133846-98-7Relevant articles and documents
Synthesis of Schiff bases of 4-Amino-3-mercapto-5-pyridin-4yl-4H-1,2,4-triazole and their evaluation as SAR inducers
Majumder, Sujan,Bashyal, Bishnu Maya,Gupta
, p. 1260 - 1274 (2015/11/25)
A series of twenty five Schiff bases 6a-y of 4-Amino-3-mercapto-5-pyridin-4yl-4H-1,2,4-triazole having different substitution in the aryl ring attached to imine group designed incorporating the isonicotinic acid moiety present in INA, a known SAR inducer have been synthesized and characterized using 1H and 13C NMR, FT-IR spectroscopy and elemental analysis. All twenty five Schiff bases, 4-Arylideneamino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazoles have been screened for systemic acquired resistance (SAR) inducing activity against sheath blight of rice and five potential compounds viz. 6f, 6g, 6r, 6t and 6u analogues have been further evaluated. All the five compounds have considerably decreased the relative lesion height (RLH) as compared to control with maximum reduction in RLH shown by compound 6u (47.15%). These five potential compounds have been further studied for their effect on phenol content, PAL and peroxidase activity. The compound 6u has been identified as the most potent SAR inducer both based on phenotypic and biochemical study and also does not show direct fungicidal activity against R. solani. Its RI activity is found better than 2,6-dichloroisonicotinic acid (INA), a resistance inducing chemical used as standard.
Synthesis, antibacterial and antifungal activity of novel 4-aminosubstituted-1,2,4-triazole-3-thiol derivatives
Sabale, Prafulla M.,Mehta, Pooja
, p. 149 - 154 (2019/01/21)
The synthesis of a series of novel substituted-1,2,4-triazole-3-thiol derivatives were described. One of the easiest way of constructing 1,3,4-oxadiazoles is by reacting hydrazides with carbon disulfide in presence of potassium hydroxide. It is then converted to 4-amino-1,2,4-triazole (3) by reacting hydrazine hydrate. Target compounds 4-(4- substituted benzylideneamino)-5-(pyridine-4-yl)-4H-1,2,4-triazole-3-thiols (4a-f) were afforded by reacting 4-amino-1,2,4-triazole (3) with aromatic aldehydes. The selection of aromatic aldehydes is based on the electron releasing and electron withdrawing groups on aromatic ring, which would help in drawing important conclusion regarding structure activity relationship (SAR) studies during the investigation of biological activities. All synthesized compounds were confirmed by physicochemical and spectral analysis. The synthesized compounds were tested for their in vitro antibacterial activity against the Gram-positive (Bacillus subtilis and Staphylococcus aureus) and Gramnegative (Salmonella typhi and Escherichia coli) bacteria. Among all the compounds synthesized, compound (4c) was found most active against Gram-positive bacterial strains. Also the compound (4e) gives a better antifungal activity against fungi (C. albicans and A. niger) than other synthesized compounds.
Synthesis, anti-inflammatory, analgesic, and antibacterial activities of some triazole, triazolothiadiazole, and triazolothiadiazine derivatives
Hussein, Mostafa A.,Shaker, Refaat M.,Ameen, Mohammed A.,Mohammed, Mohammed F.
experimental part, p. 1239 - 1250 (2012/05/20)
This study is concerned with the synthesis of new 1,2,4-triazoles, 1,3,4-thiadiazoles, and 1,3,4- thiadiazines derivatives. Derivatives 3a-i were obtained by condensation of 4-amino-3-(4-pyridine)- 5-mercapto-1,2,4-triazole 1 with the appropriate aldehyde
Synthesis of some 5-substituted-1,2,4-triazole-3-thiones, containing thiourea, arylidenamino and morpholin-4-yl methyl fragments
Koparir, Metin,Koparir, Pelin,Cansiz, Ahmet,Temuz, Mehmet Mursit
experimental part, p. 6059 - 6066 (2010/12/24)
In this study, first 4-amino-5-(pyridine-4yl)-4H-1,2,4-triazole-3- thione (1) and 4-amino-5-(2-hydroxyphenyl)-4H-1,2,4-triazole-3-thione (2) were synthesized. In the second step (1) and (2) compounds undergo reaction with aryl isothiocyanates in dry C6H6 to give corresponding N-substituted thiourea derivatives (3a-d and 4a-d). In addition, in the another reaction (1) and (2) compounds were reacted with some aromatic aldehyde in anhydrous ethanol to give corresponding arylidenamino compounds (5a-d and 6a-d). In the third step, aminomethylation derivatives (7a-d and 8a-d) were obtained by the Mannich reactions of arylidenamino compounds (5a-d and 6a-d), with formaldehyde/ morpholine in ethanol. The structures of all the synthesized compounds were confirmed by elemental analyses, FT-IR, 1H and 13C NMR spectra.
Efficient and convenient protocol for the synthesis of novel 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines
Foroughifar, Naser,Mobinikhaledi, Akbar,Ebrahimi, Sattar
experimental part, p. 2421 - 2428 (2010/09/05)
The novel triazolothiadiazine analogs 5a-p were obtained via a multistep synthetic sequence beginning with 5-substituted 4-amino-1,2,4-triazole-3-thiols 1. Compound 1, in reaction with various aromatic aldehydes 2 in acetic acid, afforded Schiff bases 3a-
Synthesis and in vitro antimicrobial activity of some triazole derivatives
Mishra, Ravinesh,Kumar, Rajiv,Kumar, Suresh,Majeed, Jaseela,Rashid, Mohd,Sharma, Sameer
experimental part, p. 359 - 362 (2011/10/18)
Some 4-[{l-(substituted)methylidine}-amino]-3-(4-pyridyl)-5-mercapto-4H-l, 2,4-triazol (3a- 3f) and N-[5-(4-substituted)-lH-l,2,3-triazol-l-yl] isonicotinamide derivatives (5a- 5e) were synthesized by a sequence of reactions starting from isonicotinic acid hydrazide and is illustrated in scheme l and 2. The antibacterial and antifungal activities of newly synthesized compounds were tested by the disc diffusion method using nutrient agar medium against various microorganisms such as gram positive Staphylococcus aureus and Bacillus subtilis, gram negative Escherichia coli and the fungi Aspergillus niger and Candida albicans. Ciprofloxacin and Fluconazole at 50 μg/mL were used as standard drugs for antibacterial and antifungal activities, respectively. All the synthesized compounds showed significant activity against various microorganisms.
Synthesis, biological and computational study of new Schiff base hydrazones bearing 3-(4-pyridine)-5-mercapto-1,2,4-triazole moiety
Khanmohammadi, Hamid,Abnosi, Mohammad H.,Hosseinzadeh, Ali,Erfantalab, Malihe
experimental part, p. 1474 - 1480 (2009/02/06)
A series of new Schiff base hydrazones (compounds 1-16) were synthesized by condensation reaction of 4-amino-3-(4-pyridine)-5-mercapto-1,2,4-triazole with various aldehydes and/or dialdehydes. The structure of the prepared compounds was confirmed by means of 1H NMR, 13C NMR, UV-vis, IR and elemental analyses. The all prepared compounds were assayed for antibacterial (Escherichia coli and Staphylococcus aureus) and antifungal (Candida albicans) activities by disc diffusion method. The results indicate that all tested compounds did not show any antibacterial activity against E. coli, as gram negative bacteria, and antifungal activity against C. albicans. But the compounds 2, 3, 4, 6 and 8 containing 4-Cl, 4-Me, 4-MeO, 2,4-di-Cl and 2-OH substituted phenyl moiety, respectively, showed good inhibition against S. aureus as compare to standard drugs. The structure of all biologically active compounds has also been theoretically studied by ab initio Hartree-Fock (HF) methods.
