Synthesis of Some Thiadiazolotriazinone Derivatives as Possible Antimicrobial Agents

Prasad, D. Jagadeesh; Karthikeyan, Mari Sithambaram; Karegoudar, Prakash; Poojary, Boja; Holla, B. Shivarama; Kumari, N. Suchetha

doi:10.1080/10426500601096435

Cited by 14 publications

(8 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Recently, significant activities have been directed toward this class of compounds, in particular, 4-amino-1,2,4-triazin-5(2H)-one derivatives which have considerable interest because of their herbicidal [6,7], antimicrobial [8][9][10], anti-HIV [11] and anticancer activities [12,13]. On the other hand, heterocyclic systems containing phosphorus atoms have considerable attention due to a large variety of interesting pharmacological and biological activities, such as herbicidal [14][15][16], insecticidal [17], antimicrobial [18] and anticancer properties [19].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antibacterial activity of some new thiadiaza/triazaphospholes, thiadiaza/triaza/tetrazaphosphinines and thiadiaza/tetrazaphosphepines containing 1,2,4-triazinone moiety

Ali

2009

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

Section: Introductionmentioning

confidence: 99%

Synthesis and antibacterial activity of some new thiadiaza/triazaphospholes, thiadiaza/triaza/tetrazaphosphinines and thiadiaza/tetrazaphosphepines containing 1,2,4-triazinone moiety

Ali

2009

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

“…The versatile pyrazole synthesis allowed generation of a variety of analogues including the unsubstituted phenyl and 3-methoxy-and 4-methoxyphenyl, as well as the 3,5-dichlorophenyl, 3-chloro-, and 4-chlorophenyl compounds. The phenylfuran N-caps were also synthesized through a diazotization of the requisite aniline, followed by reaction with furoic acid (Scheme 3); 17 the phenylpyrrole was generated through cyclization of appropriate aniline with 2,5dimethoxytetrahydrofuran-3-carbaldehyde in acetic acid (Scheme 4); 18 and the phenylimidazole was synthesized through cyclization of 3-fluoro-N′-hydroxybenzimidamide and ethyl propiolate (Scheme 5). 19 Structure−Activity Relationship of Substituted Phenylheterocyclic Isosteres as N-Terminal Capping Groups.…”

Section: ■ Resultsmentioning

confidence: 99%

“…Preparation of Phenylfuran N-Capping Groups (Scheme 3) 17 (5768 and 5769). Synthesis of 5-(3,5-Dichlorophenyl)furan-2-carboxylic acid (6).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Optimization of Non-ATP Competitive CDK/Cyclin Groove Inhibitors through REPLACE-Mediated Fragment Assembly

et al. 2013

View full text Add to dashboard Cite

A major challenge in drug discovery is to develop and improve methods for targeting protein-protein interactions. Further exemplification of the REPLACE strategy for generating inhibitors of protein-protein interactions demonstrated that it can be used to optimize fragment alternatives of key determinants, to combine these in an effective way and was achieved for compounds targeting the CDK2 substrate recruitment site on the cyclin regulatory subunit. Phenylheterocyclic isosteres replacing a critical charge-charge interaction provided new structural insights for binding to the cyclin groove. In particular, these results shed light onto the key contributions of a H-bond observed in crystal structures of N-terminally capped peptides. Furthermore the structure-activity relationship of a bisarylether C-terminal capping group mimicking dipeptide interactions, was probed through ring substitutions, allowing increased complementarity with the primary hydrophobic pocket. This study further validates REPLACE as an effective strategy for converting peptidic compounds to more pharmaceutically relevant compounds.

show abstract

“…Various substituted 1,2,4‐triazinone derivatives have a great importance as biological agents in medicinal and agricultural fields . Furthermore, significant activities have been focused towards this specific substances, particularly, 4‐amino‐1,2,4‐triazin‐5‐one derivatives that have predominate interest because of the herbicidal , antimicrobial , anti‐HIV , and anticancer activities . 1,2,4‐Triazole is an important template that is connected with several biological activities as antibacterial, anticholinergic, analgesic, and antiasthmatic .…”

Section: Introductionmentioning

confidence: 99%

Synthetic Approach to Some New Annulated 1,2,4‐Triazine Skeletons with Antimicrobial and Cytotoxic Activities

Hamama

El‐Bana

Shaaban

et al. 2018

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

in Wiley Online Library (wileyonlinelibrary.com).The synthesis of some triazolotriazine, tetrazolotriazine, triazinotetrazine, and triazinotetrazepinoindole by the reaction of 4-amino-6-benzyl-3-hydrazinyl-1,2,4-triazin-5(4H)-one (2) with different reagents is described. The synthesized compounds were screened for their antimicrobial activity using the minimum inhibition concentration method by serial dilution technique. Two of these compounds showed higher activity than that of standard drug, and they were further evaluated for their cytotoxic activities against human cancer cells (MCF-7, HCT116, and HepG2), which indicate strong effect on these cancer cell lines. J. Heterocyclic Chem., 55, 971 (2018). and the carbonyl group of acid to form hydrazone intermediate, which underwent a cyclization reaction between the secondary amine and the hydroxyl group of the acid function affording 3, following pathway A. The constitution of 3 was deduced from its spectral data. Its 1 H NMR spectrum showed a singlet signal at δ = 2.49 and 6.05 ppm corresponding to CH 3 and NH 2 , Scheme 2. Action of 1,2-diketonic compounds on the triazino hydrazine derivative 2 to form the corresponding hydrazones 7, 8, 9, and 11. Scheme 1. Heterocyclization reaction of 2 with various reagents. Scheme 3. Alkylation of hydrazine derivative 2 with halo compounds. 972W.

show abstract

Synthesis of Some Thiadiazolotriazinone Derivatives as Possible Antimicrobial Agents

Cited by 14 publications

References 9 publications

Synthesis and antibacterial activity of some new thiadiaza/triazaphospholes, thiadiaza/triaza/tetrazaphosphinines and thiadiaza/tetrazaphosphepines containing 1,2,4-triazinone moiety

Synthesis and antibacterial activity of some new thiadiaza/triazaphospholes, thiadiaza/triaza/tetrazaphosphinines and thiadiaza/tetrazaphosphepines containing 1,2,4-triazinone moiety

Optimization of Non-ATP Competitive CDK/Cyclin Groove Inhibitors through REPLACE-Mediated Fragment Assembly

Synthetic Approach to Some New Annulated 1,2,4‐Triazine Skeletons with Antimicrobial and Cytotoxic Activities

Contact Info

Product

Resources

About