Eine einfache Synthese von 4-Chromanonen

Kabbe, Hans‐Joachim

doi:10.1055/s-1978-24924

Cited by 88 publications

(29 citation statements)

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“…Thin layer chromatography (TLC) was done by silica gel plates 60 GF254, cellulose plates (20 × 20 cm) from Sigma-Aldrich company for chemicals and ethyl acetate/hexane were used as the eluting system. (Kabbe, 1978). Pyrrolidine (4.2 mL, 0.05 mol) was added under stirring to a mixture of N-Boc piperidone (5 g, 0.0249 mol) and 2-hydroxyacetophenone (3.4 g, 0.0249 mol) in anhydrous methanol (40 mL) at rt.…”

Section: Chemistrymentioning

confidence: 99%

“…The starting spiro material, tert-butyl 4-oxospiro[chroman-2,4'-piperidine]-1'-carboxylate 12, was prepared using the reported multi-component reaction developed by Kabbe where a thermal condensation reaction of 2-hydroxyacetophenone and N-Boc piperidone in methanol was carried out in presence of pyrrolidine (Kabbe, 1978). The furnished spiro protected compound 12 was subjected to a deprotecting process using TFA in DCM to give the free-boc intermediate 13 in a quantitative yield which in turn was coupled with the appropriate acid chloride or sulfonyl chloride reagents in presence of TEA affording the final targeted compounds (14-18) in good yields.…”

Section: Chemistrymentioning

confidence: 99%

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Synthesis And Anticancer Screening Of Novel Spiro[Chroman-2,4'- Piperidin]-4-One Derivatives With Apoptosis-Inducing Activity

2018

J App Pharm Sci

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A novel series of spiro[chroman-2,4′-piperidin]-4-one derivatives was synthesized and evaluated as cytotoxic agents against three human cancer cell lines; MCF-7 (human breast carcinoma), A2780 (human ovarian cancer) and HT-29 (human colorectal adenocarcinoma) using MTT assay. Compound 16 with a sulfonyl spacer exhibited the most potent activity with IC 50 values between 0.31 and 5.62 μM. However, the trimethoxyphenyl derivative 15 was the least potent with IC 50 values between 18.77 and 47.05 μM. The most active compound 16 was selected for further mechanistic studies, which revealed that it induced more than three folds early apoptosis in MCF-7 cells treated for 24 h. Additionally, it increased MCF-7 cells in the sub-G1 and G2-M cell cycle phases, following the same treatment duration. Together, these compounds could be promising cytotoxic candidates, thus further structural optimization, in vitro and in vivo studies are recommended to be developed into potential cytotoxic agents.

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Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Synthesis And Anticancer Screening Of Novel Spiro[Chroman-2,4'- Piperidin]-4-One Derivatives With Apoptosis-Inducing Activity

2018

J App Pharm Sci

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“…(Micro-analytical Center of Cairo University). Compounds 1a [13], 1b [14] were prepared according methods described in the literature.…”

Section: Experimental Generalmentioning

confidence: 99%

4‐Chloro‐2,2‐disubstituted Chromen‐3‐carboxaldehyde: Synthesis of some Fused Polycyclic Heterocycles as Anti‐inflammatory, Analgesic, Anticonvulsant, and Antiparkinsonian Agents

Hegab¹,

Abdulla²

2006

Archiv der Pharmazie

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Some new aldazino 4, pyrazolo 5, thieno 8, and thiooxopyrimidino chromenes 10 were prepared via reaction of the corresponding beta-chlorocarboxaldehyde 3 with hydrazine hydrate, mercaptoacetic acid, and thiourea, respectively. Wherever, 4-chlorochromene derivatives 2 along with 4-chlorochromen-3-carboxaldehyde derivatives 3 were prepared from the corresponding ketone 1 with Vilsmeier-Haack reagent. Some of the new products showed good anti-inflammatory, analgesic, anticonvulsant, and antiparkinsonian activities comparable to indomethacin, diclofenace, carbamazepine, and benztropine.

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“…Chromanones are formed by the condensation of a phenol with 3,3-dimethyl acrylic acid in the presence of an acid catalyst such as H F (23), zinc chloride -phosphoryl chloride (24), polyphosphoric acid (25), BF, etherate (26), or methanesulphonic acid (27) (which is now the reagent of choice). Alternately, pyrrolidine catalysed condensation of an ortho-hydroxy acetophenone with ketones also affords chromanones in high yields (28).…”

Section: R1mentioning

confidence: 99%

The synthesis of 5-hydroxy chromenes

ApSimon¹,

Herman²,

Huber³

1985

Can. J. Chem.

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The synthesis of 2,2-dimethyl-5-hydroxychromene ( I d ) is described. The synthesis of the analogous 5,7-dihydroxy derivatives, using similar conditions, yields the adduct 9 derived via a Bucherer type reaction. X-ray analysis of 9 demonstrated that a pyrrolidine group was in the 7-position, and that the 5-hydroxyl group was involved in a strong intramolecular hydrogen bond to the 4-keto oxygen atom.

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Eine einfache Synthese von 4-Chromanonen

Cited by 88 publications

References 0 publications

Synthesis And Anticancer Screening Of Novel Spiro[Chroman-2,4'- Piperidin]-4-One Derivatives With Apoptosis-Inducing Activity

Synthesis And Anticancer Screening Of Novel Spiro[Chroman-2,4'- Piperidin]-4-One Derivatives With Apoptosis-Inducing Activity

4‐Chloro‐2,2‐disubstituted Chromen‐3‐carboxaldehyde: Synthesis of some Fused Polycyclic Heterocycles as Anti‐inflammatory, Analgesic, Anticonvulsant, and Antiparkinsonian Agents

The synthesis of 5-hydroxy chromenes

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