Synthesis and Biological Activity of 4,5‐Dihydro‐1,2,4‐triazole‐5‐thione Schiff Base

Sun, Xiaohong; Yan, Binbin; Liu, Yuanfa; Chen, Bang; Jia, Yi‐Xia; Zeng, Zhenfang

doi:10.1002/cjoc.200990234

Cited by 8 publications

(5 citation statements)

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“…Phosphate Buffer Solution (PBS) was made from Na 2 HPO 4 , KH 2 PO 4 , NaCl, KCl and Millipore ultrapure water according to the standard procedure. CBTZ (C 10 H 8 Cl 2 N 4 S; MW = 287.17 g mol 1 ) was synthesized by Northwest University, China and its molecular structure is presented in Figure 1 [8].…”

Section: Chemicals and Instrumentsmentioning

confidence: 99%

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Biophysical studies of the interaction between a triazole derivative and bovine serum albumin by multi-spectroscopic and molecular modeling methods

Wang

et al. 2011

Sci. China Chem.

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The interaction between 3-thiol-4-(2,4-dichlorobenzylideneamino)-5-methyl-4H-1,2,4-triazole (CBTZ) and bovine serum albumin (BSA) under physiological conditions was investigated by fluorescence, UV-vis absorption and circular dichroism (CD) spectroscopy as well as molecular modeling methods. The result of fluorescence experiment indicates the static quenching as a result of the formation of the CBTZ-BSA complex. The binding constants (K a ) at different temperatures were calculated according to the modified Stern-Volmer equation. The enthalpy change (H) and entropy change (S) were determined based on the van′t Hoff equation. Both negative H and S indicated that van der Waals and hydrogen-bonding forces were the dominant intermolecular forces to stabilize the CBTZ-BSA complex. Site marker competitive replacement experiments demonstrated that binding of CBTZ to BSA primarily took place in sub-domain IIA (Sudlow's site I). The binding distance (r = 7.2 nm) between CBTZ and the tryptophan residue of BSA was estimated according to the theory of fluorescence resonance energy transfer (FRET). The conformational studies by circular dichroism (CD) and three-dimensional fluorescence spectroscopy showed that the presence of CBTZ induced minor changes of the secondary structure of BSA. Molecular modeling study further confirmed the binding mode obtained experimentally. triazole, bovine serum albumin, fluorescence quenching, binding site, molecular modeling

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Section: Chemicals and Instrumentsmentioning

confidence: 99%

“…The content of -helix can be obtained from the above eqs. (8), (9), and other secondary-structure parameters (-pleat sheet, turn and unordered) can be quantified by the algorithm SELCON3 through the CD spectroscopic data (Table S1). The secondary-structure contents are closely related to the biological activity of protein.…”

Section: Conformation Changementioning

confidence: 99%

Biophysical studies of the interaction between a triazole derivative and bovine serum albumin by multi-spectroscopic and molecular modeling methods

Wang

et al. 2011

Sci. China Chem.

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“…182.5～183.7 ; ℃ 2h: 产率 56.68%, m.p. 187.3～189.5 ℃(文献值 [12] : 190.0～191.0 ); [1,2,4] OS: C 57.94,H 4.58,N 23.85;found C 57.92,H 4.61,N 23.82. 3-(5H-苯并咪唑 -2-亚甲硫基 )-5-(4-甲基苯氧甲基)- [1,2,4] 3184,3136,2920,2860,1614,1588,1510,1454,1078,814,740, 684 cm -1 . Anal.…”

Section: 6～2738 ;unclassified

Synthesis, Structure and Their Biological Activities of 3-[(5-H/methyl-benzoimidazol-2-yl)methylthio]-5-substituted-1,2,4-triazol-4-amine Derivatives

安悦¹,

张婷²,

姜华³

et al. 2012

Chin. J. Org. Chem.

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Seventeen 3-[(5-H/methyl-benzoimidazol-2-yl)methylthio]-5-substituted-1,2,4-triazol-4-amine derivatives were synthesized by the reaction of 4-amino-5-substituted-1,2,4-triazole-3-thiol with 2-chloromethyl-5-substituted-benzoimidazole in sodium hydroxide solution. All the compounds were characterized by 1 H NMR and IR spectra, and elemental analysis. Moreover, one novel cobalt(II) compound was obtained with the target compound 3f by solution method, and its structure was characterized by X-ray single crystal diffraction analysis. Besides, the results of primary biological activity experiments on wheat gemma and germination process of mung bean showed that these synthesized compounds had good activity, and the compounds 3d and 3i even have inhibiting effect on Staphylococcus aureus.

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“…Compounds with the structure of AC=NB are known as Schiff bases, which arouse considerable interest due to their antifungal, anticancer and antibacterial activities [1][2][3][4][5] . The Schiff bases compounds can be synthesized from the condensation of primary amines and active carbonyl groups.…”

Section: Introductionmentioning

confidence: 99%

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Characterization and Biological Evaluation of Structurally Modified Taurine using Benzaldehydes

Yao¹,

Wang²,

Du³

et al. 2013

Asian J. Chem.

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INTRODUCTIONCompounds with the structure of AC=NB are known as Schiff bases, which arouse considerable interest due to their antifungal, anticancer and antibacterial activities [1][2][3][4][5] . The Schiff bases compounds can be synthesized from the condensation of primary amines and active carbonyl groups.Taurine (2-aminoethane sulfonic acid), which belongs to an organic acid widely distributed in animal tissues, is a nonprotein β-amino acid, playing an important role in many physiological processes i.e., regulation of cardiovascular responses and neuronal excitability, maintenance of structure and function of photoreceptors, modulation of neurotransmitter and hormone release [6][7][8][9] . Taurine has primary amino groups on its side chain and is widely used as an organic ligand. Relevant documents have reported that taurine forms multiple types of Schiff base compounds [10][11][12] . However, these studies focus mainly on the synthesis, crystallization, antifungal, anticancer and antibacterial activities. Based on that taurine is found to modulate smooth muscle contraction [13][14][15][16] , while the effect of Schiff base on contractility of isolated jejunal segment is rarely reported and our preliminary assay found that Schiff bases slightly inhibited the contractility of smooth muscle. These lead us to suspect the possible effect of taurine Schiff base on the contractility of smooth muscle.

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Synthesis and Biological Activity of 4,5‐Dihydro‐1,2,4‐triazole‐5‐thione Schiff Base

Cited by 8 publications

References 2 publications

Biophysical studies of the interaction between a triazole derivative and bovine serum albumin by multi-spectroscopic and molecular modeling methods

Biophysical studies of the interaction between a triazole derivative and bovine serum albumin by multi-spectroscopic and molecular modeling methods

Synthesis, Structure and Their Biological Activities of 3-[(5-H/methyl-benzoimidazol-2-yl)methylthio]-5-substituted-1,2,4-triazol-4-amine Derivatives

Characterization and Biological Evaluation of Structurally Modified Taurine using Benzaldehydes

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