Backbone-modified oligopeptidic bioregulators. The synthesis and configuration of thioamide, amidoxime, cyanoamidine, and amidrazone analogs of the chemotactic peptide N-formyl-methionyl-leucyl-phenylalanine (f-Met-Leu-Phe-OR)

1985 ◽  
Vol 63 (11) ◽  
pp. 3089-3101 ◽  
Author(s):  
Gilles Sauvé ◽  
Vanga S. Rao ◽  
Gilles Lajoie ◽  
Bernard Belleau
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Biological Activity ◽  
Magnetic Resonance ◽  
Peptide Bond ◽  
Chemotactic Peptide ◽  
Reaction Conditions ◽  
Nuclear Magnetic

Reaction conditions for the synthesis of thioamide, amidoxime, and N-substituted amidine analogs of the peptide bond are described. Several new amidine analogs of the chemotactic peptide f-Met-Leu-Phe-OR were synthesized using the thioamides as precursors. The assignment of the E/Z configuration was accomplished by nuclear magnetic resonance. The biological activity of these analogs is briefly described.

A highly stereoselective intramolecular aldol condensation. Part I. Nuclear magnetic resonance spectroscopic investigation of the stereochemistry of the products derived from the reaction of 2,2′-O-methylene-bis-D-glycerose with base

1982 ◽  
Vol 60 (4) ◽  
pp. 390-414 ◽  
Author(s):  
Walter A. Szarek ◽  
B. Mario Pinto ◽  
Alan H. Haines ◽  
T. Bruce Grindley
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Spectroscopic Investigation ◽  
Driving Force ◽  
Aldol Condensation ◽  
Reaction Times ◽  
Reaction Conditions ◽  
Cannizzaro Reaction ◽  
High Degree ◽  
Nuclear Magnetic

The intramolecular aldol condensation of 2,2′-O-methylene-bis-D-glycerose has been found to yield only two of the four possible diastereomeric products. At higher base concentration or prolonged reaction times, these products undergo a Cannizzaro reaction. The stereochemistry of the products derived from the aldol condensation has been established by means of labelling experiments and by examination of the products by 1Hmr and 13Cmr spectroscopy. The major and minor products of the reaction have been identified as being 2-C-hydroxymethyl-2,4-O-methylene-D,L-ribose (7) and 2-C-hydroxymethyl-2,4-O-methylene-D,L-xylose (8), respectively. The preferential stabilization of these products in the reaction by means of intramolecular hemiacetal formation is proposed as a driving force for the high degree of stereoselectivity; this possibility is supported by the isolation of the bicyclic systems expected from such a reaction. Conditions have been chosen such that 7 is formed exclusively.

SYNTHESIS OF 1-ARYL SUBSTITUTED 9H-PYRIDO[3,4-b]INDOLES

1965 ◽  
Vol 43 (8) ◽  
pp. 2251-2253 ◽  
Author(s):  
W. A. Skinner ◽  
R. M. Parkhurst
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Hydrochloric Acid ◽  
Reaction Conditions ◽  
Aryl Group ◽  
Nuclear Magnetic Resonance Spectra ◽  
Substituted Benzaldehydes ◽  
Magnetic Resonance Spectra ◽  
Nuclear Magnetic

A series of 1-aryl substituted 9H-pyrido[3,4-b]indoles (1,2,3,4-tetrahydro-β-carbolines) were synthesized by cyclization of tryptamine with a number of substituted benzaldehydes in the presence of hydrochloric acid. Four modifications of reaction conditions were found necessary in order to obtain the desired products containing a variety of substituents on the 1-aryl group. Nuclear magnetic resonance spectra of the products enabled definitive assignment of structure.

Synthesis and properties of N-Phenyl derivatives of 4,4'-Diaminobenzophenone

1983 ◽  
Vol 36 (2) ◽  
pp. 409 ◽  
Author(s):  
NA Evans
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Mass Spectra ◽  
Reaction Conditions ◽  
Satisfactory Yield ◽  
13C Nuclear Magnetic Resonance ◽  
Derivatives Of ◽  
Nuclear Magnetic

Variations in the reaction conditions during the Ullmann condensation of 4,4'-diaminobenzophenone with iodobenzene and the Goldberg diphenylamine synthesis with 4,4'-dibromobenzophenone and acetanilide or 4,4'-bis(acetamido)benzophenone and iodobenzene yielded the five possible partially and completely N-phenylated 4,4'- diaminobenzophenones. By choice of starting materials, 4,4'-bis(phenylamino)benzophenone could be obtained in satisfactory yield. The infrared, ultraviolet, 1H and 13C nuclear magnetic resonance and mass spectra of the benzophenones are reported.

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