Browse
Submit Data
Databases
API
Help

Dataset Information

9 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

A practical and efficient approach to imidazo[1,2-a]pyridine-fused isoquinolines through the post-GBB transformation strategy.

ABSTRACT: Diversity-oriented synthesis of the biologically intriguing imidazo[1,2-a]pyridine-fused isoquinoline systems from readily available starting materials was achieved through the Groebke-Blackburn-Bienaymé reaction followed by a gold-catalyzed cyclization strategy. The synthetic approach is characterized by mild reaction conditions and a broad substrate scope, allowing for the rapid construction of structurally complex and diverse heterocycles in moderate to good yields.

SUBMITTER: Shao T

PROVIDER: S-EPMC5433183 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

A practical and efficient approach to imidazo[1,2-a]pyridine-fused isoquinolines through the post-GBB transformation strategy.

Shao Taofeng T Gong Zhiming Z Su Tianyi T Hao Wei W Che Chao C

Beilstein journal of organic chemistry 20170504

Diversity-oriented synthesis of the biologically intriguing imidazo[1,2-a]pyridine-fused isoquinoline systems from readily available starting materials was achieved through the Groebke-Blackburn-Bienaymé reaction followed by a gold-catalyzed cyclization strategy. The synthetic approach is characterized by mild reaction conditions and a broad substrate scope, allowing for the rapid construction of structurally complex and diverse heterocycles in moderate to good yields. ...[more]

PMID: 28546839

Similar Datasets

2-Phenyl-imidazo[1,2-a]pyridine-3-carbaldehyde.

Project description:In the title compound, C(14)H(10)N(2)O, the dihedral angle between the imidazo[1,2-a]pyridine and phenyl rings is 28.61 (4)° The mol-ecules are connected into broad chains parallel to the a axis by weak C-H⋯O and C-H⋯N hydrogen bonds. The linking of the ribbons is provided by π-π stacking inter-actions between neighbouring pyridine rings, with a centroid-centroid distance of 3.7187 (7) Å.

| S-EPMC2961188 | biostudies-literature

Ethyl 5-methyl-imidazo[1,2-a]pyridine-2-carboxyl-ate.

Project description:The title compound, C(11)H(12)N(2)O(2), was synthesized from the reaction of 6-methyl-pyridin-2-amine and ethyl 3-bromo-2-oxopropionate. In the mol-ecular structure, the six- and five-membered rings are individually almost planar with r.m.s. deviations of 0.003 and 0.002?Å, respectively. The two rings are almost coplanar, the dihedral angle between their planes being 1.4?(3)°. Inter-molecular C-H?O and C-H?N hydrogen bonds are present in the crystal structure.

| S-EPMC3007311 | biostudies-literature

Imidazo[1,2-a]pyridine-based peptidomimetics as inhibitors of Akt.

Project description:We report the design, synthesis, and biological evaluation of imidazopyridine-based peptidomimetics based on the substrate consensus sequence of Akt, an AGC family serine/threonine kinase hyperactivated in over 50% of human tumors. Our ligand-based approach led to the identification of novel substrate mimetic inhibitors of Akt1 featuring an unnatural extended dipeptide surrogate. Compound 11 inhibits Akt isoforms in the sub-micromolar range and exhibits improved proteolytic stability relative to a parent pentapeptide.

| S-EPMC4176526 | biostudies-literature

2-(Ethyl-sulfin-yl)imidazo[1,2-a]pyridine-3-sulfonamide.

Project description:The supra-molecular structure of the title compound, C(9)H(11)N(3)O(3)S(2), is defined by two inter-molecular hydrogen bonds. Pairs of N-H⋯N hydrogen bonds link the mol-ecules into centrosymmetric dimers and N-H⋯O hydrogen bonds link the dimers into a tubular chain structure running parallel to the a axis.

| S-EPMC3344477 | biostudies-literature

Metal-free, efficient hydrazination of imidazo[1,2-a]pyridine with diethyl azodicarboxylate in neutral media.

Project description:The first example of metal-free regioselective hydrazination of imidazo[1,2-a]pyridine with diethyl azodicarboxylate is accomplished. This procedure is chemically appealing due to the high degree of functional group tolerance and efficiency in expanding the molecular diversity.

| S-EPMC4675458 | biostudies-other

Gold Catalysed Redox Synthesis of Imidazo[1,2-a]pyridine using Pyridine N-Oxide and Alkynes.

Project description:A mild, catalytic, atom economical synthesis of imidazo[1,2-a]pyridines has been developed: catalytic PicAuCl2 in the presence of an acid produces a range imidazo[1,2-a]pyridines in good yield. This strategy is mild and forseen to be of particular use for the installation of stereogenic centers adjacent to the imidazo[1,2-a]pyridine ring without loss of enantiomeric excess.

| S-EPMC4019451 | biostudies-literature

Scaffold-switching: an exploration of 5,6-fused bicyclic heteroaromatics systems to afford antituberculosis activity akin to the imidazo[1,2-a]pyridine-3-carboxylates.

Project description:A set of 5,6-fused bicyclic heteroaromatic scaffolds were investigated for their in vitro anti-tubercular activity versus replicating and non-replicating strains of Mycobacterium tuberculosis (Mtb) in an attempt to find an alternative scaffold to the imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrimidines that were previously shown to have potent activity against replicating and drug resistant Mtb. The five new bicyclic heteroaromatic scaffolds explored in this study include a 2,6-dimethylimidazo[1,2-b]pyridazine-3-carboxamide (7), a 2,6-dimethyl-1H-indole-3-carboxamide (8), a 6-methyl-1H-indazole-3-carboxamide (9), a 7-methyl-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide (10), and a 5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxamide (11). Additionally, imidazo[1,2-a]pyridines isomers (2 and 12) and a homologous imidazo[1,2-a]pyrimidine isomer (6) were prepared and compared. Compounds 2 and 6 were found to be the most potent against H37Rv Mtb (MIC's of 0.1 μM and 1.3 μM) and were inactive (MIC >128 μM) against Staphylococcus aureus, Escherichia coli and Candida albicans. Against other non-tubercular mycobacteria strains, compounds 2 and 6 had activity against Mycobacterium avium (16 and 122 μM, respectively), Mycobacterium kansasii (4 and 19 μM, respectively), Mycobacterium bovis BCG (1 and 8 μM, respectively) while all the other scaffolds were inactive (>128 μM).

| S-EPMC4096046 | biostudies-literature

Iodine catalyzed synthesis of imidazo[1,2-a]pyrazine and imidazo[1,2-a]pyridine derivatives and their anticancer activity.

Project description:An efficient iodine-catalyzed method for synthesizing imidazo[1,2-a]pyrazines and imidazo[1,2-a]pyridines via one-pot three-component condensations has been reported. The product, generated in situ by the reaction between an aryl aldehyde and 2-aminopyridine or 2-aminopyrazine, undergoes [4 + 1] cycloaddition with tert-butyl isocyanide, affording the corresponding imidazopyrazine and imidazopyridine derivatives in good yields. The photophysical properties of these new fluorescent derivatives are also presented. The anti-cancer activities of the synthesized compounds (10a-m) and (12a-l) were evaluated against four cancer cells (Hep-2, HepG2, MCF-7, A375) and the normal Vero cell. Significant anti-cancer activities were observed and compared with the standard drug Doxorubicin. In vitro experimental results revealed that compound 12b is a promising lead with IC50 values of 11 μM, 13 μM, 11 μM, 11 μM, and 91 μM against Hep-2, HepG2, MCF-7, A375, and Vero, respectively.

| S-EPMC10718296 | biostudies-literature

Synthesis, study of antileishmanial and antitrypanosomal activity of imidazo pyridine fused triazole analogues.

Project description:Four groups, thirty-five compounds in total, of novel 1,2,3-triazole analogues of imidazo-[1,2-a]-pyridine-3-carboxamides were designed and synthesized using substituted pyridine, propargyl bromide, 2-azidoethyl 4-methyl benzenesulfonate and substituted acetylenes. These compounds were characterized using 1H NMR, 13C NMR, LCMS and elemental analyses and a crystal structure was obtained for one of the significantly active compounds, 8f. All the synthesized and characterized compounds were screened in vitro for antileishmanial and antitrypanosomal activity against Leishmania major and Trypanosoma brucei parasites, respectively. Among the tested analogues, five compounds (8d, 8f, 8j, 10b and 10d) exhibited significant antileishmanial activity while three compounds (10b, 11a and 11b) showed substantial activity against T. brucei parasite. In silico ADME prediction studies depicted that the essential compounds obeyed Lipinski's rule of five. The predicted in silico toxicity profile suggested that the tested compounds would be non-toxic, which was confirmed experimentally by the lack of cytotoxicity against HeLa cells. Finally, a molecular docking study was also performed, for 10d the most active antileishmanial compound, to study its putative binding pattern at the active site of the selected leishmanial trypanothione reductase target.

| S-EPMC9057266 | biostudies-literature

2-Methyl-6-(trifluoro-meth-yl)imidazo[1,2-a]pyridine-3-carbonitrile.

Project description:In the title compound, C(10)H(6)F(3)N(3), the imidazo[1,2-a]pyridine group is essentially planar with a maximum deviation of 0.021 (1) Å. The F atoms in the trifluoro-methyl group and the methyl H atoms are each disordered over two sets of sites with refined site occupancies of 0.68 (1):0.32 (1). In the crystal, mol-ecules are linked into infinite chains through two C-H⋯N inter-actions forming R(2) (2)(12) and R(2) (2)(8) hydrogen-bond ring motifs. These chains are stacked along the a axis.

| S-EPMC3052008 | biostudies-literature