The Reactions of Unsaturated Ketones and Derivatives with Amino Compounds. Amino Ketones.

Cromwell, Norman H.

doi:10.1021/cr60119a003

Cited by 76 publications

(24 citation statements)

References 68 publications

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“…Removal of the methyl group (9) produced a cytotoxic activity comparable to 1. Moreover, either the introduction of differently sterically-hindered alkyls (11)(12)(13) or a phenyl group (14) slightly reduced the cytotoxicity. In contrast, replacement of the methyl group with an acetyl group (10) completely abolished activity.…”

Section: Biological Evaluationmentioning

confidence: 99%

“…1 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 (14). 14 was prepared according to the general procedure for the synthesis of secondary amines, starting from 32c (74.1 mg, 0.25 mmol), 31b (45.0 mg, 0.25 mmol) and NaBH(OAc) 3 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 …”

Section: -[[[1-(2-fluorophenyl)cyclopentyl]amino]methyl]-2-(piperazimentioning

confidence: 99%

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Synthesis and in Vitro Anticancer Activity of the First Class of Dual Inhibitors of REV-ERBβ and Autophagy

et al. 2015

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Autophagy inhibition is emerging as a promising anticancer strategy. We recently reported that the circadian nuclear receptor REV-ERBβ plays an unexpected role in sustaining cancer cell survival when the autophagy flux is compromised. We also identified 4-[[[1-(2-fluorophenyl)cyclopentyl]amino]methyl]-2-[(4-methylpiperazin-1-yl)methyl]phenol, 1 (ARN5187), as a novel dual inhibitor of REV-ERBβ and autophagy. 1 had improved cytotoxicity against BT-474 breast cancer cells compared to chloroquine, a clinically relevant autophagy inhibitor. Here, we present the results of structure-activity studies, based around 1, that disclose the first class of dual inhibitors of REV-ERBβ and autophagy. This study led to identification of 18 and 28, which were more effective REV-ERBβ antagonists than 1 and were more cytotoxic to BT-474. The combination of optimal chemical and structural moieties of these analogs generated 30, which elicited 15-fold greater REV-ERBβ inhibitory and cytotoxic activities compared to 1. Furthermore, 30 induced death in a panel of tumor cell lines at doses 5-50 times lower than an equitoxic amount of chloroquine but did not affect the viability of normal mammary epithelial cells.

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Section: Biological Evaluationmentioning

confidence: 99%

Section: -[[[1-(2-fluorophenyl)cyclopentyl]amino]methyl]-2-(piperazimentioning

confidence: 99%

Synthesis and in Vitro Anticancer Activity of the First Class of Dual Inhibitors of REV-ERBβ and Autophagy

et al. 2015

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“…-ketoimines are common Schiff bases that can be obtained from traditional 1 : 1 (50% mole excess) condensation of a -diketone with primary amine [20]. These bases have three tautomers (Schiff base, ketamine and enimine), and they can exist in any of three forms.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structure and olefin polymerization catalysis of nickel(II) complexes bearing N,O-chelate ligands

Gui

Bao

Gao

et al. 2006

Journal of Coordination Chemistry

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Four -ketoimine ligands (two series) were prepared through traditional condensation reactions of -diketones with 2,6-substituted anilines. Reaction took place only at the cyclohexanone carbonyl rather than at the acetyl or benzoyl carbonyl, even if more than two equivalents of the amines were added. Consequently, four new moisture-and air-stable bis(-ketoamino)nickel(II) complexes, Ni[2-CH 3 C(O)C 6 H 8 (¼NAr)] 2 (Ar ¼ 2, 6-iPr 2 C 6 H 3 , (1); Ar ¼ 2, 6-Me 2 C 6 H 3 , (2) and Ni[2-PhC(O)C 6 H 8 (¼NAr)] 2 (Ar ¼ 2, 6-iPr 2 C 6 H 3 , (3); Ar ¼ 2, 6-Me 2 C 6 H 3 , (4) were obtained and characterized. The solid-state structures of complex 1, 2 and 3 have been determined by single-crystal X-ray diffraction. Additionally, these complexes can be applied as highly active catalyst precursors for vinyl polymerization of norbornene (NBE) after activation with methylaluminoxane (MAO).

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“…Diese Resultate bestatigen die heute vorherrschende Auffassung [ 2 ] , [6], [12], [13], dass vinyloge h i d e praktisch vollstandig in der Enonamin-Form 2a vorliegen, wie auf Grund der durch Mesomerie gemass 18 und 19 modifizierten Bindungsenergien der beiden Formen zu erwarten wares). Ein von dieser Regel abweichendes Verhalten wird nur in Fallen beobachtet, in welchen die Enolimin-Form aus besonderen Grunden eine Stabilisierung erfahrt.…”

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Die Enonamin‐Enolimin‐Tautomerie

Grob

Wilkens

1967

Helvetica Chimica Acta

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A study of the ultraviolet, infrared, and nuclear magnetic resonance spectra of Δ8,9‐octahydro‐7‐quinolone (7a) and of the corresponding N‐ and O‐ethyl derivatives 8 and 9, respectively, confirms that in cases of potential enonamine‐enolimine tautomerism the enonamine form predominates. This also applies to vinylogous amides capable of intramolecular hydrogen bonding, such as 2‐benzylaminomethylene‐ and 2‐phenylaminomethylene‐cyclohexanone, 10 and 11, respectively. Exeptions are only observed in cases where the enolimine form is stabilized by special factors, such as aromaticity.

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The Reactions of Unsaturated Ketones and Derivatives with Amino Compounds. Amino Ketones.

Cited by 76 publications

References 68 publications

Synthesis and in Vitro Anticancer Activity of the First Class of Dual Inhibitors of REV-ERBβ and Autophagy

Synthesis and in Vitro Anticancer Activity of the First Class of Dual Inhibitors of REV-ERBβ and Autophagy

Synthesis, structure and olefin polymerization catalysis of nickel(II) complexes bearing N,O-chelate ligands

Die Enonamin‐Enolimin‐Tautomerie

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