Regioselectivity in the Addition of Grignard Reagents to Bis(2‐benzothiazolyl) Ketone: <i>C</i>‐ vs. <i>O</i>‐Alkylation Using Aryl Grignard Reagents

Boga, Carla; Micheletti, Gabriele

doi:10.1002/ejoc.201000764

Cited by 3 publications

(2 citation statements)

References 27 publications

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“…Pentatomic-aza-heteroaromatics bearing two different heteroatoms, such as thiazoles or imidazoles, together with their benzocondensated derivatives, are also found in many natural compounds and are of great importance as bioactive compounds [7,8]. For a long time, our interest focused on the synthesis and reactivity of thiazoles and benzothiazole derivatives [9][10][11][12][13][14][15]. Recently, we performed a S N Ar reaction between 2-aminobenzothiazole derivatives and 7-chloro-4,6-dinitrobenzofuroxan, and we exploited the action of the products toward the natural strain in Vibrio genus and different bacterial lux-biosensors [16].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Structural Hybrids between Aza-Heterocycles and Azelaic Acid Moiety with a Specific Activity on Osteosarcoma Cells

et al. 2020

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Nine compounds bearing pyridinyl (or piperidinyl, benzimidazolyl, benzotriazolyl) groups bound to an azelayl moiety through an amide bond were synthesized. The structural analogy with some histone deacetylase inhibitors inspired their syntheses, seeking new selective histone deacetylase inhibitors (HDACi). The azelayl moiety recalls part of 9-hydroxystearic acid, a cellular lipid showing antiproliferative activity toward cancer cells with HDAC as a molecular target. Azelayl derivatives bound to a benzothiazolyl moiety further proved to be active as HDACi. The novel compounds were tested on a panel of both normal and tumor cell lines. Non-specific induction of cytotoxicity was observed in the normal cell line, while three of them induced a biological effect only on the osteosarcoma (U2OS) cell line. One of them induced a change in nuclear shape and size. Cell-cycle alterations are associated with post-transcriptional modification of both H2/H3 and H4 histones. In line with recent studies, revealing unexpected HDAC7 function in osteoclasts, molecular docking studies on the active molecules predicted their proneness to interact with HDAC7. By reducing side effects associated with the action of the first-generation inhibitors, the herein reported compounds, thus, sound promising as selective HDACi.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Structural Hybrids between Aza-Heterocycles and Azelaic Acid Moiety with a Specific Activity on Osteosarcoma Cells

et al. 2020

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“…More recently, we discovered that phenyl lithium and phenyl Grignard reagents also produced a mixture of C - and O -alkylation species; the relative ratio is dependent on the substituent on the phenyl ring [ 13 ].…”

Section: Introductionmentioning

confidence: 99%

Regioselectivity in Reactions between Bis(2-benzothiazolyl)ketone and Vinyl Grignard Reagents: C- versus O-alkylation—Part III

et al. 2018

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Abstract:The reaction between bis(2-benzothiazolyl)ketone and vinyl Grignard reagents bearing different substituents on the vinyl moiety gave the product derived from attack on the carbonylic carbon-and/or oxygen-atom. The regioselectivity of the attack depends on the kind of substituents bound to the vinylic carbon atoms and on their relative position. The reaction between vinylmagnesium bromide and 2-methyl-1-propenylmagnesium bromide was carried out under different experimental conditions and in the presence of radical scavengers. The results indicate a plausible mechanistic pathway involving radical intermediates in the case of O-alkylation, but a polar ones in the case of classic C-alkylation. This agrees with our previous reports indicating a key role played by the delocalization ability of the substituents bound to the carbonyl group in driving the regioselectivity of the vinylmagnesium bromide attack towards O-alkylation. Further support of this was obtained by diffractometric analysis of four distinct bis(heteroaryl)ketones.

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Asymmetric addition of benzothiazole to N-tert-butanesulfinyl imine for the synthesis of chiral α-branched heteroaryl amines

Zhang

Yang

Mei

et al. 2012

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Regioselectivity in the Addition of Grignard Reagents to Bis(2‐benzothiazolyl) Ketone: C‐ vs. O‐Alkylation Using Aryl Grignard Reagents

Cited by 3 publications

References 27 publications

Synthesis of Novel Structural Hybrids between Aza-Heterocycles and Azelaic Acid Moiety with a Specific Activity on Osteosarcoma Cells

Synthesis of Novel Structural Hybrids between Aza-Heterocycles and Azelaic Acid Moiety with a Specific Activity on Osteosarcoma Cells

Regioselectivity in Reactions between Bis(2-benzothiazolyl)ketone and Vinyl Grignard Reagents: C- versus O-alkylation—Part III

Asymmetric addition of benzothiazole to N-tert-butanesulfinyl imine for the synthesis of chiral α-branched heteroaryl amines

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