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Literature DB >> 26327521

Click with a boronic acid handle: a neighboring group-assisted click reaction that allows ready secondary functionalization.

Alexander B Draganov¹, Ke Wang, Jalisa Holmes, Krishna Damera, Danzhu Wang, Chaofeng Dai, Binghe Wang.

Abstract

The feasibility of a neighboring boronic acid-facilitated facile condensation of an aldehyde is described. This reaction is bio-orthogonal, complete at room temperature within minutes, and suitable for bioconjugation chemistry. The boronic acid group serves the dual purpose of catalyzing the condensation reaction and being a handle for secondary functionalization.

Entities: Chemical Disease Gene

Mesh：

Substances：

Year: 2015 PMID： 26327521 PMCID： PMC4603419 DOI： 10.1039/c5cc05890b

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

56 in total

1. Synthesis, characterization and biological evaluation of some thiourea derivatives bearing benzothiazole moiety as potential antimicrobial and anticancer agents.

Authors: Sohail Saeed; Naghmana Rashid; Peter G Jones; Muhammad Ali; Rizwan Hussain
Journal: Eur J Med Chem Date: 2009-12-16 Impact factor: 6.514

2. A new fluorescent probe for gasotransmitter H₂S: high sensitivity, excellent selectivity, and a significant fluorescence off-on response.

Authors: Jingyu Zhang; Wei Guo
Journal: Chem Commun (Camb) Date: 2014-04-25 Impact factor: 6.222

3. Synthesis and anticancer activity evaluation of 4-thiazolidinones containing benzothiazole moiety.

Authors: Dmytro Havrylyuk; Ludmyla Mosula; Borys Zimenkovsky; Olexandr Vasylenko; Andrzej Gzella; Roman Lesyk
Journal: Eur J Med Chem Date: 2010-08-12 Impact factor: 6.514

4. Riluzole series. Synthesis and in vivo "antiglutamate" activity of 6-substituted-2-benzothiazolamines and 3-substituted-2-imino-benzothiazolines.

Authors: P Jimonet; F Audiau; M Barreau; J C Blanchard; A Boireau; Y Bour; M A Coléno; A Doble; G Doerflinger; C D Huu; M H Donat; J M Duchesne; P Ganil; C Guérémy; E Honor; B Just; R Kerphirique; S Gontier; P Hubert; P M Laduron; J Le Blevec; M Meunier; J M Miquet; C Nemecek; S Mignani
Journal: J Med Chem Date: 1999-07-29 Impact factor: 7.446

5. Copper-mediated cross-coupling of aryl boronic acids and alkyl thiols.

Authors: P S Herradura; K A Pendola; R K Guy
Journal: Org Lett Date: 2000-07-13 Impact factor: 6.005

Review 6. Suzuki-Miyaura cross-coupling reactions in aqueous media: green and sustainable syntheses of biaryls.

Authors: Vivek Polshettiwar; Audrey Decottignies; Christophe Len; Aziz Fihri
Journal: ChemSusChem Date: 2010-05-25 Impact factor: 8.928

7. Rapid and specific post-synthesis modification of DNA through a biocompatible condensation of 1,2-aminothiols with 2-cyanobenzothiazole.

Authors: Yunfeng Cheng; Hanjing Peng; Weixuan Chen; Nanting Ni; Bowen Ke; Chaofeng Dai; Binghe Wang
Journal: Chemistry Date: 2013-02-28 Impact factor: 5.236

8. Heterogeneous Pd/C-catalyzed ligand-free, room-temperature Suzuki-Miyaura coupling reactions in aqueous media.

Authors: Tomohiro Maegawa; Yoshiaki Kitamura; Satoko Sako; Takahiro Udzu; Ai Sakurai; Asami Tanaka; Yusuke Kobayashi; Koichi Endo; Utpal Bora; Takanori Kurita; Atsushi Kozaki; Yasunari Monguchi; Hironao Sajiki
Journal: Chemistry Date: 2007 Impact factor: 5.236

9. Synthesis and evaluation of 11C-labeled 6-substituted 2-arylbenzothiazoles as amyloid imaging agents.

Authors: Chester A Mathis; Yanming Wang; Daniel P Holt; Guo-Feng Huang; Manik L Debnath; William E Klunk
Journal: J Med Chem Date: 2003-06-19 Impact factor: 7.446

10. Genetic Encoding of bicyclononynes and trans-cyclooctenes for site-specific protein labeling in vitro and in live mammalian cells via rapid fluorogenic Diels-Alder reactions.

Authors: Kathrin Lang; Lloyd Davis; Stephen Wallace; Mohan Mahesh; Daniel J Cox; Melissa L Blackman; Joseph M Fox; Jason W Chin
Journal: J Am Chem Soc Date: 2012-06-13 Impact factor: 15.419

8 in total

8. Observation of the generation of peroxynitrite in mouse liver after acetaminophen overdose with a boronate-based ratiometric fluorescence probe.

Authors: Ying Ma; Haigang Tian; Zhengyu Jin; Xiaoyong Li; Yiping Li
Journal: RSC Adv Date: 2019-02-25 Impact factor: 4.036

8 in total

Click with a boronic acid handle: a neighboring group-assisted click reaction that allows ready secondary functionalization.

1. Synthesis, characterization and biological evaluation of some thiourea derivatives bearing benzothiazole moiety as potential antimicrobial and anticancer agents.

2. A new fluorescent probe for gasotransmitter H₂S: high sensitivity, excellent selectivity, and a significant fluorescence off-on response.

3. Synthesis and anticancer activity evaluation of 4-thiazolidinones containing benzothiazole moiety.

4. Riluzole series. Synthesis and in vivo "antiglutamate" activity of 6-substituted-2-benzothiazolamines and 3-substituted-2-imino-benzothiazolines.

5. Copper-mediated cross-coupling of aryl boronic acids and alkyl thiols.

Review 6. Suzuki-Miyaura cross-coupling reactions in aqueous media: green and sustainable syntheses of biaryls.

7. Rapid and specific post-synthesis modification of DNA through a biocompatible condensation of 1,2-aminothiols with 2-cyanobenzothiazole.

8. Heterogeneous Pd/C-catalyzed ligand-free, room-temperature Suzuki-Miyaura coupling reactions in aqueous media.

9. Synthesis and evaluation of 11C-labeled 6-substituted 2-arylbenzothiazoles as amyloid imaging agents.

10. Genetic Encoding of bicyclononynes and trans-cyclooctenes for site-specific protein labeling in vitro and in live mammalian cells via rapid fluorogenic Diels-Alder reactions.

1. Borylated oximes: versatile building blocks for organic synthesis.

2. Biocompatible conjugation of Tris base to 2-acetyl and 2-formyl phenylboronic acid.

3. Versatile Bioconjugation Chemistries of ortho-Boronyl Aryl Ketones and Aldehydes.

4. High-fidelity carbon dots polarity probes: revealing the heterogeneity of lipids in oncology.

5. Fast and selective labeling of N-terminal cysteines at neutral pH via thiazolidino boronate formation.

6. Iminoboronates are efficient intermediates for selective, rapid and reversible N-terminal cysteine functionalisation.

7. Design and Development of an HBT-Based Ratiometric Fluorescent Probe to Monitor Stress-Induced Premature Senescence.

8. Observation of the generation of peroxynitrite in mouse liver after acetaminophen overdose with a boronate-based ratiometric fluorescence probe.