- Twofold Radical-Based Synthesis of N, C-Difunctionalized Bicyclo[1.1.1]pentanes
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Bicyclo[1.1.1]pentylamines (BCPAs) are of growing importance to the pharmaceutical industry as sp3-rich bioisosteres of anilines and N-tert-butyl groups. Here we report a facile synthesis of 1,3-disubstituted BCPAs using a twofold radical functionalization strategy. Sulfonamidyl radicals, generated through fragmentation of α-iodoaziridines, undergo initial addition to [1.1.1]propellane to afford iodo-BCPAs; the newly formed C-I bond in these products is then functionalized via a silyl-mediated Giese reaction. This chemistry also translates smoothly to 1,3-disubstituted iodo-BCPs. A wide variety of radical acceptors and iodo-BCPAs are accommodated, providing straightforward access to an array of valuable aniline-like isosteres.
- Anderson, Edward A.,Mousseau, James. J.,Nugent, Jeremy,Owen, Benjamin,Pickford, Helena D.,Smith, Russell C.
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supporting information
p. 9729 - 9736
(2021/07/19)
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- MACROCYCLIC COMPOUNDS AND THEIR USE IN THE TREATMENT OF DISEASE
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The invention relates to heterocyclic compounds of the formula (I), in which all of the variables are as defined in the specification; capable of modulating the activity of CFTR. The invention further provides a method for manufacturing compounds of the invention, and its therapeutic uses. The invention further provides methods to their preparation, to their medical use, in particular to their use in the treatment and management of diseases or disorders including Cystic fibrosis and related disorders.
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Page/Page column 65
(2020/07/14)
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- Consecutive Aminolithiation-Carbolithiation of a Linear Aminoalkene Bearing Terminal Vinyl Sulfide Moiety to Give Hydro-indolizine
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Aminolithiation-carbolithiation tandem cyclization of an aminoalkene bearing vinyl sulfide moiety proceeded smoothly using stoichiometric amounts of BuLi. Both aminolithiation and carbo-lithiation were in equilibrium at room temperature, and the stereoche
- Yamamoto, Yasutomo,Yamaguchi, Tatsuya,Kaneshige, Atsunori,Hashimoto, Aiko,Kaibe, Sachiho,Miyawaki, Akari,Yamada, Ken-Ichi,Tomioka, Kiyoshi
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supporting information
p. 2913 - 2917
(2017/12/14)
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- DIAZABICYCLO[4.3.1]DECANE DERIVATIVES FOR TREATMENT OF PSYCHIATRIC DISORDERS
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The present invention relates to diazabicyclo[4.3.1]decane derivatives, pharmaceutically acceptable salts of these compounds and pharmaceutical compositions containing at least one of these compounds together with pharmaceutically acceptable carrier, excipient and/or diluents. Said diazabicyclo[4.3.1]decane derivatives can be used for prophylaxis and/or treatment of psychiatric disorders and neurodegenerative diseases, disorders and conditions.
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Paragraph 0143-0147
(2017/01/23)
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- An Enantioselective Cascade Cyclopropanation Reaction Catalyzed by Rhodium(I): Asymmetric Synthesis of Vinylcyclopropanes
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N-Tosylhydrazone-yne-ene substrates are satisfactorily prepared and their cyclization under rhodium catalysis is evaluated. A cascade process involving rhodium vinyl carbene formation – through carbene/alkyne metathesis – and cyclopropanation has been dev
- Torres, òscar,Roglans, Anna,Pla-Quintana, Anna
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supporting information
p. 3512 - 3516
(2016/11/25)
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- DIAZABICYCLO[4.3.1]DECANE DERIVATIVES FOR TREATMENT OF PSYCHIATRIC DISORDERS
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The present invention relates to diazabicyclo[4.3.1 ]decane derivatives (I), pharmaceutically acceptable salts of these compounds and pharmaceutical compositions containing at least one of these compounds together with pharmaceutically acceptable carrier, excipient and/or diluents. Said diazabicyclo[4.3.1]decane derivatives are specific inhibitors of the FK506 binding proteins (FKBP's) and can be used for prophylaxis and/or treatment of psychiatric disorders and neurodegenerative diseases, disorders and conditions.
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Page/Page column 72; 73
(2015/08/06)
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- Diazabicyclo[4.3.1]decane derivatives for treatment of psychiatric disorders
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The present invention relates to diazabicyclo[4.3.1]decane derivatives of formula (I), pharmaceutically acceptable salts of these compounds and pharmaceutical compositions containing at least one of these compounds together with pharmaceutically acceptable carrier, excipient and/or diluents. Said diazabicyclo[4.3.1]decane derivatives are inhibitors of the FK506 binding protein (FKBP's) and can be used for prophylaxis and/or treatment of psychiatric disorders and neurodegenerative diseases, disorders and conditions.
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Paragraph 0097; 0098
(2015/08/06)
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- Chemoselective hydrogenation reaction of unsaturated bonds in the presence of an o-nitrobenzenesulfonyl group
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Chemoselective hydrogenation of unsaturated compounds bearing an o-nitrobenzenesulfonyl (Ns)-amide moiety, affording the corresponding saturated compounds, was accomplished efficiently without loss of the nitro group by using the Pd/MS3A catalyst and a H2 balloon. Partial hydrogenation of alkynes bearing an Ns group to corresponding cis alkenes was achieved with the combination of the Pd/BN catalyst and an additive (diethylenetriamine or acetic acid).
- Kawanishi, Akinori,Miyamoto, Chiyako,Yabe, Yuki,Inai, Makoto,Asakawa, Tomohiro,Hamashima, Yoshitaka,Sajiki, Hironao,Kan, Toshiyuki
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p. 1306 - 1309
(2013/05/09)
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- Effect of added salt on ring-closing metathesis catalyzed by a water-soluble hoveyda-grubbs type complex to form N-containing heterocycles in aqueous media
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The efficiency of ring-closing metathesis catalyzed by a Hoveyda-Grubbs type catalyst in water can be enhanced by addition of a chloride salt under neutral conditions. UV-vis spectroscopic study showed that a characteristic band of the catalyst around 380 nm remained over 16 h in the presence of KCl, whereas the band distinctly decreased in the absence of KCl. The disappearance of the band is ascribed to a displacement of a chloride ligand by a water molecule or a hydroxide anion. The spectral changes can be related to the metathesis activity. The experimental results indicate that avoidance of the chloride ligand loss is important to maintain the metathesis activity in water.
- Matsuo, Takashi,Yoshida, Takefumi,Fujii, Akira,Kawahara, Keiya,Hirota, Shun
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p. 5313 - 5319
(2013/11/06)
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- Regioselectivity in the intramolecular heck reaction of a series of cyclic sulfonamides: An experimental and computational study
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Regioselectivity in the intramolecular Heck reaction of a series of N-sulfonyl-2,5-dihydro-3-substituted pyrroles was studied. These substrates are unbiased in terms of the formed ring size of the new heterocycle. Results indicate that high levels of regi
- Geoghegan, Kimberly,Evans, Paul,Rozas, Isabel,Alkorta, Ibon
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supporting information
p. 13379 - 13387
(2012/11/07)
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- FUROPYRIDINE COMPOUNDS AND USES THEREOF
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The present invention provides a compound of formula (I); a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.
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Page/Page column 179-180
(2011/11/06)
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- Design and synthesis of all diastereomers of cyclic pseudo-dipeptides as mimics of cyclic CXCR4 pentapeptide antagonists
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The four diastereomers of 2,5-bis[(3-guanidino)propyl]-1-[3-(4- hydroxyphenyl)propionyl]-7-(2-naphthylacetyl)-1,4,7-triazacycloundec-9-en-3-one (54-57) and of 2,5-bis[(3-guanidino)propyl]-1-(4-hydroxyphenylacetyl)-7-(2- naphthylacetyl)-1,4,7-triazacycloundec-9-en-3-one (58-61) were synthesized by a divergent methodology from l- and d-glutamic acids. The 11-membered ring core was made by ring closing metathesis of linear bis(allylamines), and the guanidyl functions were introduced by a simultaneous double Mitsunobu reaction using bis(Boc)guanidine. These compounds were designed to mimic cyclic pentapeptide FC131 (c[Gly-d-Tyr-Arg-Arg-Nal]). The Royal Society of Chemistry.
- Cluzeau, Jerome,Oishi, Shinya,Ohno, Hiroaki,Wang, Zixuan,Evans, Barry,Peiper, Stephen C.,Fujii, Nobutaka
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p. 1915 - 1923
(2008/02/10)
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- Gold(l)-catalyzed cascade cyclization reaction: Highly regio- and diastereoselective intermodular addition of water and alcohols to epoxy alkynes
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We have developed a novel access to ketal skeletons through a highly regio- and diastereoselective intermolecular addition of water and alcohols to alkynyl epoxides catalyzed by goid(l). This procedure involves a domino three-membered ring-opening, 6-exo-
- Dai, Lun-Zhi,Qi, Ming-Juan,Shi, Yong-Ling,Liu, Xu-Guang,Shi, Min
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p. 3191 - 3194
(2008/02/11)
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- BICYCLIC PIPERAZINE COMPOUND AND USE THEREOF
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The present invention provides a compound represented by the formula: wherein R1 is an acyl group, R2 is a hydrocarbon group which may be substituted or the like, R3 is a hydrocarbon group which may be substituted or the like, R4 is a hydrocarbon group which may be substituted or the like, n is from 0 to 4, and X is an oxygen atom, a sulfur atom or the like, or a salt thereof. The invention also provides a compound which has a TGR23 antagonist activity and thus is useful for prevention and treatment of cancer.
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Page/Page column 53
(2010/11/08)
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- Iododediazoniation of Arenediazonium Salts Accompanied by Aryl Radical Ring Closure
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Treatment of o-(allyloxy)benzenediazonium tetrafluoroborate (1a) with sodium iodide in acetone affords the cyclized iodide 2a in good yield by a mechanism involving the generation and exo cyclization of the aryl radical 6a.Other diazonium salts (1b-i) containing suitable unsaturated side chains behave similarly, but those (1l,1m) in which there is an N-allylsulfonamido group yield mainly products formed by endo cyclization.The diazonium salts 1j and 1k do not give cyclized products.Factors affecting the mechanism, rates, and regiochemistry of the reaction are discussed.
- Beckwith, Athelstan L. J.,Meijs, Gordon F.
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p. 1922 - 1930
(2007/10/02)
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