The Pschorr Synthesis

Leake, Preston H.

doi:10.1021/cr50007a002

Cited by 62 publications

(18 citation statements)

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“…IR value of carbonyl shifted to 1,763 from 1,710 because of lactone formation. Further Pschorr reaction [24] is fully supported in the condensation of phenyl acetic acid with aldehyde, resulting into combretastatin with cis configuration. When 2-hdroxybenzaldehyde is used for the condensation with phenyl acetic acid, no lactone formation occurred (Figure 4).…”

Section: Resultsmentioning

confidence: 99%

Novel indole-bearing combretastatin analogues as tubulin polymerization inhibitors

Kumar

Mehndiratta

Nepali

et al. 2013

Organic and Medicinal Chemistry Letters

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BackgroundThe combretastatins are a class of natural stilbenoids. These molecules generally share three common structural features: a trimethoxy "A"-ring, a "B"-ring containing substituent often at C3′ and C4′, and an ethene bridge between the two rings, which provides necessary structural rigidity. Members of the combretastatin family possess varying ability to cause vascular disruption in tumors. Combretastatin binds to the colchicine binding site of β-subunit of tubulin. Despite having a similar name, combretastatin is unrelated to statins, a family of cholesterol-lowering drugs.ResultsNew combretastatin 2-(1-acetyl-1H-indole-3-yl)-3-(phenyl) propenoic analogues (2a to 2y), bearing indole moiety at the place of ring A of combretastatin (CA4), were synthesized and evaluated for anticancer activity against various cancer cell lines such as THP-1 (leukemia), A-549 (lung), IGROV-1 (ovary), HEP-2 (liver), MCF-7 (breast), and DU-145 (prostate). Compound 2d showed anti-cancer activity against THP-1 and MCF-7 with IC50 0.80 and 0.37 μM, respectively, and 2y showed against MCF-7 with IC50 3.60 μM comparable to paclitaxel.ConclusionsThe target compounds bind to the colchicine binding site which is situated at α and β interface of tubulin and prevent polymerization as it was confirmed by immunofluorescence technique. The molecular docking further confirmed the binding of the potent compound 2d to the colchicine binding site at α and β interface of tubulin.

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Section: Resultsmentioning

confidence: 99%

Novel indole-bearing combretastatin analogues as tubulin polymerization inhibitors

Kumar

Mehndiratta

Nepali

et al. 2013

Organic and Medicinal Chemistry Letters

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“…Its presence increase the yields of products from 21% to 86% for 3-ethyl 1,1,2,2-tetracyanocyclopropane 2k and from 43% to 86% for 1,1,2,2-tetracyanospiro[2.5]octane 2p . Earlier NaOAc was used as a catalyst in the Perkin condensation [14] and in the Knoevenagel reaction [15]. …”

Section: Resultsmentioning

confidence: 99%

New Way to Substitute Tetracyanocyclopropanes: One-Pot Cascade Assembling of Carbonyls and Malononitrile by the Only Bromine Direct Action

Vereshchagin

Elinson

Stepanov

et al. 2011

ISRN Organic Chemistry

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The new type of the chemical cascade reaction was found: formation of cyclopropanes from carbonyl compounds and CH acid by the only bromine direct action. The action of aqueous bromine on the carbonyl compounds and malononitrile in EtOH-H2O solutions in the presence of NaOAc results in the formation of 3-substituted 1,1,2,2-tetracyanocyclopropanes in 48–93% yields. The latter are well-known precursors for the different bicyclic heterosystems, among them those containing cyclopropane ring and those possessing different types of pharmacological activity.

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“…Pschorr, however, was the first to realise the potentialities of this process as a IE ECmethod for the unambiguous synthesis of derivatives of phenanthrene in which the positions of the substituents are known, and in a series of papers, with various collaborators, described the preparation of a large number of these derivatives, in particular, of degradation products of morphine. A number of reviews of the Pschorr reaction have been published recently (Fieser and Fieser, 1949;Saunders, 1949;Leake, 1956;De Tar, 1957), which together provide an adequate account of the experimental aspects of reactions of internuclear cyclisation. De Tar's review, for example, includes a tabular summary of the results of reactions reported up to 1956, as well as a discussion of the scope and limitations of the reaction, and the various side reactions which may occur.…”

Section: Introductionmentioning

confidence: 99%

Intramolecular Arylation

Williams

1960

Homolytic Aromatic Substitution

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The Pschorr Synthesis

Cited by 62 publications

References 61 publications

Novel indole-bearing combretastatin analogues as tubulin polymerization inhibitors

Novel indole-bearing combretastatin analogues as tubulin polymerization inhibitors

New Way to Substitute Tetracyanocyclopropanes: One-Pot Cascade Assembling of Carbonyls and Malononitrile by the Only Bromine Direct Action

Intramolecular Arylation

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