1-(3-Acetylphenyl)-2-(2-oxidonaphthalen-1-yl)diazen-1-ium

Bougueria, Hassiba; Benosmane, Ali; Benaouida, Mohamed Amine; Bouchoul, Abd el kader; Bouaoud, Salah-Eddine

doi:10.1107/s1600536813014918

Cited by 6 publications

(4 citation statements)

References 8 publications

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“…The N1-N2, C1-N1, C7-N2 and C8-O1 bond lengths are 1.312 (4), 1.394 (5), 1.330 (5) and 1.276 (5) A ˚, respectively, indicating that the dye compound has crystallized in the hydrazone tautomeric form (i.e. proton transfer from the naphthol group to the azo group); bond lengths and angles are within normal ranges and are comparable to those reported for other azo compounds (Benaouida et al, 2013;Bougueria, Benosmane et al, 2013;Mili et al, 2013;Xu et al, 2010). The molecule adopts an s-trans conformation, with the two aryl groups residing on the opposite side of the azo group.…”

Section: Structural Commentarysupporting

confidence: 74%

Crystal structure and Hirshfeld surface analysis of 1-[(E)-2-(3-nitrophenyl)diazen-1-yl]naphthalen-2-ol

et al. 2023

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The title compound, C16H11N3O3, belongs to the family of azo dyes. In the light of a single-crystal X-ray study, it is evident that of the tautomeric forms (azo–hydrazone), the hydrazone form is the predominant form in the solid state, namely, (1E)-1-[2-(3-nitrophenyl)hydrazin-1-ylidene]-1,2-dihydronaphthalen-2-one. The naphthol and benzene fragments attached to the –N=N– moiety adopt the s-trans conformation. Furthermore, the molecules are nearly coplanar, subtending a dihedral angle of 2.63 (5)°. An intramolecular N—H...O hydrogen bond occurs. There are only two types of intermolecular interactions in the crystal structure: strong hydrogen-bonding C—H...O interactions and π–π stacking interactions. The importance of C—H...O interactions in the molecular packing is reflected by the relatively high contributions (28.5%) made by O...H/H...O contacts to the Hirshfeld surface.

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Section: Structural Commentarysupporting

confidence: 74%

Crystal structure and Hirshfeld surface analysis of 1-[(E)-2-(3-nitrophenyl)diazen-1-yl]naphthalen-2-ol

et al. 2023

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“…Consequently, the CCDC was searched for phenylazopyrimidine scaffolds and azo scaffolds containing desired functional groups, but none were found. The CCDC entries AFIHAA, KEBJIM, POQFIM, and YEJNAC − provided the best scaffolds for comparison with the four analog dyes. C.I.…”

Section: Resultsmentioning

confidence: 99%

Toward the Rational Design of Sustainable Hair Dyes Using Cheminformatics Approaches: Step 2. Identification of Hair Dye Substance Database Analogs in the Max Weaver Dye Library

Williams

Driessche

Valery

et al. 2018

ACS Sustainable Chem. Eng.

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We report on part 2 of the cheminformatics-assisted development of sustainable hair dyes with enhanced technical and toxicological properties. In this study, an initial similarity search analysis was performed using two reference probes (C.I. Basic Orange 1 and Orange 2) as structural templates for the identification of potential analogs among the Max Weaver Dye Library (MWDL). The analysis revealed an interesting subset of 158 MWDL compounds that were close analogs of the classical aminoazobenzene dyes. A more detailed similarity search analysis of this subset ultimately led to the selection of four dyes for further in silico quantum calculations and experimental dye uptake (color depth on hair) studies. Results from quantum calculations indicated that the ESP surface properties of these dyes were consistent with nonionic interactions between dye and keratin. Among the four dye analogs, 2-amino-6-methyl-5-(phenyldiazenyl)pyrimidin-4-ol and 2-amino-4-chloro-1,6-dimethyl-5-(phenyldiazenyl)-pyrimidin-1-ium methyl sulfate achieved the best dye uptake on hair (∑K/S 227.31 and 149.26). The results of this study show that cheminformatics-based tools can be used to both build and screen dye databases containing potential alternatives to colorants believed to pose environmental concerns, providing a more sustainable (green) approach to hair dye design, by reducing the number of compounds requiring synthesis and analysis before suitable replacements are identified.

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“…The 2D structures were converted into 3D, then reduced, minimized, and optimized using MMFF94 force field through Avogadro software (Ver. 1.2.0) [26]. Blind docking was performed using a web-based program called CB-DOCK, accessed on 24 December 2021, and 15 and 16 January 2022 (http://clab.labshare.cn/cb-dock/php/).…”

Section: Molecular Dockingmentioning

confidence: 99%

EGFR and COX-2 Dual Inhibitor: The Design, Synthesis, and Biological Evaluation of Novel Chalcones

et al. 2022

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For most researchers, discovering new anticancer drugs to avoid the adverse effects of current ones, to improve therapeutic benefits and to reduce resistance is essential. Because the COX-2 enzyme plays an important role in various types of cancer leading to malignancy enhancement, inhibition of apoptosis, and tumor-cell metastasis, an indispensable objective is to design new scaffolds or drugs that possess combined action or dual effect, such as kinase and COX-2 inhibition. The start compounds A1 to A6 were prepared through the diazo coupling of 3-aminoacetophenone with a corresponding phenol and then condensed with two new chalcone series, C7–18. The newly synthesized compounds were assessed against both COX-2 and epidermal growth factor receptor (EGFR) for their inhibitory effect. All novel compounds were screened for cytotoxicity against five cancer cell lines. Compounds C9 and G10 exhibited potent EGFR inhibition with IC50 values of 0.8 and 1.1 µM, respectively. Additionally, they also displayed great COX-2 inhibition with IC50 values of 1.27 and 1.88 µM, respectively. Furthermore, the target compounds were assessed for their cytotoxicity against pancreatic ductal cancer (Panc-1), lung cancer (H-460), human colon cancer (HT-29), human malignant melanoma (A375) and pancreatic cancer (PaCa-2) cell lines. Interestingly, compounds C10 and G12 exhibited the strongest cytotoxic effect against PaCa-2 with average IC50 values of 0.9 and 0.8 µM, respectively. To understand the possible binding modes of the compounds under investigation with the receptor cites of EGFR and COX-2, a virtual docking study was conducted.

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1-(3-Acetylphenyl)-2-(2-oxidonaphthalen-1-yl)diazen-1-ium

Cited by 6 publications

References 8 publications

Crystal structure and Hirshfeld surface analysis of 1-[(E)-2-(3-nitrophenyl)diazen-1-yl]naphthalen-2-ol

Crystal structure and Hirshfeld surface analysis of 1-[(E)-2-(3-nitrophenyl)diazen-1-yl]naphthalen-2-ol

Toward the Rational Design of Sustainable Hair Dyes Using Cheminformatics Approaches: Step 2. Identification of Hair Dye Substance Database Analogs in the Max Weaver Dye Library

EGFR and COX-2 Dual Inhibitor: The Design, Synthesis, and Biological Evaluation of Novel Chalcones

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