Synthesis, antimicrobial and molecular docking studies of enantiomerically pure N-alkylated β-amino alcohols from phenylpropanolamines

Rao, K. Chennakesava; Arun, Y.; Easwaramoorthi, K.; Balachandran, C.; Prakasam, Tangirala; Yuvaraj, T. Eswara; Perumal, Paramasivan T.

doi:10.1016/j.bmcl.2014.05.027

Cited by 15 publications

(7 citation statements)

References 20 publications

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“…Reduced from a chiral pool such as the l -amino acids, β-amino alcohols serve as chiral auxiliaries or ligands for asymmetric catalysis . Various amino alcohol derivatives also exhibit antimicrobial and antifungal activity. As a result, the amino alcohol group has been adopted in several antibiotics, including ethambutol prescribed for treatment of tuberculosis and other infections.…”

Section: Introductionmentioning

confidence: 99%

Broadband Microwave Spectroscopy of Prototypical Amino Alcohols and Polyamines: Competition between H-Bonded Cycles and Chains

2015

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The rotational spectra of the amino alcohols d-allo-threoninol, 2-amino-1,3-propanediol, and 1,3-diamino-2-propanol and the triamine analog, propane-1,2,3-triamine, have been investigated under jet-cooled conditions over the 7.5-18.5 GHz frequency range using chirped-pulsed Fourier transform microwave spectroscopy. Microwave transitions due to three conformers of d-allothreoninol, four conformers of 2-amino-1,3-propanediol, four conformers of 1,3-diamino-2-propanol, and four conformers of propane-1,2,3-triamine have been identified and assigned, aided by comparison of the fitted experimental rotational constants with the predictions for candidate structures based on an exhaustive conformational search using force field, ab initio and DFT methods. Distinctions between conformers with similar rotational constants were made on the basis of the observed nuclear quadrupole splittings and relative line strengths, which reflect the direction of the permanent dipole moment of the conformers. With three adjacent H-bonding substituents along the alkyl chain involving a combination of OH and NH2 groups, hydrogen-bonded cycles (3 H-bonds) and chains (2 H-bonds) remain close in energy, no matter what the OH/NH2 composition. Two families of H-bonded chains are possible, with H-bonding substituents forming curved chain or extended chain structures. Percent populations of the observed conformers were extracted from the relative intensities of their microwave spectra, which compare favorably with relative energies calculated at the B2PLYP-D3BJ/aug-cc-pVTZ level of theory. In glycerol (3 OH), d-allothreoninol (2 OH, 1 NH2), 2-amino-1,3-propanediol (2 OH, 1 NH2), and 1,3-diamino-2-propanol (1 OH, 2 NH2), H-bonded cycles are most highly populated, followed by curved chains (3 OH or 2 OH/1 NH2) or extended chains (1 OH/2 NH2). In propane-1,2,3-triamine (3 NH2), H-bonded cycles are pushed higher in energy than both curved and extended chains, which carry all the observed population. The NH2 group serves as a better H-bond acceptor than donor, as is evidenced by optimized structures in which H-bond lengths fall into the following order: r(OH···N) ≈ r(OH···O) < r(NH···N) ≈ r(NH···O).

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Section: Introductionmentioning

confidence: 99%

Broadband Microwave Spectroscopy of Prototypical Amino Alcohols and Polyamines: Competition between H-Bonded Cycles and Chains

2015

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“…The major objective of this work was to improve benzotriazole chemistry , in order to create various types of β-amino alcohol analogues with 1,2,3-benzotriazole as the main heterocyclic component (for antibacterial screening, etc.). There are few reports in the literature that demonstrates the antibacterial activity of β-amino alcohols. − Therefore, to create medicinally advantageous antibacterial benzotriazole β-blocker analogues 4 and their equivalent oxazolidines 5 , a well-planned retrosynthetic technique was used to introduce a powerful β-amino alcohol unit into the benzotriazole nucleus (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…In light of the aforementioned biological applications, the benzotriazole moiety has been frequently used to construct biologically potent molecules which not only imparts significant properties like hydrophilicity, lipophilicity, and minimal side effects but also enhances their bioactivities. − Additionally, this will help to curb the drug-resistant pathogens, which will boost the prospects of developing superior drug alternatives. , On the other hand, β-amino alcohols are an elite class of compounds that have a wide range of medicinal applications. − Additionally, they were extensively used in the synthesis of unnatural amino acids , as well as in asymmetric synthesis such as chiral ligands and auxiliaries. , Therefore, it is anticipated that the addition of a biologically active β-amino alcohol moiety to a benzotriazole scaffold will complement their action, perhaps improving the total pharmacological activity. It is important to note that screening of powerful and hybrid heterocycles has developed into a modern trend in biomedical development programs. − …”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Molecular Docking, and In Vitro Antibacterial Evaluation of Benzotriazole-Based β-Amino Alcohols and Their Corresponding 1,3-Oxazolidines

Singh,

Abrol,

Parihar

et al. 2023

ACS Omega

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In the present study, a series of benzotriazole-based β-amino alcohols were efficiently synthesized in excellent yields via aminolysis of benzotriazolated epoxides under catalyst-and solventfree conditions. Further these β-amino alcohols were successfully utilized to synthesize the corresponding benzotriazole-based oxazolidine heterocyclic derivatives. All the synthesized compounds were characterized by various spectroscopic techniques such as 1 H NMR, 13 C NMR, and mass spectroscopy for structure elucidation. The compounds were subjected to a microtiter plate-based antimicrobial assay. The antimicrobial activity results reveal that the compounds 4a, 4e, and 5f were found to be active against Staphylococcus aureus (ATCC-25923) with minimum inhibitory concentrations (

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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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Synthesis, antimicrobial and molecular docking studies of enantiomerically pure N-alkylated β-amino alcohols from phenylpropanolamines

Cited by 15 publications

References 20 publications

Broadband Microwave Spectroscopy of Prototypical Amino Alcohols and Polyamines: Competition between H-Bonded Cycles and Chains

Broadband Microwave Spectroscopy of Prototypical Amino Alcohols and Polyamines: Competition between H-Bonded Cycles and Chains

Design, Synthesis, Molecular Docking, and In Vitro Antibacterial Evaluation of Benzotriazole-Based β-Amino Alcohols and Their Corresponding 1,3-Oxazolidines

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

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