scholarly journals New 4-iminohydantoin sulfamide derivatives with antiviral and anticancer activity

2021 ◽  
Vol 16 (1) ◽  
pp. 10-17
Author(s):  
Yurii Kornii ◽  
Oleh Shablykin ◽  
Olga Shablykina ◽  
Volodymyr Brovarets
Keyword(s):  
Amino Acids ◽  
Anticancer Activity ◽  
Carboxylic Acids ◽  
Human Cytomegalovirus ◽  
Methyl Esters ◽  
Amino Group ◽  
Secondary Amino

A number of sulfamides were obtained by reaction of (5-(dichloromethylene)-2-oxoimidazolidin-4-ylidene)sulfamoyl chloride with anilines, benzylamines, Boc-protected piperazine, methylalylamine, and amino acids methyl esters with primary and secondary amino group. The antiviral and anticancer activity of new derivatives was evaluated. The most effective compounds against Human cytomegalovirus were sulfamides based on anisidine (1b), N-Boc-piperazine (1h), and the derivatives 1n,o with fragments of nipecotic and azetidine-3-carboxylic acids, respectively. Anticancer activity was most significant for sulfamides based on p-methoxybenzylamine (compound 1d), benzylmethylamine (compound 1f), and allylmethylamine (compound 1g).

THE INFRARED SPECTRA OF SECONDARY AMINES AND THEIR SALTS

1956 ◽  
Vol 34 (12) ◽  
pp. 1782-1795 ◽  
Author(s):  
R. A. Heacock ◽  
Léo Marion
Keyword(s):  
Amino Acids ◽  
Secondary Amine ◽  
Infrared Spectra ◽  
Secondary Amines ◽  
Amino Group ◽  
Absorption Bands ◽  
Secondary Amino ◽  
Amine Salts

The infrared spectra of a number of secondary bases and of their salts have been examined. The spectra of the salts differ from those of the corresponding bases in containing several absorption bands that are absent from the latter. Those of the new bands occurring in the region 1620 to 1560 cm.−1, which are due to NH2+ deformation vibrations, are characteristic of secondary amine salts, and can be used to detect the presence of a secondary amino group in the original molecule. With aromatic bases the spectra are complicated because the ring absorption occurs in the same region, but in many cases the assignment can still be made, although with less certainty. In zwitterionic substances such as the secondary aliphatic amino acids, the function is more difficult to detect.

Azides of N-substituted aziridine-2-carboxylic acids. Reaction with methyl esters of amino acids

1980 ◽  
Vol 16 (10) ◽  
pp. 1023-1025
Author(s):  
A. V. Eremeev ◽  
I. V. Solodin ◽  
F. D. Polyak
Keyword(s):  
Amino Acids ◽  
Carboxylic Acids ◽  
Methyl Esters

Identification of Ornithine and Arginine Conjugates of Cholic Acid by Mass Spectrometry

1975 ◽  
Vol 53 (5) ◽  
pp. 583-590 ◽  
Author(s):  
J. J. Myher ◽  
L. Marai ◽  
A. Kuksis ◽  
I. M. Yousef ◽  
M. M. Fisher
Keyword(s):  
Mass Spectrometry ◽  
Amino Acids ◽  
Methyl Ester ◽  
Mass Spectra ◽  
Methyl Esters ◽  
Isolated Perfused Rat Liver ◽  
Amino Group ◽  
Perfused Rat Liver ◽  
Direct Insertion Probe ◽  
Dibasic Amino Acids

Nα-Cholylornithine, -arginine, and -histidine were prepared according to a method previously employed for the chemical synthesis of the monoamino acid conjugates of bile acids. The products were shown to involve the α amino group of the dibasic amino acids by examination of the mass spectra of the original compounds, their lactams, their methyl esters and the methyl ester acetates. Only the methyl ester acetates gave detectable amounts of molecular ion. The free acids and the methyl esters of Nα-cholylornithine and -arginine gave identical lactams upon sublimation from the direct insertion probe. The synthetic Nα-cholylarginine was shown to yield a mass spectrum identical to that of an arginocholic acid recovered from the bile of an isolated perfused rat liver.

scholarly journals Propylphosphonic acid anhydride–mediated amidation of Morita–Baylis–Hillman–derived indolizine-2-carboxylic acids

2021 ◽  
pp. 174751982098715
Author(s):  
Khethobole C Sekgota ◽  
Michelle Isaacs ◽  
Heinrich C Hoppe ◽  
Ronnett Seldon ◽  
Digby F Warner ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Coupling Agent ◽  
Methyl Esters ◽  
Acid Anhydride

Propylphosphonic acid anhydride has been successfully used as a coupling agent in the synthesis of a series of indolizine-2-carboxamido derivatives from indolizine-2-carboxylic acid and its 3-acetylated analogue. The acid substrates were obtained by saponification of the corresponding methyl esters produced, in turn, selectively and efficiently, by time-controlled cyclisation of a single Morita–Baylis–Hillman adduct. Various amino and hydrazino compounds with medicinal potential have been used to prepare indolizine-2-carboxamido and hydrazido derivatives.

Sodium borohydride: A versatile reagent in the reductive N-monoalkylation of α-amino acids and α-amino methyl esters

2002 ◽  
Vol 80 (7) ◽  
pp. 779-788 ◽  
Author(s):  
Giancarlo Verardo ◽  
Paola Geatti ◽  
Elena Pol ◽  
Angelo G Giumanini
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Sodium Borohydride ◽  
Carbonyl Compounds ◽  
Condensation Reaction ◽  
Methyl Esters ◽  
Reducing Agent ◽  
Reductive Condensation ◽  
Versatile Reagent

α-Amino acids and α-amino methyl esters are easily converted to their N-monoalkyl derivatives by a reductive condensation reaction using several carbonyl compounds in the presence of sodium borohydride. This reducing agent has shown a wide versatility with minor but essential procedural variations. The reaction allows the α-monodeuterium labeling of the new N-substituent by use of sodium borodeuteride.Key words: α-amino acid, α-amino methyl esters, sodium borohydride, reductive N-monoalkylation, carbonyl compounds.

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