Tag: M.W=200-250

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

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

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

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

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

Hedidi, Madani published the artcileSynthesis of C,N’-linked bis-heterocycles using a deprotometalation-iodination-N-arylation sequence and evaluation of their antiproliferative activity in melanoma cells, Application In Synthesis of 69626-75-1, the publication is Bioorganic & Medicinal Chemistry (2014), 22(13), 3498-3507, database is CAplus and MEDLINE.

Benzothiophene, benzofuran, benzothiazole, and benzoxazole were deprotometalated using the lithium-zinc combination prepared from ZnCl₂.TMEDA (TMEDA = N,N,N’,N’-tetramethylethylenediamine, 1 equiv) and lithium 2,2,6,6-tetramethylpiperidide (LiTMP, 3 equiv). Subsequent interception of the 2-metalated derivatives using iodine as electrophile led to the iodides in 81%, 82%, 67%, and 42% yields, resp. These yields are higher (10% more) than those obtained using ZnCl₂.TMEDA (0.5 equiv) and LiTMP (1.5 equiv), except in the case of benzoxazole (10% less). The crude iodides were involved in the N-arylation of pyrrole, indole, carbazole, pyrazole, indazole, imidazole, and benzimidazole in the presence of Cu (0.2 equiv) and Cs₂CO₃ (2 equiv), and using acetonitrile as solvent (no other ligand) to provide after 24 h reflux the expected N-arylated azoles in yields ranging from 33% to 81%. Using benzotriazole also led to N-arylation products, but in lower 34%, 39%, 36%, and 6% yields, resp. A further study with this azole showed the impact of 2,2,6,6-tetramethylpiperidine on the N-arylation yields. Most of the C,N’-linked bis-heterocycles thus synthesized (in particular those containing benzimidazole) induced a high growth inhibition of A2058 melanoma cells after a 72 h treatment at 10^-5 M.

Bioorganic & Medicinal Chemistry 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, Application In Synthesis of 69626-75-1.

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

L’Helgoual’ch, Jean-Martial published the artcileDeprotonative cadmation of functionalized aromatics, Computed Properties of 69626-75-1, the publication is Chemical Communications (Cambridge, United Kingdom) (2008), 5375-5377, database is CAplus and MEDLINE.

This communication describes the deproto-metalation of a large range of aromatics including heterocycles using a newly developed lithium-cadmium base; the reaction proceeds at room temperature with an excellent chemoselectivity and efficiency, and proved to be regioselective in most cases. Thus, treatment of PhOMe with CdCl₂·TMEDA/LiTMP in THF at room temperature followed by quenching with I₂ gave 74% 2-IC₆H₄OMe.

Chemical Communications (Cambridge, United Kingdom) 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, Computed Properties of 69626-75-1.

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

Baillie, Sharon E. published the artcilePotassium-alkyl magnesiates: synthesis, structures and Mg-H exchange applications of aromatic and heterocyclic substrates, Recommanded Product: 2-Iodobenzofuran, the publication is Chemical Communications (Cambridge, United Kingdom) (2014), 50(85), 12859-12862, database is CAplus and MEDLINE.

Using structurally well-defined dipotassium-tetra(alkyl)magnesiates, a new straightforward methodol. to promote regioselective Mg-H exchange reactions of a wide range of aromatic and heteroaromatic substrates is disclosed. E.g., reaction of anisole with (PMDETA)₂K₂Mg(CH₂SiMe₃)₂ in hexane at 20° followed by excess I₂ gave p-IC₆H₂OMe in 92% yield. Contacted ion pair intermediates probably are involved, with K being the key to facilitate the magnesiation processes.

Chemical Communications (Cambridge, United Kingdom) 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

Nicolle, Edwige published the artcileBreast cancer resistance protein (BCRP/ABCG2): New inhibitors and QSAR studies by a 3D linear solvation energy approach, Category: benzofurans, the publication is European Journal of Pharmaceutical Sciences (2009), 38(1), 39-46, database is CAplus and MEDLINE.

A series of compounds derived from naturally occurring flavonoids and synthetic analogs have been evaluated on cell lines overexpressing the wild-type breast cancer resistance protein (BCRP/ABCG2) half-transporter. Human ABCG2-transfected cells were used for screening their inhibitory activity. Five new natural compounds obtained from Morus mesozygia Stapf and one synthetic chromone, comprising a flavonoidic scaffold, were also evaluated. Based on the results obtained with a total of 34 compounds, a 3D linear solvation energy QSAR was investigated by VolSurf descriptors of mol.-interaction fields (MIFs) related to hydrophobic-interaction forces, polarizability and hydrogen-bonding capacity. Accuracy of the constructed 3D-QSAR model was attested by a correlation coefficient r² of 0.77. Shape parameters and hydrophobicity were revealed to be major physicochem. parameters responsible for the inhibition activity of flavonoid derivatives and synthetic analogs towards ABCG2, whereas hydrogen-bond donor capacity appeared highly unfavorable.

European Journal of Pharmaceutical Sciences 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