Regioselectivity of the 1,3-dipolar cycloaddition of fluorinated fluoren-9-iminium ylides to heteroelement-containing dipolarophiles: Experimental and quantum-chemical study

Новиков, Михаил С.; Хлебников, А. Ф.; Egarmin, M. A.; Shevchenko, M. V.; Khlebnikov, V. A.; Kostikov, R. R.; Vidović, Denis

doi:10.1134/s1070428006120086

Cited by 4 publications

(3 citation statements)

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“…The dipolarophile can be almost any double or triple bond, containing functionality such as C≡C, 48 C=C, 49 C≡N, 50 C=N, 51 C=O, 5 and C=S. 52 The -bond may be isolated, conjugated 53 or part of a cumulene 54 system.…”

Section: The Dipolarophilementioning

confidence: 99%

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Asymmetric 1,3-dipolar cycloadditions of acrylamides

2010

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This critical review, which is relevant to researchers in synthetic organic chemistry, focuses on asymmetric 1,3-dipolar cycloadditions with acrylamides. The use of chiral acrylamides as dipolarophiles leads to high levels of stereocontrol, due to conformational constraint in the acrylamides. Employment of chiral tertiary acrylamides containing nitrogen heterocycles is particularly effective in controlling the stereoselectivity. Following a general overview of 1,3-dipolar cycloadditions, the main body of the review focuses on asymmetric 1,3-dipolar cycloadditions of acrylamides with nitrile oxides, nitrones, diazoalkanes and azomethine ylides, with particular emphasis on the rationale for the observed stereocontrol (215 references)

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Section: The Dipolarophilementioning

confidence: 99%

“…The 2p component of the 1,3-dipolar cycloaddition is commonly known as the dipolarophile. The dipolarophile can be almost any double or triple bond, containing functionality such as CRC, 48 CQC, 49 CRN, 50 CQN, 51 CQO, 5 and CQS. 52 The p-bond may be isolated, conjugated 53 or part of a cumulene 54 system.…”

Section: The Dipolarophilementioning

confidence: 99%

Asymmetric 1,3-dipolar cycloadditions of acrylamides

2010

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“…Fluorene-containing compounds have unique chemical behaviours and physical properties due to the unusual geometric structure of fluorene [1]. Fluorene and its derivatives are important materials that are used in organic synthesis, the pharmaceutical and synthetic resin industries, and conductivity research [2][3][4].…”

Section: Introductionmentioning

confidence: 99%

In vitro inhibition of purified human carbonic anhydrase I and II by novel fluorene derivatives

Demirhan

Arslan

Kaya

et al. 2014

Maced. J. Chem. Chem. Eng.

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In this study, 9-benzylidene-9H-fluorene-substituted urea (5a-p) and thiourea derivatives (5q-v) were synthesized and their inhibitory effects on the activity of human carbonic anhydrase (hCA) I and II were evaluated. hCA I and II were purified from human erythrocytes using a Sepharose 4B-L-tyrosinesulphanilamide affinity column. All the synthesized compounds inhibited the activity of the hCA I and II isoenzymes. Among the synthesized compounds, 5f was found to be the most active (IC 50 = 21.4 μM) for inhibition of hCA I and 5s was the most active (IC 50 = 25.3 μM) for inhibition of hCA II. IN VITRO ИНХИБИЦИЈА НА ПРЕЧИСТЕНА ЧОВЕЧКА КАРБОНСКА АНХИДРАЗА I И II СО НОВИ ФЛУОРЕНСКИ ДЕРИВАТИВо оваа студија беа синтетизирани деривати на уреа (5a-p) и тиоуреа (5q-v) добиени со супституција на 9-безилиден-9H-флуорен и беше проценет нивниот инхибиторен ефект врз човечка карбонска анхидраза (hCA) I и II. HCA I и II беа пречистени од човечки еритроцити со употреба на афинитетната колона Sepharose 4B-L-тирозин-сулфаниламид. Сите синтетизирани соединенија ја инхибираа активноста на изоензимите на hCA I и II. Од синтетизираните соединенија, 5f се покажа најактивно (IC 50 = 21,4 μM) за инхибиција на hCA I, додека 5s беше најактивно (IC 50 = 25,3 μM) за инхибиција на hCA II.Клучни зборови: 9-безилиден-9H-флуорен; уреа; тиоуреа; карбонска анхидраза; инхибиција

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