Synthesis of enantiomers of 2′-aminomethyl-5-benzylacyclouridine (AM-BAU) and 2′-aminomethyl-5-benzyloxybenzylacyclouridine (AM-BBAU). Potent inhibitors of uridine phosphorylase

Racemic 2′-aminomethyl-5-benzyl-acyclouridine (AM-BAU, 5 ) and 2′-aminomethyl-5-benzyloxybenzyla-cyclouridine (AM-BBAU, 6 ) have been found to be very active inhibitors of uridine phosphorylase [1]. Their enantiomers were synthesized from chiral 2,2-dimethyl-1,3-dioxolane-4-methanol ( 7a,b ). S-(—)-AM-BAU ( 5a ) and S-(—)-AM-BBAU ( 6a ) were prepared from the R-(—) isomer 7a , and R(+)-AM-BAU ( 5b ) and R-(+)-AM-BBAU (6b) from the S-(+) isomer 7b . A different route from the S-(+) isomer 7b to S-(—)-AM-BBAU ( 6a ) was also determined to be feasible.     

Synthesis and monolayer characterization of phosphorylated amino acid analogs

The synthesis of a series of thiols containing phosphorylated and non-phosphorylated serine, threonine, and tyrosine amino acid residues is described. The synthesized molecules, based on 3-mercaptopropionic acid, were assembled onto gold and subsequently characterized using infrared reflection-absorption spectroscopy, ellipsometry, X-ray photoelectron spectroscopy, and contact angle goniometry. The ellipsometric analysis indicates that they form densely packed and well-oriented monolayers on gold, with thicknesses that are in good agreement with estimated values from space-filling models. The bulky and space-demanding phosphorylated threonine analog was, however, found to be an exception. The increase in layer thickness when adding a phosphate group to the threonine is only 35% of that observed for the two other analogs. A detailed infrared examination of the influence of cation coordination to the phosphorylated serine analog using calcium and magnesium reveals structural similarities to those of the inorganic phosphate compound calcium hydroxy apatite. We furthermore discuss the application of these monolayers as soft templates for biomineralization.     

Synthesis of phosphinic analogs of sulfur-containing amino acids

Phosphinic analogs of the key compounds of the metabolism of methionine were synthesized. The compounds obtained were selectively oxidized either at the phosphinic group or at the sulfur-containing fragment. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1360–1363, July, 1999.     

Synthesis of 5-ethylpyrimidine nucleoside analogs

This paper describes the synthesis of acyclic, cyclic, and deoxy sugar nucleosides of 5-ethylpyrimidine, i.e., i) 1-(2-hydroxyethoxymethyl), 1-(2-methoxyethoxymethyl), and 1-ethoxyethyl derivatives of 5-ethyl-uracil and 5-ethylcytosine, ii) 5-ethyl-1-(tetrahydro-2H-pyran-2-yl)- and -1-(tetrahydrofuran-2-yl)uracils, and iii) 5-ethyl-2′-deoxyuridine.     

Synthesis of phosphinic and phosphonic analogs of aromatic amino acids

The reaction of aryl and aralkyl aldoximes with hypophosphorous acid resulted in aminophosphinic acids, which were oxidized into the corresponding aminophosphonic acids. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 137–140, January, 1997.     

Synthesis of new nucleoside analogs containing amino bisphosphonic groups

Adenosine derivatives containing a 2,2-bis(diethoxyphosphoryl)ethyl or 2,2-diphosphonoethyl group on the amino nitrogen atom were synthesized for the first time by reaction of 5′-chloro-5′-deoxy- and 5′-hydroxy-2′,3′-isopropylideneadenosine with tetraethyl ethene-1,1-diylbis(phosphonate) or tetrakis(trimethylsilyl) ethene-1,1-diylbis(phosphonate).     

Synthesis of aminomethyl derivatives of sophoricoside

Aminomethylation of the natural isoflavonoid sophoricoside (genistein-4-O-β-D-glucoside) was studied. It was shown that the most convenient method for performing the aminomethylation was the use of aminals. 6,8-bis-Substituted derivatives of sophoricoside were synthesized.     

4-(N-对三氟甲基苯基)氨甲基-5-取代苯基硫吡唑衍生物的合成及生物活性

为了寻找高效低毒的农药,以3-甲基-1-取代苯基-5-吡唑酮、硫酚、对三氟甲基苯胺等为原料,通过4步反应,合成了5个3-甲基-1-取代苯基-4-(N-对三氟甲基苯基)氨甲基-5-取代苯硫基吡唑化合物,其结构经元素分析、1H NMR、IR确证。初步生物活性测试表明,部分化合物具有一定的杀菌活性。     

Synthesis and characterization of ethidium analogs: Emphasis on amino and azido substituents

A series of eight ethidium derivatives has been synthesized in which the substituents at R₃ and R₈ have been varied with hydrogen, azido and amino functions. Three of these compounds are new and their synthesis and characterization by uv-visible, ir and ¹H nmr spectroscopy are presented. The synthesis and characterization of the other compounds are also given for comparison, because the compounds served as precursors, or the synthetic route undertaken for these compounds differed from that reported previously.     

Synthesis and spectrophotometric study of some amino derivatives of thiophene analogs of chalcone

Eight amino derivatives of thiophene analogs of chalcone were obtained by reduction of the corresponding nitro derivatives with stannous chloride in concentrated hydrochloric acid, and their UV absorption spectra in dioxane were measured. The long-wave band was assigned to the corresponding fragments of the molecule on the basis of a comparison of the absorption curves of the investigated compounds with the curves of simpler compounds — aminoacetophenone, aminobenzalacetone, acetothienone, etc.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 198–203, February, 1977.     

Synthesis of analogs of pyridoxal 5′-phosphate and pyridoxamine 5′-phosphate

The following analogs of pyridoxamine 5′-phosphate (PAMP) have been synthesized by the direct phosphorylation of the corresponding amines: 2-nor-PAMP, 6-methyl-2-nor-PAMP, and 6-methyl-PAMP. A method for the synthesis of analogs of pyridoxal 5′-phosphate (PLP) by the phosphorylation of the Schiff's bases of the corresponding aldehydes with p-phenetidine and subsequent hydrolysis on a sulfonated resin has been worked out. 2-Nor-PLP, 6-methyl-2-nor-PLP, and 6-methyl-PLP have been obtained with yields of 53–73%. The spectral properties of the compounds obtained have been investigated.     

Synthesis of analogs of pyridoxal 5′-phosphate and pyridoxamine 5′-phosphate

The following analogs of pyridoxamine 5-phosphate (PAMP) have been synthesized by the direct phosphorylation of the corresponding amines: 2-nor-PAMP, 6-methyl-2-nor-PAMP, and 6-methyl-PAMP. A method for the synthesis of analogs of pyridoxal 5-phosphate (PLP) by the phosphorylation of the Schiff's bases of the corresponding aldehydes with p-phenetidine and subsequent hydrolysis on a sulfonated resin has been worked out. 2-Nor-PLP, 6-methyl-2-nor-PLP, and 6-methyl-PLP have been obtained with yields of 53–73%. The spectral properties of the compounds obtained have been investigated.The authors heartily thank Academician A. E. Braunshtein for his constant interest in this work and for valuable advice.     

Synthesis of symmetrical amino and aminomethyl derivatives of Tröger's base via Pd-catalyzed C-C and C-N bond formation

In this paper, we report the synthesis of amino and aminomethyl derivatives of Tröger's base (±)-1 and (±)-2. The key steps in the synthesis of (±)-1 and (±)-2 are Pd-catalyzed amination and cyanation, respectively, of the easily accessible dihalo derivatives (±)-3. These compounds are important intermediates in the synthesis of new ligands and building blocks for H-bonded supramolecular architectures.     

Synthesis of biologically active analogs of luliberin with shortened amino acid sequences

Two new analogs of the releasing factor of the luteinizing hormone with shortened amino acid sequences have been synthesized by the methods of classical peptide chemistry. The influence of the preparations on the action of chorionic gonadotropin and on the course of processes of ovulation in experimental animals has been studied. The promising nature in this direction of the search for active analogs for luliberin has been shown.     

Synthesis and hypotensive activity of new amino derivatives of terpenoids and their structural analogs

Thirty-five new salts of amino ester derivatives of terpenoids have been synthesized and their influence on the level of arterial pressure has been investigated.Institute of Physical Organic Chemistry, BSSR Academy of Sciences, Minsk. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 190–193, March–April, 1988.     

Synthesis of benzo(aminomethyl)indoles

The benzene ring in indoles has been aminomethylated in high yield by reaction with methylolphthalimide followed by hydrazinolysis of the phthalimidomethyl derivatives. In the hydrazinolysis of one of the phthalimidomethyl compounds, an intermediate product (the amino-methylindole phthalazine) was isolated and characterized.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, 1218–1221, September, 1985.     

Synthesis of chalcone analogs -4- and 5-nitropyrrole derivatives

Nitropyrrole analogs of chalcone have been synthesized by aldol condensation in basic medium from 5-nitropyrrole-2-carboxaldehyde, 4- and 5-nitro-2-acetylpyrrole, and the corresponding aromatic aldehydes and methyl ketones; their 2, 4-dinitrophenylhydrazones have been obtained. Some considerations are expressed concerning the reactivity of pyrrole-2-carboxaldehyde, 2-acetylpyrrole, and their nitro derivatives.     

Synthesis of anabasine-containing aminomethyl derivatives of 6-hydroxyaurones

Chemistry of Heterocyclic Compounds - Aminomethylation of aurones was studied by using anabasine. The reaction in the case of 6-hydroxyaurones was shown to selectively provide...     

Organophosphorus analogs of amino acids and peptides

A method for obtaining phosphorus analogs of homoproline was developed, and the complexing properties of these compounds were studied. An effective method for obtaining optically active 1-aminoalkylphosphonic acids that is based on the stereoselective enzymatic hydrolysis of their N-acyl derivatives is proposed. New approaches to the synthesis of phosphonopeptides using privalyl chloride as the condensing agent, silylated amino phosphonic acids as the amino components of peptide synthesis, and the proteinase papain as the stereoselective catalyst for the formation of the peptide bond were developed.Institute of Bioorganic Chemistry and Petrochemistry, Academy of Sciences of the Ukrainian SSR, Kiev. Translated from Teoreticheskaya i Éksperimental'naya Khimiya, Vol. 27, No. 3, pp. 288–293, May–June, 1991. Original article submitted February 8, 1991.