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Twelve novel triazolothiadiazole derivatives were synthesized from 4-amino-5-substituted-4H-1,2,4-triazole-3-thiols with various aromatic carboxylic acids by cyclization in the presence of phosphorous oxychloride. All the newly synthesized compounds were characterized by FTIR, ¹H NMR, mass spectroscopy and elemental analysis. The antimicrobial acti...
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... A limited number of second-order nonlinear optical (NLO) active and biologically active D-π-A system potential NLO organic compounds have been reported in the literature [27][28][29][30][31][32]. Recently, [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazole, an azo class constituent unit of a few chemical systems, has become of particular interest in this system. ...
... Radwan et al. studied the biological characteristics of 1,3,4-thiadiazole-and 1,2,4-triazole-3(4H)-thionecontaining salicylate compounds for antifungal applications [28]. Additionally, 3,6-disubstituted-1,2,4-triazolo-1,3,4thiadiazole and 3,6-distributed 1,2,4-traizolo [3,4-b]1,3,4thiadiazole compound derivatives are showed excellent antimicrobial activities [29,30]. The results of experimental research on 4-amino-5-mercapto-1,2,4-triazoles suggest that these compounds are appropriate for use in anticancer applications [33]. ...
Many organic chromophores possess excellent nonlinear optical (NLO) properties. In spite of this, the performance of these chromophores in second-order nonlinear optical applications is limited due to the high symmetry and short dipole moment of the parent molecules, which can lead to a weak response or high susceptibility to molecular orientation dependency. To address this challenge, we designed a series of new [1,2,4] triazolo[3,4-b] [1,3,4] thiadiazole derivative chromophores C1–C7 and studied their second-order NLO property through density functional theory (DFT) by substitution of different donor functional groups. To this end, several hybrid functionals such as B3LYP/6–311 + + G (d, p), CAM B3LYP/6–311 + + G (d, p), and ωB97XD/6–311 + + G (d, p) were employed to carry out quantum chemical calculations, which included calculations and evaluations of frequency-dependent dipole moment, linear polarizability, and first hyperpolarizability values. In addition, natural bond orbital (NBO) analysis, intramolecular charge transfer (ICT) mechanism, electronic charge density analysis, highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), and vertical energy transitions are studied with time-independent and time-dependent level density functional theory. The results demonstrate that C7 is the most efficient chromophore among the other chromophores investigated, with a significant first hyperpolarizability value of 105,032.98 × 10⁻³⁴. This study provides insights into how to design second-order NLO active organic chromophores with better performance for optoelectronic applications.
... Especially, compounds 52e and 52k exhibited excellent antibacterial and antifungal activities among these triazolothiadiazole derivatives. 45 A series of novel 5-amino-1,3,4-thiadiazole-2-thiol derivatives 53 and 1,3,4-thiadiazole-2,5-dithiol derivatives 54 of benzimidazole (Scheme 28) were synthesized through nucleophilic substitution reaction of 5-substituted-2-(chloromethyl)-1H-benzimidazole. All the target compounds were screened for their antibacterial activity toward gram-negative (E. ...
3-Chloro-3-chlorosulfenyl-4′-methylspiro[chroman-2,1′-cyclohexane]-4-one (4) was prepared from the reaction of spiro 4′-methylcyclohexan-1′,2-chroman-4-one (3) with thionyl chloride according to reported method. Furthermore, treatment of compound 4 with potassium iodide gave 1,2-bis (3-chloro-4′-methylspirochroman-2,1′-cyclohexyl-4-one)disulfane (6) in addition to 4,4‴-dimethyltrispiro[cyclohexane-1,2′-chroman-3′,2″-2H-chromeno[3,4-e][1,3,4]-oxadithiin-5″,1‴-cyclohexan]-4′-one (5). The formation of compound 5 could be presumably explained via the formation of unstable intermediate oxo-thioketone A. The formation of the latter intermediate A was confirmed chemically through the thermal reaction of compound 5, or compound 6 with 1,3-homodiene such as: 1,3-cyclohexadiene, isoprene, and 2,3-dimethyl-1,3-butadiene to afford the products 7–9, respectively. The chemical structures of the newly prepared compounds were confirmed by spectroscopic methods (IR, ¹H & ¹³C NMR, and MS). The synthesized compounds were evaluated against lung (A549), prostate (PC3), pancreatic (PACA2), and breast (MDA) cancer cell lines. Compound 3 exhibited prominent cytotoxicity against A549, PC3, and PACA2 cancer cell lines with IC50 values from 12.4 to 16.1 µM, which was comparable or superior to the reference drug (Doxorubicin). Compounds 7–9 showed better cytotoxicity against breast (MDA) cancer cell line than the reference drug (Doxorubicin).
... Especially, compounds 52e and 52k exhibited excellent antibacterial and antifungal activities among these triazolothiadiazole derivatives. 45 A series of novel 5-amino-1,3,4-thiadiazole-2-thiol derivatives 53 and 1,3,4-thiadiazole-2,5-dithiol derivatives 54 of benzimidazole (Scheme 28) were synthesized through nucleophilic substitution reaction of 5-substituted-2-(chloromethyl)-1H-benzimidazole. All the target compounds were screened for their antibacterial activity toward gram-negative (E. ...
... showed that the compounds with phenyl-substituent were more active than the analogs with benzyl moiety [36,37]. The second chloro onto the phenyl ring was found disfavourable to the activity. ...
... Chemical structures of 1,2,4-triazole-thiazole and triazolothiadiazole hybrids 5e8[32][33][34][35][36][37]. ...
Antibiotics are commonly used to fight against bacterial infections, but bacteria have already been resistant to almost all antibiotics due to abuse of antibiotics. 1,2,4-Triazole derived compounds possess chemotherapeutic effects including potential antibacterial activities against drug-sensitive as well as drug-resistant pathogens. Hybridization displays a high potential to develop novel drugs with the capacity to overcome drug resistance, reduce toxicity and improve pharmacokinetic profiles. More effective antibacterial candidates might be obtained by the hybridization of 1,2,4-triazole with other antibacterial pharmacophores. This review summarizes the recent advances of 1,2,4-triazole derivatives as potential antibacterial compounds, and the structure-activity relationship is also discussed.
... In last decades chemistry of triazole compounds has been greatly developed and is well studied [1][2][3]. Many of the medications, which contain compounds with 1,2,4-triazole ring, were discovered and applied in practice [3][4][5][6]. ...
... In last decades chemistry of triazole compounds has been greatly developed and is well studied [1][2][3]. Many of the medications, which contain compounds with 1,2,4-triazole ring, were discovered and applied in practice [3][4][5][6]. In that way, pharmaceuticals like vorazole [7] and anastrozole [6] demonstrate antitumor activity, trazodone, alprazolam show antidepressant effects [4,8]. ...
Objective: It has now been demonstrated that compound 4-((5-(decylthio)-4-methyl-4H-1,2,4-triazol-3-yl)methyl)morpholine shows antifungal and antimicrobial activities. This study was aimed to estimate toxicity values of novel oil liniment, which is based on mentioned compound and has antifungal effect. Material and Method: Research was held in accordance with guidelines “Toxicological screening of new substances for animal safety products” and “Preclinical esearch of veterinary drugs”. Toxicity level (amount of toxic doses) and benchmark doses for subacute study were assessed in conditions of acute study. Experiments were conducted on male wistar rats using karber method. Result and Discussion: Findings in the research of the acute effect have shown that studied substance belongs to the group of low-toxic compounds in conditions of intragastric administration. All rats survived and completed subacute study, and daily administration of oil liniment in duration of 14 days did not cause possible changes in body and organ weight among animals in experimental groups. It was demonstrated that prolonged exposure to the liniment caused possible increase of ALP and LDH on the background of possible cholesterol decrease, which may be the evidence of cholestatic liver disease, and enhancement of permeability of the cell membranes, which may be highlighted by destructive changes in liver.
... In last decades chemistry of triazole compounds has been greatly developed and is well studied [1][2][3]. Many of the medications, which contain compounds with 1,2,4-triazole ring, were discovered and applied in practice [3][4][5][6]. ...
... In last decades chemistry of triazole compounds has been greatly developed and is well studied [1][2][3]. Many of the medications, which contain compounds with 1,2,4-triazole ring, were discovered and applied in practice [3][4][5][6]. In that way, pharmaceuticals like vorazole [7] and anastrozole [6] demonstrate antitumor activity, trazodone, alprazolam show antidepressant effects [4,8]. ...
A series of novel 6-sulfonyl-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole derivatives were designed and synthesized. CoMFA models were established to analyze the quantitative structure-activity relationships on the basis of the EC50 values of the compounds. The models were used to design and synthesize compounds 32 and 33 with higher activities. The EC50 values of compound 33 against Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas oryzae pv. oryzicola (Xoc) were 0.59 and 1.63 mg/L, respectively, which were higher than those of thiodiazole copper (90.43 and 97.93 mg/L) and bismerthiazol (68.37 and 75.59 mg/L). Moreover, protective activities of compound 33 against bacterial leaf streak (BLS) and bacterial leaf blight (BLB) were 49.65% and 49.42%, respectively, which were superior to those of thiodiazole copper (44.28% and 41.51%) and bismerthiazol (38.89% and 40.09%). Protective activity of compound 33 against BLS was closely related to the improvement of defense-related enzyme activities, chlorophyll content, and photosynthesis activation. This is consistent with the upregulated expression of defense responses and photosynthesis-related proteins.
Background
The present research work is focused on development of the alternative antioxidant and anti-inflammatory agents. The review of literature reveals that many benzofused thiazole analogues have been used as lead molecules for the design and development of therapeutic agents including anticancer, anti-inflammatory, antioxidant and antiviral. The synthesized benzofused thiazole derivatives are evaluated for in vitro antioxidant, anti-inflammatory activities and molecular docking study. Thus the present research work aims to synthesis of benzofused thiazole derivatives and to test their antioxidant and anti-inflammatory activities.
Objective
To design and synthesize an alternative antioxidant and anti-inflammatory agents.
Methods
The substituted benzofused thiazoles 3a-g were prepared by cyclocondensation reaction of appropriate carboxylic acid with 2-aminothiophenol in POCl3 and heated for about 2-3 h to offered benzofused thiazole derivatives 3a-g. All the newly synthesized compounds were in vitro screened for their anti-inflammatory and antioxidant activities by using known literature method.
Results
At the outset the study of in vitro indicated that the compounds code 3c, 3d and 3e possessed distinct anti-inflammatory activity as it compared to standard reference. All the tested compounds show potential antioxidant activity against one or more reactive (H2O2, DPPH, SO and NO) radical scavenging species. Additionally, docking simulation is further performed to position of compounds 3d & 3e into the anti-inflammatory active site to determine the probable binding model.
Conclusion
New anti-inflammatory and antioxidant agents were need of tense; we proved that benzofused thiazole derivatives were 3c, 3d and 3e constituted as an interesting template for the evaluation of new anti-inflammatory agents and an antioxidant’s work also may provide an interesting template for further development.
