Journal ArticleDOI
Novel Orthogonal Synthesis of a Tagged Combinatorial Triazine Library via Grignard Reaction
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TLDR
In this article, a novel orthogonal synthesis via Grignard monoalkylation or monoarylation of cyanuric chloride in solution was employed to prepare aryl- or alkyl-substituted triazine building blocks.Abstract:
To expand the diversity of 1,3,5-triazine libraries to aryl and alkyl functionalities through the C–C bond, we employed a novel orthogonal synthesis via Grignard monoalkylation or monoarylation of cyanuric chloride in solution to prepare aryl- or alkyl-substituted triazine building blocks. These aryl- or alkyl-substituted triazine building blocks were captured by a resin-bound amine, followed by amination and acidic cleavage with high purity. Herein, we demonstrate a novel orthogonal synthesis of a tagged aryl- and alkyl-triazine library on solid support, utilizing building blocks prepared via Grignard reaction in solution. Through incorporation of a triethylene glycol linker at one of the alternate sites on the triazine scaffold we explored an intrinsic tagged library approach.read more
Citations
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Comprehensive Survey of Chemical Libraries for Drug Discovery and Chemical Biology: 2009
Dolle Roland E,Bertrand Le Bourdonnec,Karin Worm,Guillermo A. Morales,Craig J. Thomas,Wei Zhang +5 more
TL;DR: This is the thirteenth installment of the comprehensive survey series in high throughput chemistry, where 370 libraries and 24 molecular probes extracted from 355 literature citations are presented.
Journal ArticleDOI
A Chemical Screen Identifies Novel Compounds That Overcome Glial-Mediated Inhibition of Neuronal Regeneration
Lynn Usher,Andrea L. Johnstone,Ali Ertürk,Ying Hu,Dinara Strikis,Ina B. Wanner,Ina B. Wanner,Sanne Moorman,Jae Wook Lee,Jae Wook Lee,Jaeki Min,Hyung-Ho Ha,Y. Duan,Stanley Hoffman,Jeffrey L. Goldberg,Frank Bradke,Young-Tae Chang,Vance Lemmon,John L. Bixby +18 more
TL;DR: A novel triazine library is screened, based on the ability of compounds to increase neurite outgrowth from cerebellar neurons on inhibitory myelin substrates, to provide insight into the mechanisms through which glial-derived inhibitors of regeneration act, and could lead to the development of novel therapies for CNS injury.
Journal ArticleDOI
Combinatorial Solid-Phase Synthesis of 6-Aryl-1,3,5-triazines via Suzuki Coupling
Jae Wook Lee,Hyung-Ho Ha,Hyung-Ho Ha,Marc Vendrell,Jacqueline T. Bork,Young-Tae Chang,Young-Tae Chang +6 more
TL;DR: This work optimized the combinatorial derivatization of the triazine core using Suzuki cross-coupling and adapted this approach to polymer-supported amino acids and prepared aryl triazines with different charge distribution.
Journal ArticleDOI
Combinatorial Solid-Phase Synthesis of 4,6-Diaryl and 4-Aryl, 6-Alkyl-1,3,5-triazines and Their Application to Efficient Biofuel Production
Jaoon Y.H. Kim,Jae Wook Lee,Woo Sirl Lee,Hyung-Ho Ha,Marc Vendrell,Jacqueline T. Bork,Youngsook Lee,Young-Tae Chang,Young-Tae Chang +8 more
TL;DR: Through an unbiased phenotypic screening for improved biofuel generation in oleaginous yeast, it is found one diaryl triazine derivative (E4) which increased the biolipid production up to 86%.
Journal ArticleDOI
Specific Triazine Herbicides Induce Amyloid-β42 Production.
Erik Portelius,Emilie Durieu,Marion Bodin,Morgane Cam,Josef Pannee,Charlotte Leuxe,Aloϊse Mabondzo,Nassima Oumata,Hervé Galons,Jung Yeol Lee,Young-Tae Chang,Kathrin Stϋber,Philipp Koch,Gaëlle Fontaine,Marie-Claude Potier,Antigoni Manousopoulou,Spiros D. Garbis,Adrian Covaci,Debby Van Dam,Peter Paul De Deyn,Frank Karg,Marc Flajolet,Chiori Omori,Saori Hata,Toshiharu Suzuki,Kaj Blennow,Henrik Zetterberg,Henrik Zetterberg,Laurent Meijer +28 more
TL;DR: Several widely used triazines enhance the production of toxic, aggregation prone Aβ42/Aβ43 amyloids, suggesting the possible existence of environmental "Alzheimerogens" which may contribute to the initiation and propagation of the amyloidogenic process in late-onset AD.
References
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Journal ArticleDOI
A High-Throughput Screen for Compounds That Inhibit Aggregation of the Alzheimer's Peptide
Woojin Kim,Yunkyoung Kim,Jaeki Min,Dong-Jin Kim,Young-Tae Chang,Young-Tae Chang,Michael H. Hecht +6 more
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A Novel Microtubule Destabilizing Entity from Orthogonal Synthesis of Triazine Library and Zebrafish Embryo Screening
Ho-Sang Moon,Eric M. Jacobson,Sonya M. Khersonsky,Michael R. Luzung,Daniel P. Walsh,Wennan Xiong,Jae Wook Lee,Puja B. Parikh,Jennifer C. Lam,Tae-Wook Kang,Gustavo R. Rosania,Alexander F. Schier,Young-Tae Chang +12 more
TL;DR: The first orthogonal combinatorial synthesis of a high-purity triazine library was demonstrated and novel triazine-based microtubule inhibitors were discovered by an efficient zebrafish embryo screening and in vitro microtubules polymerization assay.
Journal ArticleDOI
A new series of estrogen receptor modulators that display selectivity for estrogen receptor beta.
Brad R. Henke,Thomas G. Consler,Ning Go,Ron L. Hale,Dana R Hohman,Stacey A. Jones,Amy T. Lu,Linda B. Moore,John T. Moore,Lisa A. Orband-Miller,R. Graham Robinett,Jean Shearin,Paul Kenneth Spearing,Eugene L. Stewart,Philip Stewart Turnbull,Susan L. Weaver,Shawn P. Williams,G. Bruce Wisely,Millard H. Lambert +18 more
TL;DR: The X-ray crystal structure of compound 15 complexed with the ligand binding domain of ERbeta has been solved and was utilized in the design of more conformationally restrained analogues such as 31 in an attempt to increase selectivity for the ERbeta subtype.
Journal ArticleDOI
Synthesis and Biological Evaluation of s-Triazine Substituted Polyamines as Potential New Anti-Trypanosomal Drugs
TL;DR: The use of the melamine motif, a substrate of the P2 transporter, as a potential tool to selectively deliver polyamine analogues to the parasites is described and a number of compounds were shown to competitively inhibit uptake of adenosine, indicating that they are recognized by the transporter.
Journal ArticleDOI
Evolution of Anti-HIV Drug CandidatesPart 2: Diaryltriazine (DATA) Analogues
Donald William Ludovici,Robert W. Kavash,Michael J. Kukla,Chih Y. Ho,Hong Ye,Bart De Corte,Koen Andries,Marie-Pierre de Béthune,Hilde Azijn,Rudi Pauwels,Henry E.L. Moereels,Jan Heeres,Lucien Maria Henricus Koymans,Marc René De Jonge,Koen Jeanne Alfons Van Aken,Frederik Frans Desire Daeyaert,Paul J. Lewi,Kalyan Das,Edward Arnold,Paul Adriaan Jan Janssen +19 more
TL;DR: A synthesis program directed toward improving the stability of imidoyl thiourea based non-nucleoside reverse transcriptase inhibitors led to the discovery of diaryltriazines (DATAs), a new class of potent NNRTIs.