2515-30-2Relevant academic research and scientific papers
Design, discovery, modelling, synthesis, and biological evaluation of novel and small, low toxicity s-triazine derivatives as HIV-1 non-nucleoside reverse transcriptase inhibitors
Viira, Birgit,Selyutina, Anastasia,García-Sosa, Alfonso T.,Karonen, Maarit,Sinkkonen, Jari,Merits, Andres,Maran, Uko
, p. 2519 - 2529 (2016/05/09)
A set of top-ranked compounds from a multi-objective in silico screen was experimentally tested for toxicity and the ability to inhibit the activity of HIV-1 reverse transcriptase (RT) in cell-free assay and in cell-based assay using HIV-1 based virus-like particles. Detailed analysis of a commercial sample that indicated specific inhibition of HIV-1 reverse transcription revealed that a minor component that was structurally similar to that of the main compound was responsible for the strongest inhibition. As a result, novel s-triazine derivatives were proposed, modelled, discovered, and synthesised, and their antiviral activity and cellular toxicity were tested. Compounds 18a and 18b were found to be efficient HIV-1 RT inhibitors, with an IC50 of 5.6 ± 1.1 μM and 0.16 ± 0.05 μM in a cell-based assay using infectious HIV-1, respectively. Compound 18b also had no detectable toxicity for different human cell lines. Their binding mode and interactions with the RT suggest that there was strong and adaptable binding in a tight (NNRTI) hydrophobic pocket. In summary, this iterative study produced structural clues and led to a group of non-toxic, novel compounds to inhibit HIV-RT with up to nanomolar potency.
Antimalarial activity and docking studies of novel bi-functional hybrids derived from 4-aminoquinoline and 1,3,5-triazine against wild and mutant malaria parasites as pf-DHFR inhibitor
Bhat, Hans Raj,Singh, Udaya Pratap,Gahtori, Prashant,Ghosh, Surajit Kumar,Gogoi, Kabita,Prakash, Anil,Singh, Ramendra K.
, p. 2942 - 2952 (2013/05/08)
Bi-functional conjugates comprised of 4-aminoquinoline and 1,3,5-triazine were synthesized through facile synthetic routes. These compounds were rigorously screened for determination of their antimalarial activity against wild and mutant cultured Plasmodium falciparum. The results disclosed that the conjugates have considerable antimalarial activity against both wild and mutant parasites with marked variation on changing the pattern of substitutions. The observed activity profiles were additionally substantiated by docking studies on both wild and quadruple mutant P. falciparum dihydrofolate reductase thymidylate synthase (pf-DHFR-TS).
4-Aminoquinoline-1,3,5-triazine: Design, synthesis, in vitro antimalarial activity and docking studies
Bhat, Hans Raj,Singh, Udaya Pratap,Gahtori, Prashant,Ghosh, Surajit Kumar,Gogoi, Kabita,Prakash, Anil,Singh, Ramendra K.
, p. 2654 - 2662 (2013/09/12)
A series of hybrid 4-aminoquinoline 1,3,5-triazine derivatives was synthesized and their chemical structure were confirmed by 1H-NMR, 13C-NMR, FT-IR and mass spectrometric analyses. In vitro antimalarial activity of these compounds was evaluated against chloroquine-sensitive (3D-7) and chloroquine resistant (RKL-2) strains of P. falciparum. Results showed that all compounds had considerable antimalarial activity against both the strains and further docking studies were performed on both wild type (1J3I.pdb) and quadruple mutant (N51I, C59R, S108 N, I164L, 3QG2.pdb) pf-DHFR-TS to quantify the structural parameter necessary for the activity.
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.
Design, Facile Synthesis, and Antibacterial Activity of Hybrid 1,3,4-thiadiazole-1,3,5-triazine Derivatives Tethered via -S- Bridge
Dubey, Vaibhav,Pathak, Manish,Bhat, Hans R.,Singh, Udaya P.
, p. 598 - 604 (2012/11/07)
Some hybrid 1,3,4-thiadiazole-1,3,5-triazine derivatives tethered via -S- bridge were synthesized and characterized with the aid of spectroscopic and elemental analysis. These hybrid conjugates were then investigated for their antibacterial activity against selected Gram-positive and Gram-negative bacteria. Excellent to moderate antibacterial activity was presented by the target compounds.
Synthesis and bioevaluation of hybrid 4-aminoquinoline triazines as a new class of antimalarial agents
Kumar, Ashok,Srivastava, Kumkum,Raja Kumar,Puri,Chauhan, Prem M.S.
scheme or table, p. 6530 - 6533 (2009/09/06)
The emergence and rapid spread of chloroquine resistant strains of Plasmodium falciparum has dramatically reduced the chemotherapeutic options. Towards this goal, a series of new class of hybrid 4-aminoquinoline triazines were synthesized and screened aga
An efficient, "green" approach to aryl amination of cyanuric chloride using acetic acid as solvent
Kolmakov, Kirill A.
, p. 533 - 539 (2008/09/18)
(Chemical Equation Presented) Acetic acid is an inexpensive and environmentally friendly solvent for facile, clean and high-yielding aryl amination of cyanuric chloride with aromatic amines, including nitroanilines. Aryl animation in acetic acid medium and isolation protocol are greatly simplified as compared to previously reported procedures. Under proper conditions, it is possible to attach the same or different aniline residues in a controlled way to obtain in excellent yields symmetrical and unsymmetrical 1,3,5-triazine derivatives, respectively.
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.
