122234-46-2Relevant articles and documents
Fluorodibenzocyclooctynes: A Trackable Click Reagent with Enhanced Reactivity
Li, Wei,Zou, Juan,Zhu, Shiyu,Mao, Xianxian,Tian, Hongyan,Wang, Xiaojian
, p. 10328 - 10332 (2019)
Bioorthogonal reactions have widespread applications in biological systems, and development of new bioorthogonal reactions has been of great interest over the past two decades. In this work, the design and synthesis of a family of fluorinated dibenzocyclooctynes (FDIBOs) are reported. The electron-deficient nature of fluorine atoms significantly accelerated the reaction of cyclooctynes in 1,3-dipolar cycloadditions, with either benzyl azide or ethyl diazoacetate, compared to conventional dibenzocyclooctyne (DIBO). In addition, FDIBOs showed unique trackable properties owing to the high NMR sensitivity of the naturally abundant 19F isotope. Biological molecules, including a monosaccharide, a peptide, and a protein, were tested with FDIBOs, and these reactions could be easily monitored by 19F NMR spectroscopy to evaluate the progress of the conjugation reactions. In addition, labeling of live cells was also demonstrated with metabolically modified bacteria to expand the possible applications of FDIBOs.
Antibodies against 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and metabolites thereof
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, (2009/02/10)
The present invention relates to compounds, methods for their preparation, conjugates obtainable by coupling the compounds to immunogenic carriers, pharmaceutical compositions comprising the conjugates, the use of the conjugates for treating and/or preventing disorders associated with tobacco specific nitrosamine exposure, methods for the preparation of the conjugates, antibodies which can be obtained using the conjugates, a method for the preparation of the antibodies and a method of detecting 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), a metabolite or an adduct comprising a pyridyloxobutyl group derived from NNK, wherein the antibodies are employed. The present invention also relates to a method of detecting antibodies specific for NNK, non-detoxified metabolites or the above adducts thereof, wherein the conjugates are employed.
Thiomaleic anhydride: A convenient building block for the synthesis of α-substituted γ- and δ-lactones through free-radical addition, nucleophilic ring opening, and subsequent thiocarboxylate manipulation
Crich, David,Rahaman, Md. Yeajur
supporting information; experimental part, p. 6792 - 6796 (2009/12/31)
(Chemical Equation Presented) Iodoalkyl tert-butyl carbonates and carbamates undergo clean free-radical addition to thiomaleic anhydride to give substituted thiosuccinic anhydrides in high yield on treatment with tris-(trimethylsilyl)silane and a radical initiator. After removal of the tert-butyloxycarbonyl group, cyclization then affords lactones or lactams substituted in the α-position by a thiocarboxylic acid residue. This group is converted to amides through reaction with electron-deficient sulfonamides or to aldehydes and/or ketones by the reaction of derived thioesters with either thiophenol, an electron-deficient allyl phenyl sulfide, or phenylboronic acid.
ALKYLOXY SUBSTITUTED THIAZOLOQUINOLINES AND THIAZOLONAPHTHYRIDINES
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Page/Page column 101, (2008/06/13)
Thiazoloquinolines and thiazolonaphthyridines with an alkoxy substituent at the 6, 7, 8, or 9-position, pharmaceutical compositions containing the compounds, intermediates, methods of making and methods of use of these compounds as immunomodulators, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.
ALKOXY SUBSTITUTED IMIDAZOQUINOLINES
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Page/Page column 87, (2008/06/13)
Imidazoquinoline compounds with an alkoxy substituent at the 6, 7, 8, or 9-position, pharmaceutical compositions containing the compounds, intermediates, methods of making, and methods of use of these compounds as immunomodulators, for inducing or inhibit
Efficient synthesis of protected β-phenylethylamines, enantiomerically pure protected β-phenyl-α-benzylethylamines and β-phenyl-α-isopropylethylamines using organozinc chemistry
Hunter, Christopher,Jackson, Richard F. W.,Rami, Harshad K.
, p. 219 - 223 (2007/10/03)
The β-aminoalkylzinc reagents 9a, 10 and 11 have been efficiently prepared using DMF as a solvent. Palladium-catalysed coupling of these reagents with substituted aryl iodides, under mild and convenient conditions, gives protected β-phenylethylamines 6 in
New Inhibitors of Human Renin That Contain Novel Replacements at the P2 Site
Doherty, Annette M.,Kaltenbronn, James S.,Hudspeth, James P.,Repine, Joseph T.,Roark, William H.,et al.
, p. 1258 - 1271 (2007/10/02)
A series of renin inhibitors with novel modifications at the P2 site has been prepared.Structure-activity relationships reveal that for a particular P2 fragment the in vitro potency is highly dependent on the nature of the P2' portion in addition to the P1-P1' group.The length of the P2 side chain and choice of ε-N P2 substitution have been found to be important for in vitro potency although the degree of unsaturation in the P2 side chain is not particularly significant.Molecular modeling studies have shown that it is possible for the P2 side chain to interact unfavorably with the P2' bi nding site.It has been possible to control the specificity for renin over cathepsin D by correct modification at the P2' and P1-P1' sites.Variations at the P4 site have been utilized to lower the log P values of these renin inhibitors while maintaining high potency.Compound 42, which exhibited an IC50 of 3.70 nM, log P of 2.3, and showed high specificity for renin, was selected for further studies.It was found to be very stable under neutral, acidic, and basic conditions.In simulated intestinal juice, compound 42 had a half-life of 37 min while it was virtually unaffected by simulated gastric juice after 4 h.Compound 42 produced a significant hypotensive response upon intravenous administration to the salt-depleted normotensive cynomolgus monkey.
