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. 2022 Oct 28:10:1046120.
doi: 10.3389/fchem.2022.1046120. eCollection 2022.

Poly(aniline- co-melamine)@MnFe2O4 nanocatalyst for the synthesis of 4,4'-(arylmethylene) bis (1H-pyrazole-5-ol) derivatives, and 1,4- dihydropyrano[2,3- c]pyrazoles and evaluation of their antioxidant, and anticancer activities

Shefa Mirani Nezhad  1 , Seied Ali Pourmousavi  1 , Ehsan Nazarzadeh Zare  1 , Golnaz Heidari  1 , Hamed Manoochehri  2 , Esmaeel Sharifi  3
Affiliations

Poly(aniline- co-melamine)@MnFe2O4 nanocatalyst for the synthesis of 4,4'-(arylmethylene) bis (1H-pyrazole-5-ol) derivatives, and 1,4- dihydropyrano[2,3- c]pyrazoles and evaluation of their antioxidant, and anticancer activities

Shefa Mirani Nezhad et al. Front Chem. .

Abstract

In this work, magnetic poly(aniline-co-melamine) nanocomposite as an efficient heterogeneous polymer-based nanocatalyst was fabricated in two steps. First, poly(aniline-co-melamine) was synthesized through the chemical oxidation by ammonium persulfate, then the magnetic nanocatalyst was successfully prepared from the in-situ coprecipitation method in the presence of poly(aniline-co-melamine). The resulting poly(aniline-co-melamine)@MnFe2O4 was characterized by FTIR, FESEM, XRD, VSM, EDX, TGA, and UV-vis analyses. The catalytic activity of poly(aniline-co-melamine)@MnFe2O4 was investigated in the synthesis of 4,4'-(arylmethylene)bis(1H-pyrazole-5-ol) derivatives, and new alkylene bridging bis 4,4'-(arylmethylene)bis(1H-pyrazole-5-ol) derivatives in excellent yields. The yield of 1,4-dihydropyrano[2,3-c]pyrazoles, 4,4'-(arylmethylene)bis(1H-pyrazol-5-ol), yields, and new alkylene bridging bis 4,4'-(arylmethylene)bis(1H-pyrazol-5-ol) derivatives were obtained 89%-96%, 90%-96%, and 92%-96%, respectively. The poly(aniline-co-melamine)@MnFe2O4 nanocatalyst can be recycled without pre-activation and reloaded up to five consecutive runs without a significant decrease in its efficiency. In addition, the antioxidant activity of some derivatives was evaluated by DPPH assay. Results showed that the maximum antioxidant activity of 4,4'-(arylmethylene)bis(1H-pyrazole-5-ol) derivatives and 1,4-dihydropyrano[2,3-c]pyrazoles were 75% and 90%, respectively. Furthermore, 4,4'-(arylmethylene)bis(1H-pyrazole-5-ol) derivatives and 1,4-dihydropyrano[2,3-c]pyrazoles showed good potential for destroying colon cancer cell lines. Consequently, the poly(aniline-co-melamine)@MnFe2O4 nanocomposite is an excellent catalyst for green chemical processes owing to its high catalytic activity, stability, and reusability.

Keywords: anticancer; antioxidant; nanocatalyst; poly(aniline-co-melamine)@MnFe2O4 nanocomposite; pyrazole derivatives.

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Conflict of interest statement

The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest. The reviewer AM declared a past co-authorship with the author EN to the handling editor.

Figures

FIGURE 1
FIGURE 1
Preparation of poly(aniline-co-melamine)@MnFe2O4 nanocomposite in two steps (A), synthesis of 1,4-dihydropyrano[2,3-c]pyrazoles (B), synthesis of 4,4′-(arylmethylene)bis(1H-pyrazole-5-ol) derivatives (C), and synthesis of bis 4,4′-(arylmethylene)bis(1H-pyrazole-5-ol) derivatives (D).
FIGURE 2
FIGURE 2
FTIR spectra of the prepared MnFe2O4 (A), poly(aniline-co-melamine) (B), and poly(aniline-co-melamine) @MnFe2O4 (C)
FIGURE 3
FIGURE 3
XRD patterns of the prepared MnFe2O4 (A), poly(aniline-co-melamine) (B), and poly(aniline-co-melamine) @MnFe2O4 (C).
FIGURE 4
FIGURE 4
TGA (A), and DTG thermograms (B) of the prepared MnFe2O4, poly(aniline-co-melamine), and poly(aniline-co-melamine) @MnFe2O4.
FIGURE 5
FIGURE 5
VSM curves of the prepared MnFe2O4 and poly(aniline-co-melamine)@MnFe2O4.
FIGURE 6
FIGURE 6
UV-vis absorption spectra of poly(aniline-co-melamine) and poly(aniline-co-melamine)@MnFe2O4 in DMSO solvent.
FIGURE 7
FIGURE 7
EDX spectra (A), and FESEM micrographs (B) of the prepared MnFe2O4, poly(aniline-co-melamine), and poly(aniline-co-melamine) @MnFe2O4 nanocomposite.
FIGURE 8
FIGURE 8
Suggested mechanistic scheme for the synthesis of 1,4-dihydropyrano[2,3-c]pyrazole catalyzed by poly(aniline-co-melamine)@Mn(Fe2O4). ℗ represents a polymer-based catalyst.
FIGURE 9
FIGURE 9
Suggested mechanistic scheme for the synthesis of 4,4′-(arylmethylene)bis(1H-pyrazole-5-ol) derivatives catalyzed by poly(aniline-co-melamine)@Mn(Fe2O4). ℗ represents polymer-based catalyst.
FIGURE 10
FIGURE 10
The structure of bis-4,4'-(arylmethylene)-bis-(3-methyl-1H-pyrazole-5-ols).
FIGURE 11
FIGURE 11
Reusability of poly(aniline-co-melamine)@MnFe2O4 in the synthesis 6- mino-3-methyl-1,4-diphenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (4a).
FIGURE 12
FIGURE 12
The photographs (A–C) and the histograms (D–F) of the antioxidant activity of synthesized of 1,4-dihydropyrano[2,3-c]pyrazoles (4q, 4f, 4g, 4i, 4d, and 4l), 4,4′-(arylmethylene)bis(1H-pyrazole-5-ol) (5a, 5b, 5c, 5d, 5e, 5h, 5i and 5q), bis 4,4'-(arylmethylene)bis(3-methyl-1H-pyrazol-5-ols) (6a, 6b, 6c, and 6d) derivatives.
FIGURE 13
FIGURE 13
Anticancer activity of 1,4-dihydropyrano[2,3-c]pyrazoles (4q, 4d, 4o, 4l), 4,4′-(arylmethylene)bis(1H-pyrazole-5-ol) (5i, 5j, 5q), bis 4,4'-(arylmethylene)bis(3-methyl-1H-pyrazol-5-ols) (6c) derivatives against HCT116 (A,B) and L929 (C,D) cell lines.
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