Thiophenyl-substituted triazolyl-thione l-alanine: Asymmetric synthesis, aggregation and biological properties

Amino Acids

Volumn 46, Issue 10, 2014, Pages 2325-2332

  Saghyan, Ashot S ^a   Simonyan, Hayarpi M ^a   Petrosyan, Satenik G ^a   Geolchanyan, Arpine V ^a   Roviello, Giovanni N ^b   Musumeci, Domenica ^c   Roviello, Valentina ^d  

^a YEREVAN STATE UNIVERSITY   (Armenia)

^b CNR   (Italy)

^c UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^d CNR   (Italy)

Author keywords

Artificial amino acid; CD; Light scattering; RNA

Indexed keywords

ALANINE; ANTIVIRUS AGENT; AROMATIC AMINO ACID; RNA; THIOPHENE DERIVATIVE; TRIAZOLE DERIVATIVE;

ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; CONFORMATION; DRUG DESIGN; ELECTROSPRAY MASS SPECTROMETRY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOMETRY; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

ALANINE; AMINO ACIDS, AROMATIC; ANTIVIRAL AGENTS; CIRCULAR DICHROISM; DRUG DESIGN; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NEPHELOMETRY AND TURBIDIMETRY; RNA; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET; THIOPHENES; TRIAZOLES;

EID: 84921315595     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-014-1782-3     Document Type: Article

References (22)

1. Cativiela C, Díaz-de-Villegas MD, Gálvez JA, Lapeña Y (1997) On the synthesis of (S)-α-methylaspartic acid by diastereoselective alkylation of a chiral 2-cyanopropanoate. Tetrahedron 53:5891-5898
2. Desai N, Bhavsar A, Shah M, Saxena A (2008) Synthesis and QSAR studies of thiosemi-carbazides, 1,2,4-triazoles, 1,3,4-thiadiazoles and 1,3,4-oxadiazoles derivatives as potential anti-bacterial agents. Ind J Chem 47B:579-585
3. Fei Z, Liu Y, Yan Z, Fan D, Alexander A, Yang JH (2009) Targeting viral dsRNA for antiviral prophylaxis. FASEB J. doi: 10.1096/fj.09-144915
4. Harris RLN, Huppatz J (1977) Synthetic plant growth regulators. The synthesis of C-o-Carboxyphenyl derivatives of some five-membered heterocycles. Aus. J.Chem 30(10):2225-2240
5. Katritzky A, Rees C (1984) Comprehensive heterocyclic chem. chapter/thiazoles and benzothiazole derivatives by Metzyer J. 6:330-331
6. Kumar P, Raju S, Goud P, Sailaja M, Sarma M, Reddy G, Kumar M, Krishna R, Suresh T, Hegde P (2004) Synthesis and biological evaluation of thiophene [3,2-b] pyrrole derivatives as potential anti-inflammatory agents. Bioorg Med Chem 12:1221-1230
7. Queiroz M, Ferreira I, Gaetano Y, Kirsch G, Calhelha R, Estevinho L (2006) Synthesis and antimicrobial activity studies of ortho-chlorodiarylamines and heteroaromatic tetracyclic systems in the benzo[b]thiophene series. Bioorg Med Chem 14:6827-6831
8. Roviello GN, Musumeci D, Castiglione M, Bucci EM, Pedone C, Benedetti E (2009) Solid phase synthesis and RNA-binding studies of a serum-resistant nucleo-ε-peptide. J Pept Sci 15:155-160
9. Roviello GN, Musumeci D, De Cristofaro A, Capasso D, Di Gaetano S, Bucci EM, Pedone C (2010a) Alternate dab-aegPNAs: synthesis, nucleic acid binding studies and biological activity. Mol BioSyst 6:199-205
10. Roviello GN, Musumeci D, Pedone C, Bucci EM (2010b) Synthesis, characterization and hybridization studies of an alternate nucleo-epsilon/gamma-peptide: complexes formation with natural nucleic acids. Amino Acids 38:103-111
11. Roviello GN, Musumeci D, Bucci EM, Pedone C (2011a) Evidences for supramolecular organization of nucleopeptides: synthesis, spectroscopic and biological studies of a novel dithymine l-serine tetrapeptide. Mol BioSyst 7:1073-1080
12. Roviello GN, Ricci A, Bucci EM, Pedone C (2011b) Synthesis, biological evaluation and supramolecular assembly of novel analogues of peptidyl nucleosides. Mol BioSyst 7:1773-1778
13. Roviello GN, Mottola A, Musumeci D, Bucci EM, Pedone C (2012) Synthesis and aggregation properties of a novel enzymatically resistant nucleoamino acid. Amino Acids 43:1465-1470
14. Roviello GN, Musumeci D, D'Alessandro C, Pedone C (2014) Binding ability of a thymine-functionalized oligolysine towards nucleic acids. Bioorg Med Chem 22:97-1002
15. Saghyan A, Geolchanyan A, Belokon' Yu (2003) Method of synthesis of the chiral NiII complex of Schiff's base of dehydroalanine with (S)-2-N-(N'-benzylprolyl)aminobenzophenone. Armenian patent #1257 A2
16. Saghyan A, Simonyan H, Stepanyan L, Ghazaryan S, Geolchanyan A, Manasyan L, Ghochikyan V, Ghochikyan T, Hovhannisyan N, Gevorgyan A, Iaroshenko V, Langer P (2012) Asymmetric synthesis of new β-heterocyclic (S)-α-aminopropionic acids. Tetrahedron Asymmetry 23:891-897
17. Saghyan S, Mkrtchyan G, Dadayan A, Petrosyan S, Geolchanyan A, Simonyan H, Mkrtchyan A, Mkrtchyan S, Gevorgyan A, Iaroshenko V, Langer P (2013) Asymmetric synthesis of enantiomerically enriched (S)-α-aminopropionic acids containing heterocyclic side chains. Tetrahedron Asymmetry 24:229-232
18. Shashikant P, Prajact K, Nachiket D, Sunil N, Deepak M, Smita P, Daithankar A (2009) Synthesis and biologicaon of somel evaluati 1, 3, 4-thiadiazoles. J Chem Pharm Res 1:191-198
19. Shuai X, Merdan T, Unger F, Kissel T (2005) Supramolecular gene delivery vectors showing enhanced transgene expression and good biocompatibility. Bioconjug Chem 16:322-329
20. Simeone L, Milano D, De Napoli L, Irace C, Di Pascale A, Boccalon M, Tecilla P, Montesarchio D (2011) Design, synthesis and characterisation of guanosine-based amphiphiles. Chem Eur J 17(49):13854-13865
21. Simeone L, Irace C, Di Pascale A, Ciccarelli D, D'Errico G, Montesarchio D (2012) Synthesis, self-aggregation and bioactivity properties of a cationic aminoacyl surfactant, based on a new class of highly functionalized nucleolipids. Eur J Med Chem 57:429-440
22. Thomson P, Naylor M, Everett S, Stratford M, Lewis G, Hill S, Patel K, Wardman P, Davis P (2006) Synthesis and biological properties of bioreductively targeted nitrothienyl prodrugs of combretastatin A-4. Mol Cancer Therapeut 5:2886-2894