Crystal Structure of (&lt;i&gt;E&lt;/i&gt;)-1-(3,4-Methylenedioxy-6-fluorophenyl)-2-nitropropene

Guillon, Jean; Ronga, Luisa; Marchivie, Mathieu; Moreau, Stéphane

doi:10.2116/xraystruct.32.23

Cited by 1 publication

(2 citation statements)

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“…Figure 4B represents the molecular structure of compound 19f and confirmed the (E)-configuration of the nitrovinyl group together with the π-π stacking interactions (Figure 4C). The bond distances and torsional angles determined for the aromatic ring and the nitrobutene substituents in compound 19f were in close agreement with the reported values for related β-methyl-β-nitrostyrenes [39,64,65]. The nitrostyrene C=C bond was observed at 1.323(3)Å for compound 19f (C(15)-C( 16)), similar to 1.332(2) Å reported for the (E)-1-(3,4-methylene-dioxy-6-fluorophenyl)-2-nitropropene [64].…”

Section: Chemistrysupporting

confidence: 87%

“…The bond distances and torsional angles determined for the aromatic ring and the nitrobutene substituents in compound 19f were in close agreement with the reported values for related β-methyl-β-nitrostyrenes [39,64,65]. The nitrostyrene C=C bond was observed at 1.323(3)Å for compound 19f (C(15)-C( 16)), similar to 1.332(2) Å reported for the (E)-1-(3,4-methylene-dioxy-6-fluorophenyl)-2-nitropropene [64]. The nitro and ethyl substituents on the alkene were out of the plane of the anthracene ring, with a torsional angle for C( 7)-(C8)-(C15)-(C16) of 108.8(3)° (Figure 4 and Supplementary Information, Figure S21).…”

Section: Chemistrysupporting

confidence: 87%

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Synthesis and Pro-Apoptotic Effects of Nitrovinylanthracenes and Related Compounds in Chronic Lymphocytic Leukaemia (CLL) and Burkitt’s Lymphoma (BL)

Byrne,

Bright,

McKeown

et al. 2023

Molecules

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Chronic lymphocytic leukaemia (CLL) is a malignancy of the immune B lymphocyte cells and is the most common leukaemia diagnosed in developed countries. In this paper, we report the synthesis and antiproliferative effects of a series of (E)-9-(2-nitrovinyl)anthracenes and related nitrostyrene compounds in CLL cell lines and also in Burkitt’s lymphoma (BL) cell lines, a rare form of non-Hodgkin’s immune B-cell lymphoma. The nitrostyrene scaffold was identified as a lead structure for the development of effective compounds targeting BL and CLL. The series of structurally diverse nitrostyrenes was synthesised via Henry–Knoevenagel condensation reactions. Single-crystal X-ray analysis confirmed the structure of (E)-9-chloro-10-(2-nitrobut-1-en-1-yl)anthracene (19f) and the related 4-(anthracen-9-yl)-1H-1,2,3-triazole (30a). The (E)-9-(2-nitrovinyl)anthracenes 19a, 19g and 19i–19m were found to elicit potent antiproliferative effects in both BL cell lines EBV−MUTU-1 (chemosensitive) and EBV+ DG-75 (chemoresistant) with >90% inhibition at 10 μM. Selected (E)-9-(2-nitrovinyl)anthracenes demonstrated potent antiproliferative activity in CLL cell lines, with IC50 values of 0.17 μM (HG-3) and 1.3 μM (PGA-1) for compound 19g. The pro-apoptotic effects of the most potent compounds 19a, 19g, 19i, 19l and 19m were demonstrated in both CLL cell lines HG-3 and PGA-1. The (E)-nitrostyrene and (E)-9-(2-nitrovinyl)anthracene series of compounds offer potential for further development as novel chemotherapeutics for CLL.

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