- Deconstructive Oxygenation of Unstrained Cycloalkanamines
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A deconstructive oxygenation of unstrained primary cycloalkanamines has been developed for the first time using an auto-oxidative aromatization promoted C(sp3)?C(sp3) bond cleavage strategy. This metal-free method involves the substitution reaction of cycloalkanamines with hydrazonyl chlorides and subsequent auto-oxidative annulation to in situ generate pre-aromatics, followed by N-radical-promoted ring-opening and further oxygenation by 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) and m-cholorperoxybenzoic acid (mCPBA). Consequently, a series of 1,2,4-triazole-containing acyclic carbonyl compounds were efficiently produced. This protocol features a one-pot operation, mild reaction conditions, high regioselectivity and ring-opening efficiency, broad substrate scope, and is compatible with alkaloids, osamines, and peptides, as well as steroids.
- Han, Bing,He, Yi-Heng,Pan, Jia-Hao,Wang, Yuan-Rui,Yu, Wei,Zhang, Jian-Wu
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supporting information
p. 3900 - 3904
(2020/02/11)
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- Substituent effects on chiral resolutions of derivatized 1-phenylalkylamines by heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin GC stationary phase
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Chiral resolutions of trifluoroacetyl-derivatized 1-phenylalkylamines with different type and position of substituent were investigated by capillary gas chromatography by using heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin diluted in OV-1701 as a chiral stationary phase. The influence of column temperature on retention and enantioselectivity was examined. All enantiomers of meta-substituted analytes as well as fluoro-substituted analytes could be resolved. Temperature had a favorable influence on enantioselectivity for small amines with substituents at the ortho-position. The type of substituent at the stereogenic center of amines also had a crucial effect as the ethyl group led to poor enantioseparation. Among all analytes studied, trifluoroacetyl-derivatized 1-(2′-fluorophenyl)ethylamine exhibited baseline resolution with the shortest analysis time.
- Issaraseriruk, Natthapol,Sritana-anant, Yongsak,Shitangkoon, Aroonsiri
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supporting information
p. 900 - 906
(2018/05/08)
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- HETEROCYCLIC AMIDE DERIVATIVES AS P2X7 RECEPTOR ANTAGONISTS
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The invention relates to heterocyclic amide derivatives of formula (I), wherein R1, R2, R3, X and n are as defined in the description, their preparation and their use as pharmaceutically active compounds.
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Paragraph 0361; 0362; 0396
(2015/02/18)
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- HETEROCYCLIC AMIDE DERIVATIVES AS P2X7 RECEPTOR ANTAGONISTS
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The invention relates to heterocyclic amide derivatives of formula (I), wherein R1, R2, R3, X and n are as defined in the description, their preparation and their use as pharmaceutically active compounds.
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Page/Page column 64
(2013/07/31)
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- (FUSED RING ARYLAMINO AND HETEROCYCLYLAMINO) PYRIMIDYNYL AND 1,3,5-TRIAZINYL BENZIMIDAZOLES, PHARMACEUTICAL COMPOSITIONS THEREOF, AND THEIR USE IN TREATING PROLIFERATIVE DISEASES
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Provided herein are (fused ring arylamino and heterocyclylamino) pyrimidinyl and 1,3,5-triazinyl benzimidazoles, e.g., a compound of Formula (I), and their pharmaceutical compositions, preparation, and use as agents or drugs for treating proliferative diseases.
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Page/Page column 78
(2012/10/18)
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- QUINAZOLINONE DERIVATIVES AS VIRAL POLYMERASE INHIBITORS
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Compounds of formula I: (I) wherein X, R2, R3, R5 and R6 are defined herein, are useful as inhibitors of the hepatitis C virus NS5B polymerase.
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Page/Page column 102
(2011/04/19)
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- Identification of (R)-1-(5-tert-butyl-2,3-dihydro-1H-inden-1-yl)-3-(1H- indazol-4-yl)urea (ABT-102) as a potent TRPV1 antagonist for pain management
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Vanilloid receptor TRPV1 is a cation channel that can be activated by a wide range of noxious stimuli, including capsaicin, acid, and heat. Blockade of TRPV1 activation by selective antagonists is under investigation by several pharmaceutical companies in an effort to identify novel agents for pain management. Here we report that replacement of substituted benzyl groups by an indan rigid moiety in a previously described N-indazole-N′-benzyl urea series led to a number of TRPV1 antagonists with significantly increased in vitro potency and enhanced drug-like properties. Extensive evaluation of pharmacological, pharmacokinetic, and toxicological properties of synthesized analogs resulted in identification of (R)-7 (ABT-102). Both the analgesic activity and drug-like properties of (R)-7 support its advancement into clinical pain trials.
- Gomtsyan, Arthur,Bayburt, Erol K.,Schmidt, Robert G.,Surowy, Carol S.,Honore, Prisca,Marsh, Kennan C.,Hannick, Steven M.,McDonald, Heath A.,Wetter, Jill M.,Sullivan, James P.,Jarvis, Michael F.,Faltynek, Connie R.,Lee, Chih-Hung
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p. 392 - 395
(2008/09/17)
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- SUBSTITUTED FLUOROETHYL UREAS AS ALPHA 2 ADRENERGIC AGENTS
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Therapeutic compounds, and methods, compositions, and medicaments related thereto are disclosed herein.
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Page/Page column 17
(2008/12/04)
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- NOVEL 2-AMINO BENZIMIDAZOLE DERIVATIVES AND THEIR USE AS MODULATORS OF SMALL-CONDUCTANCE CALCIUM-ACTIVATED POTASSIUM CHANNELS
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This invention relates to novel 2-amino benzimidazole derivatives useful as modulators of small-conductance calcium-activated potassium channels (SK channels). In other aspects the invention relates to the use of these compounds in a method for therapy an
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Page/Page column 20
(2008/06/13)
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