68452-41-5Relevant articles and documents
CHEMOSELECTIVE SENSITIVITY BOOSTER FOR TAGGING A PEPTIDE, PEPTIDE CONJUGATE, OR SIMILAR REACTIVE MOLECULE
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Page/Page column 24; 25, (2020/12/29)
The invention pertains to chemoselective sensitivity booster for tagging a peptide, peptide conjugate, or similar reactive molecule for analysis of a peptide, protein, antibody, protein bioconjugate, antibody bioconjugate, and similar analytes. The sensitivity booster comprises of sp2 or sp3 nitrogen centers in combination with hydrophobic carbon chains linked with an electrophile or nucleophile for attachment with a peptide, peptide conjugate, or molecules with similar reactivity.
Sensitivity booster for mass detection enables unambiguous analysis of peptides, proteins, antibodies, and protein bioconjugates
Singudas, Rohith,Reddy, Neelesh C.,Rai, Vishal
supporting information, p. 9979 - 9982 (2019/08/22)
A chemical tag enhances peptide detection by multiple orders in mass spectrometry. The substantial improvement in the peptide mapping along with simplified and enhanced fragmentation pattern enables the unambiguous sequencing of a protein and antibody. The chemoselective sensitivity booster provides a tool for remarkably improved analysis of protein bioconjugates.
N-Propargylation of secondary amines directly using calcium carbide as an acetylene source
Fu, Rugang,Li, Zheng
, p. 341 - 345 (2017/06/19)
A one-pot N-propargylation of secondary amines has been achieved by heating the amine with formaldehyde and calcium carbide in DMSO in the presence of CuCl as a catalyst. Fifteen examples of propargylic tertiary amines, 12 of which are novel, were efficiently prepared in yields of 65-84%. The advantages of the method are broad substrate scope and a simple work-up procedure.
Synthesis of novel triazole-linked mefloquine derivatives: Biological evaluation against Plasmodium falciparum
Hamann, Anton R.,De Kock, Carmen,Smith, Peter J.,Van Otterlo, Willem A.L.,Blackie, Margaret A.L.
supporting information, p. 5466 - 5469 (2015/01/08)
Using 2,8-bis(trifluoromethyl)quinoline, the pharmacophore of mefloquine, as scaffold, eleven novel triazole-linked compounds have been synthesised by the application of CuAAC chemistry. The in vitro biological activity of the compounds on the Plasmodium falciparum chloroquine-sensitive strain NF54 was then determined. The compounds all showed IC50s in the lower μM range with (1R,3S,5R)-N-{[1-(2,8-bis(trifluoromethyl)quinoline-4-yl)-1H-1,2,3-triazol-4-yl]methyl}adamantan-2-amine (29) exhibiting the best activity of 1.00 μM.
A 1,3-amino group migration route to form acrylamidines
Chauhan, Dinesh Pratapsinh,Varma, Sreejith Jayasree,Vijeta, Arjun,Banerjee, Pallavi,Talukdar, Pinaki
supporting information, p. 323 - 325 (2014/01/06)
A novel 1,3-amino group migration strategy for the synthesis of acrylamidines is presented. Cu(i) catalyzed reaction of N,N-disubstituted propargylamine with tosylazide generates a highly reactive ketenimine intermediate which is trapped by a tethered amino group leading to the rearrangement reaction.
Copper(I)-catalysed deacetylenative cross-coupling reaction of terminal alkynes with propargylic amines via C(sp)-C(sp3) bond cleavage
Kim, Yongeun,Nakamura, Hiroyuki
supporting information; experimental part, p. 1686 - 1690 (2012/07/17)
The catalytic deacetylenative coupling reaction of terminal alkynes with various N-substituted propargylic amines proceeded in the presence of CuCl (10 mol%) and NaPO(4 equiv) in THF at 130 °C to give the corresponding substituted propargylic amines in go
Influence of the acetylenic substituent on the intramolecular carbolithiation of alkynes
Girard, Anne-Lise,Lhermet, Rudy,Fressigne, Catherine,Durandetti, Muriel,Maddaluno, Jacques
scheme or table, p. 2895 - 2905 (2012/06/29)
The intramolecular carbolithiation of a series of propargylic ethers has been performed to evaluate the influence of the terminal substituent on the efficiency and the stereochemical outcome of the cyclization. Our results show that only 5-exo-dig cyclizations are observed, and dihydrobenzofurans are obtained exclusively. Depending on the nature of the terminal substituent, two cases can be considered. If the terminal substituent carried by the acetylenic carbon atom is itself a carbon atom, the cyclization can occur provided the terminal propargylic position bears a coordinating element and is at least disubstituted. When the cyclization occurs, it follows an anti-carbolithiation pathway and thus leads to the E isomer of the exocyclic double bond. Only in one case (Ph) was a mixture of the E and Z isomers of the resulting olefin recovered. The cyclization can also take place if the alkyne is directly substituted by S or Si, provided the cyclization conditions are tuned. In the case of the trimethylsilyl substituent, a syn-carbolithiation was observed. If the double bond is recovered, in most cases, in the exocyclic position, the products can aromatize directly for SPh-substituted substrate 24. Furthermore, in the two latter cases, when alkylation of the vinyllithium intermediate is performed, isomerization of the double bond seems instantaneous. Copyright
Copper(I)-catalyzed substitution reactions of propargylic amines: Importance of C(sp)-C(sp3) bond cleavage in generation of iminium intermediates
Sugiishi, Tsuyuka,Kimura, Akifumi,Nakamura, Hiroyuki
supporting information; experimental part, p. 5332 - 5333 (2010/07/04)
Substitution reactions of propargylic amines proceed in the presence of copper(I) catalysts. Mechanistic studies showed that C(sp)?C(sp3) bond cleavage assisted by nitrogen lone-pair electrons is essential for the reaction, and the resulting iminium intermediates undergo amine exchange, aldehyde exchange, and alkyne addition reactions. Because iminium intermediates are key to aldehyde?alkyne?amine (A3) coupling reactions, this transformation is effective not only for reconstruction of propargylic amines but also for chiral induction of racemic compounds in the presence of chiral catalysts.
4 ( 1H) -PYRIDINONE DERIVATIVES AND THEIR USE AS ANTIMALARIA AGENTS
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Page/Page column 39, (2010/08/08)
4-pyridone (4-pyridinone) derivatives of Formula (I) and pharmaceutically acceptable derivatives thereof, processes for their preparation, pharmaceutical formulations thereof and their use in chemotherapy of certain parasitic infections such as malaria, are provided.
A gallium-catalyzed cycloisomerization/Friedel-Crafts tandem
Li, Hui-Jing,Guillot, Regis,Gandon, Vincent
supporting information; experimental part, p. 8435 - 8449 (2011/03/19)
Under noble (Au, Pt, Ru) and group 13 (Ga, In) metals catalysis, 1,6-arenynes rearrange to give 1,2-dihydronaphthalenes in a high yielding, regiocontrolled fashion. When the reaction is carried out in the presence of electron-rich arenes (anisole, phenol, indole derivatives), Friedel-Crafts addition may follow the cycloisomerization step. Only GaX3 salts proved able to catalyze these two C-C bond formation events. This specificity of gallium has been exploited for the synthesis of valuable polycyclic compounds that would be very difficult to prepare otherwise. For instance, tetrahydroisoquinolines and tetrahydrobenzoazepines have been obtained by selective 6-exo-dig or 7-endo-dig cyclization of N-tethered 1,6-arenynes. DFT calculations were carried out to shed light on the mechanism and provide a rationale for this regiodivergency. Computations also reveal the fundamental role of the tether in the stabilization of carbocationic species. Differential reactivities of other types of substrates in gallium- and gold-catalyzed cascades are also exposed, showing that the two approaches are complementary. In particular, bimolecular Friedel-Crafts additions are facilitated under gallium catalysis.
