78538-75-7

Upstream product

• 74214-62-3 ethyl 9H-pyrido[3,4-b]indole-3-carboxylate 
• 64-04-0 phenethylamine 
• 69954-48-9 methyl 9H-β-carboline-3-carboxylate 
• 21109-25-1 1-(1H-indol-2-yl)methanamine 
• 59795-89-0 phenethyl isocyanide 
• 74214-63-4 β-carboline-3-carboxylic acid 

Relevant academic research and scientific papers

Diverse Isoquinoline Scaffolds by Ugi/Pomeranz-Fritsch and Ugi/Schlittler-Müller Reactions

The Pomeranz-Fritsch reaction and its Schlittler-Müller modification were successfully applied in the Ugi postcyclization strategy by using orthogonally protected aminoacetaldehyde diethyl acetal and complementary electron rich building blocks. Several scaffolds, including isoquinolines, carboline, alkaloid-like tetrazole-fused tetracyclic compounds, and benzo[d]azepinone scaffolds, were synthesized in generally moderate to good yield. All our syntheses provide a short MCR-based sequence to novel or otherwise difficult to access scaffolds. Hence, we foresee multiple applications of these synthesis technologies.

β-carboline amides as intrinsic directing groups for C(sp2)-H functionalization

Many site-selective palladium-catalyzed C-H functionalization methods require directing groups. We report here β-carboline amides as intrinsic directing groups for C(sp2)-H functionalization. Various substrates including the natural product alangiobussinine and the marinacarboline core structure were functionalized using carboline-directed δ-C(sp2)-H alkynylations. This transformation proceeds under mild conditions and is compatible with a wide variety of β-aryIethamines. δ-Alkynylation of β-arylethamines via a six-membered palladacycle is favored over γ-C(sp2)-H bond functionalization when both positions are accessible. The versatility of β-carboline amides as directing groups is evidenced by other δ-C(sp2)-H functionalizations such as alkenylation, arylation, and C-N bond formation.

The Broad Aryl Acid Specificity of the Amide Bond Synthetase McbA Suggests Potential for the Biocatalytic Synthesis of Amides

Amide bond formation is one of the most important reactions in pharmaceutical synthetic chemistry. The development of sustainable methods for amide bond formation, including those that are catalyzed by enzymes, is therefore of significant interest. The ATP-dependent amide bond synthetase (ABS) enzyme McbA, from Marinactinospora thermotolerans, catalyzes the formation of amides as part of the biosynthetic pathway towards the marinacarboline secondary metabolites. The reaction proceeds via an adenylate intermediate, with both adenylation and amidation steps catalyzed within one active site. In this study, McbA was applied to the synthesis of pharmaceutical-type amides from a range of aryl carboxylic acids with partner amines provided at 1–5 molar equivalents. The structure of McbA revealed the structural determinants of aryl acid substrate tolerance and differences in conformation associated with the two half reactions catalyzed. The catalytic performance of McbA, coupled with the structure, suggest that this and other ABS enzymes may be engineered for applications in the sustainable synthesis of pharmaceutically relevant (chiral) amides.

β-Carbolin-3-carboxylic acid derivatives

A β-carbolin-3-carboxylic acid derivative of the formula STR1 has valuable pharmacological properties when administered to patients, e.g. humans as a drug, have been shown to possess interesting tranquilizing activity.