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

Abstract

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.

Protect to Detect: A Golgi Apparatus Targeted Probe to Image Mobile Zinc Through the Use of a Lipophilic Cell-Labile Protecting Group Strategy

“…Firstly, the cysteine thiol group was protected with a trityl group, as reported, 29 to give S2. Following protection of the carboxylic acid as its methyl ester to give S3, 30 a 'click' azide group was then introduced to give amide S4. The trityl protected probe 1 was then readily obtained by stepwise double 'click' reactions following our originally reported procedures.…”

Synthesis of 6-Membered-Ring Fused Thiazine-Dicarboxylates and Thiazole-Pyrimidines via One-Pot Three-Component Reactions

“…The Passerini and Ugi reactions have gained a great deal of attention since the early 1990s [13,14]. The versatility of these reactions relies on the dual reactivity of the isocyanide carbon atom, leading to the formation of diverse and complex products [15,16].…”

Rhodanine‐Furan Bis‐Heterocyclic Frameworks Synthesis via Green One‐Pot Sequential Six‐Component Reactions: A Synthetic and Computational Study

“…Consequently, it is highly vital to develop an efficient synthetic route for the green construction of bis ‐heterocyclic frameworks. In this context, multi‐component reactions (MCRs) strategy can be used as versatile synthetic tools for the expedient generation of structurally diverse organic compounds such as natural products, drug‐like small molecules, and bis ‐heterocyclic frameworks . Furan‐containing heterocycles show inspiring biological and medicinal activities like cytotoxic and antitumor properties and antimicrobial activities .…”

“…In this context, multi-component reactions (MCRs) strategy can be used as versatile synthetic tools for the expedient generation of structurally diverse organic compounds such as natural products, drug-like small molecules, and bis-heterocyclic frameworks. [3][4][5][6] Furan-containing heterocycles show inspiring biological and medicinal activities like cytotoxic and antitumor properties and antimicrobial activities. [7] Furthermore, functionalized furans represent synthetic scaffolds which are abundant in biologically active molecules, [8] for example, calicogorgins, αclausenan accompanied by furan fatty acids.…”