3179-31-5Relevant articles and documents
Deamination of some N-amino nitrogen heterocycles using Preyssler's anion
Heravi, Majid M.,Sadjadi, Sodeh,Hekmatshoar, Rahim,Oskooie, Hossein A.,Bamoharram, Fatemeh F.
, p. 107 - 110 (2008)
Some N-aminotriazines and -triazoles were treated with Preyssler's anion as catalyst in acetic acid to afford the corresponding deaminated triazines and triazoles. The reaction is suggested to proceed via formation of N-nitrosamines with subsequent N-NO b
Synthesis, characterization and anti-inflammatory activity evaluation of 1,2,4-triazole and its derivatives as a potential scaffold for the synthesis of drugs against prostaglandin-endoperoxide synthase
Khan, Bushra,Naiyer, Abdullah,Athar, Fareeda,Ali, Shakir,Thakur, Sonu Chand
, p. 457 - 475 (2020/01/22)
Substituted 1,2,4-triazole nucleus is common in several drugs used in a variety of clinical conditions including infections, hypoglycemia, hypertension and cancer. In this study, we synthesized 1,2,4-triazole and its 16 hydrazone derivatives (B1–B16), characterized them by IR, NMR and Mass spectroscopy, and evaluated their radical scavenging and anti-inflammatory activities in?vitro and in?vivo. Out of 16 derivatives, five (B1, B5, B6, B9, and B13) demonstrated a significant radical scavenging and anti-inflammatory activity in?vitro. B6, which possessed two electron-donating hydroxyl groups, was most active among all. Molecular docking and MD simulation of the complex of B6 with prostaglandin-endoperoxide synthase (PTGS) or cyclooxygenase (COX) showed that B6 occupied celecoxib binding site in COX with high affinity (the binding free energy of the complex with COX-1 was –10.5, and –11.2 kcal/mol with COX-2). Maximum anti-inflammatory activity was also shown by the B6 derivative in?vivo, in the rat model of carrageenan-induced inflammation. B6, along with four other derivatives (B1, B5, B9 and B13) exhibited 80–90% free radical scavenging activity. The IC50 values of these compounds were ≥40 μM. Griess nitrite and dichloro-dihydro-fluorescein-diacetate assays suggested a significant inhibition of nitric oxide and reactive oxygen species, especially by B6 and B9. Taken together, out of 16 derivatives, B6 is reported to have highest anti-inflammatory and antioxidant activity at a low dose level, which may be attributed to its two electron-donating hydroxyls. B6 is proposed to be an important scaffold for the synthesis of new drugs against PTGS for use in a myriad of inflammatory and infectious diseases. Communicated by Ramaswamy H. Sarma.
Novel panaxadiol triazole derivatives induce apoptosis in HepG-2 cells through the mitochondrial pathway
Xiao, Shengnan,Wang, Xude,Xu, Lei,Li, Tao,Cao, Jiaqing,Zhao, Yuqing
, (2020/07/23)
In this study, we introduced 1, 2, 4-triazole groups into panaxadiol (PD) to obtain 18 panaxadiol triazole derivatives. Five cancer cells and one normal cell were evaluated for cytotoxicity by MTT assay. The results showed that most of the derivatives could inhibit cancer cell proliferation, and the anti-proliferative activity of compound A1 was the most significant. For HepG-2 cells, the IC50 value was 4.21 ± 0.54 μM, which was nearly 15 times higher than the activity of PD. Further studies showed that compound A1 could induce apoptosis in HepG-2 cells, and could enhance the expression of Cl-caspase-3, Cl-caspase-9 and Cl-PARP. Moreover, Western blot analysis showed that after treating HepG-2 cells with compound A1, the expression of p53 protein was increased and the ratio of Bax/Bcl-2 was gradually increased. The cytoplasmic Bax is then translocated to the mitochondria, causing the release of Cyt c protein. Therefore, the results indicate that compound A1 induces apoptosis through the mitochondrial pathway and can be used the potential to develop new anti-proliferative agents.
Design, Synthesis, and Structure-Activity Relationship of Economical Triazole Sulfonamide Aryl Derivatives with High Fungicidal Activity
Hao, Ge-Fei,Li, Yi-Tao,Lin, Jian,Xu, Jun-Xing,Yao, Wen-Qiang,Zhou, Si
, p. 6792 - 6801 (2020/07/08)
Plant fungal diseases have caused great decreases in crop quality and yield. As one of the considerable agricultural diseases, cucumber downy mildew (CDM) caused by pseudoperonospora cubensis seriously influences the production of cucumber. Amisulbrom is a commercial agricultural fungicide developed by Nissan Chemical, Ltd., for the control of oomycetes diseases that is highly effective against CDM. However, the synthesis of amisulbrom has a high cost because of the introduction of the bromoindole ring. In addition, the continuous use of amisulbrom might increase the risk of resistance development. Hence, there is an imperative to develop active fungicides with new scaffolds but low cost against CDM. In this study, a series of 1,2,4-triazole-1,3-disulfonamide derivatives were designed, synthesized, and screened. Compound 1j showed a comparable fungicidal activity with amisulbrom, but it was low cost and ecofriendly. It has the potential to be developed as a new fungicide candidate against CDM. Further investigations of structure-activity relationship exhibited the structural requirements of 1,2,4-triazole-1,3-disulfonamide and appropriate modification in N-alkyl benzylamine groups with high fungicidal activity. This research will provide powerful guidance for the design of highly active lead compounds with a novel skeleton and low cost.
Discovery of a new fungicide by screening triazole sulfonylhydrazone derivatives and its downy mildew inhibition in cucumber
Gao, Guoliang,Jing, Dewang,Li, Yitao,Lin, Jian,Wu, Yang,Yao, Wenqiang
, (2020/03/05)
Downy mildew is a very important detrimental disease that lead reduced to fruits and vegetables. Due to the continuous growth of drug resistance, finding novel fungicides with dissimilar modes of function from present fungicides for controlling downy mildew are imminent. This work is an extension of our preceding research on the original triazole sulfonamide derivatives lead compound. Triazole sulfonamide as a remarkable nitrogen-containing heterocyclic compound opposed cucumber downy mildew (CDM) develops a quite vital part in the sphere of the study of new farm chemicals. The existing report designs a certain amount of 1,2,4-triazole-1,3-disulfonamide derivatives. Hydrazones have obtained extensive attention in the field of pharmaceutical due to its unique chemical structure and remarkable activity (insecticidal, antibacterial, antifungal and herbicidal). By means of coupling numerous hydrazone with triazole sulfonyl chloride groups, 24 novel derivatives were synthesized. Spectrum analysis of LC-MS, 1H NMR and 13C NMR were used for characterizing these new compounds. Compared with commercial Cyazofamid using bioassays, most of these compounds displayed preferable fungicidal activities. Moreover, compounds 8q illustrated the greatest CDM resistance (EC50 = 7.776 mg/L). Field efficacy trials revealed that compound 8q fungicidal activity was higher than the purchased agrochemical Cyazofamid and Amisulbrom. Thus, the research declared that 8q displayed a great potential for the application of fungicide against CDM.
Design, Synthesis, and Biological Activity of Novel Triazole Sulfonamide Derivatives Containing a Benzylamine Moiety
Li, Yitao,Yao, Wenqiang,Lin, Jian,Li, Falin,Wu, Yang,Xu, Junxing
, p. 2170 - 2178 (2019/07/09)
The triazole sulfonamide played a very important role in the field of research of new agrochemical compounds as a novel heterocyclic compound with lack of reported resistance. For the research on the innovative triazole sulfonamide fungicide effective against cucumber downy mildew (CDM), the present article designed an array of 1,2,4-triazole-1,3-disulfonamide derivatives. The derivatives were synthesized via coupling multiple benzylamine with triazole sulfonamide groups. 1H-NMR, 13C-NMR, and LC–MS spectrometry were used to characterize these synthesized compounds. Most of these derivatives exhibited better fungicidal activities than that of the commercial cyanosole using bioassays. In particular, compounds 6g and 6h showed the best fungicidal activity against CDM (EC50?=?6.91 and 10.62?mg/L). Comparative experiments demonstrated that the fungicidal activity of 6g and 6h was better than the commercial pesticides amisulbrom and cyanosole. According to the study, the compound 6g had a giant application potential on fungicide against CDM.
Triazole compounds and their use in agriculture (by machine translation)
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Paragraph 0355; 0356; 0357; 0358, (2018/11/04)
The present invention provides a triazole compound and its application in agriculture; in particular, the invention provides compounds of formula (A) indicated by the compound and its preparation method; the composition containing these compounds and preparation and their use as fungicides; wherein R1 , R2 , R3 , W, R4 , R5 , R6 , R7 , R8 , R9 , Ra , Rb And in the event of x has the meanings given by the invention. (by machine translation)
Intermediate compound, and synthetic method of prothioconazole
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Paragraph 0054; 0055; 0062; 0066; 0067; 0076; 0077, (2017/07/22)
The invention discloses an intermediate compound, and a synthetic method of prothioconazole. The method comprises the following steps: carrying out a substation reaction on 5,5'-dithio-bis(1,2,4-triazole) and 2-(1-chlorocyclopropyl)-3-chloro-1-(2-chlorophenyl)-2-propanol to obtain the key intermediate compound; and reducing the key intermediate compound to obtain the target product prothioconazole. The synthetic method has the advantages of high conversion rate, high selectivity, cheap and easily available synthesis raw materials, reduction of the production cost, mild and easily controlled technologic reaction conditions, simplicity in operation, easiness in product purification, obtaining of the product through direct re-crystallization, simple and accurate control method of intermediates in all steps, high product yield, good atom economy, avoiding of tedious post-treatment, large competition advantages and industrial production utilization values, avoiding of strong alkalis and other raw materials, extremely low three wastes, and according with the green chemistry idea.
Synthesis and biological evaluation of novel thiazolidinone derivatives as potential anti-inflammatory agents
Hu, Jie,Wang, Yi,Wei, Xiaoyan,Wu, Xixi,Chen, Gaozhi,Cao, Gaozhong,Shen, Xueqian,Zhang, Xiuhua,Tang, Qinqin,Liang, Guang,Li, Xiaokun
, p. 292 - 301 (2013/07/11)
The modulation of pro-inflammatory cytokines provides a target for controlling inflammatory diseases and attracts much attention in current anti-inflammatory drug development. Here, four series of thiazolidinone derivatives were synthesized and screened for anti-inflammatory activities. A majority of these compounds showed excellent inhibition on the expression of TNF-α and IL-6 in LPS-stimulated macrophages. Discussions are given regarding the structure-activity relationships. Compounds 12d and 12h inhibited LPS-induced TNF-α and IL-6 release in a dose-dependent manner. Furthermore, 12d exhibited a significant protection against LPS-induced septic death in mouse model. Together, these data present a series of new thiazolidinones with potential therapeutic effects in acute inflammatory diseases and they could be important leads in the continuing anti-inflammatory drug research.
Synthesis and biological screening of novel derivatives of 3-(N-substituted carboxamidoethylthio)-(4H)-1,2,4-triazoles
Manikrao, Anil M.,Fursule, Ravindra A.,Rajesh,Kunjwani, Harish K.,Sabale, Prafulla M.
experimental part, p. 1642 - 1647 (2011/03/17)
3-Mercapto-(4H)-1,2,4-triazole has been synthesized from 1-formylthiosemicarbazide. Different N-substituted β-chloropropionamides have been prepared by reacting substituted amines with β- chloropropionylchloride. Different Nsubstituted β-chloropropionamides have been condensed with 3-mercapto-(4H)-1,2,4-triazole in basic medium to obtain various 3-(N-substituted carboxamidoethylthio)-(4H)-1,2,4-triazoles. The structure of the synthesized compounds are confirmed by IR, 1H NMR spectra and elemental analysis. All the compounds have been screened for their analgesic, anti-inflammatory and anxiolytic activity.
