- Regioselective Radical Arene Amination for the Concise Synthesis ofortho-Phenylenediamines
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The formation of arene C-N bonds directly from C-H bonds is of great importance and there has been rapid recent development of methods for achieving this through radical mechanisms, often involving reactiveN-centered radicals. A major challenge associated with these advances is that of regiocontrol, with mixtures of regioisomeric products obtained in most protocols, limiting broader utility. We have designed a system that utilizes attractive noncovalent interactions between an anionic substrate and an incoming radical cation in order to guide the latter to the areneorthoposition. The anionic substrate takes the form of a sulfamate-protected aniline and telescoped cleavage of the sulfamate group after amination leads directly toortho-phenylenediamines, key building blocks for a range of medicinally relevant diazoles. Our method can deliver both free amines and monoalkyl amines allowing access to unsymmetrical, selectively monoalkylated benzimidazoles and benzotriazoles. As well as providing concise access to valuableortho-phenylenediamines, this work demonstrates the potential for utilizing noncovalent interactions to control positional selectivity in radical reactions.
- Gillespie, James E.,Morrill, Charlotte,Phipps, Robert J.
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p. 9355 - 9360
(2021/07/19)
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- STRAD-BINDING AGENTS AND USES THEREOF
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Disclosed herein, inter alia, are compounds for binding STRAD pseudokinase and uses thereof.
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Paragraph 1443-1445
(2021/08/06)
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- Chemical Methods for N- and O-Sulfation of Small Molecules, Amino Acids and Peptides
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Sulfation of the amino acid residues of proteins is a significant post-translational modification, the functions of which are yet to be fully understood. Current sulfation methods are limited mainly to O-tyrosine (sY), which requires negatively charged species around the desired amino acid residue and a specific sulfotransferase enzyme. Alternatively, for solid-phase peptide synthesis, a de novo protected sY is required. Therefore, synthetic routes that go beyond O-sulfation are required. We have developed a novel route to N-sulfamation and can dial-in/out O-sulfation (without S-sulfurothiolation), mimicking the initiation step of the ping-pong sulfation mechanism identified in structural biology. This rapid, low-temperature and non-racemising method is applicable to a range of amines, amides, amino acids, and peptide sequences.
- Benedetti, Anna Mary,Gill, Daniel M.,Tsang, Chi W.,Jones, Alan M.
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p. 938 - 942
(2020/01/24)
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- PROTEIN KINASE MKK4 INHIBITORS FOR PROMOTING LIVER REGENERATION OR REDUCING OR PREVENTING HEPATOCYTE DEATH
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The invention relates to pyrazolo-pyridine compounds which inhibit mitogen-activated protein kinase kinase 4 (MKK4) and in particular, selectively inhibit MKK4 over protein kinases JNK1 and MKK7. The compounds are useful for promoting liver regeneration or reducing or preventing hepatocyte death. They are further useful for treating osteoarthritis or rheumatoid arthritis, or CNS-related diseases.
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Page/Page column 88; 89
(2019/08/26)
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- Vicinal Diamination of Arenes with Domino Aryne Precursors
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Vicinal diamination of domino aryne precursors was achieved with sulfamides. The reaction proceeds through a two-aryne pathway, accepting two N-nucleophiles at the 1,2-positions of an arene ring. Symmetrical and unsymmetrical diaminobenzenes were readily obtained.
- Li, Lu,Qiu, Dachuan,Shi, Jiarong,Li, Yang
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supporting information
p. 3726 - 3729
(2016/08/16)
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- ANTIBACTERIAL THIAZOLECARBOXYLIC ACIDS
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Compounds of general formula (I), wherein R1, R11, Y, R2, n and A are as defined herein are useful as inhibitors or metallo-β-lactamase (MBL) enzymes and can be used for reducing or removing antibiotic resistance in bacteria.
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Page/Page column 107
(2015/01/09)
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- Preparation of Arylimidobis(sulfates)
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Seven arylimidobis(sulfates), six of which are new compounds, have been prepared by the N-sulfonation of the corresponding primary aromatic amines with 2-methylpyridine-sulfur trioxide in 60-92percent yields.
- Kanetani, Fujio
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p. 952 - 954
(2007/10/02)
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