4567-05-9

Upstream product

• 591-50-4 iodobenzene 
• 156049-34-2 (E)-methyl 3-(2-isocyanophenyl)acrylate 
• 67-56-1 methanol 
• 4662-03-7 2-phenylindole-3-acetic acid 
• 100-63-0 phenylhydrazine 
• 2051-95-8 succinylbenzene 
• 1912-33-0 Indole-3-acetic acid methyl ester 
• 106273-53-4 benzenediazonium 4-methylbenzenesulfonate 
• 13141-38-3 2-phenylethynylaniline 
• 442155-91-1 4-methyl-N-{2-(phenylethynyl)phenyl}benzenesulfonamide 
• 536-74-3 phenylacetylene 
• 88939-75-7 methyl (2E)-3-(2-aminophenyl)propenoate 
• 100-52-7 benzaldehyde 
• 108-86-1 bromobenzene 

Relevant academic research and scientific papers

Heteroaromatic Inhibitors of the Astacin Proteinases Meprin α, Meprin β and Ovastacin Discovered by a Scaffold-Hopping Approach

Astacin metalloproteinases, in particular meprins α and β, as well as ovastacin, are emerging drug targets. Drug-discovery efforts have led to the development of the first potent and selective inhibitors in the last few years. However, the most recent compounds are based on a highly flexible tertiary amine scaffold that could cause metabolic liabilities or decreased potency due to the entropic penalty upon binding to the target. Thus, the aim of this study was to discover novel conformationally constrained scaffolds as starting points for further inhibitor optimization. Shifting from flexible tertiary amines to rigid heteroaromatic cores resulted in a boost in inhibitory activity. Moreover, some compounds already exhibited higher activity against individual astacin proteinases compared to recently reported inhibitors and also a favorable off-target selectivity profile, thus qualifying them as very suitable chemical probes for target validation.

Direct C?H Arylation of Indole-3-Acetic Acid Derivatives Enabled by an Autonomous Self-Optimizing Flow Reactor

Described herein is a continuous-flow strategy for the palladium-catalyzed direct C?H arylation of indole-3-acetic acid derivatives with arenediazonium salts. A fully autonomous self-optimizing flow platform was used to efficiently optimize the coupling reaction in a three-dimensional space. The flow methodology developed is experimentally simple, mild, broad in scope, and safer than traditional batch approaches. Our continuous-flow approach is particularly convenient to prepare precursors of pharmaceutically relevant compounds. (Figure presented.).

Metal-free cascade boron–heteroatom addition and alkylation with diazo compounds

Transition metal-catalyzed carbene transfer reaction is one of the most notable advances for C?C bond formation reactionsduring the past decade, which has been widely employed in the preparation of C3-substituted indoles. Here, we described an efficient e

HETEROAROMATIC INHIBITORS OF ASTACIN PROTEINASES

The present invention relates to novel hydroxamic acid derivatives useful as inhibitors of astacin metalloproteinases, in particular procollagen C-proteinase (PCP) enzymes, meprins, ovastacin and/or nematode astacins; more particularly human or mammalian

N-Heterocyclic carbene (NHC)-catalysed atom economical construction of 2,3-disubstituted indoles

A novel organocatalytic approach, harnessing the unique reactivities of N-heterocyclic carbenes (NHCs), has been revealed for the construction of indoles. The NHC-catalysed atom economical synthesis of a wide range of 2-substituted indole-3-acetic acid derivatives is displayed. Strategic application of the developed method was demonstrated for a short synthesis of a cyclin-dependent kinase (CDK) inhibitor: paullone.

N-Heterocyclic-Carbene-Catalyzed Umpolung of Imines

N-Heterocyclic carbene (NHC) catalysis has been widely used for the umpolung of aldehydes, and recently for the umpolung of Michael acceptors. Described herein is the umpolung of aldimines catalyzed by NHCs, and the reaction likely proceeds via aza-Breslo

Palladium-catalyzed direct monoarylation of thiophene-, benzothiophene-, and indoleacetic acids through regioselective CH bond cleavage

Regioselective monoarylation of thiophene-3-acetic acid with aryl bromides proceeds efficiently under palladium catalysis to selectively give the corresponding C2-arylated thiophene derivatives. The procedure is also applicable to the C2-arylations of ben

Synthesis of 2-Boryl- and silylindoles by copper-catalyzed borylative and silylative cyclization of 2-alkenylaryl isocyanides

(Figure Presented) We have developed a method for the synthesis of 2-borylindoles via the copper(I)-catalyzed borylative cyclization of 2-alkenylphenyl isocyanides using diboronate. The reaction proceeds at room temperature under neutral conditions and exhibits high tolerance to functional groups, such as Br, CO2R, COR, CONMe2, and CN. The 2-borylindoles synthesized in the present study can be elaborated into an array of indole-based derivatives, for example, through the Suzuki-Miyaura reaction. The utility of this method is demonstrated in the rapid synthesis of a kinase inhibitor, paullone. The reaction can be extended to the synthesis of 2-hydride indole and 2-silylindole by using hydroboronate (or hydrosilane) and silylboronate, respectively. Under these copper-catalyzed conditions, a quinoxaline ring system can also be constructed by using 1,2-isocyanobenzene as a substrate.

Synthesis of 2,3-disubstituted indoles by palladium-mediated coupling of 2-iodoindoles

N-Unprotected 2-iodoindoles are synthesized by treatment of 2- stannylindoles with iodine, which in turn are prepared by tin-mediated radical cyclization of 2-alkenylphenylisocyanides. Palladium-catalyzed coupling reactions of N-unprotected 2-iodoindoles