Cyanuric Chloride Derivatives. I. Aminochloro-s-triazines

Thurston, Jack T.; Dudley, James R.; Kaiser, Donald W.; Hechenbleikner, Ingenuin; Schaefer, Frederic C.; Holm-Hansen, Dagfrid

doi:10.1021/ja01151a001

Cited by 281 publications

(102 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Ammelide and ammeline derivatives were prepared as follows. First, 2,4-dichloro-6-amino-1,3,5-triazine and 2,4-dichloro-6-(N-substitutedamino)-1,3,5-triazines were prepared from cyanuric chloride as described by Thurston et al (37), and then the amino-dichloro compounds were hydrolyzed to give the parent ammelides as described by Smolin and Rapoport (35). Ammeline derivatives were prepared as follows.…”

Section: Chemicalsmentioning

confidence: 99%

Hydroxyatrazine N -Ethylaminohydrolase (AtzB): an Amidohydrolase Superfamily Enzyme Catalyzing Deamination and Dechlorination

et al. 2007

View full text Add to dashboard Cite

Hydroxyatrazine [2-(N-ethylamino)-4-hydroxy-6-(N-isopropylamino)-1,3,5-triazine] N-ethylaminohydrolase(AtzB) is the sole enzyme known to catalyze the hydrolytic conversion of hydroxyatrazine to N-isopropylammelide. AtzB, therefore, serves as the point of intersection of multiple s-triazine biodegradative pathways and is completely essential for microbial growth on s-triazine herbicides. Here, atzB was cloned from Pseudomonas sp. strain ADP and its product was purified to homogeneity and characterized. AtzB was found to be dimeric, with subunit and holoenzyme molecular masses of 52 kDa and 105 kDa, respectively. The k cat and K m of AtzB with hydroxyatrazine as a substrate were 3 s ؊1 and 20 M, respectively. Purified AtzB had a 1:1 zinc-to-subunit stoichiometry. Sequence analysis revealed that AtzB contained the conserved mononuclear amidohydrolase superfamily active-site residues His74, His76, His245, Glu248, His280, and Asp331. An intensive in vitro investigation into the substrate specificity of AtzB revealed that 20 of the 51 compounds tested were substrates for AtzB; this allowed for the identification of specific substrate structural features required for catalysis. Substrates required a monohydroxylated s-triazine ring with a minimum of one primary or secondary amine substituent and either a chloride or amine leaving group. AtzB catalyzed both deamination and dechlorination reactions with rates within a range of one order of magnitude. This differs from AtzA and TrzN, which do not catalyze deamination reactions, and AtzC, which is not known to catalyze dechlorination reactions.

show abstract

Section: Chemicalsmentioning

confidence: 99%

Hydroxyatrazine N -Ethylaminohydrolase (AtzB): an Amidohydrolase Superfamily Enzyme Catalyzing Deamination and Dechlorination

et al. 2007

View full text Add to dashboard Cite

show abstract

“…As a result, a careful control of the temperature during the substitution reactions will allow the synthesis of 2,4,6-trisubstituted-triazines by sequential and very selective addition of amines or thiols. The first substitution of chlorine in cyanuric chloride was carried out with diethyl amine at 0°C in aqueous dioxane medium followed by simple re-crystallization to facilitate isolation of pure product 1, in 81% yield 17 . The second substitution in 1 was carried out by 4-(4′-chloro)phenylthiazolyl-2-amine and 4-(3′,4′-dichloro)phenylthiazolyl-2-amine, respectively, at room temperature to afford 19c and 28d in good yields.…”

Section: P Gahtori and S K Ghoshmentioning

confidence: 99%

Design, synthesis and SAR exploration of hybrid 4-chlorophenylthiazolyl-s-triazine as potential antimicrobial agents

Gahtori

Ghosh

2011

Journal of Enzyme Inhibition and Medicinal Chemistry

View full text Add to dashboard Cite

“…These 1,3,5-triazines have their own identity and importance in medicinal 7 , pharmaceutical 8 , agricultural 9 and industrial 10 fields few of them possesses antidiabetic [11][12] , anti-tumor [13][14][15][16] , anti-inflammatory 17 , anti-depresent 18 , hypoglycaemic 19 activities. They are also used as herbicidal [20][21][22][23][24][25][26] , fungicidal 27-29 , insecticidal 30 , anti-corrosive 31 , antimicrobial 32 and anti-convulsant 33 properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1-Substituted-2-Formamidino-4-Amino-6-Thio1,3,5-Triazines

Tayade¹,

Ingole²,

Waghmare³

2018

IJCTR

View full text Add to dashboard Cite

:Recently in this laboratory 1-substituted-2-formamidino-4-amino-6-thio-1,3,5-triazines (XIIIa-g) were synthesised by isomerisation of 2-substituted imino-4-amino-6-formamidino-1,3,5-thiadiazines (XIIa-g) successfully by refluxing with 10% aqueous ethanolic sodium bicarbonate medium. The structure of all the synthesized compounds was justified on the basis of chemical characteristics, elemental analysis and spectral studies.

show abstract

Cyanuric Chloride Derivatives. I. Aminochloro-s-triazines

Cited by 281 publications

References 0 publications

Hydroxyatrazine N -Ethylaminohydrolase (AtzB): an Amidohydrolase Superfamily Enzyme Catalyzing Deamination and Dechlorination

Hydroxyatrazine N -Ethylaminohydrolase (AtzB): an Amidohydrolase Superfamily Enzyme Catalyzing Deamination and Dechlorination

Design, synthesis and SAR exploration of hybrid 4-chlorophenylthiazolyl-s-triazine as potential antimicrobial agents

Synthesis of 1-Substituted-2-Formamidino-4-Amino-6-Thio1,3,5-Triazines

Contact Info

Product

Resources

About