Design, Synthesis, in Vitro, and in Silico Evaluation of N-Phenylacetamide-Oxindole-Thiosemicarbazide Hybrids As New Potential Tyrosinase Inhibitors

Design, Synthesis, in Vitro, and in Silico Evaluation of N-Phenylacetamide-Oxindole-Thiosemicarbazide Hybrids As New Potential Tyrosinase Inhibitors Publisher Pubmed

Yari Boroujeni S¹ ; Haghighijoo Z² ; Mohammadikhanaposhtani M³ ; Mosadeghkhah A⁴ ; Moazzam A¹ ; Yavari A¹ ; Hajimahmoodi M⁵ ; Sabourian R⁵ ; Hosseini S⁶ ; Larijani B¹ ; Hamedifar H⁷ ; Ansari S⁷ ; Mahdavi M¹

Show Affiliations

1. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, 1417653761, Iran
2. Department of Chemistry, University of Louisiana at Lafayette, Lafayette, LA 70504, United States
3. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, 4717647745, Iran
4. Endocrinology department, Aja University of Medical Science, Tehran, Iran
5. Drug and Food Control Department, Faculty of Pharmacy, and Food and Drug Administration, Tehran University of Medical Sciences, Tehran, Iran
6. Shahid Beheshti University of Medical Sciences, Tehran, Iran
7. CinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran

Source: Chemistry and Biodiversity Published:2022

Abstract

A novel series of N-phenylacetamide-oxindole-thiosemicarbazide hybrids were synthesized and evaluated for their tyrosinase inhibitory activity. According to tyrosinase inhibition results, all the synthesized compounds showed high tyrosinase inhibitory activity with IC50 values ranging from 0.8 to 3.88 μM in comparison to positive control kojic acid with IC50 value of 36.32 μM. Among tested compounds, analog 7o, containing the 2-methyl-4-nitrophenyl on N-phenylacetamide moiety displayed superior tyrosinase inhibition. This compound was around 45-fold more potent than kojic acid. The kinetic analysis of compound 7o demonstrated that this compound is a competitive inhibitor against tyrosinase. Docking study of this compound demonstrated that compound 7o interacted with critical histidine residues within tyrosinase active site. © 2022 Wiley-VHCA AG, Zurich, Switzerland.

2. Kinetic Studies, Molecular Docking, and Antioxidant Activity of Novel 1,3-Diphenyl Pyrazole-Thiosemicarbazone With Anti-Tyrosinase and Anti-Melanogenesis Properties, Bioorganic Chemistry (2024)

3. Synthesis, Biological Evaluation, and Molecular Docking Analysis of Novel 1, 3, 4-Thiadiazole -Based Kojic Acid Derivatives As Tyrosinase Inhibitors, Journal of Molecular Structure (2022)

4. Design, Synthesis, Biological Evaluation, and Molecular Docking Study of Thioxo-2,3-Dihydroquinazolinone Derivative As Tyrosinase Inhibitors, Journal of Molecular Structure (2022)

5. Design, Synthesis, in Vitro, and in Silico Studies of Novel Benzylidene 6-Methoxy-1-Tetralone Linked to Benzyloxy and Benzyl -1,2,3- Triazole Rings As Potential Tyrosinase Inhibitors, Journal of Molecular Structure (2023)

6. Novel Morpholine Containing Cinnamoyl Amides As Potent Tyrosinase Inhibitors, International Journal of Biological Macromolecules (2019)

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Mohammad Mahdavi (5)

Bagher Larijani (3)

Style	Citing Format
MLA	Yari Boroujeni S, et al.. "Design, Synthesis, in Vitro, and in Silico Evaluation of N-Phenylacetamide-Oxindole-Thiosemicarbazide Hybrids As New Potential Tyrosinase Inhibitors." Chemistry and Biodiversity, vol. 19, no. 4, 2022, pp. -.
APA	Yari Boroujeni S, Haghighijoo Z, Mohammadikhanaposhtani M, Mosadeghkhah A, Moazzam A, Yavari A, Hajimahmoodi M, Sabourian R, Hosseini S, Larijani B, Hamedifar H, Ansari S, Mahdavi M (2022). Design, Synthesis, in Vitro, and in Silico Evaluation of N-Phenylacetamide-Oxindole-Thiosemicarbazide Hybrids As New Potential Tyrosinase Inhibitors. Chemistry and Biodiversity, 19(4), -.
Chicago	Yari Boroujeni S, Haghighijoo Z, Mohammadikhanaposhtani M, Mosadeghkhah A, Moazzam A, Yavari A, Hajimahmoodi M, et al.. "Design, Synthesis, in Vitro, and in Silico Evaluation of N-Phenylacetamide-Oxindole-Thiosemicarbazide Hybrids As New Potential Tyrosinase Inhibitors." Chemistry and Biodiversity 19, no. 4 (2022): -.
Harvard	Yari Boroujeni S et al. (2022) 'Design, Synthesis, in Vitro, and in Silico Evaluation of N-Phenylacetamide-Oxindole-Thiosemicarbazide Hybrids As New Potential Tyrosinase Inhibitors', Chemistry and Biodiversity, 19(4), pp. -.
Vancouver	Yari Boroujeni S, Haghighijoo Z, Mohammadikhanaposhtani M, Mosadeghkhah A, Moazzam A, Yavari A, et al.. Design, Synthesis, in Vitro, and in Silico Evaluation of N-Phenylacetamide-Oxindole-Thiosemicarbazide Hybrids As New Potential Tyrosinase Inhibitors. Chemistry and Biodiversity. 2022;19(4):-.
BibTex	@article{ author = {Yari Boroujeni S and Haghighijoo Z and Mohammadikhanaposhtani M and Mosadeghkhah A and Moazzam A and Yavari A and Hajimahmoodi M and Sabourian R and Hosseini S and Larijani B and Hamedifar H and Ansari S and Mahdavi M}, title = {Design, Synthesis, in Vitro, and in Silico Evaluation of N-Phenylacetamide-Oxindole-Thiosemicarbazide Hybrids As New Potential Tyrosinase Inhibitors}, journal = {Chemistry and Biodiversity}, volume = {19}, number = {4}, pages = {-}, year = {2022} }
RIS	TY - JOUR AU - Yari Boroujeni S AU - Haghighijoo Z AU - Mohammadikhanaposhtani M AU - Mosadeghkhah A AU - Moazzam A AU - Yavari A AU - Hajimahmoodi M AU - Sabourian R AU - Hosseini S AU - Larijani B AU - Hamedifar H AU - Ansari S AU - Mahdavi M TI - Design, Synthesis, in Vitro, and in Silico Evaluation of N-Phenylacetamide-Oxindole-Thiosemicarbazide Hybrids As New Potential Tyrosinase Inhibitors JO - Chemistry and Biodiversity VL - 19 IS - 4 SP - EP - PY - 2022 ER -

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