Synthesis, anti-proliferative activity, theoretical and 1H NMR experimental studies of Morita–Baylis–Hillman adducts from isatin derivatives

Brito, Vinicius B M; Santos, Gilmar F; Silva, Thiago D S; Souza, Júlia L. C.; Militão, Gardênia Carmen Gadelha; Martins, Felipe Terra; Silva, Fábio P.L.; Oliveira, Boaz G.; Araújo, Edigênia C. C.; Vasconcellos, Mário L. A. A.; Lima-Júnior, Cláudio Gabriel; Filho, Edilson Beserra de Alencar

doi:10.1007/s11030-019-09950-7

Cited by 15 publications

(4 citation statements)

References 34 publications

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“…This is because of coordination (ligand to metal) which could be best explained on the basis of chelation theory. 16,51 The comparison of antibacterial activity, shown in Fig. 7 confirms that metal complex of cobalt (compound 5) was highly active than its corresponding MBHA ligand against all bacterial strains.…”

Section: Antibacterial Assaymentioning

confidence: 57%

“…Most probably, this difference is due to the coordination of water molecules into the coordination sphere. 15,16 Besides, they have different unit cell number and radius intensity ratio, because of this they belong to non-identical but unique crystal class. The resultant XRD output such as density, volume, radius intensity ratio, lattice parameters (a, b, c, α, β, γ) and probable crystal class have been given in the Table 2.…”

Section: X-ray Diffractionmentioning

confidence: 99%

“…Therefore, studies pertaining to ligands with multiple, medicinally dynamic binding sites may serve as models for ensuring biochemical processes. 11,15,16 In this context, the wide variety of potent biotic activities of MBHA encouraged us to synthesize new series of products belonging to this class of compounds, possessing different functionalities and exhibiting potential antioxidant activity. Keeping in view the significance of reported research on synthetic MBH adducts as medicinally important candidates and having the diversity of functions, we conferred them as ligands for the novel drug synthesis composed of their transition metal complexes.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization, Biological Activities and Ab-initio Study of Transition Metal Complexes of [Methyl 2-((4-chlorophenyl)(hydroxy)methyle) Acrylate]

Nisar¹,

Ishfaq

Ali³

et al. 2022

ACSi

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Taking cognizance of the medicinal significance and diverse functions of synthetic Morita-Baylis-Hillman adducts (MBHA), the title ligand was synthesized and purified through column chromatography. Cr+3, Mn+2, Co+3, Ni+2, Cu+2 complexes of the ligand were synthesized under basic conditions, subjected to characterization through spectral analyses and verified with the IR spectrum that was generated computationally by the DFT B3LYP method, with 6-311++ G (d,p) basis set and Hartree Fock (HF) B3LYP method in conjunction with 3-21G(d,p) basis set. Powder XRD helped to testify crystals of the complexes. Moreover, the antibacterial, and antioxidant characteristics of MBHA and its complexes were also established. All of them were found to be active antioxidants. The antibacterial activities, examined against S. aureus, E. coli, B. pumilis and S. typhi have revealed that its Cobalt complex has an excellent potential to act against all of them. Hence, these compounds maybe having potentialities for the discovery of new, cheaper and efficient drugs against various infectious diseases. The study also uncovers the first example of utilization of MBHA towards metal complex formation.

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Section: Antibacterial Assaymentioning

confidence: 57%

Section: X-ray Diffractionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization, Biological Activities and Ab-initio Study of Transition Metal Complexes of [Methyl 2-((4-chlorophenyl)(hydroxy)methyle) Acrylate]

Nisar¹,

Ishfaq

Ali³

et al. 2022

ACSi

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“…Herein, following the aforementioned methodology, we report the synthesis of azetidine-2-one derivative, as shown in Scheme 3 , an analogue of ezetimibe, starting from p -anisaldehyde and tert-butyl acrylate, which are used in the Baylis–Hillman reaction. In this manner, the adduct 3 was obtained, an α,β-unsaturated ester previously synthetized by Brand et al [ 21 ] in acceptable yield using phenol as an additive to improve reaction kinetics [ 22 , 23 ]. This alcohol is acetylated with acetic anhydride and pyridine, giving the acetate 4, which was treated with the chiral amide ( R) -2 to give 5 with good yield and excellent diastereomeric excess, higher than 95%.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Modeling of Ezetimibe Analogues

et al. 2021

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Ezetimibe is a well-known drug that lowers blood cholesterol levels by reducing its absorption in the small intestine when joining to Niemann-Pick C1-like protein (NPC1L1). A ligand-based study on ezetimibe analogues is reported, together with one-hit synthesis, highlighted in the study. A convenient asymmetric synthesis of (2S,3S)-N-α-(R)-methylbenzyl-3-methoxycarbonylethyl-4-methoxyphenyl β-lactam is described starting from Baylis–Hillman adducts. The route involves a domino process: allylic acetate rearrangement, stereoselective Ireland–Claisen rearrangement and asymmetric Michael addition, which provides a δ-amino acid derivative with full stereochemical control. A subsequent inversion of ester and acid functionality paves the way to the lactam core after monodebenzylation and lactam formation. It also shows interesting results when it comes to a pharmacophore study based on ezetimibe as the main ligand in lowering blood cholesterol levels, revealing which substituents on the azetidine-2-one ring are more similar to the ezetimibe skeleton and will more likely bind to NPC1L1 than ezetimibe.

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Synthesis, biological activities, and structure–activity relationships of Morita–Baylis–Hillman adducts: An update

Devi,

Pathania,

Singh

et al. 2024

Archiv der Pharmazie

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The Morita–Baylis–Hillman (MBH) reaction is a unique C–C bond‐forming technique for the generation of multifunctional allylic alcohols (MBH adducts) in a single operation. In recent years, these MBH adducts have emerged as a novel class of compounds with significant biological potential, including anticancer, anti‐leishmanial, antibacterial, antifungal, anti‐herbicidal effects and activity against Chagas disease, and so on. The aim of this review is to assimilate the literature findings from 2011 onwards related to the synthesis and biological potential of MBH adducts, with an emphasis on their structure–activity relationships (SAR). Although insight into the biological mechanisms of action for this recently identified pharmacophore is currently in its nascent stages, the mechanisms described so far are reviewed herein.

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Synthesis, anti-proliferative activity, theoretical and 1H NMR experimental studies of Morita–Baylis–Hillman adducts from isatin derivatives

Cited by 15 publications

References 34 publications

Synthesis, Characterization, Biological Activities and Ab-initio Study of Transition Metal Complexes of [Methyl 2-((4-chlorophenyl)(hydroxy)methyle) Acrylate]

Synthesis, Characterization, Biological Activities and Ab-initio Study of Transition Metal Complexes of [Methyl 2-((4-chlorophenyl)(hydroxy)methyle) Acrylate]

Synthesis and Modeling of Ezetimibe Analogues

Synthesis, biological activities, and structure–activity relationships of Morita–Baylis–Hillman adducts: An update

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