Literature DB >> 20000789

Unprecedented rearrangement of 2-(2-aminoethyl)-1-aryl-3,4-dihydropyrazino[1,2-b]indazole-2-ium 6-oxides to 2,3-dihydro-1H-imidazo[1,2-b]indazoles.

Jan Kocí1, Allen G Oliver, Viktor Krchnák.   

Abstract

Easily accessible 2-(2-aminoethyl)-1-aryl-3,4-dihydropyrazino[1,2-b]indazole-2-ium 6-oxides rearranged to 2,3-dihydro-1H-imidazo[1,2-b]indazoles under mild conditions. The rearrangement appeared to be general, tolerated a wide range of functional groups, and provided access to an as yet unexplored class of heterocycles. Herein we report the characterization of these heterocycles.

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Year:  2010        PMID： 20000789      PMCID： PMC2811364          DOI： 10.1021/jo902301x

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  25 in total

1.  Syntheses of potent, selective, and orally bioavailable indazole-pyridine series of protein kinase B/Akt inhibitors with reduced hypotension.

Authors:  Gui-Dong Zhu; Viraj B Gandhi; Jianchun Gong; Sheela Thomas; Keith W Woods; Xiaohong Song; Tongmei Li; R Bruce Diebold; Yan Luo; Xuesong Liu; Ran Guan; Vered Klinghofer; Eric F Johnson; Jennifer Bouska; Amanda Olson; Kennan C Marsh; Vincent S Stoll; Mulugeta Mamo; James Polakowski; Thomas J Campbell; Ruth L Martin; Gary A Gintant; Thomas D Penning; Qun Li; Saul H Rosenberg; Vincent L Giranda
Journal:  J Med Chem       Date:  2007-05-25       Impact factor: 7.446

2.  GdCl(3) catalysed Grieco condensation: a facile approach for the synthesis of novel pyrimidine and annulated pyrimidine fused indazole derivatives in single pot under mild conditions and their anti-microbial activity.

Authors:  T Yakaiah; B P V Lingaiah; B Narsaiah; K Pranay Kumar; U S N Murthy
Journal:  Eur J Med Chem       Date:  2007-04-14       Impact factor: 6.514

3.  Anticancer mechanisms of YC-1 in human lung cancer cell line, NCI-H226.

Authors:  Chun-Jen Chen; Mei-Hua Hsu; Li-Jiau Huang; Takao Yamori; Jing-Gung Chung; Fang-Yu Lee; Che-Ming Teng; Sheng-Chu Kuo
Journal:  Biochem Pharmacol       Date:  2007-08-17       Impact factor: 5.858

Review 4.  Pharmacological properties of indazole derivatives: recent developments.

Authors:  Hugo Cerecetto; Alejandra Gerpe; Mercedes González; Vicente J Arán; Carmen Ochoa de Ocáriz
Journal:  Mini Rev Med Chem       Date:  2005-10       Impact factor: 3.862

5.  Discovery of novel indazole-linked triazoles as antifungal agents.

Authors:  Joon Seok Park; Kyung A Yu; Tae Hee Kang; Sunghoon Kim; Young-Ger Suh
Journal:  Bioorg Med Chem Lett       Date:  2007-03-27       Impact factor: 2.823

6.  7-fluoroindazoles as potent and selective inhibitors of factor Xa.

Authors:  Yu-Kai Lee; Daniel J Parks; Tianbao Lu; Tho V Thieu; Thomas Markotan; Wenxi Pan; David F McComsey; Karen L Milkiewicz; Carl S Crysler; Nisha Ninan; Marta C Abad; Edward C Giardino; Bruce E Maryanoff; Bruce P Damiano; Mark R Player
Journal:  J Med Chem       Date:  2007-12-27       Impact factor: 7.446

7.  Fluorinated indazoles as novel selective inhibitors of nitric oxide synthase (NOS): synthesis and biological evaluation.

Authors:  Rosa M Claramunt; Concepción López; Carlos Pérez-Medina; Marta Pérez-Torralba; José Elguero; Germaine Escames; Darío Acuña-Castroviejo
Journal:  Bioorg Med Chem       Date:  2009-08-06       Impact factor: 3.641

8.  In vitro structure-activity relationship and in vivo characterization of 1-(aryl)-3-(4-(amino)benzyl)urea transient receptor potential vanilloid 1 antagonists.

Authors:  Richard J Perner; Stanley DiDomenico; John R Koenig; Arthur Gomtsyan; Erol K Bayburt; Robert G Schmidt; Irene Drizin; Guo Zhu Zheng; Sean C Turner; Tammie Jinkerson; Brian S Brown; Ryan G Keddy; Kurill Lukin; Heath A McDonald; Prisca Honore; Joe Mikusa; Kennan C Marsh; Jill M Wetter; Karen St George; Michael F Jarvis; Connie R Faltynek; Chih-Hung Lee
Journal:  J Med Chem       Date:  2007-06-21       Impact factor: 7.446

9.  Synthesis and structure-activity relationships of novel pyrimido[1,2-b]indazoles as potential anticancer agents against A-549 cell lines.

Authors:  T Yakaiah; B P V Lingaiah; B Narsaiah; B Shireesha; B Ashok Kumar; S Gururaj; T Parthasarathy; B Sridhar
Journal:  Bioorg Med Chem Lett       Date:  2007-03-30       Impact factor: 2.823

10.  Identification of (R)-1-(5-tert-butyl-2,3-dihydro-1H-inden-1-yl)-3-(1H-indazol-4-yl)urea (ABT-102) as a potent TRPV1 antagonist for pain management.

Authors:  Arthur Gomtsyan; Erol K Bayburt; Robert G Schmidt; Carol S Surowy; Prisca Honore; Kennan C Marsh; Steven M Hannick; Heath A McDonald; Jill M Wetter; James P Sullivan; Michael F Jarvis; Connie R Faltynek; Chih-Hung Lee
Journal:  J Med Chem       Date:  2008-01-10       Impact factor: 7.446
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  1 in total

1.  Synthesis of quinazolines from N-(2-nitrophenylsulfonyl)iminodiacetate and alpha-(2-nitrophenylsulfonyl)amino ketones via 2H-indazole 1-oxides.

Authors:  Sona Krupková; Greg A Slough; Viktor Krchnák
Journal:  J Org Chem       Date:  2010-07-02       Impact factor: 4.354
  1 in total

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