- A biotin-conjugated pyridine-based isatoic anhydride, a selective room temperature RNA-acylating agent for the nucleic acid separation
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Isatoic anhydride derivatives, including a biotin and a disulfide linker were specifically designed for nucleic acid separation. 2′-OH selective RNA acylation, capture of biotinylated RNA adducts by streptavidin-coated magnetic beads and disulfide chemica
- Ursuegui,Yougnia,Moutin,Burr,Fossey,Cailly,Laayoun,Laurent,Fabis
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Read Online
- Zn-Catalyzed Nicotinate-Directed Transamidations in Peptide Synthesis
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A chemoselective and catalytic transamidation for peptide synthesis is described. Transamidation under Zn catalysis is chemoselectively achieved by amino acid amide/peptidic amide derivatization with a tert-butyl nicotinate (tBu-nic) directing group. The directing group could be easily introduced on protected amino acid amides via Pd-catalyzed amidation with tert-butyl 2-chloronicotinate (tBu-nicCl). Under standard peptide coupling/deprotection conditions, the tBu-nic-equipped amino acid amides proved to be fully inert, allowing them to be easily built-in in complex molecules. The disclosed method was evaluated in the synthesis of diverse dipeptides, in dipeptide segment coupling, in side-chain modification of a solid-supported tetra-/pentapeptide, and in the macrocyclization of a heptapeptide.
- Hollanders, Charlie,Renders, Evelien,Gadais, Charlène,Masullo, Dario,Van Raemdonck, Laurent,Wybon, Clarence C. D.,Martin, Charlotte,Herrebout, Wouter A.,Maes, Bert U. W.,Ballet, Steven
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p. 4280 - 4289
(2020/05/18)
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- INHIBITORS OF INDOLEAMINE 2,3-DIOXYGENASE AND METHODS OF THEIR USE
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The present invention provides a compound of formula (II): an inhibitor of indoleamine 2,3-dioxygenase (IDO), which may be used as medicaments for the treatment of proliferative disorders, such as cancer, viral infections and/or autoimmune diseases. Its prodrugs are disclosed.
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Page/Page column 100; 101
(2019/07/20)
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- Methods of functionalization and reagents used in such methods using an aza-isatoic anhydride or a derivative thereof, biological molecules thus treated and kits
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The present invention relates to a method of functionalization of at least one ribonucleic acid (RNA) molecule, contained in a liquid sample, which includes the following steps: a) providing at least: one binding molecule consisting of an aza-isatoic anhydride or a derivative thereof, one group of interest, and one linkage joining the binding molecule to the group of interest, b) reacting the anhydride function of the binding molecule with at least one hydroxyl group carried: in position 2′ of the ribose of one of the RNA nucleotides, and/or in position(s) 2′ and/or 3′ of the ribose of the nucleotide at the terminal 3′ end of the RNA, and obtaining an aza-anthranilate that joins, by means of the linkage, the RNA to the group of interest.
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Page/Page column 18
(2019/01/20)
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- Zn-Catalyzed tert-Butyl Nicotinate-Directed Amide Cleavage as a Biomimic of Metallo-Exopeptidase Activity
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A two-step catalytic amide-to-ester transformation of primary amides under mild reaction conditions has been developed. A tert-butyl nicotinate (tBu nic) directing group is easily introduced onto primary amides via Pd-catalyzed amidation with tert-butyl 2-chloronicotinate. A weak base (Cs2CO3 or K2CO3) at 40-50 °C can be used provided that 1,1′-bis(dicyclohexylphosphino)ferrocene is selected as ligand. The tBu nic activated amides subsequently allow Zn(OAc)2-catalyzed nonsolvolytic alcoholysis in tBuOAc at 40-60 °C under neutral reaction conditions. The activation mechanism is biomimetic: the C3-ester substituent of the pyridine in the directing group populates the trans-conformer suitable for Zn-chelation, C=Oamide-Zn-Ndirecting group, and Zn-coordinated alcohol is additionally activated as a nucleophile by hydrogen bonding with the acetate ligand of the catalyst. Additionally, the acetate ligand assists in intramolecular O-to-N proton transfer. The chemoselectivity versus other functional groups and compatibility with challenging reaction partners, such as peptides, sugars, and sterols, illustrates the synthetic applicability of this two-step amide cleavage method. The tBu nic amides do not require purification before cleavage. Preliminary experiments also indicate that other weak nucleophiles can be used such as (hetero)arylamines (transamidation) as exemplified by 8-aminoquinoline.
- Wybon, Clarence C. D.,Mensch, Carl,Hollanders, Charlie,Gadais, Charlène,Herrebout, Wouter A.,Ballet, Steven,Maes, Bert U. W.
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p. 203 - 218
(2018/01/17)
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- METHOD FOR PRODUCING HETEROCYCLIC COMPOUND
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The present invention provides a production method of heterocyclic compound having an excellent CH24H inhibitory action, which is suitable for industrial production. In the present invention, a 2-halogenonicotinic acid or a reactive derivative thereof or a salt thereof is reacted with 4-benzyl-4-hydroxypiperidine acid addition salt to give a (4-benzyl-4-hydroxypiperidin-1-yl) (2-halogenopyridin-3-yl)methanone or a salt thereof, and then the obtained compound is reacted with pyridine-4-boronic acid or a reactive derivative thereof or a salt thereof in the presence of a metal catalyst and a base to give (4-benzyl-4-hydroxypiperidin-1-yl) (2,4′-bipyridin-3-yl)methanone or a salt thereof.
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Paragraph 0055
(2018/11/11)
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- PROCESS FOR THE CATALYTIC DIRECTED CLEAVAGE OF AMIDE-CONTAINING COMPOUNDS
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The present invention relates to a catalytic method for the conversion of amide-containing compouds by means of a build-in directing group and upon the action of a heteronucleophilic compound (in se an amine (RNH2 or RNHR') or an alcohol (ROH) or a thiol (RSH)) in the presence of a metal catalyst to respectively esters, thioesters, carbonates, thiocarbonates and to what is defined as amide-containing compounds (such as carboxamides, urea, carbamates, thiocarbamates). The present invention also relates to these amide-containing compounds having a build-in directing group (DG), as well as the use of such directing groups in the catalytic directed cleavage of N-DG amides with the use of heteronucleophiles (in se an amine (RNH2 or RNHR') or an alcohol (ROH) or thiol (RSH)).
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- Preparation of 2-, 4-, 5-, and 6-aminonicotinic acid tert-butyl esters
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Procedures are reported to prepare the tert-butyl esters of 2-aminonicotinic acid, 4-aminonicotinic acid, 5-aminonicotinic acid, and 6-aminonicotinic acid from 2-chloronicotinic acid, 4-chloronicotinic acid, 5-bromonicotinic acid, and 6-chloronicotinic acid, respectively, without need for purification of intermediates. Copyright
- Wright, Stephen W.
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experimental part
p. 442 - 445
(2012/06/15)
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- Claisen condensation of N-methylpyrrolidinone and α-chloronicotinic esters
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Reaction between α-halo-nicotinic esters and a nucleophilic source such as the N-methylpyrrolidin-2-one (NMP) gave unexpected results. The presence of the halide on the pyridine gave a very interesting migration reaction. Extension to 6-methylnicotinic ester derivatives lead to an unexpected carbanion condensation.
- Kaminski, Thomas,Kirsch, Gilbert
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p. 229 - 234
(2008/09/19)
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- N-substituted carbamoyloxyalkyl-azolium derivatives
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N-substituted carbamoyloxyalkyl-azolium derivatives which have antifungal activity and are useful for the treatment of fungal diseases.
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Page/Page column 21-22; 34-35
(2010/02/09)
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- Azaanalogues of ebselen as antimicrobial and antiviral agents: Synthesis and properties
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The different analogues of ebselen - unsubstituted benzisoselenazol-3(2H)- one (2a) 2-pyridylbenzisoselenazol-3(2H)-ones (2b-h) and 7-azabenzisoselenazol- 3(2H)-ones (3a-j) were designed as new selenium-containing antiviral and antimicrobial agents and synthesized. Some of them were found in the antiviral assay in vitro to be strong inhibitors of cythopatic activity of herpes simplex virus type 1 - HSV-1 (compounds 2a,b,f,h, 3a-j) and encephalomyocarditis virus - EMCV (compounds 2a,h, 3a-f,k,l). The compounds 2a,h and 3a-e,j were found to have an appreciable activity against Gram-positive bacteria (Staphylococcus aureus and Bacillus) in vitro, some of them inhibited growth of pathogenic yeasts (Candida albicans) (3a,b) and filamentous fungi (3a-e,f).
- Wojtowicz,Kloc,Maliszewska,Mlochowski,Pietka,Piasecki
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p. 863 - 868
(2007/10/03)
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- Synthesis of 7-Azabenzisoselenazol-3(2H)-ones: A New Group of Selenium Containing Antimicrobials
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A convenient, general method for synthesis of various 2-substituted 7-azabenzisoselenazol-3(2H)-ones having pyridine ring condensed with selenazolone moiety is presented. It is based on the conversion of 2-chloronicotinic acid into 2-(chloroseleno)nicotin
- Kloc, Krystian,Maliszewska, Irena,Mlochowski, Jacek
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p. 3805 - 3815
(2007/10/03)
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- Design, synthesis and antifungal activity of a novel water soluble prodrug of antifungal triazole.
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A highly potent water soluble triazole antifungal prodrug, RO0098557 (1), has been identified from its parent, the novel antifungal agent RO0094815 (2). The prodrug includes a triazolium salt linked to an aminocarboxyl moiety, which undergoes enzymatic activation followed by spontaneous chemical degradation to release 2. Prodrug 1 showed high chemical stability and water solubility and exhibited strong antifungal activity against systemic candidiasis and aspergillosis as well as pulmonary aspergillosis in rats.
- Ohwada, Jun,Tsukazaki, Masao,Hayase, Tadakatsu,Oikawa, Nobuhiro,Isshiki, Yoshiaki,Fukuda, Hiroshi,Mizuguchi, Eisaku,Sakaitani, Masahiro,Shiratori, Yasuhiko,Yamazaki, Toshikazu,Ichihara, Shigeyasu,Umeda, Isao,Shimma, Nobuo
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p. 191 - 196
(2007/10/03)
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