Nano silver particles catalyzed synthesis, molecular docking and bioactivity of α-thiazolyl aminomethylene bisphosphonates

• Published in: Phosphorus, sulfur, and silicon and the related elements Vol. 195; no. 5; pp. 409 - 420
• Main Authors: Poola, Sreelakshmi, Gundluru, Mohan, Nadiveedhi, Maheshwara Reddy, Saddala, Madhu Sudhana, P. T. S. R. K., Prasada Rao, Cirandur, Suresh Reddy
• Format: Journal Article
• Language: English
• Published: ABINGDON Taylor & Francis 03.05.2020; Taylor & Francis Ltd
• Subjects: antibacterial; antifungal; antioxidant; Antioxidants; Aromatic compounds; Ascorbic acid; Bisphosphonates; Chemical synthesis; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Crystal structure; docking studies; Fungicides; Hydrogen peroxide; Inorganic salts; Methylene; Molecular docking; nano Ag particles; Phosphonates; Physical Sciences; Science & Technology; Silver; α-Thiazolyl aminomethylenebisphosphonates; antifungal; BONE-DISEASE; alpha-Thiazolyl aminomethylenebisphosphonates; antioxidant; docking studies; antibacterial; MECHANISMS; AGENTS; INHIBITORS; nano Ag particles
• ISSN: 1042-6507; 1563-5325
• DOI: 10.1080/10426507.2019.1700413

A new series of α-thiazolyl aminomethylene bisphosphonates were synthesized by a three component reaction of 4-aryl substituted thiazol-2-amine with different dialkyl/aryl phosphites and triethyl orthoformate in the presence of Ag NPs (nano particles) as a catalyst under solvent free conditions. All the synthesized target compounds were characterized by 1 H, 13 C, 31 P, mass and elemental analysis. The target compounds were screened for their in vitro antioxidant, antibacterial and antifungal activity. Molecular docking studies were also performed. The results revealed that among the synthesized compounds tetramethyl(((4-(4-methoxyphenyl)thiazol-2-yl)amino) methylene)bis(phosphonate) (5d), tetramethyl(((4-(4-fluorophenyl)thiazol-2-yl)amino) methylene) bis(phosphonate) (5h), and tetramethyl(((4-(4-bromophenyl)thiazol-2-yl)amino)methylene) bis (phosphonate) (5j) showed remarkably higher antioxidant activity by DPPH and H 2 O 2 than the standard ascorbic acid. Compounds tetramethyl(((4-phenyl thiazol-2-yl)amino) methylene) bis(phosphonate) (5a), 5d, 5h and tetraethyl(((4-(4-bromophenyl)thiazol-2-yl) amino)methylene)bis (phosphonate) (5k) showed good antibacterial activity. 5a, 5d, and 5h also showed rather higher antifungal activity than the standard flucanozole. Computational docking methods have been used to predict how several aminomethylene bisphosphonate derivatives compete against the inhibitor BPH-1330 at the crystal enzyme structure of the 4H3A protein active site and how R and R 1 influence their binding ability.