The synthesis of 3(5)-[(2-hydroxyethoxy)methyl]pyrazole-5(3)-carboxamide, an acyclic analog of 4-deoxypyrazofurin

1990 ◽  
Vol 55 (20) ◽  
pp. 5535-5538 ◽  
Author(s):  
Daryl R. Sauer ◽  
Stewart W. Schneller
Keyword(s):  
Acyclic Analog

Synthesis and biological activity of an acyclic analog of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5-pyrimidinyl)propyl]amino]benzoyl]-L-glutamic acid

1990 ◽  
Vol 33 (2) ◽  
pp. 561-567 ◽  
Author(s):  
James L. Kelley ◽  
Ed W. McLean ◽  
Naomi K. Cohn ◽  
Mark P. Edelstein ◽  
David S. Duch ◽  
...  
Keyword(s):  
Biological Activity ◽  
Glutamic Acid ◽  
Acyclic Analog ◽  
Tetrahydrofolic Acid

Cation binding by 21,31-diphenyl-l 2,42-dioxo-7,10,13-trioxa-1,4(3,1)-diquinoxalina-2 (2,3),3(3,2)-diindolizinacyclopentadecaphane and its acyclic analog

2009 ◽  
Vol 58 (1) ◽  
pp. 89-94 ◽  
Author(s):  
V. V. Yanilkin ◽  
N. V. Nastapova ◽  
A. S. Stepanov ◽  
A. A. Kalinin ◽  
V. A. Mamedov
Keyword(s):  
Cation Binding ◽  
Acyclic Analog

Glycine methoxyamide, acyclic analog of cycloserine

1966 ◽  
Vol 22 (9) ◽  
pp. 600-601
Author(s):  
Ch. H. Stammer ◽  
C. W. Jones
Keyword(s):  
Acyclic Analog

Synthesis of an ethidium nucleoside and its acyclic analog

2003 ◽  
Vol 44 (8) ◽  
pp. 1685-1690 ◽  
Author(s):  
Nicole Amann ◽  
Hans-Achim Wagenknecht
Keyword(s):  
Acyclic Analog

Acid-catalyzed hydrolysis of 4-diazo-3-isochromanone: the effect of coplanarity on the carbon protonation of α-phenyl-α-carbonyldiazo compounds

1996 ◽  
Vol 74 (7) ◽  
pp. 1369-1372 ◽  
Author(s):  
E.A. Jefferson ◽  
A.J. Kresge ◽  
S.W. Paine
Keyword(s):  
Carbon Atom ◽  
Negative Charge ◽  
Diazo Compound ◽  
Cyclic Compound ◽  
Phenyl Group ◽  
Molecular Orbital Calculations ◽  
Am1 Calculations ◽  
Charge Delocalization ◽  
Acyclic Analog ◽  
Hydrolysis Of

Hydrolysis of the cyclic α-phenyl-α-carbonyl-diazo compound, 4-diazo-3-isochromanone, in dilute aqueous perchloric acid solutions was found to give the hydronium ion isotope effect [Formula: see text] which shows that this reaction occurs by rate-determining hydronation of the substrate on the carbon atom α to its diazo group. Comparison of the rate constant obtained, [Formula: see text] with that for the corresponding acyclic analog, methyl phenyldiazoacetate, indicates that the cyclic compound is 57 times less reactive. Semi-empirical AM1 molecular orbital calculations suggest that this difference in reactivity is caused by enforced near-coplanarity of the diazo and phenyl groups in the cyclic substrate, as opposed to a staggered arrangement of these groups in the acyclic analog; this coplanarity then enhances delocalization of negative charge from the diazo α-carbon atom into the phenyl group, which reduces the negative charge density on the α-carbon atom and slows the rate of reaction. Key words: hydrolysis, diazoalkanes, charge delocalization, AM1 calculations.

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