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Literature DB >> 27598302

Artificial Macrocycles by Ugi Reaction and Passerini Ring Closure.

Eman M M Abdelraheem^1,2, Katarzyna Kurpiewska³, Justyna Kalinowska-Tłuścik³, Alexander Dömling¹.

Abstract

Artificial macrocycles can be convergently synthesized by a sequence of an Ugi multicomponent reaction (MCR) followed by an intramolecular Passerini MCR used to close the macrocycle. Significantly, in this work, the first intramolecular macrocyclization through a Passerini reaction is described. We describe 21 macrocycles of a size of 15-20. The resulting macrocyclic depsipeptides are model compounds for natural products and could find applications in drug discovery.

Entities: Chemical Disease Gene Species

Mesh：

Substances：
Macrocyclic Compounds

Year: 2016 PMID： 27598302 PMCID： PMC6280654 DOI： 10.1021/acs.joc.6b01430

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

31 in total

1. Multicomponent Reactions with Isocyanides.

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-09-15 Impact factor: 15.336

2. Short and diverse route toward complex natural product-like macrocycles.

Authors: Barbara Beck; Gregor Larbig; Beatrice Mejat; Marina Magnin-Lachaux; Anne Picard; Eberhardt Herdtweck; Alexander Dömling
Journal: Org Lett Date: 2003-04-03 Impact factor: 6.005

Review 3. "Multi-component reactions : emerging chemistry in drug discovery" 'from xylocain to crixivan'.

Authors: Christopher Hulme; Vijay Gore
Journal: Curr Med Chem Date: 2003-01 Impact factor: 4.530

Review 4. Multicomponent Reactions, Union of MCRs and Beyond.

Authors: Tryfon Zarganes-Tzitzikas; Ajay L Chandgude; Alexander Dömling
Journal: Chem Rec Date: 2015-09-11 Impact factor: 6.771

Review 5. Therapeutic monitoring of vancomycin in adult patients: a consensus review of the American Society of Health-System Pharmacists, the Infectious Diseases Society of America, and the Society of Infectious Diseases Pharmacists.

Authors: Michael Rybak; Ben Lomaestro; John C Rotschafer; Robert Moellering; William Craig; Marianne Billeter; Joseph R Dalovisio; Donald P Levine
Journal: Am J Health Syst Pharm Date: 2009-01-01 Impact factor: 2.637

6. A rapid access to biaryl ether containing macrocycles by pairwise use of Ugi 4CR and intramolecular S(N)Ar-based cycloetherification.

Authors: P Cristau; J P Vors; J Zhu
Journal: Org Lett Date: 2001-12-13 Impact factor: 6.005

7. Quantifying the chameleonic properties of macrocycles and other high-molecular-weight drugs.

Authors: Adrian Whitty; Mengqi Zhong; Lauren Viarengo; Dmitri Beglov; David R Hall; Sandor Vajda
Journal: Drug Discov Today Date: 2016-02-15 Impact factor: 7.851

Review 8. How To Design a Successful p53-MDM2/X Interaction Inhibitor: A Thorough Overview Based on Crystal Structures.

Authors: Natalia Estrada-Ortiz; Constantinos G Neochoritis; Alexander Dömling
Journal: ChemMedChem Date: 2015-12-16 Impact factor: 3.466

9. Binding site elucidation and structure guided design of macrocyclic IL-17A antagonists.

Authors: Shenping Liu; Leslie A Dakin; Li Xing; Jane M Withka; Parag V Sahasrabudhe; Wei Li; Mary Ellen Banker; Paul Balbo; Suman Shanker; Boris A Chrunyk; Zuojun Guo; Jinshan M Chen; Jennifer A Young; Guoyun Bai; Jeremy T Starr; Stephen W Wright; Joerg Bussenius; Sheng Tan; Ariamala Gopalsamy; Bruce A Lefker; Fabien Vincent; Lyn H Jones; Hua Xu; Lise R Hoth; Kieran F Geoghegan; Xiayang Qiu; Mark E Bunnage; Atli Thorarensen
Journal: Sci Rep Date: 2016-08-16 Impact factor: 4.379

10. Artificial Macrocycles as Potent p53-MDM2 Inhibitors.

Authors: Natalia Estrada-Ortiz; Constantinos G Neochoritis; Aleksandra Twarda-Clapa; Bogdan Musielak; Tad A Holak; Alexander Dömling
Journal: ACS Med Chem Lett Date: 2017-09-20 Impact factor: 4.345

15 in total

1. With unprotected amino acids to tetrazolo peptidomimetics.

Authors: Rudrakshula Madhavachary; Qian Wang; Alexander Dömling
Journal: Chem Commun (Camb) Date: 2017-07-27 Impact factor: 6.222

2. Two-Step Synthesis of Complex Artificial Macrocyclic Compounds.

Authors: Rudrakshula Madhavachary; Eman M M Abdelraheem; Arianna Rossetti; Aleksandra Twarda-Clapa; Bogdan Musielak; Katarzyna Kurpiewska; Justyna Kalinowska-Tłuścik; Tad A Holak; Alexander Dömling
Journal: Angew Chem Int Ed Engl Date: 2017-08-01 Impact factor: 15.336

3. Artificial Macrocycles by Ugi Reaction and Passerini Ring Closure.

Authors: Eman M M Abdelraheem; Katarzyna Kurpiewska; Justyna Kalinowska-Tłuścik; Alexander Dömling
Journal: J Org Chem Date: 2016-09-15 Impact factor: 4.354

4. Functionalized Spiroindolines with Anticancer Activity through a Metal-Free Post-Ugi Diastereoselective One-Pot Cascade Reaction.

Authors: Zhi-Gang Xu; Shi-Qiang Li; Jiang-Ping Meng; Dian-Yong Tang; Liu-Jun He; Jie Lei; Hui-Kuan Lin; Hong-Yu Li; Zhong-Zhu Chen
Journal: Chemistry Date: 2018-04-20 Impact factor: 5.236