Reactions of 4-oxo-1,3-benzoxazinium perchlorates with guanidines

Suvorova, E. Yu.; Vikrishchuk, N. I.; Попов, Л. Д.; Starikova, Z. A.; Vikrishchuk, A. D.; Zhdanov, Yu. A.

doi:10.1134/s1070428007100259

Cited by 10 publications

(6 citation statements)

References 3 publications

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“…A typical example with Z 0 = 3 is found for 2-isopropyl-5-methyl-cyclohexanol (CSD: BAVLOZ, Bombicz et al, 1999) with homomeric Á Á ÁAÁ Á ÁAÁ Á Á, Á Á ÁBÁ Á ÁBÁ Á Á and Á Á ÁCÁ Á ÁCÁ Á Á chains. Structures with two (or more) independent twodimensional hydrogen-bonded layers appear, however, to be very rare, but 4-((E)-2-(4-chlorophenyl)ethenyl)-(1,3,5)triazino(1,2-a)benzimidazol-2-amine is another example (also with Z 0 = 4; CSD: EFOMUI, Suvorova et al, 2007). 2 Among amino acid and peptides with Z 0 > 1 l-Abu is probably the first compound with two such layers.…”

Section: Figurementioning

confidence: 99%

L-2-Aminobutyric acid: two fully ordered polymorphs withZ′ = 4

Görbitz

2010

Acta Crystallogr Sect B

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The crystal structure of L-2-aminobutyric acid, an L-alanine analogue with an ethyl rather than a methyl side chain, has proved elusive owing to problems growing diffraction quality crystals. Good diffraction data have now been obtained for two polymorphs, in space groups P2(1) and I2, revealing surprisingly complex, yet fully ordered crystalline arrangements with Z' = 4. The closely related structures are divided into hydrophilic and hydrophobic layers, the latter being the thinnest ever found for an amino acid (other than alpha-glycine). The hydrophobic layers furthermore contain conspicuous pseudo-centers-of-symmetry, leading to overall centrosymmetric intensity statistics. Uniquely, the four molecules in the asymmetric unit can be divided into two pairs that each forms an independent hydrogen-bond network.

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Section: Figurementioning

confidence: 99%

L-2-Aminobutyric acid: two fully ordered polymorphs withZ′ = 4

Görbitz

2010

Acta Crystallogr Sect B

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“…For example, KG3 was inactive in the one assay listed in PubChem and the corresponding quinazolinones were screened in only five assays and appear to inhibit tubulin polymerization. With its scarcity of sp 3 carbon atoms (22), KG3 clearly has some structural liabilities. Similar to KG3, almost no biological data has been published for KG7 and its analogs (23).…”

Section: Discussionmentioning

confidence: 99%

Novel Toxoplasma gondii inhibitor chemotypes

Sanford

Schulze

Potluri

et al. 2018

Parasitology International

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We profiled three novel T. gondii inhibitors identified from an antimalarial phenotypic high throughput screen (HTS) campaign: styryl 4-oxo-1,3-benzoxazin-4-one KG3, tetrahydrobenzo[b]pyran KG7, and benzoquinone hydrazone KG8. These compounds inhibit T. gondii in vitro with IC values ranging from 0.3 to 2μM, comparable to that of 0.25 to 1.5μM for the control drug pyrimethamine. KG3 had no measurable cytotoxicity against five mammalian cell lines, whereas KG7 and KG8 inhibited the growth of 2 of 5 cell lines with KG8 being the least selective for T. gondii. None of the compounds were mutagenic in an Ames assay. Experimental gLogD and calculated PSA values for the three compounds were well within the ranges predicted to be favorable for good ADME, even though each compound had relatively low aqueous solubility. All three compounds were metabolically unstable, especially KG3 and KG7. Multiple IP doses of 5mg/kg KG7 and KG8 increased survival in a T. gondii mouse model. Despite their liabilities, we suggest that these compounds are useful starting points for chemical prospecting, scaffold-hopping, and optimization.

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“…The synthesis of perchlorates IIa-IIf was described previously [1,2], and 1,2,4-triazoles Ia-If were prepared according to the procedure reported in [3].…”

Section: Methodsmentioning

confidence: 99%

“…was obtained by heating 2-methyl-4-oxo-1,3-benzoxazinium perchlorate with hydrazine hydrate in glacial acetic acid according to the procedure described in [2]. 13 [3-(2-Hydroxyphenyl)-5-methyl-1H-1,2,4-triazol-1-yl]acetonitrile (IIIa).…”

Section: -(3-methyl-1h-124-triazol-5-yl)phenol (Ia)mentioning

confidence: 99%

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Synthesis and properties of substituted [3-(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]acetonitriles

et al. 2010

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Alkylation of 3-substituted 5-(2-hydroxyphenyl)-1H-1,2,4-triazoles with chloroacetonitrile gave hitherto unknown N-cyanomethyl derivatives whose structure was determined by X-ray analysis and 1 H and 13 C NMR spectroscopy. Condensation of substituted [3-(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]acetonitriles at the activated methylene group with acetone led to the formation of new 3-methyl-2-triazolylbut-2-enenitrile derivatives.Scheme 1.

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Reactions of 4-oxo-1,3-benzoxazinium perchlorates with guanidines

Cited by 10 publications

References 3 publications

L-2-Aminobutyric acid: two fully ordered polymorphs withZ′ = 4

L-2-Aminobutyric acid: two fully ordered polymorphs withZ′ = 4

Novel Toxoplasma gondii inhibitor chemotypes

Synthesis and properties of substituted [3-(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]acetonitriles

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