Literature DB >> 25267862

L-Proline catalyzed one-step synthesis of 4,5-diaryl-2H-1,2,3-triazoles from heteroaryl cyanostilbenes via [3+2] cycloaddition of azide.

Narsimha Reddy Penthala1, Nikhil Reddy Madadi1, Venumadhav Janganati1, Peter A Crooks1.   

Abstract

Use of a novel reagent has been established for the synthesis of a series of 4,5-diaryl-2H-1,2,3-triazoles (6a-i and 9a-e) from cyanostilbene analogs of benzo[b]thiophene, benzo[b]furan and indole, catalyzed by L-proline via Lewis base-catalyzed one-step [3+2]cycloaddition of azide. This method provides an efficient, simple and environmentally benign procedure that affords good yields and relatively short reaction times.

Entities:  

Keywords:  4,5-Diaryl-2H-1,2,3-triazoles; Heteroaryl cyanostilbenes; L-Proline; Sodium azide; [3+2] Cycloaddition of azide

Year:  2014        PMID： 25267862      PMCID： PMC4175744          DOI： 10.1016/j.tetlet.2014.08.027

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


  21 in total

1.  Novel cyanocombretastatins as potent tubulin polymerisation inhibitors.

Authors:  Pouria H Jalily; John A Hadfield; Nicholas Hirst; Steven B Rossington
Journal:  Bioorg Med Chem Lett       Date:  2012-09-07       Impact factor: 2.823

2.  A study of the scope and regioselectivity of the ruthenium-catalyzed [3 + 2]-cycloaddition of azides with internal alkynes.

Authors:  Max M Majireck; Steven M Weinreb
Journal:  J Org Chem       Date:  2006-10-27       Impact factor: 4.354

3.  Highly potent triazole-based tubulin polymerization inhibitors.

Authors:  Qiang Zhang; Youyi Peng; Xin I Wang; Susan M Keenan; Sonia Arora; William J Welsh
Journal:  J Med Chem       Date:  2007-01-24       Impact factor: 7.446

4.  Synthesis and evaluation of a series of benzothiophene acrylonitrile analogs as anticancer agents.

Authors:  Narsimha Reddy Penthala; Vijayakumar N Sonar; Jamie Horn; Markos Leggas; Jai Shankar K B Yadlapalli; Peter A Crooks
Journal:  Medchemcomm       Date:  2013-07-01       Impact factor: 3.597

5.  Synthesis of some new 4-styryltetrazolo[1,5-a]quinoxaline and 1-substituted-4-styryl[1,2,4]triazolo[4,3-a]quinoxaline derivatives as potent anticonvulsants.

Authors:  Shivananda Wagle; Airody Vasudeva Adhikari; Nalilu Suchetha Kumari
Journal:  Eur J Med Chem       Date:  2008-06-20       Impact factor: 6.514

6.  Cytotoxic 2-phenyacrylnitriles, the importance of the cyanide moiety and discovery of potent broad spectrum cytotoxic agents.

Authors:  Mark Tarleton; Jayne Gilbert; Jennette A Sakoff; Adam McCluskey
Journal:  Eur J Med Chem       Date:  2012-09-18       Impact factor: 6.514

7.  Novel combretastatin analogues effective against murine solid tumors: design and structure-activity relationships.

Authors:  K Ohsumi; R Nakagawa; Y Fukuda; T Hatanaka; Y Morinaga; Y Nihei; K Ohishi; Y Suga; Y Akiyama; T Tsuji
Journal:  J Med Chem       Date:  1998-07-30       Impact factor: 7.446

8.  One step cascade synthesis of 4,5-disubstituted-1,2,3-(NH)-triazoles.

Authors:  Sujata Sengupta; Haifeng Duan; Weibing Lu; Jeffrey L Petersen; Xiaodong Shi
Journal:  Org Lett       Date:  2008-03-11       Impact factor: 6.005

9.  1,5-Disubstituted 1,2,3-triazoles as cis-restricted analogues of combretastatin A-4: Synthesis, molecular modeling and evaluation as cytotoxic agents and inhibitors of tubulin.

Authors:  Kristin Odlo; Jean Hentzen; Jérémie Fournier dit Chabert; Sylvie Ducki; Osman A B S M Gani; Ingebrigt Sylte; Martina Skrede; Vivi Ann Flørenes; Trond Vidar Hansen
Journal:  Bioorg Med Chem       Date:  2008-03-23       Impact factor: 3.641

10.  Synthesis of functionalized bisphosphonates via click chemistry.

Authors:  Hanna Skarpos; Sergey N Osipov; Daria V Vorob'eva; Irina L Odinets; Enno Lork; Gerd-Volker Röschenthaler
Journal:  Org Biomol Chem       Date:  2007-06-21       Impact factor: 3.876
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  5 in total

1.  Synthesis and biological evaluation of novel 4,5-disubstituted 2H-1,2,3-triazoles as cis-constrained analogues of combretastatin A-4.

Authors:  Nikhil R Madadi; Narsimha R Penthala; Kevin Howk; Amit Ketkar; Robert L Eoff; Michael J Borrelli; Peter A Crooks
Journal:  Eur J Med Chem       Date:  2015-08-29       Impact factor: 6.514

2.  Synthesis and anti-cancer screening of novel heterocyclic-(2H)-1,2,3-triazoles as potential anti-cancer agents.

Authors:  Narsimha Reddy Penthala; Leena Madhukuri; Shraddha Thakkar; Nikhil Reddy Madadi; Gauri Lamture; Robert L Eoff; Peter A Crooks
Journal:  Medchemcomm       Date:  2015-06-30       Impact factor: 3.597

3.  Crystal structures of (Z)-5-[2-(benzo[b]thio-phen-2-yl)-1-(3,5-di-meth-oxy-phen-yl)ethen-yl]-1H-tetra-zole and (Z)-5-[2-(benzo[b]thio-phen-3-yl)-1-(3,4,5-tri-meth-oxy-phen-yl)ethen-yl]-1H-tetra-zole.

Authors:  Narsimha Reddy Penthala; Jaishankar K B Yadlapalli; Sean Parkin; Peter A Crooks
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2016-04-08

4.  Comparison of crystal structures of 4-(benzo[b]thio-phen-2-yl)-5-(3,4,5-tri-meth-oxy-phen-yl)-2H-1,2,3-triazole and 4-(benzo[b]thio-phen-2-yl)-2-methyl-5-(3,4,5-tri-meth-oxy-phen-yl)-2H-1,2,3-triazole.

Authors:  Narsimha Reddy Penthala; Nikhil Reddy Madadi; Shobanbabu Bommagani; Sean Parkin; Peter A Crooks
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-10-24

5.  Crystal structure of 4,5-bis-(3,4,5-tri-meth-oxy-phen-yl)-2H-1,2,3-triazole methanol monosolvate.

Authors:  Nikhil Reddy Madadi; Narsimha Reddy Penthala; Shobanbabu Bommagani; Sean Parkin; Peter A Crooks
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-09-24
  5 in total

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