Synthesis, biological evaluation, and docking studies of N-substituted acetamidines as selective inhibitors of inducible nitric oxide synthase.

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Maccallini C, Patruno A, Besker N, Ali JI, Ammazzalorso A, De Filippis B, Franceschelli S, Giampietro L, Pesce M, Reale M, Tricca ML, Re N, Felaco M, Amoroso R

Synthesis, biological evaluation, and docking studies of N-substituted acetamidines as selective inhibitors of inducible nitric oxide synthase.

J Med Chem. 2009 Mar 12;52(5):1481-5. doi: 10.1021/jm800846u.

PubMed ID

19203270 [ View in PubMed

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Abstract

New acetamidines structurally related to N-(3-(aminomethyl)benzyl)acetamidine (1, W1400) were designed as inhibitors of inducible nitric oxide synthase (iNOS). Six compounds were found to be selective for iNOS over endothelial nitric oxide synthase (eNOS), and among them, the most active and selective compound was the N-benzylacetamidine 2. A docking study was also performed to shed light on the effects of the structural modifications on the interaction of the designed inhibitors with the NOS.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
N-[3-(aminomethyl)benzyl]acetamidine	Nitric oxide synthase, endothelial	IC 50 (nM)	1100000	N/A	N/A	Details
N-[3-(aminomethyl)benzyl]acetamidine	Nitric oxide synthase, inducible	IC 50 (nM)	330	N/A	N/A	Details