Literature DB >> 23160888

Face selective reduction of the exocyclic double bond in isatin derived spirocyclic lactones.

Sandeep Rana1, Amarnath Natarajan.   

Abstract

We report an unusual face selective reduction of the exocyclic double bond in the α-methylene-γ-butyrolactone motif of spiro-oxindole systems. The spiro-oxindoles were assembled by an indium metal mediated Barbier-type reaction followed by an acid catalyzed lactonization.

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Year:  2012        PMID： 23160888      PMCID： PMC3535013          DOI： 10.1039/c2ob27008k

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  22 in total

Review 1.  The renaissance of alpha-methylene-gamma-butyrolactones: new synthetic approaches.

Authors:  Russell R A Kitson; Alessia Millemaggi; Richard J K Taylor
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

2.  Pharmacodynamic-mediated effects of the angiogenesis inhibitor SU5416 on the tumor disposition of temozolomide in subcutaneous and intracerebral glioma xenograft models.

Authors:  Jianguo Ma; Shaolan Li; Karin Reed; Ping Guo; James M Gallo
Journal:  J Pharmacol Exp Ther       Date:  2003-03-06       Impact factor: 4.030

3.  Dramatic rate enhancement with preservation of stereospecificity in the first metal-catalyzed additions of allylboronates.

Authors:  Jason W J Kennedy; Dennis G Hall
Journal:  J Am Chem Soc       Date:  2002-10-02       Impact factor: 15.419

4.  A novel cdk2-selective inhibitor, SU9516, induces apoptosis in colon carcinoma cells.

Authors:  M E Lane; B Yu; A Rice; K E Lipson; C Liang; L Sun; C Tang; G McMahon; R G Pestell; S Wadler
Journal:  Cancer Res       Date:  2001-08-15       Impact factor: 12.701

Review 5.  Paraherquamides, brevianamides, and asperparalines: laboratory synthesis and biosynthesis. An interim report.

Authors:  Robert M Williams; Rhona J Cox
Journal:  Acc Chem Res       Date:  2003-02       Impact factor: 22.384

6.  Antitumor agents. 16. Steroidal alpha-methylene-gamma-lactones.

Authors:  K H Lee; T Ibuka; S H Kim; B R Vestal; I H Hall; E S Huang
Journal:  J Med Chem       Date:  1975-08       Impact factor: 7.446

Review 7.  Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents.

Authors:  Chris V Galliford; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

8.  Hybrid alpha-bromoacryloylamido chalcones. Design, synthesis and biological evaluation.

Authors:  Romeo Romagnoli; Pier Giovanni Baraldi; Maria Dora Carrion; Olga Cruz-Lopez; Carlota Lopez Cara; Jan Balzarini; Ernest Hamel; Alessandro Canella; Enrica Fabbri; Roberto Gambari; Giuseppe Basso; Giampietro Viola
Journal:  Bioorg Med Chem Lett       Date:  2009-02-12       Impact factor: 2.823

9.  Next-Generation Antimalarial Drugs: Hybrid Molecules as a New Strategy in Drug Design.

Authors:  Francis W Muregi; Akira Ishih
Journal:  Drug Dev Res       Date:  2010-02       Impact factor: 4.360

10.  The p65 subunit is responsible for the strong transcription activating potential of NF-kappa B.

Authors:  M L Schmitz; P A Baeuerle
Journal:  EMBO J       Date:  1991-12       Impact factor: 11.598
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  8 in total

1.  Modified synthesis of NOP receptor antagonist SB612111.

Authors:  David A Perrey; Jun-Xu Li; Yanan Zhang
Journal:  Synthesis (Stuttg)       Date:  2016-12-19       Impact factor: 3.157

2.  Dimers of isatin derived α-methylene-γ-butyrolactone as potent anti-cancer agents.

Authors:  Sandeep Rana; Smit Kour; Smitha Kizhake; Hannah M King; Jayapal Reddy Mallareddy; Adam J Case; Tom Huxford; Amarnath Natarajan
Journal:  Bioorg Med Chem Lett       Date:  2022-04-01       Impact factor: 2.940

3.  Spirocyclic dimer SpiD7 activates the unfolded protein response to selectively inhibit growth and induce apoptosis of cancer cells.

Authors:  Smit Kour; Sandeep Rana; Sydney P Kubica; Smitha Kizhake; Mudassier Ahmad; Catalina Muñoz-Trujillo; David Klinkebiel; Sarbjit Singh; Jayapal Reddy Mallareddy; Surabhi Chandra; Nicholas T Woods; Adam R Karpf; Amarnath Natarajan
Journal:  J Biol Chem       Date:  2022-04-01       Impact factor: 5.486

4.  Symbiotic prodrugs (SymProDs) dual targeting of NFkappaB and CDK.

Authors:  Sandeep Rana; Smit Kour; Yogesh A Sonawane; Caroline M Robb; Jacob I Contreras; Smitha Kizhake; Muhammad Zahid; Adam R Karpf; Amarnath Natarajan
Journal:  Chem Biol Drug Des       Date:  2020-04-22       Impact factor: 2.817

5.  Isatin Derived Spirocyclic Analogues with α-Methylene-γ-butyrolactone as Anticancer Agents: A Structure-Activity Relationship Study.

Authors:  Sandeep Rana; Elizabeth C Blowers; Calvin Tebbe; Jacob I Contreras; Prakash Radhakrishnan; Smitha Kizhake; Tian Zhou; Rajkumar N Rajule; Jamie L Arnst; Adnan R Munkarah; Ramandeep Rattan; Amarnath Natarajan
Journal:  J Med Chem       Date:  2016-04-26       Impact factor: 7.446

6.  Regio- and stereoselective synthesis of spiropyrrolidine-oxindole and bis-spiropyrrolizidine-oxindole grafted macrocycles through [3 + 2] cycloaddition of azomethine ylides.

Authors:  Perumal Prabhakaran; Perumal Rajakumar
Journal:  RSC Adv       Date:  2020-03-10       Impact factor: 4.036

7.  Stapling proteins in the RELA complex inhibits TNFα-induced nuclear translocation of RELA.

Authors:  Smit Kour; Sandeep Rana; Smitha Kizhake; Dragana Lagundžin; David Klinkebiel; Jayapal Reddy Mallareddy; Tom Huxford; Nicholas T Woods; Amarnath Natarajan
Journal:  RSC Chem Biol       Date:  2021-10-28

8.  Structure activity relationship (SAR) study identifies a quinoxaline urea analog that modulates IKKβ phosphorylation for pancreatic cancer therapy.

Authors:  Satish Sagar; Sarbjit Singh; Jayapal Reddy Mallareddy; Yogesh A Sonawane; John V Napoleon; Sandeep Rana; Jacob I Contreras; Christabelle Rajesh; Edward L Ezell; Smitha Kizhake; Jered C Garrison; Prakash Radhakrishnan; Amarnath Natarajan
Journal:  Eur J Med Chem       Date:  2021-05-30       Impact factor: 7.088
  8 in total

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