Synthesis, characterization, computational studies and biological evaluation of S-benzyl-β-N-[3-(4-hydroxy-3-methoxy-phenylallylidene)]dithiocarbazate

Bhat, Rayees Ahmad; Kumar, Dinesh; Malla, Manzoor Ahmad; Bhat, Sami Ullah; Khan, Shad Ahmad; Manzoor, Ovais; Srivastava, Anurag; Naikoo, Rawoof Ahmad; Mohsin, Mohd; Mir, Muzzaffar Ahmad

doi:10.1016/j.molstruc.2017.11.051

Cited by 8 publications

(3 citation statements)

References 35 publications

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“…Region with low potential or higher than average electrostatic potential energy has strong influence of positively charged particles and vice versa. The biological activity recognition and reactivity towards positive and negative charged regions can be forecasted through pictorial illustration by quantum‐chemical simulations . The substantial positive potential and electron deficient coded in the form of light blue color lie mainly on the terminated hydrogen atoms attached to N, allyl group and benzene carbon atoms however, the S, N and C atoms having yellow and green color of HL are under intermediary potential regime.…”

Section: Resultsmentioning

confidence: 99%

Experimental, DFT Studies and Biological Evaluation of S‐methyl‐β‐N‐(3‐(2‐nitrophenyl)allylidene)dithiocarbazate

et al. 2018

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S‐Methyl‐β‐N‐(3‐(2‐nitrophenyl)allylidene)dithiocarbazate (HL), Schiff base of S‐methyl dithiocarbazate, was synthesized by 1:1 condensation between S‐methyl dithiocarbazate and trans‐o‐Nitrocinnamaldehyde. It's in‐vitro cytotoxicity is assayed against two habitually infection causing bacteria strains including gram‐positive Staphylococcus aureus and gram‐negative Escherichia coli for antibacterial activity. The results showed appreciable biological activity and the activity increased with increase in concentration. This nitrogen‐sulfur based Schiff base (HL) was characterized by Mass, FT‐IR, 1H‐NMR, 13C‐NMR, Raman, and UV‐Vis spectroscopic techniques. Theoretical quantum chemical calculation has been performed using DFT in combination with B3LYP exchange correlation functional and 6‐311++ G (d, p) basis sets level. The computed parameters were: Chemical potential of compound (μ) −0.174 eV, HOMO‐LUMO energy gap −0.11093 eV, chemical hardness (ɳ) −0.055 eV, softness (S) 2.164 eV, ionization energy (IE) −0.23026 eV, electron affinity (EA) −0.11933 eV, the electronegativity (EN) 0.174 eV, dipole moment (D) 1.3383 Debye and relative stabilization energy −1536.982 eV. In the theoretical FT‐IR spectrum analysis 81 fundamental vibrational modes has be observed because of non‐linear structure of HL, with potential energy distribution percentage (PED%) by using VEDA‐4 (Vibrational energy distribution analysis) software. Theoretically calculated parameters like 1H‐NMR, 13C‐NMR, FT‐IR, UV‐VIS, Raman, electrostatic potential and HOMO‐LUMO energy gap were in conformity with experimental results.

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Section: Resultsmentioning

confidence: 99%

Experimental, DFT Studies and Biological Evaluation of S‐methyl‐β‐N‐(3‐(2‐nitrophenyl)allylidene)dithiocarbazate

et al. 2018

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“…2, where the Schiff base showed a medium intensity absorption band at 3111 cm -1 , corresponding to the ν(N-H) stretching frequency that was absent in the complexes, suggesting that the ligand underwent coordination through the thiolate anion [27,28]. The Schiff base contained strong bands at 1502 and 1094 cm -1 for the ν(C=N) and ν(C=S) stretches, respectively [27][28][29]. The absence of ν(C=S) band in the complexes also indicated thiolate binding with the respective metal ions in the complexes [27,28].…”

Section: Ir Spectramentioning

confidence: 99%

Studies on Coordination Chemistry and Antibacterial Activity of Bidentate NS Schiff Base Derived From SBDTC and 4-Benzyloxybenzaldehyde

2019

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The condensation of 4-benzyloxybenzaldehyde with S-benzyl dithiocarbazate (SBDTC) in absolute ethanol afforded the Schiff base, S-benzyl-β-N-(4-benzyloxyphenyl)methylene-dithiocarbazate (1). The ligand on further reaction with metal ions in absolute ethanol [for Ni(II), Cu(II), Zn(II)] and in methanol [Pd(II)] resulted in the formation of the corresponding four coordinate complexes. The ligand and its complexes were characterized by physico-chemical techniques, viz., molar conductance, magnetic susceptibility measurement, IR, NMR and solution UV/Vis spectroscopic techniques. The complexes demonstrated stronger antibacterial activity than the free ligand indicating that coordination with these metal ions has enhanced biological potential of the ligand. All the compounds exhibited more or less moderate activity against the test organisms.

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“…Different ligands can be obtained by introducing different organic substituents, which causes variation in their biological properties, although they may differ only slightly in their molecular structures (Ali et al, 1977;Tarafder et al, 2001Tarafder et al, , 2002. Interest in this class of compound remains high as studies have shown that they possess anti-cancer (Mirza et al, 2014), anti-bacterial (Bhat et al, 2018), anti-fungal (Nithya et al, 2017), anti-viral (Chew et al, 2004) and anti-inflammatory (Zangrando et al, 2015) properties. Pyridine derivatives have also been a subject of much interest since the 1930 0 s with the discovery of niacin for the treatment of dermatitis and dementia (Henry, 2004).…”

Section: Chemical Contextmentioning

confidence: 99%

S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]dithiocarbazate: crystal structure and Hirshfeld surface analysis

et al. 2018

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In the title dithiocarbazate ester, C 16 H 17 N 3 S 2 (systematic name: (Z)-{[(benzylsulfanyl)methanethioyl]amino}[1-(6-methylpyridin-2-yl)ethylidene]amine), the central methylidenehydrazinecarbodithioate (C 2 N 2 S 2 ) core is almost planar (r.m.s. deviation = 0.0111 Å ) and forms dihedral angles of 71.67 (3) with the approximately orthogonally inclined thioester phenyl ring, and 7.16 (7) with the approximately coplanar substituted pyridyl ring. The latter arrangement and the Z configuration about the imine-C N bond allows for the formation of an intramolecular hydrazine-N-HÁ Á ÁN(pyridyl) hydrogen bond that closes an S(6) loop. In the crystal, phenyl-C-HÁ Á ÁS(thione), methylene-C-HÁ Á Á(pyridyl), methylene-and phenyl-C-HÁ Á Á(phenyl) contacts connect molecules into supramolecular layers propagating in the bc plane; the layers stack along the a axis with no directional interactions between them. The analysis of the Hirshfeld surface indicates the relative importance of an intralayer phenyl-HÁ Á ÁH(pyridyl) contact upon the molecular packing.

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Synthesis, characterization, computational studies and biological evaluation of S-benzyl-β-N-[3-(4-hydroxy-3-methoxy-phenylallylidene)]dithiocarbazate

Cited by 8 publications

References 35 publications

Experimental, DFT Studies and Biological Evaluation of S‐methyl‐β‐N‐(3‐(2‐nitrophenyl)allylidene)dithiocarbazate

Experimental, DFT Studies and Biological Evaluation of S‐methyl‐β‐N‐(3‐(2‐nitrophenyl)allylidene)dithiocarbazate

Studies on Coordination Chemistry and Antibacterial Activity of Bidentate NS Schiff Base Derived From SBDTC and 4-Benzyloxybenzaldehyde

S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]dithiocarbazate: crystal structure and Hirshfeld surface analysis

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