Tag: M.W=200-250

Zhang, Hua published the artcileA Construction of α-Alkenyl Lactones via Reduction Radical Cascade Reaction of Allyl Alcohols and Acetylenic Acids, Formula: C8H5IO, the publication is Organic Letters (2020), 22(21), 8337-8344, database is CAplus and MEDLINE.

An iron-catalyzed cascade reaction of radical reduction of allyl alcs. and acetylenic acids to construct polysubstituted α-alkenyl lactones has been developed. In this paper, various allyl alcs. can form allyl ester intermediates and are further transformed into alkyl radicals, which form products through intramol. reflex-Michael addition In addition, this method can be used to prepare spirocycloalkenyl lactones. Interestingly, this protocol can be used to synthesize the skeleton structure of natural products. Moreover, the product can be further transformed into a β-methylene THF and THF diene.

Organic Letters 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 C10H19NO3, Formula: C8H5IO.

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

Yang, Pei-Song published the artcileTwo new 2-arylbenzofurans from the stems of Nicotiana tabacum and their bioactivities, SDS of cas: 56317-21-6, the publication is Heterocycles (2016), 92(8), 1462-1467, database is CAplus.

Two new 2-arylbenzofurans, 4-(7-methoxy-3,5-dimethyl-benzofuran-2-yl)phenol (1), 4-(6-methoxy-3,5-dimethylbenzofuran-2-yl)-phenol (2), together with two known 2-arylbenzofurans (3 and 4) were isolated from the stems of Nicotiana tabacum. Their structures were determined by means of HRESIMS and extensive 1D and 2D NMR spectroscopic studies. Compounds 1-4 were tested for their anti-TMV and cytotoxicity activities. The results showed that compound 2 exhibited high anti-TMV activities with inhibition rates of 36.4% at the concentration of 20 μM. This rate is higher than that of pos. control. Compounds 1-4 showed moderate-to-weak cytotoxicities against some tested human tumor cell lines with IC50 values in the range of 2.2-8.4 μM.

Heterocycles 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 C15H20BNO3, SDS of cas: 56317-21-6.

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

Jing, Ying published the artcileChemical constituents from the leaves of Morus mongolica, Category: benzofurans, the publication is Tianran Chanwu Yanjiu Yu Kaifa (2010), 22(2), 181-184, database is CAplus.

Chem. constituents of the leaves of Morus mongolica were isolated and purified by ion-exchange resin, silica gel, ODS and Sephadex LH-20 column chromatogs. Their structures were elucidated on the basis of physico-chem. properties and spectral data. Ten compounds were identified as 1-deoxynojirimycin (1), fagomine (2), myoinositol (3), moracin M (4), 3-O-β-D-glucopyranoside (5), umbelliferone (6), scopoletin (7), syringaresinol (8), 2,4,2′,4′-tetrahydroxychalcone (9), and daucosterol (10), resp. Compounds 2, 3, 5-10 were isolated from this plant for the first time, and compound 9 is a new natural product.

Tianran Chanwu Yanjiu Yu Kaifa 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

Chen, Shang-Ke published the artcileMoracin M from Morus alba L. is a natural phosphodiesterase-4 inhibitor, Application In Synthesis of 56317-21-6, the publication is Bioorganic & Medicinal Chemistry Letters (2012), 22(9), 3261-3264, database is CAplus and MEDLINE.

Phosphodiesterase-4 (PDE4) has been identified to be a promising target for treatment of asthma. Moracin M extracted from Chinese herbal drug ‘Sang-Bai-Pi’ (Morus alba L.) was studied for the inhibitory affinity towards PDE4. It inhibited PDE4D2, PDE4B2, PDE5A1, and PDE9A2 with the IC₅₀ values of 2.9, 4.5, >40, and >100 μM, resp. Our mol. docking and 8 ns mol. dynamics (MD) simulations demonstrated that moracin M forms three hydrogen bonds with Gln369, Asn321, and Asp318 in the active site and stacks against Phe372. In addition, comparative kinetics anal. of its analog moracin C was carried out to qual. validate their inhibitory potency as predicted by the binding free energy calculations after MD simulations.

Bioorganic & Medicinal Chemistry 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, Application In Synthesis of 56317-21-6.

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

Varga, Balint published the artcileSynthesis and Photochemical Application of Hydrofluoroolefin (HFO) Based Fluoroalkyl Building Block, COA of Formula: C8H5IO, the publication is Organic Letters (2021), 23(12), 4925-4929, database is CAplus and MEDLINE.

A novel fluoroalkyl iodide, 3-chloro-1,1,1,2-tetrafluoro-2-iodopropane was synthesized on multigram scale from refrigerant gas HFO-1234yf as cheap industrial starting material in a simple, solvent-free, and easily scalable process. Here, its applicability in a metal-free photocatalytic ATRA reaction demonstrated to synthesize valuable fluoroalkylated vinyl iodides RCH(I)=CHC(F)(CF₃)CH₂Cl (R = n-Bu, Ph, pyridin-3-yl, etc.) and proved the straightforward transformability of the products in cross-coupling chem. to obtain conjugated systems R¹C(CCR²)=CHC(F)(CF₃)CH₂Cl (R¹ = Ph, n-Bu, 1-naphthyl, etc.; R² = n-Bu, TMS, Ph, 2-thienyl, etc.); R¹C(Ar)=CHC(F)(CF₃)CH₂Cl (Ar = Ph, furan-3-yl, 3-methyl-3H-imidazo[4,5-b]pyridine-6-yl, etc.).

Organic Letters 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 C7H5Br2F, COA of Formula: C8H5IO.

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

Xu, Bin published the artcilePhotocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes, Formula: C8H5IO, the publication is Journal of the American Chemical Society (2020), 142(13), 6206-6215, database is CAplus and MEDLINE.

Endergonic isomerizations are thermodynamically unfavored processes that are difficult to realize under thermal conditions. A photocatalytic and diastereoselective isomerization of acyclic cinnamyl chlorides to strained cyclopropanes is reported. Quantum mech. calculations (uM06-2X and DLPNO), including TD-DFT calculations, and exptl. studies provide evidence for the energy transfer from an iridium photocatalyst to the allylic chloride substrate followed by C-Cl homolytic cleavage. Subsequent Cl^• radical migration forms a localized triplet 1,3-diradical intermediate that, after intersystem crossing, undergoes ring-closing to form the desired product. The mild reaction conditions are compatible with a broad range of functional groups to generate chlorocyclopropanes in high yields and diastereoselectivities. A more efficient process is developed by addition of a catalytic amount of a nickel complex, and we propose a novel role for this cocatalyst to recycle an allyl chloride byproduct generated in the course of the reaction. The reaction is also shown to be stereoconvergent, as an E/Z mixture of cinnamyl chlorides furnish the anti-chlorocyclopropane product in high diastereoselectivity. The use of a visible light activated photocatalyst to transform substrates in combination with a transition metal catalyst to recycle byproducts back into the catalytic cycle will provide unique opportunities for the discovery of new reactivity is anticipated.

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 C15H12O6, Formula: C8H5IO.

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

Naka, Hiroshi published the artcileAn Aluminum Ate Base: Its Design, Structure, Function, and Reaction Mechanism, HPLC of Formula: 69626-75-1, the publication is Journal of the American Chemical Society (2007), 129(7), 1921-1930, database is CAplus and MEDLINE.

An Al ate base, i-Bu₃Al(TMP)Li, was designed and developed for regio- and chemoselective direct generation of functionalized aromatic Al compounds Direct alumination followed by electrophilic trapping with I₂, Cu/Pd-catalyzed C-C bond formation, or direct oxidation with mol. O₂ proved to be a powerful tool for the preparation of 1,2-di- or 1,2,3-trisubstituted aromatic compounds This deprotonative alumination using i-Bu₃Al(TMP)Li is effective in aliphatic chem. as well, enabling regio- and chemoselective addition of functionalized allylic ethers and carbamates to aliphatic and aromatic aldehydes. A combined multinuclear NMR spectroscopy, x-ray crystallog., and theor. study showed that the Al ate base is a Li/Al bimetallic complex bridged by the N atom of TMP and the α-C of an i-Bu ligand and that the Li exclusively serves as a recognition point for electroneg. functional groups or coordinative solvents. The mechanism of directed ortho alumination reaction of functionalized aromatic compounds was studied by NMR and in situ FTIR spectroscopy, x-ray anal., and DFT calculation The reaction proceeds with facile formation of an initial adduct of the base and aromatic, followed by deprotonative formation of the functionalized aromatic Al compound Deprotonation by the TMP ligand rather than the iso-Bu ligand was suggested and reasoned by spectroscopic and theor. study. The remarkable regioselectivity of the ortho alumination reaction was explained by a coordinative approximation effect between the functional groups and the counter Li⁺ ion, enabling stable initial complex formation and creation of a less strained transition state structure.

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, HPLC of Formula: 69626-75-1.

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

Arias, Leire published the artcileRegioselective Preparation of Benzo[b]furans from Phenols and α-Bromoketones, Related Products of benzofurans, the publication is Journal of Organic Chemistry (2012), 77(1), 266-275, database is CAplus and MEDLINE.

A fully regiocontrolled synthesis of either 2- and 3-substituted benzo[b]furans is described. Direct reaction between phenols and α-bromoacetophenones in the presence of neutral alumina yields 2-substituted benzo[b]furans with complete regiocontrol. When a basic salt such as potassium carbonate is used, the corresponding 2-oxoether is obtained. Cyclization of these latter compounds promoted by neutral alumina yields the corresponding 3-substituted benzo[b]furans. Using the former method, Moracin M and other analogs can be obtained from com. sources in two preparative steps. DFT calculations provide reasonable reaction paths to understand the formation of 2-substituted benzo[b]furans.

Journal of Organic Chemistry 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, Related Products of benzofurans.

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

Guo, Zhengwei published the artcileSynthesis of reversible PAD4 inhibitors via copper-catalyzed C-H arylation of benzimidazole, Formula: C8H5IO, the publication is Science China: Chemistry (2019), 62(5), 592-596, database is CAplus.

A Cu-catalyzed C-H arylation reaction of N-heteroarene I [R = H; R¹ = H₃CO] has been applied to the synthesis of complex non-covalent PAD4 inhibitors I [R = 1-benzyl-1H-indol-2-yl, naphthalen-2-yl, pyrazin-2-yl, etc.; R¹ = (3S,4R)-3-amino-4-hydroxypiperidin-1-yl] bearing a bi-heteroaryl pharmacophore. This strategy access various analogs of C₂-aryl substituted benzimidazoles I [R¹ = OH, H₃CO] from a common benzimidazole core I [R = H; R¹ = H₃CO] and easily accessible aryl iodides RI. Preliminary SAR studies revealed that the indole motif of GSK-484 is critical to its activity. Replacing the N-cyclopropylmethyl group to N-benzyl group on the indole ring of GSK-484 resulted in more than 5-fold increase in cell killing efficacy against 4T1 cell line.

Science China: 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, Formula: C8H5IO.

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

Arung, Enos Tangke published the artcileArtocarpus plants as a potential source of skin whitening agents, HPLC of Formula: 56317-21-6, the publication is Natural Product Communications (2011), 6(9), 1397-1402, database is CAplus.

Artocarpus plants were a focus of constant attention due to the potential for skin whitening agents. In the in vitro experiment, compounds from the Artocarpus plants, such as artocarpanone, norartocarpetin, artocarpesin, artogomezianol, andalasin, artocarbene, and chlorophorin showed tyrosinase inhibitory activity. Structure-activity investigations revealed that the 4-substituted resorcinol moiety in these compounds was responsible for their potent inhibitory activities on tyrosinase. In the in vitro assay, using B16 melanoma cells, the prenylated polyphenols isolated from Artocarpus plants, such as artocarpin, cudraflavone C, 6-prenylapigenin, kuwanon C, norartocarpin, albanin A, cudraflavone B, and brosimone I showed potent inhibitory activity on melanin formation. Structure-activity investigations revealed that the introduction of an isoprenoid moiety to a non-isoprenoid-substituted polyphenol enhanced the inhibitory activity of melanin production in B16 melanoma cells. In the in vivo investigation, the extract of the wood of Artocarpus incisus and a representative isolated compound from it, artocarpin had a lightening effect on the skin of guinea pigs’ backs. Other in vivo experiments using human volunteers have shown that water extract of Artocarpus lakoocha reduced the melanin formation in the skin of volunteers. These results indicate that the extracts of Artocarpus plants are potential sources for skin whitening agents.

Natural Product Communications 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, HPLC of Formula: 56317-21-6.

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