Molecular and crystal structure of 5-amino-1H-[1,2,4]triazole-3-carboxylic acid derivatives

Zeitschrift fur Kristallographie

Volumn 218, Issue 7, 2003, Pages 480-487

  Wawrzycka Gorczyca, I ^a   Rzeszotarska, B ^b   Dzygiel, A ^b   Masiukiewicz, E ^b   Koziol A E ^a  

^a MARIA CURIE SK ODOWSKA UNIVERSITY   (Poland)

^b UNIVERSITY OF OPOLE   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

1 ACETYL 5 AMINO 3 CARBOMETHOXY 1H 1,2,4 TRIAZOLE; 1,2,4 TRIAZOLE DERIVATIVE; 5 ACETYLAMINO 3 CARBOMETHOXY 1 METHYL 1H 1,2,4 TRIAZOLE; 5 AMINO 1H 1,2,4 TRIAZOLE 3 CARBOXYLIC ACID DERIVATIVE; 5 AMINO 3 CARBOMETHOXY 1 METHYL 1H 1,2,4 TRIAZOLE; CARBOXYLIC ACID DERIVATIVE; PROTON; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; CRYSTAL STRUCTURE; MOLECULAR INTERACTION; STRUCTURE ANALYSIS;

EID: 0042304013     PISSN: 00442968     EISSN: None     Source Type: Journal    
DOI: 10.1524/zkri.218.7.480.20717     Document Type: Article

References (43)

1. Dervan, P. B.: Molecular recognition of DNA by small molecules. Bioorg. Med. Chem. 9 (2001) 2215-2235.
2. Kopka, M. L.; Goodsell, D. S.; Han, G. W.; Chiu, T. K.; Lown, J. W.; Dickerson, R. E.: Defining GC-specificity in the minor groove: side-by-side binding of the di-imidazole lexitropsin to C-A-T-G-G-C-C-A-T-G. Structure 5 (1997) 1033-1046.
3. Johnson, D. S.; Boger, D. L.: DNA binding agents. In: Comprehensive Supramolecular Chemistry (Eds. J.-M. Lehn, J. L. Atwood, J. E. D. Davies, D. D. Macnicol, F. Vögtle), Vol. 4, pp. 73-176, Pergamon, Oxford 1996.
4. Voyer, N.: The development of peptide nanostructures. In: Topics in Current Chemistry (Ed. F. P. Schmidtchen), Vol. 184, pp. 1-37, Springer, Berlin 1997.
5. Janecka, A.; Janecki, T.; Shan, S.; Bowers, C.; Folkers, K.: Novel, potent luteinizing hormone-releasing hormone antagonists with improved solubility in water. J. Med. Chem. 37 (1994) 2238-2241.
6. Ishida, H.; Inoue, T.: Artificial peptides with unnatural components designed for materializing protein function. Biopolymers (Peptide Science) 55 (2000) 469-478.
7. Kubik, S.; Goddard, R.: Fine tuning of the cation affinity of artificial receptors based on cyclic peptides by intramolecular conformational control. Eur. J. Org. Chem. 2 (2001) 311-322.
8. Kirsten, Ch. N.; Schrader, T. H.: Intermolecular β-sheet stabilization with aminopyrazoles. J. Am. Chem. Soc. 119 (1997) 12061-12068.
9. Chipen, G.; Grinstein, V.: Derivatives of 1,2,4-triazolecarboxylic-5 acid. Latvijas PSR Zinatnu Akad. Vestis, Kim. Ser. (1965) 204-208; Chem. Abst. 63 (1965) 13243g.
10. Chipen, G.; Grinstein, V.: Derivatives of 1,2,4-triazolecarboxylic-5 acid. Latvijas PSR Zinatnu Akad. Vestis, Kim. Ser. (1965) 204-208; Chem. Abst. 63 (1965) 13243g.
11. Bartroli, J.; Turmo, E.; Algueró, M.; Boncompte, E.; Vericat, M. L.; Conte, L.; Ramis, J.; Merlos, M.; García-Rafanell, J.; Forn, J.: New azole antifungals. 3. Synthesis and antifungal activity of 3-substituted-4(3H)-quinazolinones. J. Med. Chem. 41 (1998) 1869-1882.
12. Crott, S.; Cameron, C. E.; Andino, R.: RNA virus error catastrophe: direct molecular test by using ribavirin. Proc. Natl. Acad. Sci. USA 98 (2001) 6895-6900.
13. Recanatini, M.; Bisi, A.; Cavalli, A.; Belluti, F.; Gobbi, S.; Rampa, A.; Valenti, P.; Palzer, M.; Palusczak, A.; Hartmann, R. W.: A new class of nonsteroidal aromatase inhibitors: design and synthesis of chromone and xanthone derivatives and inhibition of the P450 enzymes aromatase and 17α-hydroxylase/ C17,20-lyase. J. Med. Chem. 44 (2001) 672-680.
14. Li, S.; Gao, J.; Satoh, T.; Friedman, T. M.; Edling, A. E.; Koch, U.; Choksi, S.; Han, X.; Korngold, R.; Huang, Z.: A computer screening approach to immunoglobulin superfamily structures and interaction: discovery of small non-peptidic CD4 inhibitors as novel immunotherapeutics. Proc. Natl. Acad. Sci USA 94 (1997) 73-78.
15. Ramos Tombo, G. M.; Belluš, D.: Chirality and crop protection. Angew. Chem. Int. Ed. Engl. 30 (1991) 1193-1215.
16. Saalfrank, R. W.; Wirth, U.: 4,5-Dihydro-1H-tetrazol-5-ylidene aus 3,3-Diazido-2-cyanacrylsäureestern und Hydrazinen, Hydraziden sowie O-substituierten Hydroxylaminen. Chem. Ber. 122 (1989) 519-522.
17. Kohlbau, H.-J.; Thürmer, R.; Voelter, W.: α-Carboxy Group. In: Synthesis of Peptides (Houben-Weyl Methods of Organic Chemistry; Eds. Goodman, M.; Felix, A.; Moroder, L.; Toniolo, C.) Vol. E 22a, pp. 193-237, George Thieme, Stuttgart 2002.
18. GRAMS/386 Version 3.01B, Galactic Industries Corp., Salem, NH, 1994.
19. Sheldrick, G. M.: SHELXS-86. Program for crystal structure solution, University of Göttingen, Germany 1986.
20. Sheldrick, G. M.: SHELXS-97. Program for crystal structure solution, University of Göttingen, Germany 1997.
21. Sheldrick, G. M.: SHELXL-97. Program for the refinement of crystal structures from diffraction data, University of Göttingen, Germany 1997.
22. Sheldrick, G. M.: SHELXTL/PC. User's Manual. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA 1990.
23. International Tables for Crystallography. (Ed. Wilson, J.A.C.) Vol. C. Kluwer, Dordrecht 1995.
24. Benedetti, E.: Structure and conformation of peptides as determined by X-ray crystallography. In: Chemistry and Biochemistry of Amino Acids, Peptides and Proteins (Ed. B. Weinstein), Vol. 6, pp. 105-184, Dekker, New York 1982.
25. Chakrabarti, P.; Dunitz, J. D.: Structural characteristic of the carboxylic amide group. Helv. Chim. Acta 65 (1982) 1555-1562.
26. Schweizer, W. B.; Dunitz, J. D.: Structural characteristics of the carboxylic ester group. Helv. Chim. Acta 65 (1982) 1547-1554.
27. Taylor, R.; Kennard, O.: Crystallographic evidence for the existence of C-H⋯O, C-H⋯N and C-H⋯Cl hydrogen bond. J. Am. Chem. Soc. 104 (1982) 5063-5070.
28. 13 chemical shielding tensor studies. J. Crystall. Spectrosc. Res. 19 (1989) 715-723.
29. Desiraju, G. R.; Steiner, T.: The Weak Hydrogen Bond in Structural Chemistry and Biology. pp. 1-121, Oxford University Press, Oxford 1999.
30. Jeffrey, G. A.; Saenger, W.: Hydrogen bonding in biological structures. Springer-Verlag, Berlin 1991.
31. Grell, J.; Bernstein, J.; Tinhofer, G.: Graph-set analysis of hydrogen-bond patterns: some mathematical concepts. Acta Cryst. B55 (1999) 1030-1043 (Erratum: Acta Cryst. B56(2000) 166).
32. Hunter, C. A.; Sanders, J. K. M.: The nature of π-π interaction. J. Am. Chem. Soc. 112 (1990) 5525-5534.
33. Hunter, C. A.; Lawson, K. R.; Perkins, J., Urch, C. J.: Aromatic interactions. J. Chem. Soc., Perkin Trans. 2 (2001) 651-669.
34. Gaughey, G. B.; Gagne, M., Rappe, A. K.: π-Stacking interactions. J. Biol. Chem. 273 (1998) 15458-15463.
35. Tsuzuki, S., Honda, K.; Uchimaru, T.; Mikami, M.; Tanabe, K.: Origin of attraction and directionality of the π/π interaction model chemistry calculations of benzene dimer interaction. J. Am. Chem. Soc. 124 (2002) 104-112.
36. Jeffrey, G. A.; Ruble, J. R.; Yates, J. H.: Neutron diffraction at 15 and 120 K and ab initio molecular-orbital studies of the molecular structure of 1,2,4-triazole. Acta Cryst. B38 (1983) 388-394.
37. Toda, F.; Tanaka, K.; Elguero, J.; Nassimbeni, L.; Niven, M.: Freezing the equilibrium of 1,2,4-triazole by complex formation with 1,1-bis(2,4-dimethylphenyl)-2-butyn-1-ol, and X-ray crystal structure of the complex. Chem. Lett. (1987) 2317-2320.
38. Starova, G. L.; Frank-Kamenetskaya, O. V.; Makarskii, V. V.; Lopyrev, V. A.: The crystal and molecular structure of 5-amino-1-hydrogen-1,2,4-triazole. Kristallografiya 23 (1978) 849-850.
39. Lyuboradskii, R.; Lipkowskii, Ya.; Simonov, Yu, A.; Fonar', M. S.; Ganin, E. V.; Yavolowskii, A. A.: Structures of the molecular complexes of 18-crown-6 with five-membered heterocyclic molecules: 5-amino-1H-tetrazole and 5-amino-1,2,4-triazole. Kristallografiya 42 (1997) 77-87.
40. 5). Kristallografiya 25 (1980) 1292-1295.
41. Kálmán, A.; Argay, Gy.: A survey of the lone pair effect on the ring geometry of 1,2,4-triazoles and analogous 1,2,3-triazoles and imidazoles. J. Mol. Struc. 102 (1983) 391-402.
42. Ribar, B.; Stankovic, S.; Argay, Gy.; Kálmán, A.; Koczo, E: Structure of 5-amino-1-(2,6-dimethylphenyl)-3-methylthio-1H-1,2,4-triazole. Acta Cryst. C43 (1987) 1712-1713.
43. Borbulevych, O. Ya; Shishkin, O. V.; Desenko S. M.; Chernenko, V. N.; Orlov, V. D.: 5-Amino-3-trifluoromethyl-1H-1,2,4-triazole. Acta Cryst. C54 (1998) 442-444.