Literature DB >> 28190224

One-pot synthesis of novel (2R,4S)-N-aryl-4-hydroxy-1-(2,2,2-trifluoroacetyl) pyrrolidine-2-carboxamides via TiO₂-NPs and Pd(PPh₃)₂Cl₂ catalysts and investigation of their biological activities.

Ali Darehkordi1, Mahin Ramezani2.   

Abstract

A new class of (2R,4S)-N-aryl-4-hydroxy-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxamide compounds was synthesized by a facile one-pot reaction of trans-4-hydroxy proline and trifluoroacetimidoyl chlorides in the presence of [Formula: see text]-nanoparticles as a catalyst and sodium bicarbonate as a base. Synthesized compounds showed cytotoxicity with [Formula: see text] values of 15.3-70.3 [Formula: see text] against K562 (Homo sapiens, human) cells. The results of the study provide a valuable method for one-pot synthesis of trans-4-hydroxy proline-based N-(2,2,2-trifluoroacetylated) compounds. Also, these compounds show significant pharmaceutical activities as antibacterial and antifungal reagents.

Entities:  

Keywords:  -nanoparticles; Bis(triphenylphosphine)palladium(II)dichloride; K562 (Homo sapiens, human)  cells; Pharmaceutical

Mesh:

Substances:

Year:  2017        PMID: 28190224     DOI: 10.1007/s11030-017-9726-y

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


  13 in total

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Authors:  Daniel J Pippel; Lana K Young; Michael A Letavic; Kiev S Ly; Bita Naderi; Aki Soyode-Johnson; Emily M Stocking; Nicholas I Carruthers; Neelakandha S Mani
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Review 2.  Nanocatalysis: mature science revisited or something really new?

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Journal:  Angew Chem Int Ed Engl       Date:  2004-03-19       Impact factor: 15.336

Review 3.  Nanoparticles as recyclable catalysts: the frontier between homogeneous and heterogeneous catalysis.

Authors:  Didier Astruc; Feng Lu; Jaime Ruiz Aranzaes
Journal:  Angew Chem Int Ed Engl       Date:  2005-12-09       Impact factor: 15.336

4.  A new class of angiotensin-converting enzyme inhibitors.

Authors:  A A Patchett; E Harris; E W Tristram; M J Wyvratt; M T Wu; D Taub; E R Peterson; T J Ikeler; J ten Broeke; L G Payne; D L Ondeyka; E D Thorsett; W J Greenlee; N S Lohr; R D Hoffsommer; H Joshua; W V Ruyle; J W Rothrock; S D Aster; A L Maycock; F M Robinson; R Hirschmann; C S Sweet; E H Ulm; D M Gross; T C Vassil; C A Stone
Journal:  Nature       Date:  1980-11-20       Impact factor: 49.962

5.  Design, synthesis, and evaluation of proline and pyrrolidine based melanocortin receptor agonists. A conformationally restricted dipeptide mimic approach.

Authors:  Xinrong Tian; Timothy B Field; Adrian G Switzer; Adam W Mazur; Frank H Ebetino; John A Wos; Steve M Berberich; Lalith R Jayasinghe; Cindy M Obringer; Martin E Dowty; Beth B Pinney; Julie A Farmer; Doreen Crossdoersen; Russell J Sheldon
Journal:  J Med Chem       Date:  2006-07-27       Impact factor: 7.446

6.  Mannich-type reaction with trifluoromethylated N,O-hemiacetal: facile preparation of beta-amino-beta-trifluoromethyl carbonyl compounds

Authors: 
Journal:  Org Lett       Date:  2000-06-01       Impact factor: 6.005

7.  Discovery of (2S,4R)-1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxylic acid hydrochloride (GAP-134)13, an orally active small molecule gap-junction modifier for the treatment of atrial fibrillation.

Authors:  John A Butera; Bjarne Due Larsen; James K Hennan; Edward Kerns; Li Di; Asaf Alimardanov; Robert E Swillo; Gwen A Morgan; Kun Liu; Qiang Wang; Eric I Rossman; Rayomand Unwalla; Leonard McDonald; Christine Huselton; Jørgen S Petersen
Journal:  J Med Chem       Date:  2009-02-26       Impact factor: 7.446

8.  In vitro stereoselective metabolism of the psychotomimetic amine, 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane. An apparent enantiomeric interaction.

Authors:  N P McGraw; S C Callery; N Castagnoli
Journal:  J Med Chem       Date:  1977-02       Impact factor: 7.446

9.  Derivatization of chiral amines with (S,S)-N-trifluoroacetylproline anhydride for GC estimation of enantiomeric composition.

Authors:  J D Adams; T F Woolf; A J Trevor; L R Williams; N Castagnoli
Journal:  J Pharm Sci       Date:  1982-06       Impact factor: 3.534

10.  A general and efficient copper catalyst for the amidation of aryl halides.

Authors:  Artis Klapars; Xiaohua Huang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2002-06-26       Impact factor: 15.419

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  2 in total

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Journal:  Iran Biomed J       Date:  2017-08-12

2.  The New Compound of (2R, 4S)-N-(2, 5-difluorophenyl)-4-Hydroxy-1-(2, 2, 2-Trifluoroacetyl) Pyrrolidine-2-Carboxamide to Mediate the Expression of Some Apoptosis Genes by the HepG2 Cell Line

Authors:  Mahnaz Ramezani; Mahin Ramezani; Ali Darekordi; Gholamhossein Hassanshahi; Mohammad Reza Mirzaei
Journal:  Asian Pac J Cancer Prev       Date:  2019-05-25
  2 in total

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