Synthesis and Reactions of 2-[1-Methyl-1-(pyrrolidin-2-yl)ethyl]-1H-pyrrole and Some Derivatives with Aldehydes: Chiral Structures Combining a Secondary-Amine Group with an 1H-Pyrrole Moiety as Excellent H-Bond Donor

2012 ◽  
Vol 95 (11) ◽  
pp. 2249-2264 ◽  
Author(s):  
Anca Pordea ◽  
Helen Stoeckli-Evans ◽  
Claudio Dalvit ◽  
Reinhard Neier
Keyword(s):  
Secondary Amine ◽  
Amine Group ◽  
Secondary Amine Group ◽  
Chiral Structures

ChemInform Abstract: Novel Syntheses of Monofunctionalized Triaza-Crowns and Cyclams with a Secondary Amine Group on a Side Chain.

ChemInform ◽  
1990 ◽  
Vol 21 (4) ◽  
Author(s):  
K. E. KRAKOWIAK ◽  
J. S. BRADSHAW ◽  
N. K. DALLEY ◽  
W. JIANG ◽  
R. M. IZATT
Keyword(s):  
Secondary Amine ◽  
Side Chain ◽  
Amine Group ◽  
Secondary Amine Group

Novel syntheses of monofunctionalized triaza-crowns and cyclams with a secondary amine group on a side chain

1989 ◽  
Vol 30 (22) ◽  
pp. 2897-2900 ◽  
Author(s):  
Krzysztof E. Krakowiak ◽  
Jerald S. Bradshaw ◽  
N.Kent Dalley ◽  
Weiming Jiang ◽  
Reed M. Izatt
Keyword(s):  
Secondary Amine ◽  
Side Chain ◽  
Amine Group ◽  
Secondary Amine Group

scholarly journals Development of high-affinity ligands and photoaffinity labels for the d-fructose transporter GLUT5

2002 ◽  
Vol 367 (2) ◽  
pp. 533-539 ◽  
Author(s):  
Jing YANG ◽  
James DOWDEN ◽  
Arnaud TATIBOUËT ◽  
Yasumaru HATANAKA ◽  
Geoffrey D. HOLMAN
Keyword(s):  
Secondary Amine ◽  
Chinese Hamster Ovary Cells ◽  
Chinese Hamster ◽  
Amine Group ◽  
Ovary Cells ◽  
Affinity Ligands ◽  
High Affinity ◽  
Ring Form ◽  
Secondary Amine Group ◽  
Specific Uptake

The GLUT5 transporter catalyses the specific uptake of d-fructose and can accept this hexose in its furanose and pyranose ring forms. The transporter does not accept fructose epimers and has very limited tolerance of bulky groups substituted at the 2-, 3-, 4- and 5-OH positions [Tatibouët, Yang, Morin and Holman (2000) Bioorg. Med. Chem. 8, 1825—1833]. To further explore whether bulky groups can be tolerated at the primary OH positions, a d-fructose analogue with an allylamine group substitution to replace the 1-OH group was synthesized and was found to be quite well tolerated (Ki = 27.1mM). However, this analogue occurs in multiple ring forms. By contrast, 2,5-anhydro-d-mannitol is a symmetrical molecule that occurs only in a furanose ring form in which C-1 and C-6 are equivalent. We have therefore synthesized new 2,5-anhydro-d-mannitol analogues (substituted at the equivalent of the 6-OH of d-fructose) and from studies in Chinese hamster ovary cells expressing GLUT5 cells report that (i) the allylamine derivative of 2,5-anhydro-d-mannitol is well tolerated (Ki = 2.66mM); (ii) introduction of a di-nitrophenyl-substituted secondary amine group enhances affinity (Ki = 0.56mM); (iii) introduction of amide-linked biotinylated photolabel moieties is possible without loss of affinity relative to 2,5-anhydro-d-mannitol but a small secondary amine spacer between the biotinylated photolabelling moiety and the fructofuranose ring increases affinity (fructose photolabel 2; Ki = 1.16mM); (iv) introduction of a hydrophilic tartarate spacer between biotin and the diazirine photoreactive groups can be accomplished without reduction in affinity and (v) photoactivation of biotinylated fructose photolabels leads to specific biotin tagging of GLUT5. These data suggest that substitution of a secondary amine group (-NH) to replace the C-6 (or C-1) -OH of 2,5-anhydro-d-mannitol results in compounds of high affinity; the affinity is enhanced over 10-fold compared with d-fructose.

Synthesis of Indolo[1,2-a]quinoxalinones through Palladium/Copper-Cocatalyzed Oxidative Isocyanide-Insertion Cyclization of Indoles and Hydrolysis of Enamines

Synlett ◽  
2020 ◽  
Author(s):  
Xuan Sha ◽  
Jie Ren ◽  
Fei Ji ◽  
Yi-ran Hu ◽  
Yun-yi Zhao ◽  
...  
Keyword(s):  
Acid Medium ◽  
Secondary Amine ◽  
Amine Group ◽  
Secondary Amine Group ◽  
Hydrolysis Of ◽  
Co Gas

AbstractA novel Pd/Cu-cocatalyzed isocyanide-insertion cyclization of indoles and hydrolysis of enamines has been developed for the construction of indolo[1,2-a]quinoxalinones. A secondary amine group on the N-phenylindole skeleton acts as an important directing groups that participates in activation of the C(2)-position of the indole and the subsequent isocyanide-insertion cyclization. The fragile generated enamine bond is easily hydrolyzed by the acid medium to give the corresponding quinoxalinone skeleton. This regioselective and high-yielding transformation, which avoids the use of hazardous CO gas, might be extendable to syntheses of natural polycyclic products.

Characterization of the Minor cis Isomer of a Dipendant Polyamino Acid Macrocycle as a Dimeric Nickel(II) Complex

2000 ◽  
Vol 53 (6) ◽  
pp. 517 ◽  
Author(s):  
Eric N. Wilkes ◽  
Trevor W. Hambley ◽  
Geoffrey A. Lawrance ◽  
Marcel Maeder
Keyword(s):  
Secondary Amine ◽  
Nickel Atom ◽  
Crystal Structure Analysis ◽  
Amine Group ◽  
X Ray ◽  
Polyamino Acid ◽  
Secondary Amine Group ◽  
Amine Groups ◽  
Cis Isomer

The dipendant-arm polyamino acid macrocycle 13-amino-13-methyl-1,4,8,11-tetraazacyclotetradecane-6-carboxylate (acammac), characterized earlier as the major trans isomer (3), has been isolated as the minor cis isomer (4) by crystallization as the [Ni(4)](ClO4) complex. The complex has been examined by an X-ray crystal structure analysis, and the cation exists as a dimer with each carboxylate group bound both to its ‘parent’ nickel atom and bridging to the adjacent nickel atom. The macrocycle adopts a folded geometry, each nickel atom appearing as a cis-NiN4O2 chromophore. The pendant primary amine group and three of the four secondary amine groups are also coordinated, whereas the fourth secondary amine group is not coordinated but stabilized by a proton bridging within a superbase between the uncoordinated amine and one of the coordinated amines.

Infrared spectra of the interactions of aniline and porous glass surfaces

1969 ◽  
Vol 47 (8) ◽  
pp. 1281-1287 ◽  
Author(s):  
M. J. D. Low ◽  
V. V. Subba Rao
Keyword(s):  
Nitrogen Atom ◽  
Aromatic Ring ◽  
Secondary Amine ◽  
Infrared Spectra ◽  
Porous Glass ◽  
Weak Interactions ◽  
Amine Group ◽  
Oh Groups ◽  
Glass Surfaces ◽  
Adsorption And Dissociation

Infrared spectra were recorded of aniline sorbed on highly dehydroxylated, deuterated, and on fluoridated porous glass as well as on pure and boria-impregnated silica. The results suggest that two types of weak interactions involving the surface SiOH and B—OH groups occurred; the nitrogen atom of the amine was hydrogen bonded to surface OH and there was an interaction between OH groups and the π system of the aromatic ring. Some aniline chemisorbed on surface boron via the nitrogen atom of the amine group. Some aniline chemisorbed dissociatively to form secondary amine structures bonded through the nitrogen to surface boron atoms and new B—OH groups formed. Surface boron impurity acted as an adsorption and dissociation center.

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