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. 2010 Apr 28;15(5):3121-34.
doi: 10.3390/molecules15053121.

Synthesis of N-(methoxycarbonylthienylmethyl)thioureas and evaluation of their interaction with inducible and neuronal nitric oxide synthase

Ghadeer A R Y Suaifan  1 , Claire L M Goodyer, Michael D Threadgill
Affiliations

Synthesis of N-(methoxycarbonylthienylmethyl)thioureas and evaluation of their interaction with inducible and neuronal nitric oxide synthase

Ghadeer A R Y Suaifan et al. Molecules. .

Abstract

Two isomeric N-(methoxycarbonylthienylmethyl)thioureas were synthesised by a sequence of radical bromination of methylthiophenecarboxylic esters, substitution with trifluoroacetamide anion, deprotection, formation of the corresponding isothiocyanates and addition of ammonia. The interaction of these new thiophene-based thioureas with inducible and neuronal nitric oxide synthase was evaluated. These novel thienylmethyl-thioureas stimulated the activity of inducible Nitric Oxide Synthase (iNOS).

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Figures

Figure 1
Figure 1
Structures of the iNOS-selective inhibitor 1400W 1, the nNOS-selective lower homologue 2 and the iNOS stimulators 3 and 4. R = 3-NH2, 4-NH2=, 3-CO2H, 4-CO2H.
Scheme 1
Scheme 1
Synthetic route to target thioureidomethylthiophene 13.
Scheme 2
Scheme 2
Synthetics route to target thioureidomethylthiophene 25.
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