Synthesis of BF3 catalyzed Mannich derivatives with excellent ee from phenylpropanolamine, study of their antimicrobial activity and molecular docking

Rao, K. Chennakesava; Easwaramoorthi, K.; Arun, Y.; Balachandran, C.; Rao, K. Srinivasa; Govindhan, M.; Emi, Nobuhiko; Prakasam, Tangirala; Perumal, Paramasivan T.

doi:10.1016/j.bmcl.2015.07.096

Cited by 4 publications

(1 citation statement)

References 37 publications

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“…The synthesized compounds were subjected to molecular docking studies [15] with the DNA topoisomerase IV [21,22,23] and anaplastic lymphoma kinase [24] receptors in order to rationalize the biological studies. The docking study of the synthesized compounds was performed using AutoDock Tools (ADT) version 1.5.6 and AutoDock version 4.2.5.1 docking program [25,26] with the crystal structure of DNA topoisomerase IV (PDB ID: 4EMV) and anaplastic lymphoma kinase (PDB ID: 2XP2) [27].…”

Section: Resultsmentioning

confidence: 99%

A New Class of β–Pyrrolidino-1,2,3-Triazole Derivatives as β-Adrenergic Receptor Inhibitors: Synthesis, Pharmacological, and Docking Studies

Easwaramoorthi¹,

Rajendran²,

Rao

et al. 2019

Molecules

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New 1,4-disubstituted β-pyrrolidino-1,2,3-triazoles were synthesized using a reusable copper-iodide-doped neutral alumina catalyst. Synthesis of diversely substituted triazoles and recyclability of CuI catalyst explains the broad scope of this protocol. The synthesized compounds were screened for their antimicrobial and anticancer properties. Most of the compounds showed significant antimicrobial activities against all the tested microorganisms compared to standard drugs. Furthermore, compounds 5a, 5e, 5g, 5h, 5i, and 5j showed moderate to potent activities against A549 and HepG-2 cells. In addition, compounds 5g and 5h displayed potential cytotoxicity activity against A549 cells with IC50 values of 72 ± 3.21 and 58 ± 2.31 µM, respectively. The molecular docking study revealed that some of the synthesized compounds exhibited comparable binding as co-crystalized ligands with the DNA topoisomerase IV and anaplastic lymphoma kinase receptors.

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Section: Resultsmentioning

confidence: 99%

A New Class of β–Pyrrolidino-1,2,3-Triazole Derivatives as β-Adrenergic Receptor Inhibitors: Synthesis, Pharmacological, and Docking Studies

Easwaramoorthi¹,

Rajendran²,

Rao

et al. 2019

Molecules

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ChemInform Abstract: Synthesis of BF₃ Catalyzed Mannich Derivatives with Excellent ee from Phenylpropanolamine, Study of Their Antimicrobial Activity and Molecular Docking.

et al. 2016

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Antimicrobial agents [(IV) and (VI)] are synthesized with 100% e.e. by BF 3-catalyzed three-component one-pot Mannich reaction in good yields. The products are shown to exhibit good to very high potential activity against microbes and significant minimum inhibitory concentration values against Gram positive and Gram negative bacteria. -(CHENNAKESAVA RAO, K.; EASWARAMOORTHI, K.; ARUN, Y.; BALACHANDRAN, C.; MURALIDHARA RAO, K. S.; GOVINDHAN, M.; EMI, N.; PRAKASAM, T.; PERUMAL*, P. T.; Bioorg. Med. Chem. Lett. 25 (2015) 19, 4232-4238, http://dx.

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An Efficient Synthesis of 1,3‐Diphenyl‐3‐phenylamino‐propan‐1‐one and its Derivatives by Mannich Reaction in the Presence of Doped Porous Carbon by Nitrogen and Sulfur (NS‐PCS) as Catalyst

Mansoori

Lari

2017

J Chinese Chemical Soc

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Synthesis of BF3 catalyzed Mannich derivatives with excellent ee from phenylpropanolamine, study of their antimicrobial activity and molecular docking

Cited by 4 publications

References 37 publications

A New Class of β–Pyrrolidino-1,2,3-Triazole Derivatives as β-Adrenergic Receptor Inhibitors: Synthesis, Pharmacological, and Docking Studies

A New Class of β–Pyrrolidino-1,2,3-Triazole Derivatives as β-Adrenergic Receptor Inhibitors: Synthesis, Pharmacological, and Docking Studies

ChemInform Abstract: Synthesis of BF₃ Catalyzed Mannich Derivatives with Excellent ee from Phenylpropanolamine, Study of Their Antimicrobial Activity and Molecular Docking.

An Efficient Synthesis of 1,3‐Diphenyl‐3‐phenylamino‐propan‐1‐one and its Derivatives by Mannich Reaction in the Presence of Doped Porous Carbon by Nitrogen and Sulfur (NS‐PCS) as Catalyst

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Synthesis of BF3 catalyzed Mannich derivatives with excellent ee from phenylpropanolamine, study of their antimicrobial activity and molecular docking

Cited by 4 publications

References 37 publications

A New Class of β–Pyrrolidino-1,2,3-Triazole Derivatives as β-Adrenergic Receptor Inhibitors: Synthesis, Pharmacological, and Docking Studies

A New Class of β–Pyrrolidino-1,2,3-Triazole Derivatives as β-Adrenergic Receptor Inhibitors: Synthesis, Pharmacological, and Docking Studies

ChemInform Abstract: Synthesis of BF3 Catalyzed Mannich Derivatives with Excellent ee from Phenylpropanolamine, Study of Their Antimicrobial Activity and Molecular Docking.

An Efficient Synthesis of 1,3‐Diphenyl‐3‐phenylamino‐propan‐1‐one and its Derivatives by Mannich Reaction in the Presence of Doped Porous Carbon by Nitrogen and Sulfur (NS‐PCS) as Catalyst

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ChemInform Abstract: Synthesis of BF₃ Catalyzed Mannich Derivatives with Excellent ee from Phenylpropanolamine, Study of Their Antimicrobial Activity and Molecular Docking.