2272-24-4Relevant articles and documents
Design, synthesis, biological evaluation, and molecular docking study on triazine based derivatives as anti-inflammatory agents
Alvani, Mohsen,Asadi, Parvin,Hajhashemi, Valiollah,Khodarahmi, Ghadamali,Rostami, Mahboubeh
, (2021/07/01)
In an attempt to develop new anti-inflammatory agents, design, synthesis, pharmacological activities, and docking study of two groups of triazine-based derivatives were reported. Nine compounds (5a-5d and 10a-10e) consisting of triazine, vanillin, and phenylpyrazole were synthesized through the pharmacophore hybridization method. After confirmation of the structure of the synthesized compounds using spectroscopic methods (FT-IR, and NMR spectral data), their anti-inflammatory activity was evaluated using carrageenan-induced paw edema model in male Wistar rats (200–220 g) administered intraperitoneally at doses of 100 and 200 mg/kg. A group of rats received indomethacin (10 mg/kg) as the standard drug. Among compounds 5a to 5d, only compounds 5c and 5d showed a significant anti-inflammatory effect (p 0.01). Also compound 10a at a dose of (200 mg/kg) and compounds 10b, 10c, 10d and 10e at both doses showed significant anti-inflammatory activity and this effect for 10a (200 mg/kg) and both doses of 10b and 10e was comparable with indomethacin. While indomethacin reduced paw edema by 90%, 10b as the most potent tested compound reduced edema by 93%. The synthesized compounds were docked into the binding sites of both cyclooxygenase-1- and 2- isoenzymes (COX-1 and COX-2) to explore their binding mode and possible interactions of these ligands.
PIKFYVE INHIBITORS
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Page/Page column 42; 43; 64, (2020/01/31)
The present application provides, inter alia, a compound of Formula (I) or a pharmaceutically acceptable salt thereof, wherein Y, Ar, X1, X2, X3, R1, R2, R3, R4, R5, a
Design and development of novel thiazolidin-4-one-1,3,5-triazine derivatives as neuro-protective agent against cerebral ischemia–reperfusion injury in mice via attenuation of NF-?B
Lu, Min,Qi, Yujun,Han, Yu,Yi, Qiong,Xu, Lei,Sun, Wenlin,Ni, Guihua,Ni, Xiaoyu,Xu, Changsong
, p. 1315 - 1327 (2020/07/13)
The present study enumerates the discovery and development of novel thiazolidin-4-one-1,3,5-triazine as neuro-protective agent against cerebral ischemia–reperfusion injury in mice. These compounds showed significant inhibition of NF-?B transcriptional activity in LPS-stimulated RAW264.7 cells, displaying compound 8k as most potent inhibitor among the tested derivative. The compound 8k was further studied in in vivo middle cerebral artery occlusion (MCAO) mice model for neuro-protective action. Results suggest that compound 8k causes attenuation of inflammation (TNF-α, IL-β, and IL-6), oxidative stress (SOD, GSH, and MDA), and apoptosis (Bcl-2, Bax, and cleaved caspase-3) in MCAO mice in concentration-dependent manner. Collectively, our results documented that compound 8k pre-treatment protects cerebral I/R. This novel lead scaffold may be helpful for investigation of new neuro-protective agent by inactivation of NF-?B.
Tailoring the Substitution Pattern on 1,3,5-Triazine for Targeting Cyclooxygenase-2: Discovery and Structure-Activity Relationship of Triazine-4-Aminophenylmorpholin-3-one Hybrids that Reverse Algesia and Inflammation in Swiss Albino Mice
Singh, Palwinder,Kaur, Sukhmeet,Kumari, Priya,Kaur, Baljit,Kaur, Manpreet,Singh, Gurjit,Bhatti, Rajbir,Bhatti, Manpreet
, p. 7929 - 7941 (2018/09/06)
Here, we report analgesic and anti-inflammatory activity of a series of compounds obtained by appending 4-aminophenylmorpholin-3-one and acyclic, cyclic, or heterocyclic moieties on 1,3,5-triazine. The structures of compounds 4b and 6b are optimized for the best inhibition of COX-2 with IC50 values of 0.06 and 0.08 μM, respectively, and selectivity over COX-1 of 166 and >125, respectively. At the dose of 5 mg kg-1, these compounds significantly reduced acetic acid induced writhings, and their ED50 values were found to be 2.2 and 1.9 mg kg-1, respectively. Besides the cell-based and animal-based experiments showing the modes of action of these compounds targeting COX-2, the interaction behavior of 4b with COX-2 was also characterized, with physicochemical experiments including ITC, NMR, UV-vis, and molecular-modeling studies. Characteristically, these compounds interact with R120, Y355, and W385, the residues responsible for holding the substrate and mediating the process of electron transfer during the metabolic phase of the enzyme.
Rational design, synthesis and biological screening of triazine-triazolopyrimidine hybrids as multitarget anti-Alzheimer agents
Jameel, Ehtesham,Meena, Poonam,Maqbool, Mudasir,Kumar, Jitendra,Ahmed, Waqar,Mumtazuddin, Syed,Tiwari, Manisha,Hoda, Nasimul,Jayaram
, p. 36 - 51 (2017/05/09)
In our endeavor towards the development of potent multitarget ligands for the treatment of Alzheimer's disease, a series of triazine-triazolopyrimidine hybrids were designed, synthesized and characterized by various spectral techniques. Docking and scoring techniques were used to design the inhibitors and to display their interaction with key residues of active site. Organic synthesis relied upon convergent synthetic routes were mono and di-substituted triazines were connected with triazolopyrimidine using piperazine as a linker. In total, seventeen compounds were synthesized in which the di-substituted triazine-triazolopyrimidine derivatives 9a-d showed better acetylcholinesterase (AChE) inhibitory activity than the corresponding tri-substituted triazine-triazolopyrimidine derivatives 10a-f. Out of the disubstituted triazine-triazolopyrimidine based compounds, 9a and 9b showed encouraging inhibitory activity on AChE with IC50 values 0.065 and 0.092?μM, respectively. Interestingly, 9a and 9b also demonstrated good inhibition selectivity towards AChE over BuChE by ～28 folds. Furthermore, kinetic analysis and molecular modeling studies showed that 9a and 9b target both catalytic active site as well as peripheral anionic site of AChE. In addition, these derivatives effectively modulated Aβ self-aggregation as investigated through CD spectroscopy, ThT fluorescence assay and electron microscopy. Besides, these compounds exhibited potential antioxidants (2.15 and 2.91 trolox equivalent by ORAC assay) and metal chelating properties. In silico ADMET profiling highlighted that, these novel triazine derivatives have appropriate drug like properties and possess very low toxic effects in the primarily pharmacokinetic study. Overall, the multitarget profile exerted by these novel triazine molecules qualified them as potential anti-Alzheimer drug candidates in AD therapy.
Synthesis of 4-amino-6-chloro-1,3,5-triazin-2(1H)-ones
Bakharev,Gidaspov,Parfenov,Ulyankina,Zavodskaya,Selezneva,Suponitskii,Sheremetev
, p. 99 - 112 (2013/01/15)
Conditions for selective substitution for one chlorine atom in 2-(R,R-amino)-4,6-dichloro-1,3,5-triazines with a hydroxide ion were elaborated. Spectral and calculation methods showed that the products formed are in the lactam form, i.e., have the structure of 4-chloro-6-(R,R- amino)-1,3,5-triazin-2(1H)-ones.
Synthesis and antibacterial activity studies of some 2-(substitutedphenyl)- 3-bis2, 4-(4'-methylphenylamino)-s-triazine-6-ylaminobenzoylamino-5-H-4- thiazolidinone
Ahirwar, Mukesh Kumar,Shrivastava
experimental part, p. 988 - 992 (2012/07/28)
Some 4-thiazolidinone derivatives 6(a-l) have been prepared bearing s-triazine moiety by the condensation of Schiff bases from bis-2,4 (4'-methyl-phenylamino)-s-triazine-6-ylaminobenzoyl substituted benzylhydrazone 5(a-l) with thioglycolic acid. The structures of synthesized compounds have been characterized by IR, 1HNMR spectral studies. The synthesized compounds 6(a-l) have been screened for antibacterial activity.
Design, facile synthesis, antibacterial activity and structure-activity relationship of novel di- and tri-substituted 1,3,5-triazines
Ghosh, Surajit Kumar,Saha, Ashmita,Hazarika, Bornali,Singh, Udaya Pratap,Bhat, Hans Raj,Gahtori, Prashant
experimental part, p. 329 - 335 (2012/05/20)
Due to overwhelming generation of drug resistant microorganisms, there is an urgent need to develop novel chemotherapeutic agents. In continuation of our research on discovery of novel heterocyclic scaffolds from 1,3,5-triazine, present study deals with design and development of some novel di- and tri-substituted 1,3,5-triazine derivatives. The synthesis of title analogues were accomplished by SNAr reaction and subsequently underwent rigorous antibacterial screening against a panel of representative Gram-negative and Gram-positive bacteria. Screening results revealed that minor structural variation may induce drastic changes in activity. Whereas, amine bridge and piprazine was termed as pivotal structural fragments necessary for generation and escalation of bio-activity. The structures of newly synthesized compounds were ascertained on the basis of their analytical and spectral profiles.
4-Anilinoquinoline triazines: A novel class of hybrid antimalarial agents
Kumar, Ashok,Srivastava, Kumkum,Raja Kumar,Siddiqi,Puri, Sunil K.,Sexana, Jitendra K.,Chauhan, Prem M.S.
experimental part, p. 676 - 690 (2011/03/21)
A novel class of hybrid 4-anilinoquinoline triazines have been synthesized and evaluated in vitro for their antimalarial activity against CQ-sensitive 3D7 strain of P. falciparum as well as for their cytotoxicity toward VERO cell line. Five compounds (19,
Simple and efficient synthetic routes to bioactive s-triazinyl dithiocarbamate derivatives
Desai,Dodiya,Trivedi,Shah
, p. 495 - 506 (2008/12/23)
Series of 2,4-diarylamino-6-[N-(3′-methylphenyl)dithiocarbamoyl]-s- triazines (4a-l) and 2,4-bis[N-(3′-methylphenyl)dithiocarbamoyl]-6- arylamino-s-triazines (7a-l) were synthesized by two different synthetic routes. In the first route (A), 2,4,6-tricholoro-s-triazine (1) was condensed with N-(3-methylphenyl)ammoniumdithiocarbamate to afford compounds 3 or 6, which on reaction with different aryl amines afforded compounds 4a-l or 7a-l. In the second route (B), condensation of 1 with different aryl amines yielded compounds 2a-l or 5a-l. On further treatment with N-(3-methylphenyl) ammoniumdithiocarbamate these afforded compounds 4a-l or 7a-l. The newly synthesized compounds 4a-l and 7a-l were characterized by elemental analyses, infrared (IR), and 1H nuclear magnetic resonance (NMR) spectroscopic investigation. All the products were evaluated for their antibacterial and antifungal activity.
