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Literature DB >> 21401025

One-pot synthesis of 2-imidazolines via the ring expansion of imidoyl chlorides with aziridines.

Michael R Kuszpit¹, William D Wulff, Jetze J Tepe.

Abstract

We herein report a simple and convenient one-pot synthesis of highly substituted 2-imidazolines in a regiocontrolled and stereospecific matter through the ring expansion reaction of an imidoyl chloride with an aziridine, analogous to the Heine reaction.

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Year: 2011 PMID： 21401025 PMCID： PMC3074022 DOI： 10.1021/jo200101q

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

16 in total

Review 1. Enhancement of chemotherapeutic efficacy by small molecule inhibition of NF-kappaB and checkpoint kinases.

Authors: Vasudha Sharma; Christopher D Hupp; Jetze J Tepe
Journal: Curr Med Chem Date: 2007 Impact factor: 4.530

2. Sensitization of cancer cells to DNA damaging agents by imidazolines.

Authors: Vasudha Sharma; Satyamaheshwar Peddibhotla; Jetze J Tepe
Journal: J Am Chem Soc Date: 2006-07-19 Impact factor: 15.419

3. Design and synthesis of novel imidazoline derivatives with potent antihyperglycemic activity in a rat model of type 2 diabetes.

Authors: Louis Crane; Maria Anastassiadou; Salomé El Hage; Jean Luc Stigliani; Geneviève Baziard-Mouysset; Marc Payard; Jean Michel Leger; Jean-Guy Bizot-Espiard; Alain Ktorza; Daniel-Henri Caignard; Pierre Renard
Journal: Bioorg Med Chem Date: 2006-08-02 Impact factor: 3.641

Review 4. The MDM2 inhibitor Nutlins as an innovative therapeutic tool for the treatment of haematological malignancies.

Authors: Paola Secchiero; Maria Grazia di Iasio; Arianna Gonelli; Giorgio Zauli
Journal: Curr Pharm Des Date: 2008 Impact factor: 3.116

5. A new class of analgesic agents toward prostacyclin receptor inhibition: synthesis, biological studies and QSAR analysis of 1-hydroxyl-2-substituted phenyl-4,4,5,5-tetramethylimidazolines.

Authors: Ming Zhao; Zheng Li; Li Peng; Yu-Rong Tang; Chao Wang; Ziding Zhang; Shiqi Peng
Journal: Eur J Med Chem Date: 2007-07-27 Impact factor: 6.514

6. Discovery of tetrasubstituted imidazolines as potent and selective neuropeptide Y Y5 receptor antagonists: reduced human ether-a-go-go related gene potassium channel binding affinity and potent antiobesity effect.

Authors: Nagaaki Sato; Makoto Ando; Shiho Ishikawa; Makoto Jitsuoka; Keita Nagai; Hirobumi Takahashi; Aya Sakuraba; Hiroyasu Tsuge; Hidefumi Kitazawa; Hisashi Iwaasa; Satoshi Mashiko; Akira Gomori; Ryuichi Moriya; Naoko Fujino; Tomoyuki Ohe; Akane Ishihara; Akio Kanatani; Takehiro Fukami
Journal: J Med Chem Date: 2009-05-28 Impact factor: 7.446

7. Structural-activity relationship study of highly-functionalized imidazolines as potent inhibitors of nuclear transcription factor-kappaB mediated IL-6 production.

Authors: Daljinder K Kahlon; Theresa A Lansdell; Jason S Fisk; Jetze J Tepe
Journal: Bioorg Med Chem Date: 2009-03-09 Impact factor: 3.641

One-pot synthesis of 2-imidazolines via the ring expansion of imidoyl chlorides with aziridines.

Review 1. Enhancement of chemotherapeutic efficacy by small molecule inhibition of NF-kappaB and checkpoint kinases.

2. Sensitization of cancer cells to DNA damaging agents by imidazolines.

3. Design and synthesis of novel imidazoline derivatives with potent antihyperglycemic activity in a rat model of type 2 diabetes.

Review 4. The MDM2 inhibitor Nutlins as an innovative therapeutic tool for the treatment of haematological malignancies.

5. A new class of analgesic agents toward prostacyclin receptor inhibition: synthesis, biological studies and QSAR analysis of 1-hydroxyl-2-substituted phenyl-4,4,5,5-tetramethylimidazolines.

6. Discovery of tetrasubstituted imidazolines as potent and selective neuropeptide Y Y5 receptor antagonists: reduced human ether-a-go-go related gene potassium channel binding affinity and potent antiobesity effect.

7. Structural-activity relationship study of highly-functionalized imidazolines as potent inhibitors of nuclear transcription factor-kappaB mediated IL-6 production.

8. Nuclear factor-kappaB mediated inhibition of cytokine production by imidazoline scaffolds.

9. Enantioselective chemoenzymatic synthesis of trans-aziridines.

Review 10. Nutlins and ionizing radiation in cancer therapy.

Review 1. Transition metal-free one-pot synthesis of nitrogen-containing heterocycles.

2. (Z)-N-(2,6-Diiso-propyl-phen-yl)-4-nitro-benzimidoyl chloride.

3. Palladium-catalyzed multicomponent synthesis of 2-imidazolines from imines and acid chlorides.