Literature DB >> 20335958

Synthesis of 1-(4-trifluoromethoxyphenyl)-2,5-dimethyl-3-(2-R-thiazol-4-yl)-1H-pyrroles via chain heterocyclization.

Mykhaylo V Vovk1, Oleksandr M Pinchuk, Andrij O Tolmachov, Andrei A Gakh.   

Abstract

The title compounds, (4-trifluoromethoxyphenyl)-2,5-dimethyl-3-(2-R-thiazol-4-yl)-1H-pyrroles, were prepared in four steps starting from commercially available 4-trifluoromethoxyaniline. The pyrrole (second ring) was added in one step using the Paal-Knorr method. The thiazole (third ring) was added in three steps using chloroacylation with chloroacetonitrile followed by heterocyclization with thioamides/thioureas.

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 20335958      PMCID： PMC6263183          DOI： 10.3390/molecules15020997

Source DB:  PubMed          Journal:  Molecules        ISSN： 1420-3049            Impact factor:   4.411


  11 in total

Review 1.  Chemistry and biology of roseophilin and the prodigiosin alkaloids: a survey of the last 2500 years.

Authors:  Alois Fürstner
Journal:  Angew Chem Int Ed Engl       Date:  2003-08-11       Impact factor: 15.336

Review 2.  Alpha-fluorinated ethers, thioethers, and amines: anomerically biased species.

Authors:  Frédéric Leroux; Peter Jeschke; Manfred Schlosser
Journal:  Chem Rev       Date:  2005-03       Impact factor: 60.622

3.  New pyrrole inhibitors of monoamine oxidase: synthesis, biological evaluation, and structural determinants of MAO-A and MAO-B selectivity.

Authors:  Giuseppe La Regina; Romano Silvestri; Marino Artico; Antonio Lavecchia; Ettore Novellino; Olivia Befani; Paola Turini; Enzo Agostinelli
Journal:  J Med Chem       Date:  2007-01-26       Impact factor: 7.446

Review 4.  Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2006.

Authors:  Roland E Dolle; Bertrand Le Bourdonnec; Allan J Goodman; Guillermo A Morales; Joseph M Salvino; Wei Zhang
Journal:  J Comb Chem       Date:  2007-09-19

5.  Four new bioactive pyrrole-derived alkaloids from the marine sponge Axinella brevistyla.

Authors:  S Tsukamoto; K Tane; T Ohta; S Matsunaga; N Fusetani; R W van Soest
Journal:  J Nat Prod       Date:  2001-12       Impact factor: 4.050

6.  Novel small-molecule inhibitors of anthrax lethal factor identified by high-throughput screening.

Authors:  Igor A Schepetkin; Andrei I Khlebnikov; Liliya N Kirpotina; Mark T Quinn
Journal:  J Med Chem       Date:  2006-08-24       Impact factor: 7.446

7.  Oxocyclostylidol, an intramolecular cyclized oroidin derivative from the marine sponge Stylissa caribica.

Authors:  Achim Grube; Matthias Köck
Journal:  J Nat Prod       Date:  2006-08       Impact factor: 4.050

8.  Selective PPARgamma modulators with improved pharmacological profiles.

Authors:  Kun Liu; Regina M Black; John J Acton; Ralph Mosley; Sheryl Debenham; Ramon Abola; Meng Yang; Richard Tschirret-Guth; Lawrence Colwell; Cherrie Liu; Margaret Wu; Chuanlin F Wang; Karen L MacNaul; Margaret E McCann; David E Moller; Joel P Berger; Peter T Meinke; A Brian Jones; Harold B Wood
Journal:  Bioorg Med Chem Lett       Date:  2005-05-16       Impact factor: 2.823

9.  De novo discovery of serotonin N-acetyltransferase inhibitors.

Authors:  Lawrence M Szewczuk; S Adrian Saldanha; Surajit Ganguly; Erin M Bowers; Margarita Javoroncov; Balasubramanyam Karanam; Jeffrey C Culhane; Marc A Holbert; David C Klein; Ruben Abagyan; Philip A Cole
Journal:  J Med Chem       Date:  2007-10-09       Impact factor: 7.446

10.  GROWTH RETARDANTS: Effects on Gibberellin Biosynthesis and Other Metabolic Pathways.

Authors:  Wilhelm Rademacher
Journal:  Annu Rev Plant Physiol Plant Mol Biol       Date:  2000-06
View more
  2 in total

1.  Antiproliferative 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides, a new tubulin inhibitor chemotype.

Authors:  Mikhail Krasavin; Andrey V Sosnov; Ruben Karapetian; Igor Konstantinov; Olga Soldatkina; Elena Godovykh; Fedor Zubkov; Ruoli Bai; Ernest Hamel; Andrei A Gakh
Journal:  Bioorg Med Chem Lett       Date:  2014-08-08       Impact factor: 2.823

2.  Identification of diaryl 5-amino-1,2,4-oxadiazoles as tubulin inhibitors: the special case of 3-(2-fluorophenyl)-5-(4-methoxyphenyl)amino-1,2,4-oxadiazole.

Authors:  Andrei A Gakh; Andrey V Sosnov; Mikhail Krasavin; Tam Luong Nguyen; Ernest Hamel
Journal:  Bioorg Med Chem Lett       Date:  2013-01-11       Impact factor: 2.823
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.