Synthesis, Crystal Structure, and Photophysical Properties of 4-(4-(Dimethylamino)phenyl)-6-phenylpyrimidin-2-amine

Mellado, Marco; Sariego-Kluge, Rafaela; Valdés-Navarro, Franco; Sánchez‐González, Rodrigo; Fuentealba, Mauricio; Bravo, Manuel; Aguilar, Luís Fuentes

doi:10.1016/j.molstruc.2020.129340

Cited by 8 publications

(5 citation statements)

References 34 publications

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“…Synthesis of the chalcones 5a–u was carried out using the Claisen‐Schmidt reaction in alkaline media according to previous reports from our research group (see Supporting Information). [ 13,14,30 ]…”

Section: Methodsmentioning

confidence: 99%

“…reaction in alkaline media according to previous reports from our research group (see Supporting Information). [13,14,30] The designed compounds were synthesized according to Schemes 1 and 2. Natural acetophenone 6 was isolated from Senecio graveolens according to a previous report by our research group.…”

Section: S C H E M E 2 Synthetic Steps To Obtain Chalcone Derivatives...mentioning

confidence: 99%

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QSAR‐driven synthesis of antiproliferative chalcones against SH‐SY5Y cancer cells: Design, biological evaluation, and redesign

Mellado

Reyna-Jeldes

Weinstein‐Oppenheimer

et al. 2022

Archiv der Pharmazie

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Neuroblastoma is one of the most frequent types of cancer found in infants, and traditional chemotherapy has limited efficacy against this pathology. Thus, the development of new compounds with higher activity and selectivity than traditional drugs is a current challenge in medicinal chemistry research. In this study, we report the synthesis of 21 chalcones with antiproliferative activity and selectivity against the neuroblastoma cell line SH‐SY5Y. Then, we developed three‐dimensional quantitative structure–activity relationship models (comparative molecular field analysis and comparative molecular similarity index analysis) with high‐quality statistical values (q2 > 0.7; r2 > 0.8; r2pred > 0.7), using IC50 and selectivity index (SI) data as dependent variables. With the information derived from these theoretical models, we designed and synthesized 16 new molecules to prove their consistency, finding good antiproliferative activity against SH‐SY5Y cells on these derivatives, with three of them showing higher SI than the referential drugs 5‐fluorouracil and cisplatin, displaying also a proapoptotic effect comparable to these drugs, as proven by measuring their effects on executor caspases 3/7 activity induction, Bcl‐2/Bax messenger RNA levels alteration, and DNA fragmentation promotion.

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Section: Methodsmentioning

confidence: 99%

Section: S C H E M E 2 Synthetic Steps To Obtain Chalcone Derivatives...mentioning

confidence: 99%

QSAR‐driven synthesis of antiproliferative chalcones against SH‐SY5Y cancer cells: Design, biological evaluation, and redesign

Mellado

Reyna-Jeldes

Weinstein‐Oppenheimer

et al. 2022

Archiv der Pharmazie

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“…The photophysical properties of the iron (III) complex (C1) were assessed from a stock dissolution at a concentration of 1.0 × 10 −2 M in DMSO and stored in the dark at −4 °C [24][25][26]. From the stock solution, absorption properties were measured using dilutions…”

Section: Photophysical Characterization and Chemosensing Capacity Ass...mentioning

confidence: 99%

“…The photophysical properties of the iron (III) complex (C1) were assessed from a stock dissolution at a concentration of 1.0 × 10 −2 M in DMSO and stored in the dark at −4 • C [24][25][26]. From the stock solution, absorption properties were measured using dilutions in acetonitrile, obtaining a maximum absorption wavelength at λ Abs = 330 nm and an absorption coefficient ε = 5358.5 M −1 •cm −1 corresponding to the π → π* transition, while the maximum absorption wavelength at λ Abs = 504 nm with an absorption coefficient ε = 1812.3 M −1 •cm −1 could be assigned to the charge-transfer transition metal → ligand (Figure S3) [22].…”

Section: Photophysical Characterization and Chemosensing Capacity Ass...mentioning

confidence: 99%

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A pH-Sensitive Fluorescent Chemosensor Turn-On Based in a Salen Iron (III) Complex: Synthesis, Photophysical Properties, and Live-Cell Imaging Application

Nilo,

Reyna-Jeldes,

Covarrubias

et al. 2023

Molecules

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pH regulation is essential to allow normal cell function, and their imbalance is associated with different pathologic situations, including cancer. In this study, we present the synthesis of 2-(((2-aminoethyl)imino)methyl)phenol (HL1) and the iron (III) complex (Fe(L1)2Br, (C1)), confirmed by X-ray diffraction analysis. The absorption and emission properties of complex C1 were assessed in the presence and absence of different physiologically relevant analytes, finding a fluorescent turn-on when OH− was added. So, we determined the limit of detection (LOD = 3.97 × 10−9 M), stoichiometry (1:1), and association constant (Kas = 5.86 × 103 M−1). Using DFT calculations, we proposed a spontaneous decomposition mechanism for C1. After characterization, complex C1 was evaluated as an intracellular pH chemosensor on the human primary gastric adenocarcinoma (AGS) and non-tumoral gastric epithelia (GES-1) cell lines, finding fluorescent signal activation in the latter when compared to AGS cells due to the lower intracellular pH of AGS cells caused by the increased metabolic rate. However, when complex C1 was used on metastatic cancer cell lines (MKN-45 and MKN-74), a fluorescent turn-on was observed in both cell lines because the intracellular lactate amount increased. Our results could provide insights about the application of complex C1 as a metabolic probe to be used in cancer cell imaging.

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A high‐yielding protocol for the synthesis of 4,5‐diarylpyrimidin‐2‐amine derivatives from chalcones

Unni

Menon

George

et al. 2021

Journal of Heterocyclic Chem

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Synthesis, Crystal Structure, and Photophysical Properties of 4-(4-(Dimethylamino)phenyl)-6-phenylpyrimidin-2-amine

Cited by 8 publications

References 34 publications

QSAR‐driven synthesis of antiproliferative chalcones against SH‐SY5Y cancer cells: Design, biological evaluation, and redesign

QSAR‐driven synthesis of antiproliferative chalcones against SH‐SY5Y cancer cells: Design, biological evaluation, and redesign

A pH-Sensitive Fluorescent Chemosensor Turn-On Based in a Salen Iron (III) Complex: Synthesis, Photophysical Properties, and Live-Cell Imaging Application

A high‐yielding protocol for the synthesis of 4,5‐diarylpyrimidin‐2‐amine derivatives from chalcones

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