Synthesis, characterizations, biological activities and docking studies of novel dihydroxy derivatives of natural phenolic monoterpenoids containing azomethine linkage

Rajput, Jamatsing D.; Bagul, Suresh D.; Hosamani, Amar A.; Patil, Manohar

doi:10.1007/s11164-017-2933-4

Cited by 22 publications

(19 citation statements)

References 32 publications

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“…[60]), e) (i) LICTMEDA, THF, 0 °C; (ii) DMF, 0 °C; (iii) HCl (carried out in accordance with [58]), f) AlCl3, DCM (carried out in accordance with [57]), g) HCHO, H2O, 80 °C , 1h (carried out in accordance with [56]), h) MnO2, acetone, RT, 6h (carried out in accordance with [59]). 5-Bromosalicylaldehyde (6d) and 3-isopropyl-6-methylsalicylaldehyde (7e) were prepared by the Reimer-Tiemann formylation of 4-bromophenol (10d) [55] and thymol (11e) [64], respectively. 2,6-Dimethoxybenzaldehyde (6f) was prepared from resorcinol dimethyl ether by regiospecific LICTMEDA lithiation at position 2, followed by DMF formylation [58].…”

Section: Methodsmentioning

confidence: 99%

“…Methods of preparation of the hydrazides 4b-c and aldehydes of choice 6a-b, 6d-f, 7a-b, and 7d-f were adapted from the original literature [54][55][56][57][58][59][60][61][62][63][64]. 4-Methoxy-and 3-hydroxybenzoic acid hydrazides 4b and 4c were prepared in 67-85% yields from the appropriate benzoic acid methyl esters 8b and 8c and hydrazine monohydrate following a literature procedure [63].…”

Section: Syntheses and Characterizationsmentioning

confidence: 99%

“…Absorption maxima are reported in wavenumbers (cm −1 ). 1 H-and 13 C-NMR spectra (399.78 for 1 H and 100.52 for 13 C) were recorded on a 400YH (JEOL, Tokyo, Japan) or an Avance 600 Spectrometer (600.58 for 1 H and 151.03 for 13 [63], aldehydes 6a [54], 6b [54], 6d [55], 6e [58], 6f [58], 7a [59], 7b [56], 7d [60,61], 7e [64], 7f [62], and benzoic acid methyl ester 8b-c [65] (see Section 4.1.1. of [65]). Purity and homogeneity of known compounds were confirmed by measuring their m.p.…”

Section: Reagents and Materialsmentioning

confidence: 99%

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Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor

et al. 2020

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A series of hydrazide-hydrazones 1–3, the imine derivatives of hydrazides and aldehydes bearing benzene rings, were screened as inhibitors of laccase from Trametes versicolor. Laccase is a copper-containing enzyme which inhibition might prevent or reduce the activity of the plant pathogens that produce it in various biochemical processes. The kinetic and molecular modeling studies were performed and for selected compounds, the docking results were discussed. Seven 4-hydroxybenzhydrazide (4-HBAH) derivatives exhibited micromolar activity Ki = 24–674 µM with the predicted and desirable competitive type of inhibition. The structure–activity relationship (SAR) analysis revealed that a slim salicylic aldehyde framework had a pivotal role in stabilization of the molecules near the substrate docking site. Furthermore, the presence of phenyl and bulky tert-butyl substituents in position 3 in salicylic aldehyde fragment favored strong interaction with the substrate-binding pocket in laccase. Both 3- and 4-HBAH derivatives containing larger 3-tert-butyl-5-methyl- or 3,5-di-tert-butyl-2-hydroxy-benzylidene unit, did not bind to the active site of laccase and, interestingly, acted as non-competitive (Ki = 32.0 µM) or uncompetitive (Ki = 17.9 µM) inhibitors, respectively. From the easily available laccase inhibitors only sodium azide, harmful to environment and non-specific, was over 6 times more active than the above compounds.

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Section: Methodsmentioning

confidence: 99%

Section: Syntheses and Characterizationsmentioning

confidence: 99%

Section: Reagents and Materialsmentioning

confidence: 99%

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Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor

et al. 2020

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“…The synthesis of sulfonyl hydrazone based ligands was prepared by multistep process reaction. In the first step, the synthesis of ortho formyl phenolic monoterpenoids (ortho formyl thymol (2-hydroxy-3-isopropyl-6-methylbenzaldehyde) or ortho formyl carvacrol (2-hydroxy-6-isopropyl-3-methylbenzaldehyde)) was carried out using a previously reported method [18][19][20]. In the second step, synthesis of substituted sulfonyl hydrazides (2,4,6-trimethylbenzenesulfonohydrazide and 4-methylbenzenesulfonohydrazide) [19] was carried out in which hydrazine hydrate (0.25 mol, 2.5 equiv.)…”

Section: Synthesis Of Ligandsmentioning

confidence: 99%

Synthesis, crystal structures and antimicrobial activity of palladium metal complexes of sulfonyl hydrazone ligands

Tadavi¹,

Bendre

Patil

et al. 2020

Eur J Chem

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Palladium complexes of sulfonyl hydrazone based ligands have been prepared by refluxing with the corresponding ligands and Pd(II) salt in 2:1 ratio. The compounds have been characterized by FT-IR and UV-Vis spectroscopic methods. The crystal structure of the prepared palladium complexes has been determined by single-crystal X-ray crystallographic technique. Crystal data for C40H50N4O6PdS2 (PMHT-Pd(II) complex): triclinic, space group P-1 (no. 2), a = 7.1561(6) Å, b = 12.1300(11) Å, c = 12.6117(17) Å, α = 63.498(11)°, β = 86.694(9)°, γ = 81.451(7)° and Z = 1. The final R1 was 0.0699 (I > 2σ(I)) and wR2 was 0.1834 (all data). Crystal data for C36H42N4O6PdS2 (PTHC-Pd(II) complex): monoclinic, space group P21/n (no. 14), a = 8.6726(2) Å, b = 20.8824(4) Å, c = 10.3351(2) Å, β = 104.429(2)° and Z = 2. The final R1 was 0.0344 (I > 2σ(I)) and wR2 was 0.0840 (all data). Crystal data for C36H42N4O6PdS2 (PTHT-Pd(II) complex): monoclinic, space group P21/n (no. 14), a = 9.7658(2) Å, b = 10.0488(3) Å, c = 18.7714(4) Å, β = 99.602(2)° and Z = 2. The final R1 was 0.0334 (I > 2σ(I)) and wR2 was 0.0832 (all data). Crystal data for C40H50N4O6PdS2 (PMHC-Pd(II) complex): triclinic, space group P-1 (no. 2), a = 10.2070(9) Å, b = 12.1841(13) Å, c = 16.8879(19) Å, α = 109.005(6)°, β = 90.061(5)°, γ = 99.032(5)° and Z = 2. The final R1 was 0.0822 (I > 2σ(I)) and wR2 was 0.2293 (all data). The single-crystal structure data showed a good agreement with the experimental results. The synthesized complexes were screened for their in vitro antibacterial activity against one Gram-negative (Escherichia coli) and two Gram-positive (Bacillus subtilis and Staphylococcus aureus) bacterial strains and for in vitro antifungal activity against Aspergillus niger, Aspergillus flavus and Aspergillus fumigatus. The PTHC-Pd(II) complex possesses the nearby significant antifungal activity analogous to the standard drug fluconazole against selected fungal strains Aspergillus niger, Aspergillus Flavus and Aspergillus fumigatus as well as the same complex showed the antibacterial activity for Staphylococcus aureus as comparable to standard ofloxacin drug.

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“…However, the efficiency of these compounds in treatment is limited due to their poor water solubility and the requirement of high concentrations to reach a therapeutic effect [10,11]. Carvacrol, 5-isopropyl-3-methylphenol (Figure 1 (1)) is a major constituent of organo oil [12][13][14][15]. It is a phenolic monoterpenoid that exhibits several interesting biological activities [16][17][18].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Antioxidant Activity of Carvacrol Based Sulfonates

Bagul¹,

Rajput²,

Patil³

et al. 2017

Med chem

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Synthesis, characterizations, biological activities and docking studies of novel dihydroxy derivatives of natural phenolic monoterpenoids containing azomethine linkage

Cited by 22 publications

References 32 publications

Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor

Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor

Synthesis, crystal structures and antimicrobial activity of palladium metal complexes of sulfonyl hydrazone ligands

Synthesis, Characterization and Antioxidant Activity of Carvacrol Based Sulfonates

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