Literature DB >> 21275426

Synthesis and diversification of 1,2,3-triazole-fused 1,4-benzodiazepine scaffolds.

James R Donald1, Stephen F Martin.   

Abstract

A substituted heterocyclic scaffold comprising a 1,4-benzodiazepine fused with a 1,2,3-triazole ring has been synthesized and diversified via a variety of refunctionalizations. The strategy features the rapid assembly of the scaffold by combining 3-4 reactants in an efficient multicomponent assembly process, followed by an intramolecular Huisgen cycloaddition.

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Year:  2011        PMID： 21275426      PMCID： PMC3045640          DOI： 10.1021/ol1028404

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


  19 in total

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Authors:  Bruce L Grasberger; Tianbao Lu; Carsten Schubert; Daniel J Parks; Theodore E Carver; Holly K Koblish; Maxwell D Cummings; Louis V LaFrance; Karen L Milkiewicz; Raul R Calvo; Diane Maguire; Jennifer Lattanze; Carol F Franks; Shuyuan Zhao; Kannan Ramachandren; Gwendolyn R Bylebyl; Marie Zhang; Carl L Manthey; Eugene C Petrella; Michael W Pantoliano; Ingrid C Deckman; John C Spurlino; Anna C Maroney; Bruce E Tomczuk; Christopher J Molloy; Roger F Bone
Journal:  J Med Chem       Date:  2005-02-24       Impact factor: 7.446

2.  A potent nonpeptide cholecystokinin antagonist selective for peripheral tissues isolated from Aspergillus alliaceus.

Authors:  R S Chang; V J Lotti; R L Monaghan; J Birnbaum; E O Stapley; M A Goetz; G Albers-Schönberg; A A Patchett; J M Liesch; O D Hensens
Journal:  Science       Date:  1985-10-11       Impact factor: 47.728

3.  Synthesis of Diverse Heterocyclic Scaffolds via Tandem Additions to Imine Derivatives and Ring-Forming Reactions.

Authors:  James D Sunderhaus; Chris Dockendorff; Stephen F Martin
Journal:  Tetrahedron       Date:  2009-09-15       Impact factor: 2.457

4.  The structure of anthramycin.

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Journal:  J Am Chem Soc       Date:  1965-12-20       Impact factor: 15.419

5.  Scope and limitations of the Pd/BINAP-catalyzed amination of aryl bromides.

Authors:  J P Wolfe; S L Buchwald
Journal:  J Org Chem       Date:  2000-02-25       Impact factor: 4.354

Review 6.  Privileged scaffolds for library design and drug discovery.

Authors:  Matthew E Welsch; Scott A Snyder; Brent R Stockwell
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7.  Palladium-catalyzed intramolecular C-arylation of benzylic carbon: synthesis of 3-benzoxazolylisoindolinones by a sequence of Ugi-4CR/postfunctionalization.

Authors:  Angela Salcedo; Luc Neuville; Jieping Zhu
Journal:  J Org Chem       Date:  2008-04-02       Impact factor: 4.354

8.  Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds.

Authors:  James D Sunderhaus; Stephen F Martin
Journal:  Chemistry       Date:  2009       Impact factor: 5.236

9.  Click chemistry based rapid one-pot synthesis and evaluation for protease inhibition of new tetracyclic triazole fused benzodiazepine derivatives.

Authors:  Debendra K Mohapatra; Pradip K Maity; M Shabab; M I Khan
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10.  1,2,3-Triazolo[1,5-a][1,4]- and 1,2,3-triazolo[1,5-a]-[1,5]benzodiazepine derivatives: synthesis and benzodiazepine receptor binding.

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  24 in total

1.  Multicomponent assembly strategies for the synthesis of diverse tetrahydroisoquinoline scaffolds.

Authors:  Brett A Granger; Kyosuke Kaneda; Stephen F Martin
Journal:  Org Lett       Date:  2011-08-11       Impact factor: 6.005

2.  Application of a sequential multicomponent assembly process/huisgen cycloaddition strategy to the preparation of libraries of 1,2,3-triazole-fused 1,4-benzodiazepines.

Authors:  James R Donald; Rebekah R Wood; Stephen F Martin
Journal:  ACS Comb Sci       Date:  2012-02-01       Impact factor: 3.784

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4.  Novel fused 1,2,3-triazolo-benzodiazepine derivatives as potent anticonvulsant agents: design, synthesis, in vivo, and in silico evaluations.

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5.  Multicomponent, Mannich-type assembly process for generating novel, biologically-active 2-arylpiperidines and derivatives.

Authors:  Simon Hardy; Stephen F Martin
Journal:  Tetrahedron       Date:  2014-10-07       Impact factor: 2.457

6.  Azo-triazolide bis-cyclometalated Ir(iii) complexes via cyclization of 3-cyanodiarylformazanate ligands.

Authors:  Ge Mu; Zhili Wen; Judy I-Chia Wu; Thomas S Teets
Journal:  Dalton Trans       Date:  2019-11-27       Impact factor: 4.390

7.  One-pot, two-step cascade synthesis of quinazolinotriazolobenzodiazepines.

Authors:  Kathryn G Guggenheim; Hannah Toru; Mark J Kurth
Journal:  Org Lett       Date:  2012-06-29       Impact factor: 6.005

8.  Synthesis of saturated 1,4-benzodiazepines via Pd-catalyzed carboamination reactions.

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Journal:  Org Lett       Date:  2011-03-29       Impact factor: 6.005

9.  A one-pot-three-step route to triazolotriazepinoindazolones from oxazolino-2H-indazoles.

Authors:  Wayne E Conrad; Kevin X Rodriguez; Huy H Nguyen; James C Fettinger; Makhluf J Haddadin; Mark J Kurth
Journal:  Org Lett       Date:  2012-07-23       Impact factor: 6.005

10.  Facile one-pot assembly of imidazotriazolobenzodiazepines via indium(III)-catalyzed multicomponent reactions.

Authors:  Huy H Nguyen; Teresa A Palazzo; Mark J Kurth
Journal:  Org Lett       Date:  2013-08-20       Impact factor: 6.005
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