ArticleJournal of medicinal chemistry2011
Design, synthesis, and biological evaluation of 3,4-dihydroquinolin-2(1H)-one and 1,2,3,4-tetrahydroquinoline-based selective human neuronal nitric oxide synthase (nNOS) inhibitors.
Article in Journal of medicinal chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 31 citations in OpenAlex.
- Progress in the Stereoselective Synthesis Methods of Pyrrolidine-Containing Drugs and Their Precursors.International journal of molecular sciences · 2024Review
- Exploring the synthetic potential of epoxide ring opening reactions toward the synthesis of alkaloids and terpenoids: a review.RSC advances · 2024Review
- Nitric oxide synthase and its function in animal reproduction: an update.Frontiers in physiology · 2023Review
- Genipin Derivatives Protect RGC-5 from Sodium Nitroprusside-Induced Nitrosative Stress.International journal of molecular sciences · 2016Article
- 2-Aminopyridines with a Truncated Side Chain To Improve Human Neuronal Nitric Oxide Synthase Inhibitory Potency and Selectivity.Journal of medicinal chemistry · 2015Article
- Development of nitric oxide synthase inhibitors for neurodegeneration and neuropathic pain.Chemical Society reviews · 2014Review
- Combination of chiral linkers with thiophenecarboximidamide heads to improve the selectivity of inhibitors of neuronal nitric oxide synthase.Bioorganic & medicinal chemistry letters · 2014Article
- The discovery of potentially selective human neuronal nitric oxide synthase (nNOS) Inhibitors: a combination of pharmacophore modelling, CoMFA, virtual screening and molecular docking studies.International journal of molecular sciences · 2014Article
- Potent and selective double-headed thiophene-2-carboximidamide inhibitors of neuronal nitric oxide synthase for the treatment of melanoma.Journal of medicinal chemistry · 2014Article
- An Accessible Chiral Linker to Enhance Potency and Selectivity of Neuronal Nitric Oxide Synthase Inhibitors.ACS medicinal chemistry letters · 2014Article
- Recent advances toward improving the bioavailability of neuronal nitric oxide synthase inhibitors.Current topics in medicinal chemistry · 2013Review
Corrections and comments
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Authors and funding
16 authors at 2 institutions in 2 countries.
Funding
Abstract
Neuronal nitric oxide synthase (nNOS) inhibitors are effective in preclinical models of many neurological disorders. In this study, two related series of compounds, 3,4-dihydroquinolin-2(1H)-one and 1,2,3,4-tetrahydroquinoline, containing a 6-substituted thiophene amidine group were synthesized and evaluated as inhibitors of human nitric oxide synthase (NOS). A structure-activity relationship (SAR) study led to the identification of a number of potent and selective nNOS inhibitors. Furthermore, a few representative compounds were shown to possess druglike properties, features that are often difficult to achieve when designing nNOS inhibitors. Compound (S)-35, with excellent potency and selectivity for nNOS, was shown to fully reverse thermal hyperalgesia when given to rats at a dose of 30 mg/kg intraperitonieally (ip) in the L5/L6 spinal nerve ligation model of neuropathic pain (Chung model). In addition, this compound reduced tactile hyperesthesia (allodynia) after oral administration (30 mg/kg) in a rat model of dural inflammation relevant to migraine pain.
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Registered trials
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