9/17/21 News Extracurricular laboratory:new discovery of 569-31-3

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7-Methoxyphthalide (3a) and meconine (3b) have been synthesised by the lithiation of appropriate N,N-dimethylbenzylamines (1a and 1b) followed by the reaction of the lithium derivatives with ethylchloroformate.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H3147O – PubChem

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The addition of t-BuLi to a low-temperature THF solution of o-bromocarbamates 2 leads to ortho-lithiated intermediates 3, in which internal trapping by the electrophile on the side chain then takes place.This novel Parham-type anionic cyclization procedure affords the variously substituted phthalides 5 in high yields and can also be used for the preparation of lactones 8, which are useful for the synthesis of aristocularine alkaloids.

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Benzofuran – Wikipedia,
Benzofuran | C8H3152O – PubChem

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Poppy (Papaver somniferum) is a traditional source of isoquinoline alkaloids, especially morphine, codeine and papaverine that exhibit a wide spectrum of therapeutic effects. Due to beneficial properties, poppy has been used by humankind for several thousand years and is still being used around the world. The present study was aimed to investigate alkaloid composition and biological activity of various parts of the plant (leaves, stems, roots, capsules, flowers, seeds) in an ornamental variety of P. somniferum. The alkaloid content rangedwithin 0.16 ? 6.5 mg/g fresh weight of raw plant material. The major components of the alkaloid fraction were papaverine (37.7 ? 2062.9 mug/g), codeine (7.4 ? 1280.5 mug/g) and morphine (3.25 ? 929.3 mug/g). The P. somniferum alkaloid extract produced a strong antioxidant effect, which was evaluated using the radical-scavenging DPPH, ABTS and FRAP assays. The antioxidant properties were characterized by IC50 values ranging within 35.1 ? 157.6 mug/mL for DPPH radical and 138.5 ? 306.3 mug/mL for ABTS??+ radical scavenging. The ferric reducing antioxidant power (FRAP) values varied from 59.75 to 1348.71 mM FeSO4/g extract. The alkaloid extract was active against all human tumor cell lines studied (HeLa, Caco-2, MCF-7, CCRF-CEM and CEM/ADR 5000). The methanol extract exhibited a pronounced cytotoxicity against most of cancer cell lines studied, especially those with a low expression of ABC transporters.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H3154O – PubChem

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The annulation of phthalides with alpha-alkyl/arylacrylates in the presence of LDA/LHMDS is shown to directly give alkyl/aryl-1-naphthols. The method involving a novel dealkoxycarbonylation obviates the regiochemical issues in the synthesis of polysubstituted naphthalenes, and it forms the key step in a three-step total synthesis of arnottin I, a naphthobenzopyranone natural product.

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The lithium salts derived from position 3 of phthalides react with arynes to form adducts, which, upon aerial oxidation, produce anthraquinones in moderate to good yields.Substituted phthalides and arynes also participate in this general reaction.The addition to unsymmetrically substituted arynes shows regioselectivity, whilst the availability of a new general route to phthalides extends the scope of this reaction.

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Benzofuran – Wikipedia,
Benzofuran | C8H3130O – PubChem

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An acid-catalyzed stereoselective epoxide ring-opening/intramolecular transesterification cascade cyclization reaction and N-Boc deprotection was found to be a successful strategy to construct the phthalide tetrahydroisoquinoline skeleton in one pot. Based on this strategy, the unified and highly diastereoselective routes for the total syntheses of (±)-beta-Noscapine and (±)-beta-Hydrastine were exploited.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H3136O – PubChem

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Phthalideisoquinoline alkaloids have been synthesized by coupling appropriately substituted 3-halophthalides and 2-methyl-3,4-dihydroisoquinolinium salts in the presence of Zn(Cu) couple or metallic Zn.Both erythro and threo isomers are formed in the reaction.The nmr spectra of the (+/-)-erythro- and (+/-)-threo-isocordrastines have been reinvestigated.The results, which differ from those previously reported, lead to a different conclusion regarding the conformations of the molecules.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H3156O – PubChem

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beta-Hydrastine (I) is an erythro compound, the chiral centres at C-1 and C-9 having R and S configurations respectively.Its conversion into the hitherto unknown threo-isomer by the reduction of the corresponding immonium derivative (II) with zinc and acetic acid has met with failure.Surprisingly, II with Zn/ AcOH regenerates beta-hydrastine.During this reduction II rather suffers reductive cleavage yielding the non-nitrogenous lactone, meconine (IV).Sodium borohydride and catalytic reductions of II also fail to afford the threo-isomer.The latter is found to be extremely unstable as revealed from Dreiding model because of the severe steric interaction between the axial hydrogen at C-4 and the C1′-C2’bond.Benzylic oxidation of beta-hydrastine (I) with MnO2, instead of producing the desired 4-oxo derivative (VI), gives 6,7-methylenedioxyisoquinoline arising out of cleavage at C1-C9 bond.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H3127O – PubChem

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A new acid-catalyzed method for the synthesis of (Z)-3-butylidenephthalides 5 and a novel and general route to 3-alkyl-8-hydroxy/methoxyisocoumarins 6-8 from phthalides 9 is described. The hydroxyphthalides 4 and 10 were obtained by condensation of the phthalide anion with butyraldehyde and acetaldehyde. Reaction of hydroxyphthalides 4 with a mixture of orthophosphoric acid and formic acid gave the (Z)-3-butylidenephthalides 5, while the hydroxyphthalides 4 and 10 on reaction with p-toluenesulfonic acid provided the 3-alkylisocoumarins 6-8. The present approaches permit variation of the 3-substituent in isocoumarin and the pattern of functionalization on the aromatic rings of both isocoumarins and alkylidenephthalides.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H3141O – PubChem

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The compounds of formula (I) of the subject invention are related to 2-substituted cephem compounds, which have a wide antimicrobial spectrum, in particular exhibit potent antimicrobial activity against beta-lactamase producing Gram negative bacteria, and pharmaceutical compositions comprising the same.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H3124O – PubChem