Heterocyclic Building Block-benzofuran

Brikci-Nigassa, Nahida Mokhtari published the artcile2-Aminophenones, a common precursor to N-aryl isatins and acridines endowed with bioactivities, Formula: C8H5IO, the publication is Tetrahedron (2018), 74(15), 1785-1801, database is CAplus.

Because N-arylation of isatin only worked with iodoferrocene (and in low yield), N-arylation of 2-aminophenones and subsequent oxidative cyclization was employed to access the various N-arylated isatins. It was observed that N-arylation using 2-iodofuran, 2-iodobenzofuran and 2-iodobenzothiophene did not lead to the expected derivatives, but (benzo)furo- and (benzo)thieno[2,3-b]quinolines were formed. Sep. cyclization was also performed under acidic conditions on 2-(arylamino)phenones in order to obtain acridines and related compounds Most of the synthesized compounds were screened for their antiproliferative activity in A2058 melanoma cells and against a panel of disease-relevant kinases such as mammalian CDK5/p25, PIM1, CLK1, DYRK1A, GSK3α/β, Haspin and leishmanial CK1. The biol. results were reported.

Tetrahedron published new progress about 69626-75-1. 69626-75-1 belongs to benzofurans, auxiliary class Iodide,Benzofuran, name is 2-Iodobenzofuran, and the molecular formula is C8H5IO, Formula: C8H5IO.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Bouarfa, Salima published the artcileIodothiophenes and Related Compounds as Coupling Partners in Copper-Mediated N-Arylation of Anilines, Name: 2-Iodobenzofuran, the publication is Synthesis (2021), 53(7), 1271-1284, database is CAplus.

N-Arylation of various 2-acylated anilines 2-NH₂-5-R-C₆H₃C(O)R¹ (R = H, Cl; R¹ = H, Me, Ph) with different electron-rich heteroaryl iodides R²I (R² = thiophen-2-yl, 1-benzothiophen-3-yl, furan-2-yl, etc.) was achieved by using activated copper and potassium carbonate in di-Bu ether at reflux. The reactivity of the different heteroaryl iodides and anilines employed was discussed and rationalized on the basis of their electronic features. Subsequent cyclization by aromatic electrophilic substitution easily took place in the case of C2-free (benzo)thienyl I (X = O, S) or C3-free (benzo)furyl derivatives, II affording original tri- and tetracycles. The antiproliferative activity of most of them was evaluated in A2058 melanoma cells and revealed four chlorinated tetracycles as effective growth inhibitors.

Synthesis published new progress about 69626-75-1. 69626-75-1 belongs to benzofurans, auxiliary class Iodide,Benzofuran, name is 2-Iodobenzofuran, and the molecular formula is C8H5IO, Name: 2-Iodobenzofuran.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Amara, Rim published the artcileSynthesis of N-Aryl and N-Heteroaryl γ-, δ-, and ε-Lactams Using Deprotometalation-Iodination and N -Arylation, and Properties Thereof, Recommanded Product: 2-Iodobenzofuran, the publication is Synthesis (2017), 49(19), 4500-4516, database is CAplus.

Xanthone, thioxanthone, fluorenone, benzophenone, 2-benzoylpyridine, dibenzofuran, and dibenzothiophene were deprotonated using a base prepared in situ from MCl₂·TMEDA (M = Zn or Cd; TMEDA = N,N,N’,N’-tetramethylethylenediamine) and lithium 2,2,6,6-tetramethylpiperidide in a 1:3 ratio, as demonstrated by subsequent iodolysis. The different aryl halides were involved as partners in the N-arylation of pyrrolidin-2-one. In the presence of copper(I) iodide and tripotassium phosphate, and using DMSO as solvent, the reactions could be performed in yields ranging from 40 to 70%. Most of the products were tested for their antimicrobial, antifungal, antioxidant, and cytotoxic (MCF-7) activity.

Synthesis published new progress about 69626-75-1. 69626-75-1 belongs to benzofurans, auxiliary class Iodide,Benzofuran, name is 2-Iodobenzofuran, and the molecular formula is C8H5IO, Recommanded Product: 2-Iodobenzofuran.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Li, Wenxi published the artcileNeoveratrol A-D: Four new arylbenzofurans from Veratrum nigrum, Category: benzofurans, the publication is Phytochemistry Letters (2020), 144-147, database is CAplus.

Four new arylbenzofurans, 2-(3,5dimethoxy) phenyl-6-hydroxy-7-methoxy benzofuran (1, Neoveratrol A), 2-(3-O-β-D-glucosyl-5-hydroxy) phenyl-4,6-dimethoxy benzofuran (2, Neoveratrol B), 2-(3,5-dimethoxy) phenyl-4-O-β-D-glucosyl-6-hyroxy benzofuran (3, Neoveratrol C), 2-(3,5-dimethoxy) phenyl-6-hydroxy-7-O-β-D-glucosyl benzofuran (4, Neoveratrol D), together with nine known ones (5-13) were isolated from the dried root and rhizome of a Traditional Mongolian medicinal herb Veratrum nigrum. The structures were elucidated by various spectroscopic methods including UV, IR, NMR and HR-MS. Among these compounds, 1-3, 5, 7-9 and 11-13 showed significant inhibitory effects on lipopolysaccharide (LPS) induced nitric oxide (NO) production in RAW264.7 cells at the concentration ranging from 50.0-200.0μM. Compound 1 exhibited moderate activity against HepG2 and HCT-15. In addition, compound 5 and 6 showed inhibitory activities against human tumor cell lines HepG2, HCT-15, A549, MDA-MB-231 and SH-SY5Y with IC50 range of 40-100μM.

Phytochemistry Letters published new progress about 56317-21-6. 56317-21-6 belongs to benzofurans, auxiliary class Metabolic Enzyme,PDE,Natural product, name is 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, and the molecular formula is C14H10O4, Category: benzofurans.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Masagalli, Jagadeesh Nagarajappa published the artcileSynthesis of moracin C and its derivatives with a 2-arylbenzofuran motif and evaluation of their PCSK9 inhibitory effects in HepG2 cells, SDS of cas: 56317-21-6, the publication is Molecules (2021), 26(5), 1327, database is CAplus and MEDLINE.

Here, the synthesis of naturally occurring moracin compounds and their derivatives with a 2-arylbenzofuran motif to inhibit PCSK9 expression was reported. In addition, a short approach was discussed involving the three-step synthesis of moracin C and a divergent method to obtain various analogs from one starting material. Among the tested derivatives, 2-(3,5-dimethoxyphenyl)-6-methoxybenzofuran (97.1%) was identified as a more potent inhibitor of PCSK9 expression in HepG2 cells than berberine (60.9%). These results provided a better understanding of the structure-activity relationships of moracin derivatives for the inhibition of PCSK9 expression in human hepatocytes.

Molecules published new progress about 56317-21-6. 56317-21-6 belongs to benzofurans, auxiliary class Metabolic Enzyme,PDE,Natural product, name is 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, and the molecular formula is C14H10O4, SDS of cas: 56317-21-6.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Ghoneim, Mohamed M. published the artcilePolarographic reduction of phenolphthalein, cresolphthalein, thymolphthalein, and α-naphtholphthalein in aqueous and nonaqueous ethanolic solutions, Name: 3,3-Bis(4-hydroxynaphthalen-1-yl)isobenzofuran-1(3H)-one, the publication is Canadian Journal of Chemistry (1979), 57(11), 1294-8, database is CAplus.

The polarog. reduction of phenolphthalein, cresolphthalein, thymolphthalein, and α-naphtholphthalein was studied in ethanolic Britton-Robinson buffer series (pH 2-12), nonaqueous ethanolic medium, and aqueous EtOH. The compounds are reduced through a single 2-electron wave in nonaqueous medium, and aqueous buffered solutions of pH <9 or 1-electron steps for pH >9. The nature of the waves, mechanism of the electrode reaction, and kinetic parameters are considered.

Canadian Journal of Chemistry published new progress about 596-01-0. 596-01-0 belongs to benzofurans, auxiliary class Benzofuran,Naphthalene,Alcohol,Ester, name is 3,3-Bis(4-hydroxynaphthalen-1-yl)isobenzofuran-1(3H)-one, and the molecular formula is C28H18O4, Name: 3,3-Bis(4-hydroxynaphthalen-1-yl)isobenzofuran-1(3H)-one.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Sundarrajan, Sudharsana published the artcileA systems pharmacology perspective to decipher the mechanism of action of Parangichakkai chooranam, a Siddha formulation for the treatment of psoriasis, Quality Control of 56317-21-6, the publication is Biomedicine & Pharmacotherapy (2017), 74-86, database is CAplus and MEDLINE.

Psoriasis is a chronic relapsing immune mediated disorder of the skin. The disease presents itself with well featured clin. and histol. characteristics however the etiol. of the disease still remains obscure. The current systemic therapies aim to eliminate the symptoms of disease rather than offering a complete cure. Parangichakkai chooranam (PC), a Siddha oral herbal formulation has been widely prescribed for the treatment of psoriasis. Though the medication is highly prescribed by the Siddha healers the mechanism of PC for the treatment of psoriasis remains to be elucidated. The current study utilizes an integrated systems pharmacol. approach to decipher the mechanism of action of PC. The comprehensive network pharmacol. approach resulted in the construction of a Compound-Target network which encloses 155 compounds and 583 protein targets. A Disease-Target network was constructed by assembling disease proteins and their partners. When the compound targets were mapped to the network their involvement as controllers of the disease and triggers of disease associated comorbidities were identified. A Target-Pathway network raised from the pathway enrichment anal. not only identified disease specific pathways but also the pathways mediating secondary complications such as skin hemostasis, wound healing, desquamation and itch. The present work sheds light on the mechanism of action of PC in treating psoriasis. This work not only highlights the pharmacol. action of the formulation but also emphasis on safe herbal remedies offered by the Siddha medicinal system.

Biomedicine & Pharmacotherapy published new progress about 56317-21-6. 56317-21-6 belongs to benzofurans, auxiliary class Metabolic Enzyme,PDE,Natural product, name is 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, and the molecular formula is C19H34ClN, Quality Control of 56317-21-6.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Quasdorf, Kyle W. published the artcileSuzuki-Miyaura Cross-Coupling of Aryl Carbamates and Sulfamates: Experimental and Computational Studies, Category: benzofurans, the publication is Journal of the American Chemical Society (2011), 133(16), 6352-6363, database is CAplus and MEDLINE.

The first Suzuki-Miyaura cross-coupling reactions of the synthetically versatile aryl O-carbamate and O-sulfamate groups are described. The transformations utilize the inexpensive, bench-stable catalyst NiCl₂(PCy₃)₂ to furnish biaryls in good to excellent yields. A broad scope for this methodol. has been demonstrated. Substrates with electron-donating and electron-withdrawing groups are tolerated, in addition to those that possess ortho substituents. Furthermore, heteroaryl substrates may be employed as coupling partners. A computational study providing the full catalytic cycles for these cross-coupling reactions is described. The oxidative addition with carbamates or sulfamates occurs via a five-centered transition state, resulting in the exclusive cleavage of the aryl C-O bond. Water is found to stabilize the Ni-carbamate catalyst resting state, which thus provides rationalization of the relative decreased rate of coupling of carbamates. Several synthetic applications are presented to showcase the utility of the methodol. in the synthesis of polysubstituted aromatic compounds of natural product and bioactive mol. interest.

Journal of the American Chemical Society published new progress about 69626-75-1. 69626-75-1 belongs to benzofurans, auxiliary class Iodide,Benzofuran, name is 2-Iodobenzofuran, and the molecular formula is C8H5IO, Category: benzofurans.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Dring, Ann M. published the artcileRational quantitative structure-activity relationship (RQSAR) screen for PXR and CAR isoform-specific nuclear receptor ligands, Formula: C28H18O4, the publication is Chemico-Biological Interactions (2010), 188(3), 512-525, database is CAplus and MEDLINE.

Constitutive androstane receptor (CAR) and pregnane X receptor (PXR) are closely related orphan nuclear receptor proteins that share several ligands and target overlapping sets of genes involved in homeostasis and all phases of drug metabolism CAR and PXR are involved in the development of certain diseases, including diabetes, metabolic syndrome and obesity. Ligand screens for these receptors so far have typically focused on steroid hormone analogs with pharmacophore-based approaches, only to find relatively few new hits. Multiple CAR isoforms have been detected in human liver, with the most abundant being the constitutively active reference, CAR1, and the ligand-dependent isoform CAR3. It has been assumed that any compound that binds CAR1 should also activate CAR3, and so CAR3 can be used as a ligand-activated surrogate for CAR1 studies. The possibility of CAR3-specific ligands has not, so far, been addressed. To investigate the differences between CAR1, CAR3 and PXR, and to look for more CAR ligands that may be of use in quant. structure-activity relationship (QSAR) studies, we performed a luciferase transactivation assay screen of 60 mostly non-steroid compounds Known active compounds with different core chemistries were chosen as starting points and structural variants were rationally selected for screening. Distinct differences in agonist vs. inverse agonist/antagonist effects were seen in 49 compounds that had some ligand effect on at least one receptor and 18 that had effects on all three receptors; eight were CAR1 ligands only, three were CAR3 only ligands and four affected PXR only. This work provides evidence for new CAR ligands, some of which have CAR3-specific effects, and provides observational data on CAR and PXR ligands with which to inform in silico strategies. Compounds that demonstrated unique activity on any one receptor are potentially valuable diagnostic tools for the investigation of in vivo mol. targets.

Chemico-Biological Interactions published new progress about 596-01-0. 596-01-0 belongs to benzofurans, auxiliary class Benzofuran,Naphthalene,Alcohol,Ester, name is 3,3-Bis(4-hydroxynaphthalen-1-yl)isobenzofuran-1(3H)-one, and the molecular formula is C28H18O4, Formula: C28H18O4.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Nakamura, Naoki published the artcileThe response characteristic of optical carbon dioxide sensor using pH indicator immobilized in ethyl cellulose film, Computed Properties of 596-01-0, the publication is Transactions of the Materials Research Society of Japan (2004), 29(3), 923-926, database is CAplus.

A new optical CO₂ sensor based on the overlay of the CO₂ induced absorbance change of pH indicator α-naphtholphthalein with fluorescence of tetraphenylporphine (TPP) was developed and its CO₂ sensing characteristics were studied. The observed fluorescence intensity from TPP at 655 nm increased with increasing CO₂ concentration The I₁₀₀/I₀ value that shows the sensitivity of sensor containing 13.4 mmol dm^-3 α-naphtholphthalein concentration is estimated to be 168, where I₀ and I₁₀₀ represent observed fluorescence intensities from a film exposed to argon and CO₂ saturated condition, resp. The response time of the sensing film containing 13.4 mmol dm^-3 α-naphtholphthalein concentration was 3.8 s for switching from argon to CO₂ and the recovery time of the sensing film also was 6.8 s for switching from CO₂ to argon.

Transactions of the Materials Research Society of Japan published new progress about 596-01-0. 596-01-0 belongs to benzofurans, auxiliary class Benzofuran,Naphthalene,Alcohol,Ester, name is 3,3-Bis(4-hydroxynaphthalen-1-yl)isobenzofuran-1(3H)-one, and the molecular formula is C28H18O4, Computed Properties of 596-01-0.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem