Furan Skeleton Research Articles

Design, synthesis, in vitro, and in vivo anticancer and antiangiogenic activity of novel 3-arylaminobenzofuran derivatives targeting the colchicine site on tubulin.

A new series of compounds characterized by the presence of a 2-methoxy/ethoxycarbonyl group, combined with either no substituent or a methoxy group at each of the four possible positions of the benzene portion of the 3-(3',4',5'-trimethoxyanilino)benzo[b]furan skeleton, were evaluated for antiproliferative activity against cancer cells in culture and, for selected, highly active compounds, inhibition of tubulin polymerization, cell cycle effects, and in vivo potency. The greatest antiproliferative activity occurred with a methoxy group introduced at the C-6 position, the least with this substituent at C-4. Thus far, the most promising compound in this series was 2-methoxycarbonyl-3-(3',4',5'-trimethoxyanilino)-6-methoxybenzo[b]furan (3g), which inhibited cancer cell growth at nanomolar concentrations (IC50 values of 0.3-27 nM), bound to the colchicine site of tubulin, induced apoptosis, and showed, both in vitro and in vivo, potent vascular disrupting properties derived from the effect of this compound on vascular endothelial cells. Compound 3g had in vivo antitumor activity in a murine model comparable to the activity obtained with combretastatin A-4 phosphate.

ChemInform Abstract: Stereodivergent Organocatalytic Intramolecular Michael Addition/Lactonization for the Asymmetric Synthesis of Substituted Dihydrobenzofurans and Tetrahydrofurans.

AbstractEnone acids are used as suitable substrates for the preparation of the furan skeleton.

Computational atomistic blueprinting of novel conducting copolymers using particle swarm optimization

A proficient metaheuristic approach viz., particle swarm optimization coupled with negative factor counting technique and inverse iteration method has been employed for designing novel binary and ternary copolymers based on thiophene, pyrrole and furan skeletons. A comparative study of the electronic structures and conduction properties of neutral heterocyclic copolymers and their benzene substituted analogues is inferred using the band structure results derived from ab-initio Hartree-Fock crystal orbital calculations. The band gap value decreases as a result of substitution on the polymer backbone due to increased quinoid contributions which is expected to enhance the intrinsic conductivity of the resulting copolymers. In general, it has been found that HOMO energies have a more decisive influence than LUMO energies on the relative fraction of constituents of the respective low band gap copolymers. The trends in the electronic properties of the respective copolymers are also verified and discussed with the help of density of states. These results can help streamline scrupulous synthetic efforts providing a potent route for molecular engineering of sustainable and efficient electronic materials.

Silver-catalyzed C–C bond formation with carbon dioxide: significant synthesis of dihydroisobenzofurans

The silver salt catalyzed the C-C bond forming reaction of o-alkynylacetophenone derivatives and carbon dioxide. In this reaction, a carbonyl group and a furan skeleton were successively constructed to afford the corresponding dihydroisobenzofuran derivatives.

ChemInform Abstract: Synthesis of Functionalized and Fused Furans and Pyrans from the Morita—Baylis—Hillman Acetates of Nitroalkenes.

AbstractOpen chain and six‐membered dicarbonyl compounds (with exception of Meldrum′s and barbituric acid) react via a Michael‐5‐exo‐trig‐oxa‐Michael cascade to produce furan skeletons.

ChemInform Abstract: Ruthenium‐Catalyzed Transfer Oxygenative Cyclization of α,ω‐Diynes: Unprecedented [2 + 2 + 1] Route to Bicyclic Furans via Ruthenacyclopentatriene.

AbstractGenerally, a broad spectrum of bicyclic furan skeletons can be obtained from diynes bearing 2 terminal aryl substituents under the optimized conditions A)‐C).

Phosphine-Catalyzed [3 + 2] Annulations of γ-Functionalized Butynoates and 1C,3O-Bisnucleophiles: Highly Selective Reagent-Controlled Pathways to Polysubstituted Furans

In this paper, a reagent-controlled [3+2] annulation of γ-functionalized butynoates 1 and 1C,3O-bisnucleophiles 2 is reported, which leads to three distinct furan skeletons 3-5. A PPh(3) catalyst preferentially attached the β-position of 1a, facilitating α-addition to furnish Type I annulations. With the assistance of Ag(2)O, Type II annulations were achieved via selective γ-substitution. In the absence of the PPh(3) catalyst, the reagent Cs(2)CO(3) promoted β-addition to realize Type III annulations.

Synthesis and Evaluation of Haloacetyl, α-Bromoacryloyl and Nitrooxyacetyl Benzo[b]furan and Benzo[b]thiophene Derivatives as Potent Antiproliferative Agents Against Leukemia L1210 and K562 Cells

Identification of novel and selective anticancer agents remains an important and challenging goal in pharmacological research. In search of new compounds with strong antiproliferative activity and simple molecular structure, we have synthesized three different series of compounds in which different substituents were linked to the 3-amino position of the 2-(3', 4', 5'-trimethoxybenzoyl)-benzo[b]furan or benzo[b]thiophene ring system. These substituents, corresponding to acetyl/haloacetyl, α-bromoacryloyl and nitrooxyacetyl moieties had different electrophilic properties. The benzoheterocycle parent structures were selected because of their reported bioactivities. Compounds bearing a methoxy group at the 6-position of the benzo[b]furan skeleton, were identified as potent antiproliferative agents against the human chronic myelogenous K562 and murine L1210 leukemia cell lines. Comparison of positional isomers indicated that moving the methoxy group from the 6- to the 5- or 7-position yielded inactive compounds. The effects of a selected series of compounds on cell cycle progression correlated well with their strong antiproliferative activity and inhibition of tubulin polymerization. The analysis of structure-activity relationships observed in the series of compounds described here may represent a platform for the design of more active molecules.

Lysidicins F−H, Three New Phloroglucinols from Lysidice rhodostegia

Three new phloroglucinols, named lysidicins F-H (1-3), were isolated from the roots of Lysidice rhodostegia. These compounds have a unprecedented benzyl benzo[b]furo[3,2-d]furan skeleton, and lysidicin F (1) is the first example of natural product with trans-fused furan rings. Their structures were established on the basis of extensive spectroscopic analysis, and the absolute configurations of them were determined by computational methods. A possible biosynthetic pathway for 1-3 was also postulated.

7,8‐Dihydro‐4H‐cyclohepta[b]furan (thiophene) skeleton from furyl (thiophene)‐derived tertiary allylic alcohols

Abstract magnified image 2,6‐Dimethyl‐7,8‐dihydro‐4H‐cyclohepta[b]furan and 2,6‐dimethyl‐7,8‐dihydro‐4H‐cyclohepta[b]thiophene were prepared by direct cyclization of 3‐methyl‐5‐(5‐methylfuran‐2‐yl)‐pent‐1‐en‐3‐ol and 3‐methyl‐5‐(5‐methyltiophen‐2‐yl)‐pent‐1‐en‐3‐ol, respectively. J. Heterocyclic Chem., (2009).

JBIR-23 and -24, Novel Anticancer Agents from Streptomyces sp. AK-AB27

The screening for active compounds against malignant pleural mesothelioma (MPM) cells produced by Streptomyces sp. AK-AB27 resulted in the isolation of two compounds with a dodecahydrodibenzo[b,d]furan skeleton named JBIR-23 (1) and -24 (2). Their structures were established on the basis of extensive NMR and MS analyses. Compounds 1 and 2 exhibited cytotoxic effects against several MPM cell lines.

Synthetic Studies of Neoclerodane Diterpenes from Salvia divinorum: Selective Modification of the Furan Ring.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Synthetic studies of neoclerodane diterpenes from Salvia divinorum: Selective modification of the furan ring

A synthetic sequence has been developed to selectively functionalize the furan ring of the natural product salvinorin A ( 2a). The synthetic routes described convert the furan ring in 2a into an N-sulfonylpyrrole, oxazole or an oxadiazole. In addition, a procedure has been found to remove the furan skeleton completely. Biological results indicate that replacement of the furan ring with an N-sulfonylpyrrole leads to reduced affinity and efficacy at κ opioid receptors.

Benzo[f][1,2]oxasilepines in the Synthesis of Dihydro[b]benzofuran Neolignans

A short synthesis of neolignans with a dihydrobenzo[b]furan skeleton is described. The strategy is based on a ring-closing metathesis to produce benzo[f][1,2]oxasilepines which are condensed with aromatic aldehydes in a modified Sakurai-Hosomi reaction. Natural dihydrodehydrodiconiferyl alcohol (1) and 3-0-demethyldihydrodehydrodiconiferyl alcohol (2) have been prepared in this way.

A novel route of furan compounds syntheses

A series of compounds that contained furan skeletons were synthesized using 3,4-bis(trimethylsilyl) furan as staring material.1H NMR,13C NMR, MS and EA had identified these new molecules. The important factors that influenced reactions were discussed, and the new furan intermediates could be used in various organic syntheses.

ChemInform Abstract: Convenient Construction of Hexahydrobenzo[b]furan Skeleton Containing Heteroatoms. Choice of Mn(III)‐ and Ce(IV)‐Based Radical Cyclization.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Convenient Construction of Hexahydrobenzo[b]furan Skeleton Containing Heteroatoms. Choice of Mn(III)- and Ce(IV)-based Radical Cyclization

Convenient Construction of Hexahydrobenzo[b]furan Skeleton Containing Heteroatoms. Choice of Mn(III)- and Ce(IV)-based Radical Cyclization

Novel C19 Homolignans, Taiwanschirin A, B, and Cytotoxic Taiwanschirin C, and a New C18 Lignan, Schizanrin A, from Schizandra arisanensis

Three novel C19 homolignans with a 3,4-pentano-2,3-dihydrobenzo[b]furan skeleton, taiwanschirin A (1), taiwanschirin B (2), and taiwanschirin C (3), and a new C18 dibenzocyclooctadiene lignan, schizanrin A (4) were isolated from Schizandra arisanensis. Taiwanschirin C (3) and schizarin A (4) exhibited in vitro cytotoxicity against hepatoma (Hepa-3B, ED50 = 2.2 μg/mL for 3, and ED50 = 4.2 μg/mL for 4). Compound 4 also showed marginal activity against colon carcinoma (COLO-205, ED50 = 2.9 μg/mL). Their structural elucidation by spectral and single-crystal X-ray analyses, and structure−activity relationships are discussed.

Three novel constituents from curculigo capitulata and revision of C-2 stereochemistry in nyasicoside

Continuing study of the constituents of the rhizomes of Curculigo capitulata provided three novel compounds, including two norlignan glucosides, curcapicycloside (2) and (1S,2R)-O-methylnyasicoside (3), and a phenanthrofuran, curcapital (9). The former two compounds were characterized as their tetra-O-methyl derivatives. Compound 2 possesses a glucosyl-fused skeleton with 1R,2R configuration. Biogenetic consideration led to a revision of the previously assigned 2S configuration of nyasicoside (1) to 2R, which was confirmed by NOE studies of the acetonide of its tetra-O-methyl derivative. The 2R configuration in tetra-O-methyl-1-O-methyl curculigine (7a) and isocurculigine (8a) was also established by chemical correlation of the former with (1R, 2R)-tetra-O-methyl-1-O-methylnyasicoside (10a). Curcapital (9) represents the first natural product having a phenanthro[9,10, b]furan skeleton.

On the absolute structure of optically active neolignans containing a dihydrobenzo[ b]furan skeleton

Several optically pure neolignans containing a dihydrobenzo[ b]furan skeleton were synthesized. Based on an X-ray crystallographic study and circular dichroism results, the absolute configurations of some naturally occurring neolignans, namely balanophonin ( 1), PGI 2 inducer ( 2), dehydrodiconiferyl alcohol-4-β- d-glucoside ( 3), dehydroconiferyl alcohol ( 4) and 3′,4-di- O-methylcedrusin ( 5) have been unambiguously established.