Synthesis of fluoro-substituted symmetrical dialkylaminotriazines under interphase-catalysis conditions

Николаева, С. В.; Колбин, А. М.; Sapozhnikov, Yu. E.; Valitov, R. B.; Ivanov, V. F.

doi:10.1007/bf00472187

Cited by 6 publications

(5 citation statements)

References 2 publications

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“…Fluoroatrazine and cyanoatrazine were prepared by heating atrazine with excess potassium fluoride or cyanide in dimethyl sulfoxide at 140°C or in dimethylformamide at 120°C, respectively (16,27). Products were characterized by GC-MS and 1 H and 13 C nuclear magnetic resonance spectroscopy.…”

Section: Methodsmentioning

confidence: 99%

Substrate Specificity of Atrazine Chlorohydrolase and Atrazine-Catabolizing Bacteria

Seffernick

Johnson

Sadowsky

et al. 2000

Appl Environ Microbiol

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Bacterial atrazine catabolism is initiated by the enzyme atrazine chlorohydrolase (AtzA) in Pseudomonas sp. strain ADP. Other triazine herbicides are metabolized by bacteria, but the enzymological basis of this is unclear. Here we begin to address this by investigating the catalytic activity of AtzA by using substrate analogs. Purified AtzA from Pseudomonas sp. strain ADP catalyzed the hydrolysis of an atrazine analog that was substituted at the chlorine substituent by fluorine. AtzA did not catalyze the hydrolysis of atrazine analogs containing the pseudohalide azido, methoxy, and cyano groups or thiomethyl and amino groups. Atrazine analogs with a chlorine substituent at carbon 2 and N-alkyl groups, ranging in size from methyl to t-butyl, all underwent dechlorination by AtzA. AtzA catalyzed hydrolytic dechlorination when one nitrogen substituent was alkylated and the other was a free amino group. However, when both amino groups were unalkylated, no reaction occurred. Cell extracts were prepared from five strains capable of atrazine dechlorination and known to contain atzA or closely homologous gene sequences: Pseudomonas sp. strain ADP, Rhizobium strain PATR, Alcaligenes strain SG1, Agrobacterium radiobacter J14a, and Ralstonia picketti D. All showed identical substrate specificity to purified AtzA from Pseudomonas sp. strain ADP. Cell extracts from Clavibacter michiganensis ATZ1, which also contains a gene homologous to atzA, were able to transform atrazine analogs containing pseudohalide and thiomethyl groups, in addition to the substrates used by AtzA from Pseudomonas sp. strain ADP. This suggests that either (i) another enzyme(s) is present which confers the broader substrate range or (ii) the AtzA itself has a broader substrate range.

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Section: Methodsmentioning

confidence: 99%

Substrate Specificity of Atrazine Chlorohydrolase and Atrazine-Catabolizing Bacteria

Seffernick

Johnson

Sadowsky

et al. 2000

Appl Environ Microbiol

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“…Acetone from Fisher Scientific and ethyl acetate and methyl- tert- butyl-ether (MTBE) from Sigma-Aldrich were high-performance liquid chromatography (HPLC) grade and >99% pure. Fluoroatrazine was synthesized ( 76 ), and 1 H-NMR analysis indicated a purity of ∼90%. 4-Fluorobenzotrifluoride was purchased from Oakwood Chemical.…”

Section: Methodsmentioning

confidence: 99%

Microwell Fluoride Screen for Chemical, Enzymatic, and Cellular Reactions Reveals Latent Microbial Defluorination Capacity for −CF ₃ Groups

Bygd

Aukema

Richman

et al. 2022

Appl Environ Microbiol

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“…4-(4-Chloro-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl)morpholine ( a3 ): 23 colorless oil, yield 80%. ESI-MS m/z: 299.2 [M + H] + .…”

Section: Methodsmentioning

confidence: 99%

Synthesis and biological activity of new 2,4,6-trisubstituted triazines as potential phosphoinositide 3-kinase inhibitors

Xin

Wang

Zhang

et al. 2020

Journal of Chemical Research

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Twenty-five novel 2,4,6-trisubstituted triazines were synthesized and biologically evaluated. Most of the compounds synthesized showed good antiproliferative activity against HCT-116 and MCF-7. Compounds B18 and B19 showed the best antiproliferative activity. Further study showed B18 and B19 inhibited four phosphoinositide 3-kinase isoforms and mammalian target of rapamycin with good potency. These results demonstrate that 2,4,6-trisubstituted triazines are potentially useful phosphoinositide 3-kinase inhibitors for the development of new anticancer drugs.

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Synthesis of fluoro-substituted symmetrical dialkylaminotriazines under interphase-catalysis conditions

Cited by 6 publications

References 2 publications

Substrate Specificity of Atrazine Chlorohydrolase and Atrazine-Catabolizing Bacteria

Substrate Specificity of Atrazine Chlorohydrolase and Atrazine-Catabolizing Bacteria

Microwell Fluoride Screen for Chemical, Enzymatic, and Cellular Reactions Reveals Latent Microbial Defluorination Capacity for −CF ₃ Groups

Synthesis and biological activity of new 2,4,6-trisubstituted triazines as potential phosphoinositide 3-kinase inhibitors

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Synthesis of fluoro-substituted symmetrical dialkylaminotriazines under interphase-catalysis conditions

Cited by 6 publications

References 2 publications

Substrate Specificity of Atrazine Chlorohydrolase and Atrazine-Catabolizing Bacteria

Substrate Specificity of Atrazine Chlorohydrolase and Atrazine-Catabolizing Bacteria

Microwell Fluoride Screen for Chemical, Enzymatic, and Cellular Reactions Reveals Latent Microbial Defluorination Capacity for −CF 3 Groups

Synthesis and biological activity of new 2,4,6-trisubstituted triazines as potential phosphoinositide 3-kinase inhibitors

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About

Microwell Fluoride Screen for Chemical, Enzymatic, and Cellular Reactions Reveals Latent Microbial Defluorination Capacity for −CF ₃ Groups