Literature DB >> 28477103

Design, synthesis and fluorescence property evaluation of blue emitting triazole-linked chromene peptidomimetics.

T Jency Mohan1, D Bahulayan2.   

Abstract

A highly efficient "Click with MCR" strategy for the three-step synthesis of two types of blue emitting chromene peptidomimetics is described. The peptidomimetics were synthesized via a copper-catalyzed [3[Formula: see text]2] azide-alkyne cycloaddition between chromene alkynes obtained from a three-component reaction and the peptide azides obtained from Ugi or Mannich type multicomponent reactions. The photophysical properties of the peptidomimetics are comparable with commercial fluorophores. Computational studies using drug property descriptors support the possibility of using these molecules for modulating difficult target classes having large, flat, and groove-shaped binding sites.

Entities:  

Keywords:  Beyond rule of 5 (bRo5); Chromene; Click chemistry; MCRs; Mannich reaction; Triazole; Ugi reaction

Mesh:

Substances:

Year:  2017        PMID: 28477103     DOI: 10.1007/s11030-017-9744-9

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  45 in total

Review 1.  Target-oriented and diversity-oriented organic synthesis in drug discovery.

Authors:  S L Schreiber
Journal:  Science       Date:  2000-03-17       Impact factor: 47.728

2.  Antipyretic, analgesic, anti-inflammatory and antioxidant activities of two major chromenes from Melicope lunu-ankenda.

Authors:  Anil J Johnson; Arun Kumar R; Sherin A Rasheed; Sreeja P Chandrika; Arun Chandrasekhar; Sabulal Baby; Appian Subramoniam
Journal:  J Ethnopharmacol       Date:  2010-05-08       Impact factor: 4.360

3.  Montmorillonite K10 clay: an efficient catalyst for the one-pot stereoselective synthesis of beta-acetamido ketones.

Authors:  D Bahulayan; Saibal Kumar Das; Javed Iqbal
Journal:  J Org Chem       Date:  2003-07-11       Impact factor: 4.354

Review 4.  10 years of click chemistry: synthesis and applications of ferrocene-derived triazoles.

Authors:  Venkataraman Ganesh; V Sai Sudhir; Taraknath Kundu; Srinivasan Chandrasekaran
Journal:  Chem Asian J       Date:  2011-08-31

5.  Modern synthetic tools toward the preparation of sophisticated phthalocyanine-based photoactive systems.

Authors:  Maria-Eleni Ragoussi; Tomás Torres
Journal:  Chem Asian J       Date:  2014-06-30

6.  The power of fluorogenic probes.

Authors:  André Nadler; Carsten Schultz
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-21       Impact factor: 15.336

7.  The photochemical ring opening reaction of chromene as seen by transient absorption and fluorescence spectroscopy.

Authors:  Teja T Herzog; Gerald Ryseck; Evelyn Ploetz; Thorben Cordes
Journal:  Photochem Photobiol Sci       Date:  2013-07       Impact factor: 3.982

8.  Stereoselective synthesis of bio-hybrid amphiphiles of coumarin derivatives by Ugi-Mannich triazole randomization using copper catalyzed alkyne azide click chemistry.

Authors:  P Pramitha; D Bahulayan
Journal:  Bioorg Med Chem Lett       Date:  2012-02-09       Impact factor: 2.823

Review 9.  Click chemistry with DNA.

Authors:  Afaf H El-Sagheer; Tom Brown
Journal:  Chem Soc Rev       Date:  2010-02-09       Impact factor: 54.564

Review 10.  Diversity oriented syntheses of conventional heterocycles by smart multi component reactions (MCRs) of the last decade.

Authors:  Heiner Eckert
Journal:  Molecules       Date:  2012-01-20       Impact factor: 4.411

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