Structure−Activity Relationships of Potent, Selective Inhibitors of Neuronal Nitric Oxide Synthase Based on the 6-Phenyl-2-aminopyridine Structure

2004 ◽  
Vol 47 (6) ◽  
pp. 1575-1586 ◽  
Author(s):  
John A. Lowe ◽  
Weimin Qian ◽  
Susan E. Drozda ◽  
Robert A. Volkmann ◽  
Deane Nason ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Nitric Oxide Synthase ◽  
Neuronal Nitric Oxide Synthase ◽  
Selective Inhibitors ◽  
Structure Activity Relationships ◽  
Structure Activity ◽  
Oxide Synthase

N-Phenylamidines as Selective Inhibitors of Human Neuronal Nitric Oxide Synthase:  Structure−Activity Studies and Demonstration of in Vivo Activity

1998 ◽  
Vol 41 (15) ◽  
pp. 2858-2871 ◽  
Author(s):  
Jon L. Collins ◽  
Barry G. Shearer ◽  
Jeffrey A. Oplinger ◽  
Shuliang Lee ◽  
Edward P. Garvey ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Nitric Oxide Synthase ◽  
Neuronal Nitric Oxide Synthase ◽  
Selective Inhibitors ◽  
Structure Activity ◽  
Oxide Synthase

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

2009 ◽  
Vol 5 ◽  
Author(s):  
Graham R Lawton ◽  
Haitao Ji ◽  
Pavel Martásek ◽  
Linda J Roman ◽  
Richard B Silverman
Keyword(s):  
Nitric Oxide ◽  
Nitric Oxide Synthase ◽  
Blood Brain Barrier ◽  
Neuronal Nitric Oxide Synthase ◽  
Lead Compound ◽  
Selective Inhibitors ◽  
Net Charge ◽  
In Vivo Efficacy ◽  
Oxide Synthase

Highly potent and selective inhibitors of neuronal nitric oxide synthase (nNOS) possessing a 2-aminopyridine group were recently designed and synthesized in our laboratory and were shown to have significant in vivo efficacy. In this work, analogs of our lead compound possessing 2- and 4-aminothiazole rings in place of the aminopyridine were synthesized. The less basic aminothiazole rings will be less protonated at physiological pH than the aminopyridine ring, and so the molecule will carry a lower net charge. This could lead to an increased ability to cross the blood-brain barrier thereby increasing the in vivo potency of these compounds. The 2-aminothiazole-based compound was less potent than the 2-aminopyridine-based analogue. 4-Aminothiazoles were unstable in water, undergoing tautomerization and hydrolysis to give inactive thiazolones.

N-Substituted acetamidines and 2-methylimidazole derivatives as selective inhibitors of neuronal nitric oxide synthase

2010 ◽  
Vol 20 (22) ◽  
pp. 6495-6499 ◽  
Author(s):  
Cristina Maccallini ◽  
Antonia Patruno ◽  
Fabio Lannutti ◽  
Alessandra Ammazzalorso ◽  
Barbara De Filippis ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Nitric Oxide Synthase ◽  
Neuronal Nitric Oxide Synthase ◽  
Selective Inhibitors ◽  
Oxide Synthase

Nω-Nitroarginine-Containing Dipeptide Amides. Potent and Highly Selective Inhibitors of Neuronal Nitric Oxide Synthase

1999 ◽  
Vol 42 (16) ◽  
pp. 3147-3153 ◽  
Author(s):  
Hui Huang ◽  
Pavel Martasek ◽  
Linda J. Roman ◽  
Bettie Sue Siler Masters ◽  
Richard B. Silverman
Keyword(s):  
Nitric Oxide ◽  
Nitric Oxide Synthase ◽  
Neuronal Nitric Oxide Synthase ◽  
Selective Inhibitors ◽  
Oxide Synthase

scholarly journals Structure-Guided Design of Selective Inhibitors of Neuronal Nitric Oxide Synthase

2013 ◽  
Vol 56 (7) ◽  
pp. 3024-3032 ◽  
Author(s):  
He Huang ◽  
Huiying Li ◽  
Pavel Martásek ◽  
Linda J. Roman ◽  
Thomas L. Poulos ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Nitric Oxide Synthase ◽  
Neuronal Nitric Oxide Synthase ◽  
Selective Inhibitors ◽  
Oxide Synthase

scholarly journals Analogues of 2-aminopyridine-based selective inhibitors of neuronal nitric oxide synthase with increased bioavailability

2009 ◽  
Vol 17 (6) ◽  
pp. 2371-2380 ◽  
Author(s):  
Graham R. Lawton ◽  
Hantamalala Ralay Ranaivo ◽  
Laura K. Chico ◽  
Haitao Ji ◽  
Fengtian Xue ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Nitric Oxide Synthase ◽  
Neuronal Nitric Oxide Synthase ◽  
Selective Inhibitors ◽  
Oxide Synthase
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