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A general synthesis of the phthalide-1,2,3,4-tetrahydroisoquinolines, including the synthesis of the alkaloid cordrastine, is described.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H3148O – PubChem

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PROBLEM TO BE SOLVED: To provide a cephem compound which has a strong antimicrobial activity, in particular effective against various beta-lactamase producing Gram negative bacteria, and a composition comprising the compound.SOLUTION: The present invention provides a pharmaceutical composition comprising a compound represented by formula (I), an ester at a carboxyl group, an amino-protected compound when the amino is present on a ring in the 7-side chain, or a pharmaceutically acceptable salt thereof.

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Benzofuran – Wikipedia,
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A compound of the formula: wherein, W is ?CH2? etc.; U is ?S? etc.; R1 is substituted or unsubstituted carbocyclyl etc.; R2A and R2B is a) or b) described in the specification; R3 is a hydrogen atom etc.; R11 is carboxylate anion (?COO?) etc.; L is substituted or unsubstituted lower alkylene etc., E is a substituted or unsubstituted divalent group containing quaternary ammonium ion; G is a single bond etc.; D is ?C(?O)?C(?O)?NR6? etc.; R10 1) to 3) described in specification; or an amino-protected compound when the amino group is present on the ring in the 7-side chain, or a pharmaceutically acceptable salt thereof.

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Reference:
Benzofuran – Wikipedia,
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BACKGROUND AND PURPOSE Noscapine is a promising anti-tumour agent. The purpose of the present study was to describe the metabolic map and investigate the bioactivation of noscapine. EXPERIMENTAL APPROACH Ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight mass spectrometry-based metabolomics was used to analyse the in vitro incubation mixtures, urine and faeces samples from mice treated with noscapine. Recombinant drug-metabolizing enzymes were employed to identify those involved in noscapine metabolism. Hepatic GSH levels and serum biochemistry were also carried out to determine reactive metabolites of noscapine. KEY RESULTS Several novel phase I metabolites of noscapine were detected after oral gavage of mice, including an N-demethylated metabolite, two hydroxylated metabolites, one metabolite undergoing both demethylation and cleavage of the methylenedioxy group and a bis-demethylated metabolite. Additionally, several novel glucuronides were detected, and their structures were elucidated through MS/MS fragmentology. Recombinant enzymes screening showed the involvement of several cytochromes P450, flavin-containing mono-oxygenase 1 and the UDP-glucuronosyltransferases UGT1A1, UGT1A3, UGT1A9 and UGT2B7, in noscapine metabolism. In vitro glutathione trapping revealed the existence of an ortho-quinone reactive intermediate formed through further oxidation of a catechol metabolite. However, this bioactivation process of noscapine does not occur in vivo. Similar to this result, altered glutathione levels in liver and serum biochemistry revealed no evidence of hepatic damage, thus indicating that, at least in mice, noscapine does not induce hepatotoxicity through bioactivation. CONCLUSIONS AND IMPLICATIONS A comprehensive metabolic map and bioactivation evaluation provides important information for the development of noscapine as an anti-tumour drug. Published 2012. This article is a U.S. Government work and is in the public domain in the USA.

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Benzofuran – Wikipedia,
Benzofuran | C8H3132O – PubChem

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Reaction of alpha-halo silanes 1 with CsF in DMF affords stilbenes 5.In the presence of added aldehydes, epoxides 6 are obtained, while with electron-deficient olefins the corresponding cyclopropanes 7 are formed.A similar reaction of 1a with iminium compounds 8 in HMPA leads to 2-phenyl-3-benzazepines 12, whereas 1b or 17 furnishes phthalidylisoquinolines 15.

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Degradation of (-)-alpha-narcotine (5), (-)-beta-narcotine (6), and (-)-beta-hydrastine (7) with ethyl chloroformate (ECF) affords the chloro-urethans 9 and 18, respectively. Diastereomer 9-I is easily hydrolyzed to the hydroxy-urethan 10, whilst 18 is converted to the methoxy-analogue 19. The stilbene lactone 11 is obtained from 9-I by treatment with DBU, the analogous stilbene 17 arises already when 7 is reacted with ECF. – Hydroxy-urethan 10 – a phenylogous aldol – is split by OH- to aldehyde 13 and to meconine (14). LiAlH4-reduction of 10 yields the stereochemically homogenous triol 15, which is cyclized to diastereomers of the 3-phenyl-isochroman 16 under acidic conditions.

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Reference:
Benzofuran – Wikipedia,
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A new, convergent total synthesis of (¡À)-alpha-noscapine was developed on a grams scale through the condensation of 3-trimethylsilyl-meconin derivative 9 and the iodized salt cotarnine derivative 20 as the key step. Staring from simple 2,3-dimethoxybenzoic acid, piperonal and 2,2-dimethoxyethanamine, through the traditional chemical processes to give the final product in 11.6% yield over 14 steps.

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(Z)-3-Butylidene-6,7-dihydroxyphthalide (2) was first synthesized from 6,7-dimethoxyphthalide (4) and its structure was synthetically confirmed.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H3149O – PubChem

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A general method for the synthesis of phthalaldehydic acids and phthalides, many of which are key intermediates in natural product synthesis, has been developed. o-Bromobenzaldehydes 1a-f were first protected in situ as alpha-morpholinoalkoxides by reaction with lithium morpholide.Treatment of the alpha-morpholinoalkoxides 3a-f with n-butyllithium (to exchange bromine with lithium) followed by sequential treatment with solid CO2 and dilute acid afforded the phthalaldehydic acids 6a-f, respectively.Reduction of 6a-f with NaBH4 in EtOH furnished the phthalides 7a-f, respectively, in nearly quantitative yields.Efficient methods for the synthesis of the o-bromobenzaldehydes 1a-d, which were not readily available, are also described.

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Reference:
Benzofuran – Wikipedia,
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A new procedure for the synthesis of 2,3-diaryl-3,4-dihydro-4-hydroxy-1(2H)-isoquinolones is described in which the cis-isomer predominates.Dehydration leads to 2,4-diarylisocarbostyrils.

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Reference:
Benzofuran – Wikipedia,
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