Browse
Submit Data
Databases
API
Help

Dataset Information

31 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Antitumor agents 270. Novel substituted 6-phenyl-4H-furo[3,2-c]pyran-4-one derivatives as potent and highly selective anti-breast cancer agents.

ABSTRACT: 6-Phenyl-4H-furo[3,2-c]pyran-4-one derivatives based on neo-tashinlactone (1) were synthesized and evaluated as novel anti-breast cancer agents. Compounds 10-13, 23, 25, and 27 showed potent inhibition against the SK-BR-3 breast cancer cell line. Importantly, 25 and 27 showed the highest cancer cell line selectivity, being approximately 100-250-fold more potent against SK-BR-3 (ED(50) 0.28 and 0.44microM, respectively) compared with other cancer cell lines tested. In addition, 25 displayed low cytotoxicity against normal breast cell lines 184A1 and MCF10A. Compounds 25 and 27 merit further investigation in our continuing program to generate and develop selective anti-breast cancer agents.

SUBMITTER: Dong Y

PROVIDER: S-EPMC2821697 | biostudies-literature | 2010 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Antitumor agents 270. Novel substituted 6-phenyl-4H-furo[3,2-c]pyran-4-one derivatives as potent and highly selective anti-breast cancer agents.

Dong Yizhou Y Shi Qian Q Nakagawa-Goto Kyoko K Wu Pei-Chi PC Morris-Natschke Susan L SL Brossi Arnold A Bastow Kenneth F KF Lang Jing-Yu JY Hung Mien-Chie MC Lee Kuo-Hsiung KH

Bioorganic & medicinal chemistry 20091202 2

6-Phenyl-4H-furo[3,2-c]pyran-4-one derivatives based on neo-tashinlactone (1) were synthesized and evaluated as novel anti-breast cancer agents. Compounds 10-13, 23, 25, and 27 showed potent inhibition against the SK-BR-3 breast cancer cell line. Importantly, 25 and 27 showed the highest cancer cell line selectivity, being approximately 100-250-fold more potent against SK-BR-3 (ED(50) 0.28 and 0.44microM, respectively) compared with other cancer cell lines tested. In addition, 25 displayed low c ...[more]

PMID: 20034799

Similar Datasets

Ethyl 2-amino-4-phenyl-4H-1-benzo-thieno[3,2-b]pyran-3-carboxyl-ate.

Project description:The title heterocyclic compound, C(20)H(17)NO(3)S, was synthesized by condensation of ethyl cyano-acetate with (Z)-2-benzyl-idenebenzo[b]thio-phen-3(2H)-one in the presence of a basic catalyst in ethanol. The phenyl and ester groups make dihedral angles of 77.67?(6) and 8.52?(6)°, respectively, with the benzothienopyran ring system [maximum r.m.s. deviation = 0.1177?(13)?Å]. In the crystal, centrosymmetric dimers are formed through pairs of N-H?O hydrogen bonds between the amine and ester groups. Inter-molecular C-H?N hydrogen bonds and C-H?? inter-actions involving the thio-phene ring are also observed.

| S-EPMC3213548 | biostudies-literature

(8aRS)-8,8a-Dihydro-furo[3,2-f]indolizine-6,9(4H,7H)-dione.

Project description:The title compound, C(10)H(9)NO(3), is a chiral mol-ecule with one stereogenic carbon atom, but which crystallizes as a racemate in the centrosymmetric space group P2(1)/n. The central six-membered ring of the indolizine moiety adopts a definite envelope conformation, while the conformation of the oxopyrrolidine ring is close to that of a flat-envelope with a maximum deviation of 0.352?(1)?Å for the flap atom.

| S-EPMC3213484 | biostudies-literature

8-Methyl-4-phenyl-2,3,3a,4,5,9b-hexa-hydro-furo[3,2-c]quinoline.

Project description:The title compound, C(18)H(19)NO, was synthesized from the multi-component one-pot reaction between p-toluidine, benzaldehyde and 2,3-dihydro-furan in the presence of palladium dichloride. There are two mol-ecules in the asymmetric unit. The crystal packing is stabilized by classical inter-molecular N-H?O hydrogen bonds.

| S-EPMC2980039 | biostudies-literature

New substituted 4H-chromenes as anticancer agents.

Project description:As a continuation of our efforts to discover and develop small molecules as anticancer agents, we identified GRI-394837 as an initial hit from similarity search on RGD and its analogs. Based on GRI-394837, we designed and synthesized a focused set of novel chromenes (4a-e) in a single step using microwave method. All five compounds showed activity in the nanomolar range (IC(50): 7.4-640 nM) in two melanoma, three prostate and four glioma cancer cell lines. The chromene 4e is active against all the cell lines and particularly against the A172 human glioma cell line (IC(50): 7.4 nM). Interestingly, in vitro tubulin polymerization assay shows 4e to be a weak tubulin polymerization inhibitor but it shows very strong cytotoxicity in cellular assays, therefore there must be additional unknown mechanism(s) for the anticancer activity. Additionally, the strong antiproliferative activity was verified by one of the selected chromene (4a) by the NCI 60 cell line screen. These results strongly suggest that the novel chromenes could be further developed as a potential therapeutic agent for a variety of aggressive cancers.

| S-EPMC3659818 | biostudies-literature

(8aR,9R)-9-Hy-droxy-7,8,8a,9-tetra-hydro-furo[3,2-f]indolizin-6(4H)-one.

Project description:The title compound, C(10)H(11)NO(3), crystallizes with four independent mol-ecules in the asymmetric unit. Their geometries are very similar and corresponding bond distances are almost identical. The central six-membered ring of the indolizine moiety adopts a envelope conformation [the displacement of the flap atom (the C atom opposite the N atom) being 0.539?(2), 0.548?(3), 0.509?(3) and 0.544?(3)?Å in the four molecules], while the conformation of the oxopyrrolidine ring is close to that of a flat envelope. The displacements of the non-fused C atom opposite the C=O group of the pyrrolidine ring of the four mol-ecules are 0.366?(3), 0.335?(3), 0.173?(3) and -0.310?(3)?Å. In the crystal, O-H?O hydrogen bonds link the mol-ecules into chains, which run parallel to the c axis. The absolute configuration was assigned from the synthesis.

| S-EPMC3470388 | biostudies-literature

Ethyl 2-amino-4-(3-nitro-phen-yl)-4H-1-benzothieno[3,2-b]pyran-3-carboxyl-ate.

Project description:The mol-ecule of the title compound, C20H16N2O5S, is built up by one fused five-membered and two fused six-membered rings linked to eth-oxy-carbonyl and 3-nitro-phenyl groups. The benzothieno-pyran ring system is nearly planar (r.m.s deviation = 0.0392?Å) and forms a dihedral angle of 86.90?(6)° with the aromatic ring of the nitro-benzene group. In the crystal, mol-ecules are linked by N-H?O hydrogen bonds and by ?-? inter-actions between the phenyl ring and the six-membered heterocyle [inter-centroid distance = 3.5819?(8)?Å], forming a three-dimensional network.

| S-EPMC4011203 | biostudies-literature

Methyl 4-phenyl-1,2,3,3a,4,4a,5,12c-octa-hydronaphtho[1',2':3,2]furo[5,4-b]pyrrolizine-4a-carboxyl-ate.

Project description:In the title compound, C(26)H(25)NO(3), both pyrrolidine rings adopt envelope conformations, whereas the dihydro-pyran ring adopts a half-chair conformation. The phenyl ring is oriented at an angle of 27.9?(1)° with respect to the naphthalene ring system. An intra-molecular C-H?O hydrogen bond is observed. The crystal packing is stabilized by weak inter-molecular C-H?? inter-actions.

| S-EPMC2979659 | biostudies-literature

Crystal structure of 2-amino-3-cyano-4-(4-meth-oxy-phen-yl)-4H-1-benzo-thieno[3,2-b]pyran.

Project description:The three fused five- and six-membered rings in the title compound, C19H14N2O2S, are virtually coplanar, with the maximum deviation from the mean plane being 0.060 (1) Å. This benzothieno[3,2-b]pyran ring system is nearly perpendic-ular to the plane of the 4-meth-oxy-phenyl ring, forming a dihedral angle of 83.65 (5)°. In the crystal, mol-ecules are linked by pairs of N-H⋯N hydrogen bonds into inversion dimers. The dimeric units are further connected by an N-H⋯O hydrogen bond into a tape running along the b axis. The tapes are linked together by C-H⋯N and π-π inter-actions [centroid-centroid distance = 3.7743 (8) Å], forming a three-dimensional network.

| S-EPMC4719970 | biostudies-literature

Crystal structure of ethyl 2-amino-4-(4-chloro-phen-yl)-4H-1-benzothieno[3,2-b]pyran-3-carboxyl-ate.

Project description:The title compound, C20H16ClNO3S, is built up from three fused rings, one five- and two six-membered rings, linked to a 3-eth-oxy-carbonyl group and to a 4-chloro-phenyl ring. The hydropyran ring has a flattened envelope conformation, with the C atom substituted by the 4-chloro-phenyl ring as the flap (displaced by 0.077 (2) Å from the plane through the other atoms). The fused three-ring system is quasi-planar (r.m.s. deviation = 0.057 Å), with the largest deviation from the mean plane being 0.106 (1) Å for the C atom substituted by the 4-chloro-phenyl ring. The 4-chloro-phenyl ring is approximately perpendicular to the mean plane of the fused ring system, as indicated by the dihedral angle of 77.32 (6)° between their mean planes. There is an intra-molecular N-H⋯O hydrogen bond forming an S(6) ring motif. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(12) ring motif. There are also short inter-molecular Cl⋯O inter-actions present [3.1226 (12) Å] between neighbouring mol-ecules.

| S-EPMC4571428 | biostudies-literature

4-(4-Meth-oxy-phen-yl)-6-methyl-amino-5-nitro-2-phenyl-4H-pyran-3-carbonitrile.

Project description:In the title compound, C20H17N3O4, the central pyran ring adopts a boat conformation with the O atom and diagonally opposite C atoms displaced by 0.1171?(1) and 0.1791?(1)?Å, respectively, from the mean plane defined by the other four atoms. The coplanar atoms of the pyran ring and the meth-oxy-benzene ring are nearly perpendicular, as evidenced by the dihedral angle 87.01?(1)°. The amine H atom forms an intra-molecular N-H?O(nitro) hydrogen bond. In the crystal, mol-ecules are linked into dimeric aggregates by N-H?O(nitro) hydrogen bonds, generating an R2(2)(12) graph-set motif.

| S-EPMC3588539 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data