ABSTRACT
α-Functionalization of carbonyl compounds is an important reaction in synthetic chemistry. However, the development of novel synthetic strategies to realize this reaction is challenging. This study describes the α-indolmethylation of carbonyl compounds using cooperative copper, amine, and hydrogen-bond catalysis. This reaction provides a novel and efficient strategy for developing indolmethylated carbonyl compounds by deaminative coupling of gramines.
ABSTRACT
The direct utilization of amines for C-C bond formation without prefunctionalization remains a significant challenge. Herein, we report the base-promoted deaminative coupling of gramines with aminomalaimides under redox-neutral conditions. In this operationally simple reaction, a series of indolmethyl-substituted aminomaleimides that emitted fluorescence were synthesized in good-to-excellent yields. Biological evaluation revealed that some products exhibited antiproliferative activity against human cancer cell lines.
ABSTRACT
Herein, we present a copper-mediated C4-benzylation of 5-aminopyrazoles with 3-indoleacetic acids. Various benzylated 5-aminopyrazoles are prepared in good-to-excellent yields under basic and ligand-free conditions in the presence of copper acetate. Moreover, this benzylation method is applicable to other substrates, including naphthylamine, 2-aminochromen-4-one, and enamines. Some products exhibit antiproliferative activities against cancer cell lines. In addition, the C4-benzylated products are cyclized into 1H-pyrazolo[4',3':6,7]azepino[3,4-b]indoles with aldehydes via one-pot two-step processes; notably, the cyclized products exhibit fluorescence emissions with large Stokes shifts.
ABSTRACT
Here, we describe a copper-mediated tandem decarboxylative coupling/annulation protocol of o-hydroxyaryl enaminones with 3-indoleacetic acids. A series of 3-indolmethyl-chromones were afforded in up to 97% yield. A one-pot method for 3-indolmethyl-chromones from o-hydroxy acetophenones, N, N-dimethylformamide dimethyl acetal, and 3-indoleacetic acids was also developed. Derivatization of the products was conducted to provide various indolmethyl-substituted pyrimidines. Moreover, a biological evaluation revealed that some compounds had anti-influenza viral activities.
Subject(s)
Chromones , Copper , Chromones/pharmacology , Cyclization , Indoleacetic Acids , PyrimidinesABSTRACT
Herein, we describe an efficient and benign protocol for direct C-3 sulfonylmethylation of imidazo[1,2-a]pyridines with glyoxylic acid and sodium sulfinates. Various sulfonylmethylated imidazo[1,2-a]pyridines were synthesized in water under transition metal catalyst-free conditions. This multicomponent reaction featured available substrates, good functional group tolerance, moderate to excellent yields, and mild reaction conditions.
Subject(s)
Pyridines , Transition Elements , Glyoxylates , Ions , Sodium , WaterABSTRACT
We herein describe a C4 sulfonylmethylation of pyrazol-5-amines with glyoxylic acid and sodium sulfinates. The reaction only needed water as a solvent, and it featured mild reaction conditions, simple operation, and high regioselectivity. Various C4 sulfonylmethylated pyrazol-5-amines were obtained in good to excellent yields. Moreover, this sulfonylmethylation method was applicable for C(sp2)-H sulfonylmethylation of other substrates such as enamines, indoles, and antipyrines by adding a catalyst and changing the solvent. Biological evaluation revealed that some products had antiproliferative activity against cancer cell lines.
Subject(s)
Amines/chemical synthesis , Antineoplastic Agents/chemical synthesis , Glyoxylates/chemistry , Pyrazoles/chemical synthesis , Sulfinic Acids/chemistry , Amines/chemistry , Amines/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Cell Line, Tumor , Cell Proliferation/drug effects , Cell Survival/drug effects , Drug Screening Assays, Antitumor , Humans , Methylation , Molecular Structure , Pyrazoles/chemistry , Pyrazoles/pharmacologyABSTRACT
A copper-mediated decarboxylative coupling reaction of 3-indoleacetic acids with pyrazolones was described. This protocol realized new functionalization of pyrazolones under simple reaction conditions and exhibited high functional group compatibility and broad substrate scope. Notably, the products displayed antiproliferative activity against cancer cells.
ABSTRACT
A copper-mediated decarboxylative coupling reaction between arylacetic acids and 1,3-dicarbonyl compounds was described. Significantly, methanocycloocta[b]indoles were also obtained by sequential intramolecular dehydrocyclization process in some cases. This protocol featured a broad substrate scope, simple operations, and good yields. Moreover, the products exhibited potent antiproliferative activity against the human cancer cell lines by a MTT assay.
ABSTRACT
A copper-catalyzed C-3 functionalization of imidazo[1,2-a]pyridines with 3-indoleacetic acids through an aerobic oxidative decarboxylative process has been developed. The protocol provided a series of 3-(1H-indol-3-ylmethyl)-imidazo[1,2-a]pyridines in moderate to good yields under simple reaction conditions. Importantly, some products exhibited potent antiproliferative activity in cancer cell lines.
Subject(s)
Copper , Pyridines , Catalysis , Indoleacetic Acids , Oxidation-ReductionABSTRACT
Herein, we describe the novel reactivity of hexafluoroisopropyl 2-aminobenzoates. The metal-free synthesis of 1,4-benzodiazepines and quinazolinones from hexafluoroisopropyl 2-aminobenzoates has been developed at room temperature. These procedures feature good functional group tolerance, mild reaction conditions, and excellent yields. The newly formed products can readily be converted to other useful N-heterocycles. Moreover, the products and their derivatives showed potent anticancer activities in vitro by MTT assay.
ABSTRACT
Flavonoids, commonly found in various plants, are a class of polyphenolic compounds having a basic structural unit of 2-phenylchromone. Flavonoid compounds have attracted much attention due to their wide biological applications. In order to facilitate further research on the biomedical application of flavonoids, we surveyed the literature published on the use of flavonoids in medicine during the past decade, documented the commonly found structures in natural flavonoids, and summarized their pharmacological activities as well as associated mechanisms of action against a variety of health disorders including chronic inflammation, cancer, cardiovascular complications and hypoglycemia. In this mini-review, we provide suggestions for further research on the biomedical applications of flavonoids.
Subject(s)
Flavonoids , Neoplasms , Flavonoids/pharmacology , Humans , PlantsABSTRACT
Herein, we present a copper-mediated decarboxylative sulfonylation of arylacetic acids with sodium sulfinates that provides viable access to sulfone compounds. This protocol features readily available feedstocks, simple operations, high regioselectivities, and moderate to good yields. The newly obtained products could be converted to other useful compounds. Importantly, the products and their derivatives exhibited potent antitumor activities in vitro, which were tested by MTT assay.