Literature DB >> 23243322

Convenient one-step synthesis of a medicinally relevant benzopyranopyridine system.

Nikolai M Evdokimov1, Artem S Kireev, Andrey A Yakovenko, Mikhail Yu Antipin, Igor V Magedov, Alexander Kornienko.   

Abstract

Benzopyrano[2,3-b]pyridine is an important privileged medicinal scaffold. A three-component reaction of salicylaldehydes, thiols and 2 equiv of malononitrile that leads to the formation of a series of compounds incorporating 2,4-diamino-3-cyano-5-sulfanylbenzopyrano[2,3-b]pyridine framework is described. A proposed mechanism with the supporting experimental data is presented.

Entities:  

Year:  2006        PMID： 23243322      PMCID： PMC3519924          DOI： 10.1016/j.tetlet.2006.10.110

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  11 in total

Review 1.  The multicomponent reactions and their libraries for natural and preparative chemistry.

Authors:  I Ugi; S Heck
Journal:  Comb Chem High Throughput Screen       Date:  2001-02       Impact factor: 1.339

Review 2.  "Multi-component reactions : emerging chemistry in drug discovery" 'from xylocain to crixivan'.

Authors:  Christopher Hulme; Vijay Gore
Journal:  Curr Med Chem       Date:  2003-01       Impact factor: 4.530

3.  Aminocyanopyridine inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2).

Authors:  David R Anderson; Shridhar Hegde; Emily Reinhard; Leslie Gomez; William F Vernier; Len Lee; Shuang Liu; Aruna Sambandam; Patricia A Snider; Liaqat Masih
Journal:  Bioorg Med Chem Lett       Date:  2005-03-15       Impact factor: 2.823

4.  Design, synthesis and antiproliferative activity of some new azapyranoxanthenone aminoderivatives.

Authors:  George Kolokythas; Nicole Pouli; Panagiotis Marakos; Harris Pratsinis; Dimitris Kletsas
Journal:  Eur J Med Chem       Date:  2005-11-21       Impact factor: 6.514

5.  NAD+-dependent DNA Ligase (Rv3014c) from Mycobacterium tuberculosis. Crystal structure of the adenylation domain and identification of novel inhibitors.

Authors:  Sandeep Kumar Srivastava; Rama Pati Tripathi; Ravishankar Ramachandran
Journal:  J Biol Chem       Date:  2005-05-17       Impact factor: 5.157

6.  Specific and potent inhibition of NAD+-dependent DNA ligase by pyridochromanones.

Authors:  Heike Brötz-Oesterhelt; Igor Knezevic; Stephan Bartel; Thomas Lampe; Ute Warnecke-Eberz; Karl Ziegelbauer; Dieter Häbich; Harald Labischinski
Journal:  J Biol Chem       Date:  2003-07-15       Impact factor: 5.157

7.  One-step, three-component synthesis of pyridines and 1,4-dihydropyridines with manifold medicinal utility.

Authors:  Nikolai M Evdokimov; Igor V Magedov; Artem S Kireev; Alexander Kornienko
Journal:  Org Lett       Date:  2006-03-02       Impact factor: 6.005

8.  Synthesis of the metabolites and degradation products of 2-amino-7-isopropyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3- carboxylic acid (Amoxanox).

Authors:  K Ukawa; T Ishiguro; H Kuriki; A Nohara
Journal:  Chem Pharm Bull (Tokyo)       Date:  1985-10       Impact factor: 1.645

9.  Gastric antisecretory agents. 2. Antisecretory activity of 9-[(aminoalkyl)thio]-9H-xanthenes and 5-[(aminoalkyl)thio]-5H-[1]benzopyrano[2,3-b]pyridines.

Authors:  J A Bristol; E H Gold; I Gross; R G Lovey; J F Long
Journal:  J Med Chem       Date:  1981-08       Impact factor: 7.446

10.  Cancer chemopreventive effect of phenothiazines and related tri-heterocyclic analogues in the 12-O-tetradecanoylphorbol-13-acetate promoted Epstein-Barr virus early antigen activation and the mouse skin two-stage carcinogenesis models.

Authors:  Magnus A Azuine; Harukuni Tokuda; Junko Takayasu; Fumio Enjyo; Teruo Mukainaka; Takao Konoshima; Hoyoku Nishino; Govind J Kapadia
Journal:  Pharmacol Res       Date:  2004-02       Impact factor: 7.658
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  6 in total

1.  Multicomponent Synthesis of 2,3-Dihydrochromeno[4,3-d]pyrazolo[3,4-b]pyridine-1,6-diones: A Novel Heterocyclic Scaffold with Antibacterial Activity.

Authors:  Liliya V Frolova; Indranil Malik; Pavel Y Uglinskii; Snezna Rogelj; Alexander Kornienko; Igor V Magedov
Journal:  Tetrahedron Lett       Date:  2011-12-07       Impact factor: 2.415

2.  Design, synthesis, and pharmacological evaluation of [1, 3] dioxolo-chromeno[2,3-b]pyridines as anti-seizure agents.

Authors:  Visarapu Malathi; Nissi Sharon; Pannala Padmaja; Deepak Lokwani; Saurabh Khadse; Prashant Chaudhari; Atul A Shirkhedkar; Pedavenkatagari Narayana Reddy; Vinod G Ugale
Journal:  Mol Divers       Date:  2022-10-10       Impact factor: 3.364

3.  A new one-pot three-component synthesis of 2,4-diamino-5H-chromeno[2,3-b]pyridine-3-carbonitrile derivatives.

Authors:  Ahmad Shaabani; Fatemeh Hajishaabanha; Hamid Mofakham; Ali Maleki
Journal:  Mol Divers       Date:  2009-05-16       Impact factor: 2.943

4.  Novel three-component synthesis and antiproliferative properties of diversely functionalized pyrrolines.

Authors:  Igor V Magedov; Giovanni Luchetti; Nikolai M Evdokimov; Madhuri Manpadi; Wim F A Steelant; Severine Van Slambrouck; Paul Tongwa; Mikhail Yu Antipin; Alexander Kornienko
Journal:  Bioorg Med Chem Lett       Date:  2008-01-11       Impact factor: 2.823

5.  Organocatalytic Fluorogenic Synthesis of Chromenes.

Authors:  Mina Raeisolsadati Oskouei; Albert M Brouwer
Journal:  J Fluoresc       Date:  2017-02-21       Impact factor: 2.217

6.  Cysteic acid grafted to magnetic graphene oxide as a promising recoverable solid acid catalyst for the synthesis of diverse 4H-chromene.

Authors:  Firouz Matloubi Moghaddam; Mohammad Eslami; Golfamsadat Hoda
Journal:  Sci Rep       Date:  2020-12-01       Impact factor: 4.379
  6 in total

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