.Peptide and peptide-like structures have drawn a great deal of attention from the scientific community especially in the area of medicinal chemistry. 1,2 While small linear peptides have shown great promise as targets for bioactivity, they intrinsically suffer from disadvantages due to their in vivo instability. Contrastingly, their cyclic analogues are usually associated with lower vulnerabilities to enzymatic degradation and a tunable lipophilicity due to their conformation and structure. 3 Small cyclic peptides recently displayed an expansive range of interesting biological activities including efficient interaction with opioid receptors, 4-6 potency in a variety of cytotoxic mechanisms in living systems, 7-11 and valuable neuroprotective properties. 12 In addition to these activities, much investigation has been given to the unique antibacterial, antifungal, antimalarial, and antiviral properties that have been associated with selected examples. [13][14][15][16][17][18] Although a wide range of cyclic oligopeptides are available from natural sources, intensive research programs have been devoted to obtain them from synthetic sources. Common methods have mainly involved three pathways: (a) head-to-tail condensation between the N-and C-termini of the corresponding linear peptides, (b) dimerization from two symmetrical peptide subunits, and (c) methods other than peptidic coupling. 1,2 Many of these syntheses start from the appropriately protected amino acid or peptidic subunits and these methods are often described in either solution or solid phases. 19 Of the synthetic methods reported in the literature, the head-to-tail condensation is of the greatest interest to us.The head-to-tail condensation is the most straightforward methodology for preparing cyclic peptides and has been widely described in previous literature. However, the head-to-tail condensation of small peptidic sequences is generally recognized as a difficult reaction. The cyclic dimer was often reported rather than the desired cyclic monomer. These undesired formations of the cyclic dimer can be reduced by carrying out the reaction in highly dilute conditions. 19 Beyond their highly constrained cyclic structure, the primary hurdle is then to bring the N-and Ctermini of the peptide in a close spatial proximity by inducing a turn in the peptidic sequence. This folding was usually induced by including specific residues in the peptide sequence such as, proline, 20 pseudoproline analogues, 21 other cyclic unnatural amino acids or other nonproteogenic residues. 22-24 Recently, Tai et al. reported the macrocyclization of linear tetrapeptides by using polymer-imprinted cavities as templates. 25 Generally, head-to-tail condensation of di-and tripeptides required...

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Efficient synthesis of 2,5-diketopiperazines using microwave assisted heating

Cited by 83 publications

References 51 publications

New diketopiperazine dimer from a filamentous fungal isolate of Aspergillus sydowii

New diketopiperazine dimer from a filamentous fungal isolate of Aspergillus sydowii

Solid-Phase and Microwave-Assisted Syntheses of 2,5-Diketopiperazines:Small Molecules with Great Potential

Efficient Synthesis of 2,5-Diketopiperazines by Staudinger-Mediated Cyclization

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