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1 article(s) from Martásek, Pavel

Synthesis and enzymatic evaluation of 2- and 4-aminothiazole- based inhibitors of neuronal nitric oxide synthase

Graham R. Lawton,
Haitao Ji,
Pavel Martásek,
Linda J. Roman and
Richard B. Silverman

Beilstein J. Org. Chem. 2009, 5, No. 28, doi:10.3762/bjoc.5.28

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Figure 1: Lead compounds 1 and 2; 2- and 4-aminothiazole analogs 3 and 4a-c.

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Figure 2: A: The docking conformation of 3 in the active site of rat nNOS; B: The docking conformation of 4b ...

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Scheme 1: Attempts to open epoxide 5 with deprotonated aminothiazoles. i) n-BuLi, 2 equiv, THF, −78 °C; ii) 5...

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Scheme 2: Assembly of 2-aminothiazole fragment. i) AllylMgBr, ether, 0 °C, 15 min.; ii) TBSCl, imidazole, DMF...

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Scheme 3: Synthesis of compound 3. i) 4-chlorobenzylchloride, EtOH, reflux, 4 h; ii) Boc₂O, TEA, MeOH, 3 h; i...

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Scheme 4: Assembly of the 4-aminothiazole fragments. i) LiCH₂CN, THF, 0 °C, 4 h; ii) (NH₄)₂S (aq), MeOH, 16 h...

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Scheme 5: Synthesis of inhibitor 4a-c. The 4-aminothiazoles were not stable in water undergoing tautomerizati...

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Published 04 Jun 2009

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