37073-15-7Relevant articles and documents
Multikilogram Synthesis of a Potent Dual Bcl-2/Bcl-xL Antagonist. 2. Manufacture of the 1,3-Diamine Moiety and Improvement of the Final Coupling Reaction
Hardouin, Christophe,Baillard, Sandrine,Barière, Fran?ois,Craquelin, Anthony,Grandjean, Mathieu,Janvier, Solenn,Le Roux, Stéphane,Penloup, Christine,Russo, Olivier
, p. 670 - 685 (2019/12/24)
This paper describes the synthesis of kilogram quantities of the sulfonamide moiety 3 involved in a coupling reaction with acid moiety 2 to provide batches of drug candidate 1 for preclinical studies and first-in-human clinical trials. A first approach relying on a chiral separation furnished the desired enantiomer of 1,3-diamine 20, precursor of sulfonamide 3. An enantiomeric synthesis of 20 using the Ellman's chiral auxiliary coupled with an aza-Reformatsky reaction to control the stereochemistry is also discussed. Coupling conditions of the final step involving EDCI to provide 1 under a cGMP process are detailed. An alternative approach using N-(1-methanesulfonyl)benzotriazole is also presented.
DOPAMINE D3 RECEPTOR ANTAGONISTS COMPOUNDS
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Page/Page column 108, (2016/05/19)
The disclosure is directed to novel dopamine D3 receptor antagonists, processes for their preparation, intermediates used in these processes, pharmaceutical compositions containing them and their use in therapy, including treating drug dependency and psychosis.
Iodine-catalyzed N-sulfonylation of benzotriazoles with sodium sulfinates under mild conditions
Wu, Si-Xue,Zhang, Yi-Kun,Shi, Hong-Wei,Yan, Jie
, p. 1519 - 1522 (2016/09/23)
A new and convenient procedure is developed for the preparation of N-sulfonylbenzotriazoles from sodium sulfinates and benzotriazoles using molecular iodine as catalyst via the S[sbnd]N bond formation reaction. This catalytic radical sulfonylation proceed
Convenient sulfonylation of benzotriazoles with the in situ–generated sulfonyl bromides
Wu, Sixue,Zhang, Yikun,Yan, Jie
supporting information, p. 1432 - 1437 (2016/09/14)
A convenient procedure is developed for the preparation of N-sulfonylbenzotriazoles from sodium sulfinates, benzotriazoles, and sodium bromide in the present of m-chloroperbenzoic acid as oxidant. This radical sulfonylation proceeds efficiently at room te
ENZYME INHIBITORS
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Paragraph 0199, (2014/07/08)
The present subject matter relates generally to compounds having the formula (I): wherein each of X, Y, R1, R2, R3, R4, and n are as defined herein. Compounds of formula (I) may act as inhibitors of the thioredoxin reductase enzyme system. The subject matter also relates to use, formulation and preparation of the compounds. The compounds may be useful in the treatment of inflammatory and oxidative diseases and conditions. The compounds may also provide useful anti-proliferative and anti- apoptotic effects.
Feruloylbenzotriazole and weinreb amide as bioinspired building blocks: A reactivity study towards O-, N-, S-, and C-nucleophiles
Roman, Bart I.,Monbaliu, Jean-Christophe,De Coen, Laurens M.,Verhasselt, Sigrid,Schuddinck, Bart,Van Hoeylandt, Evelien,Stevens, Christian V.
, p. 2594 - 2611 (2014/05/06)
A versatile route for the conversion of ferulic acid into biologically relevant molecules is presented. The compatibility of a number of protection and activation strategies with the 1,2-addition of a variety of O-, N-, S-, and C-nucleophiles to ferulic acid is evaluated. In particular, this report contains the first systematic study of the addition of (hetero)aryllithium reagents to 3-phenylpropenoyl Weinreb amides. The relevance of this "bioinspired" method is illustrated by the synthesis of a number of natural products or analogues, such as zingerone, curcuminoids, and (heteroaryl) chalcones. Feruloylbenzotriazole and Weinreb amide were converted into an array of biologically relevant molecules by addition of O-, N-, S-, and C-nucleophiles. The relevance of this bioinspired approach is illustrated by the synthesis of a number of natural products or analogues, such as zingerone, (heteroaryl) chalcones, and curcuminoids. Copyright
C5, C6 OXACYCLIC-FUSED IMINOTHIAZINE DIOXIDE COMPOUNDS AS BACE INHIBITORS
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Page/Page column 70, (2014/07/08)
In its many embodiments, the present invention provides certain C2-ring-substituted iminothiazine compounds, including compounds Formula (I): (structurally represented) or a tautomers thereof, and pharmaceutically acceptable salts of said compounds and, w
Syntheses and reactivities of non-symmetrical "active ester" bi-dentate cross-linking reagents having a phthalimidoyl and acid chloride, 2-benzothiazole, or 1-benzotriazole group
Sheikh, Md. Chanmiya,Takagi, Shunsuke,Sakai, Mebumi,Mori, Tasuya,Hayashi, Naoto,Fujie, Tetsuo,Ono, Shin,Yoshimura, Toshiaki,Morita, Hiroyuki
supporting information; experimental part, p. 1244 - 1254 (2011/04/15)
We have newly synthesized the non-symmetrical "phthalimidoyl active ester" bi-dentate cross-linking reagents having an acid chloride, 2-benzothiazole, or 1-benzotriazole group (i.e., 9, 15, and 16) on the basis of the reactivity study of the "active ester" model compounds, 11-14, toward the various nucleophiles and examined their reaction selectivity towards the same nucleophiles. Then, we applied for the modification of cholesterol at the more reactive site of the bi-dentate linkers to give 3β-cholesteryl 4-(phthalimidoyloxycarbonyl)butyrate (39), and the subsequent reaction of 39 with several amines, such as benzylamine, 4-chlorobenzylamine, 2-phenylethylamine, l-phenylalanine methyl ester, or diphenylalanine benzyl ester as a protein model of the cholesterol antigen.
Regioselective addition of thiophenol to α,β-unsaturated N-acylbenzotriazoles
Xia, Ziming,Lv, Xin,Wang, Wencun,Wang, Xiaoxia
supporting information; experimental part, p. 4906 - 4910 (2011/10/07)
Regioselective addition of thiophenol to α,β-unsaturated N-acylbenzotriazoles has been achieved by controlling the conditions. Thus, three types of products, namely α,β-unsaturated thioesters, β-thiophenoxy substituted N-acylbenzotriazoles, and β-thiophenoxy substituted thioesters were selectively obtained in good to excellent yields.
Enantioselective organocatalytic approach to the synthesis of α,α-disubstituted cyanosulfones
Cid, M. Belén,López-Cantarero, Jesús,Duce, Sara,Ruano, José Luis García
supporting information; experimental part, p. 431 - 434 (2009/04/10)
(Chemical Equation Presented) Optically pure cyano tert-alkyl sulfones have been obtained by organocatalytic enantioselective Michael addition of α-substituted cyanosulfones to vinyl ketones using cinchona alkaloids as catalysts. The best results were obt