Literature DB >> 19860389

Concise route to the chiral pyrrolidine core of selective inhibitors of neuronal nitric oxide.

Fengtian Xue1, Wenxin Gu, Richard B Silverman.   

Abstract

2-(((3R,4R)-4-(Allyloxy)-1-benzylpyrrolidin-3-yl)methyl)-6-(2,5-dimethyl-1H-pyrrol-1-yl)-4-methylpyridine (2), a key intermediate for the preparation of novel neuronal nitric oxide synthase (nNOS) inhibitors, is synthesized using diisopropyl (R)-(+)-malate as the starting material. The key steps involve a Frater-Seebach diastereoselective alkylation and a fast intramolecular cyclization.

Entities:  

Mesh：

Substances：

Year:  2009        PMID： 19860389      PMCID： PMC2783674          DOI： 10.1021/ol902109t

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  16 in total

1.  Substituted 2-aminopyridines as inhibitors of nitric oxide synthases.

Authors:  W K Hagmann; C G Caldwell; P Chen; P L Durette; C K Esser; T J Lanza; I E Kopka; R Guthikonda; S K Shah; M MacCoss; R M Chabin; D Fletcher; S K Grant; B G Green; J L Humes; T M Kelly; S Luell; R Meurer; V Moore; S G Pacholok; T Pavia; H R Williams; K K Wong
Journal:  Bioorg Med Chem Lett       Date:  2000-09-04       Impact factor: 2.823

Review 2.  Inhibition of nitric oxide synthase as a potential therapeutic target.

Authors:  A J Hobbs; A Higgs; S Moncada
Journal:  Annu Rev Pharmacol Toxicol       Date:  1999       Impact factor: 13.820

Review 3.  Blocking NO synthesis: how, where and why?

Authors:  Patrick Vallance; James Leiper
Journal:  Nat Rev Drug Discov       Date:  2002-12       Impact factor: 84.694

4.  Unexpected binding modes of nitric oxide synthase inhibitors effective in the prevention of a cerebral palsy phenotype in an animal model.

Authors:  Silvia L Delker; Haitao Ji; Huiying Li; Joumana Jamal; Jianguo Fang; Fengtian Xue; Richard B Silverman; Thomas L Poulos
Journal:  J Am Chem Soc       Date:  2010-04-21       Impact factor: 15.419

5.  Synthesis and cellular characterization of the detransformation agent, (-)-depudecin.

Authors:  J Shimada; H J Kwon; M Sawamura; S L Schreiber
Journal:  Chem Biol       Date:  1995-08

Review 6.  The nitric oxide related therapeutic phenomenon: a challenging task.

Authors:  M J Alcaraz; M I Guilln
Journal:  Curr Pharm Des       Date:  2002       Impact factor: 3.116

Review 7.  Progress in the development of selective nitric oxide synthase (NOS) inhibitors.

Authors:  L Salerno; V Sorrenti; C Di Giacomo; G Romeo; M A Siracusa
Journal:  Curr Pharm Des       Date:  2002       Impact factor: 3.116

8.  An efficient synthesis of an alphavbeta3 antagonist.

Authors:  Nobuyoshi Yasuda; Yi Hsiao; Mark S Jensen; Nelo R Rivera; Chunhua Yang; Kenneth M Wells; James Yau; Michael Palucki; Lushi Tan; Peter G Dormer; Ralph P Volante; David L Hughes; Paul J Reider
Journal:  J Org Chem       Date:  2004-03-19       Impact factor: 4.354

9.  Nitric oxide synthase activity is elevated in brain microvessels in Alzheimer's disease.

Authors:  M A Dorheim; W R Tracey; J S Pollock; P Grammas
Journal:  Biochem Biophys Res Commun       Date:  1994-11-30       Impact factor: 3.575

10.  Effects of cerebral ischemia in mice deficient in neuronal nitric oxide synthase.

Authors:  Z Huang; P L Huang; N Panahian; T Dalkara; M C Fishman; M A Moskowitz
Journal:  Science       Date:  1994-09-23       Impact factor: 47.728
View more
  5 in total

1.  Symmetric double-headed aminopyridines, a novel strategy for potent and membrane-permeable inhibitors of neuronal nitric oxide synthase.

Authors:  Fengtian Xue; Jianguo Fang; Silvia L Delker; Huiying Li; Pavel Martásek; Linda J Roman; Thomas L Poulos; Richard B Silverman
Journal:  J Med Chem       Date:  2011-03-16       Impact factor: 7.446

2.  Microwave-assisted protection of primary amines as 2,5-dimethylpyrroles and their orthogonal deprotection.

Authors:  Amit Walia; Soosung Kang; Richard B Silverman
Journal:  J Org Chem       Date:  2013-10-14       Impact factor: 4.354

3.  In search of potent and selective inhibitors of neuronal nitric oxide synthase with more simple structures.

Authors:  Qing Jing; Huiying Li; Jianguo Fang; Linda J Roman; Pavel Martásek; Thomas L Poulos; Richard B Silverman
Journal:  Bioorg Med Chem       Date:  2013-06-15       Impact factor: 3.641

4.  An Accessible Chiral Linker to Enhance Potency and Selectivity of Neuronal Nitric Oxide Synthase Inhibitors.

Authors:  Qing Jing; Huiying Li; Linda J Roman; Pavel Martásek; Thomas L Poulos; Richard B Silverman
Journal:  ACS Med Chem Lett       Date:  2014-01-09       Impact factor: 4.345

5.  Synthetic, Mechanistic, and Biological Interrogation of Ginkgo biloba Chemical Space En Route to (-)-Bilobalide.

Authors:  Robert M Demoret; Meghan A Baker; Masaki Ohtawa; Shuming Chen; Ching Ching Lam; Sophia Khom; Marisa Roberto; Stefano Forli; Kendall N Houk; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2020-10-16       Impact factor: 15.419
  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.