Cyanocarbon Chemistry. VIII.<sup>1</sup> Heterocyclic Compounds from Tetracyanoethylene

Middleton, W. J.; Engelhardt, V. A.; Fisher, B. S.

doi:10.1021/ja01544a058

Cited by 71 publications

(20 citation statements)

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“…The organic extracts were combined, dried and adsorbed onto silica. Chromatography (hexane/EtOAc, 1:1) gave 3,5-diamino-1H-pyrazole-4-carbonitrile 48 (25 mg, 86%) as colourless needles, mp 170-171 C, (lit., 88 169-170 C) (from EtOH), identical to that described above. Further elution (EtOAc, 100%), gave 3-amino-1H-pyrazole-4-carbonitrile 54 (3 mg, 13%) as a colourless powder, mp 173-174 C (lit., 89 …”

Section: -Amino-1h-pyrazole-4-carbonitrile 54mentioning

confidence: 96%

“…The residue obtained was passed through a short pad (2 cm) of silica that was then washed well with t-BuOMe. Removal of the volatiles gave the title compound 48 (24 mg, 84%) as colourless needles, mp 170-171 C, (lit., 88 169-170 C) (from EtOH); l max (t-BuOMe)/nm 276 (log 3 3.41); n max / cm À1 3236w, 3212w and 3050w (NH), 1683m, 1666s, 1648m, 1631w, 1544s, 1437w, 1367m, 1289m, 1253s, 1117m, 1049m, 984w; d H (300 MHz; DMSO-d 6 …”

Section: -Amino-5-(n-morpholino)-1h-pyrazole-4-carbonitrile 47mentioning

confidence: 99%

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The conversion of isothiazoles into pyrazoles using hydrazine

Ioannidou

Koutentis

2009

Tetrahedron

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Section: -Amino-1h-pyrazole-4-carbonitrile 54mentioning

confidence: 96%

Section: -Amino-5-(n-morpholino)-1h-pyrazole-4-carbonitrile 47mentioning

confidence: 99%

The conversion of isothiazoles into pyrazoles using hydrazine

Ioannidou

Koutentis

2009

Tetrahedron

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“…, and U0124 -U0124, U0125, and U0126 (22) were prepared by the addition of a thiol to tetracyanoethane as shown in Scheme 1. Tetracyanoethane (23) (6.5 g, 50 mmol) was dissolved in 20 ml of reagent grade acetone.…”

Section: Materials Synthesis Of U0126 (14-diamino-23-dicyano-14-bimentioning

confidence: 99%

Identification of a Novel Inhibitor of Mitogen-activated Protein Kinase Kinase

Favata¹,

Horiuchi²,

Manos³

et al. 1998

Journal of Biological Chemistry

2,835

2,077

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We further demonstrate that the two compounds bind to ⌬N3-S218E/S222D MEK in a mutually exclusive fashion, suggesting that they may share a common or overlapping binding site(s). Quantitative evaluation of the steady state kinetics of MEK inhibition by these compounds reveals that U0126 has approximately 100-fold higher affinity for ⌬N3-S218E/S222D MEK than does PD098059. We further tested the effects of these compounds on the activity of wild type MEK isolated after activation from stimulated cells. Surprisingly, we observe a significant diminution in affinity of both compounds for wild type MEK as compared with the ⌬N3-S218E/S222D mutant enzyme. These results suggest that the affinity of both compounds is mediated by subtle conformational differences between the two activated MEK forms. The MEK affinity of U0126, its selectivity for MEK over other kinases, and its cellular efficacy suggest that this compound will serve as a powerful tool for in vitro and cellular investigations of mitogen-activated protein kinase-mediated signal transduction.

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“…For the synthesis of this and related compounds via the reaction of tetracyanoethylene with hydrogen sulfide, see: Cairns et al (1957); Middleton et al (1958); Middleton (1959). For the use of this compound as a reagent, see: Nemykin et al (2012).…”

Section: Related Literaturementioning

confidence: 99%