A new and general method for the synthesis of tripeptide aldehydes based on the multi-component Ugi reaction

Mroczkiewicz, Monika; Ostaszewski, Ryszard

doi:10.1016/j.tet.2009.03.018

Cited by 25 publications

(15 citation statements)

References 30 publications

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“… 27 However, cleavable amine or aldehyde components require additional steps, and racemization is possible. 28 In principle, ammonium salts of carboxylates could be ideal components in the U-MCR due to their general and simple preparation while maintaining a neutral pH during the Ugi reactions thus avoiding racemization during the peptide synthesis. 29 Therefore, we have synthesized ammonium salt of carboxylates derived from N -protected amino acids (1.0 equiv) by the treatment of ammonium bicarbonate in a mixture of CH 3 CN:H 2 O.…”

Section: Resultsmentioning

confidence: 99%

Cysteine Isocyanide in Multicomponent Reaction: Synthesis of Peptido-Mimetic 1,3-Azoles

et al. 2017

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An alternative approach toward the simple and robust synthesis of highly substituted peptidic thiazole derivatives using Ugi-multicomponent reaction (U-MCR) is described. Thus, we introduced the enantiopure (R)-2-methyl-2-isocyano-3-(tritylthio)propanoate as a novel class of isocyanide in MCR. This bifunctional isocyanide was found to undergo mild cyclodehydration to afford thiazole containing peptidomimetics in a short synthetic sequence. Several examples of bis-heterocyclic rings were also synthesized through the proper choice of the aldehyde component in the U-4CR. The method opens a wide range of applications toward the synthesis of nonribosomal natural products and other bioactive compounds.

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Section: Resultsmentioning

confidence: 99%

Cysteine Isocyanide in Multicomponent Reaction: Synthesis of Peptido-Mimetic 1,3-Azoles

et al. 2017

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“…Therefore, we developed another procedure to complete the envisaged synthesis. Thus, the amino group in compounds 16 was transformed into an isocyanide moiety upon treatment with chloroform under phase‐transfer catalysis conditions to give isocyanides 17 , which were treated with elemental selenium to give the ω‐isoselenocyanatoalk‐1‐yl fluoroalkyl(aryl) sulfoxides 8 in reasonable yields (Scheme ). All of the target compounds synthesized are illustrated in Figure and the preparative details are presented in the Experimental Section.…”

Section: Resultsmentioning

confidence: 99%

Organofluorine Isoselenocyanate Analogues of Sulforaphane: Synthesis and Anticancer Activity

et al. 2016

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A series of previously unknown sulforaphane analogues with organofluorine substituents bonded to the sulfinyl sulfur atom, an isoselenocyanate moiety in place of the isothiocyanate group, the central sulfur atom in various oxidation states, and different numbers of methylene groups in the central alkyl chain were synthesized and fully characterized. All new compounds were tested for their biological properties in vitro and demonstrated much higher anticancer activity against two breast cancer cell lines than that shown by native sulforaphane; at the same time, the compounds were less toxic for normal cells. The influence of the particular structural changes in the molecules on the cytotoxicity is discussed.

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“…Thus, the DMB protective group proved to be a suitable amide protecting group for this type of phthalocyanine conjugate. 18 Water-soluble Pc compounds 4c and 4d were purified by means of dialysis followed by size-exclusion chromatography. Compound 4b was subsequently rinsed repeatedly with water and dichloromethane.…”

Section: Scheme 1 Synthesis and Deprotection Of Znpc-peptide Conjugatesmentioning

confidence: 99%

Microwave-Assisted Synthesis of Triazole-Linked Phthalocyanine-Peptide Conjugates as Potential Photosensitizers for Photodynamic Therapy

Sokolova¹,

Schotten

Berthold

et al. 2013

Synthesis

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A series of novel, highly symmetrical phthalocyanines bearing eight peptide residues has been prepared by microwaveassisted Cu(I)-catalyzed 1,3-dipolar cycloaddition ('click' reaction). Water-soluble conjugates were obtained after straightforward deprotection of the amine and amide functionalities. The phthalocyanine conjugates were found to be nontoxic along the whole concentration range, which makes them promising photosensitizers for therapeutic use.

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A new and general method for the synthesis of tripeptide aldehydes based on the multi-component Ugi reaction

Cited by 25 publications

References 30 publications

Cysteine Isocyanide in Multicomponent Reaction: Synthesis of Peptido-Mimetic 1,3-Azoles

Cysteine Isocyanide in Multicomponent Reaction: Synthesis of Peptido-Mimetic 1,3-Azoles

Organofluorine Isoselenocyanate Analogues of Sulforaphane: Synthesis and Anticancer Activity

Microwave-Assisted Synthesis of Triazole-Linked Phthalocyanine-Peptide Conjugates as Potential Photosensitizers for Photodynamic Therapy

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