Adducts of dichloroketene with 1,3-cyclopentadienes in the synthesis of bioactive cyclopentanoids

Loza, V. V.; Валиуллина, З. Р.; Мифтахов, М. С.

doi:10.1007/s11172-021-3052-3

Cited by 12 publications

(5 citation statements)

References 79 publications

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“…Melting points were measured on the Electrothermal 9100 apparatus. 1 H and 13 C NMR spectra were recorded on a Bruker Avance DPX-400 instrument. As internal standards served TMS for 1 H NMR and CDCl3 for 13 C NMR spectroscopy J values are given in Hz.…”

Section: Generalmentioning

confidence: 99%

“…Removing the solvent under reduced pressure gave the 7,7-dichlorobicyclo[3.2.0]heptan-6-one (3) (colorless liquid) yield of 75%. 1…”

Section: Generalmentioning

confidence: 99%

“…The target compounds 6a-d, (E)-7-arylidene-5-(hydroxy(aryl)methyl)bicyclo[3.2.0] heptan-6-ones, were prepared in three steps. In the first stage, 7,7-dichlorobicyclo[3.2.0]heptan-6-one (3) was obtained by addition of dichloroketene to cyclopentene (1). The reaction of cyclopentene (1) with trichloroacetyl chloride and zinc (Zn) in Et2O at 15 °C for 5 hours gave the dichloroketene adduct 3 in yield of 75%.…”

Section: Chemistrymentioning

confidence: 99%

“…Compounds containing cyclopentane and cyclopentene rings in their structures are widely found in nature [1]. With many bioactivities, these compounds' analogs and synthetic cyclopentane structures have important practical applications [2,3].…”

Section: Introductionmentioning

confidence: 99%

“…1 H-NMR (400 MHz, CDCl3): 𝛿 = 7.44-7.28 (m, 6H), 6.99 (d, J = 2.4 Hz, 1H), 5.00 (s, 1H), 3.75 (dd, J = 7.2, 2.4 Hz, 1H), 2.62 (s, 1H), 2.18-2.09 (m, 1H), 2.01-1.91 (m, 1H),…”

mentioning

confidence: 99%

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Synthesis of (E)-7-arylidene-5-(hydroxy(aryl)methyl)bicyclo[3.2.0] heptan-6-one derivatives as anti-cancer agents

CEYLAN,

ZORLU,

ŞAHİN YAĞLIOĞLU

et al. 2023

Journal of New Results in Science

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7,7-Dichlorobicyclo [3.2.0]heptan-6-one was prepared by adding dichloroketene to cyclopentene. Reduction of 7,7-dichlorobicyclo[3.2.0]heptan-6-one with Zn in acetic acid afforded the bicyclo[3.2.0]heptan-6-one. (E)-7-Arylidene-5-(hydroxy(aryl)methyl)bicyclo [3.2.0]heptan-6-ones were synthesized by addition of related benzaldehydes to bicyclo[3.2.0]heptan-6-one. The anti-proliferative activities of synthesized compounds were elucidated against rat brain tumor (C6) and human cervical carcinoma cells (HeLa) cell lines. The most active compound was chloro derivative against C6 cell lines with IC50 = 2.45 μM value (5-FU, IC50 = 14.82 μM). Moreover, the most active compound was methyl derivative against HeLa cell lines with IC50 = 26.30 μM (5-FU, IC50 = 29.30 μM).

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Section: Generalmentioning

confidence: 99%

“…Removing the solvent under reduced pressure gave the 7,7-dichlorobicyclo[3.2.0]heptan-6-one (3) (colorless liquid) yield of 75%. 1…”

Section: Generalmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…1 H-NMR (400 MHz, CDCl3): 𝛿 = 7.44-7.28 (m, 6H), 6.99 (d, J = 2.4 Hz, 1H), 5.00 (s, 1H), 3.75 (dd, J = 7.2, 2.4 Hz, 1H), 2.62 (s, 1H), 2.18-2.09 (m, 1H), 2.01-1.91 (m, 1H),…”

mentioning

confidence: 99%

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Synthesis of (E)-7-arylidene-5-(hydroxy(aryl)methyl)bicyclo[3.2.0] heptan-6-one derivatives as anti-cancer agents

CEYLAN,

ZORLU,

ŞAHİN YAĞLIOĞLU

et al. 2023

Journal of New Results in Science

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A new entrant in ketene family: Generation of 2‐(3‐Oxo‐allyl)‐isoindole‐1,3‐dione and their [4+2] Cycloadditions with 1,3‐Diazabuta‐1,3‐dienes

2023

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The manuscript describes a synthetic route for the formation of 5‐(methylisoindole‐1,3‐dione) pyrimidinones by [4+2] cycloaddition reactions of functionalized 1,3‐diazabuta‐1,3‐dienes with 2‐(3‐Oxo‐allyl)‐isoindole‐1,3‐dione generated in situ from phthaloylalanine and tosyl chloride using triethylamine as a base. The functionalized 5‐(methylisoindole‐1,3‐dione) pyrimidinones were further explored in the deprotection of amines to afford a variety of 5‐methylamino pyrimidinones. The synthesis of such functionalized pyrimidinones is significant as they have a wide range of pharmacological profiles and are valuable as organic synthons. Mechanistic insights are also proposed for the given synthetic methodology.

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Reactivity of alicyclic 1,5,9-triketones toward five-, six-, and seven-membered rings in acidic medium. Stereochemistry of intramolecular cyclization products

Akimova

Soldatkina

Герасименко

et al. 2021

Chem Heterocycl Comp

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Adducts of dichloroketene with 1,3-cyclopentadienes in the synthesis of bioactive cyclopentanoids

Cited by 12 publications

References 79 publications

Synthesis of (E)-7-arylidene-5-(hydroxy(aryl)methyl)bicyclo[3.2.0] heptan-6-one derivatives as anti-cancer agents

Synthesis of (E)-7-arylidene-5-(hydroxy(aryl)methyl)bicyclo[3.2.0] heptan-6-one derivatives as anti-cancer agents

A new entrant in ketene family: Generation of 2‐(3‐Oxo‐allyl)‐isoindole‐1,3‐dione and their [4+2] Cycloadditions with 1,3‐Diazabuta‐1,3‐dienes

Reactivity of alicyclic 1,5,9-triketones toward five-, six-, and seven-membered rings in acidic medium. Stereochemistry of intramolecular cyclization products

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