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Synthesis, Tautomeric Structure, Dyeing Characteristics, and Antimicrobial Activity of Novel 4-(2-Arylazophenyl)-3-(2-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones
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 Title & Authors
Synthesis, Tautomeric Structure, Dyeing Characteristics, and Antimicrobial Activity of Novel 4-(2-Arylazophenyl)-3-(2-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones
Metwally, M.A.; Bondock, S.A.; El-Desouky, S.I.; Abdou, M.M.;
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 Abstract
Novel azopyrazolin-5-one dyes 4a-f were synthesized by the regioselective reaction of phenylhydrazine with 2,3,4-chromantrione-3-arylhydrazones 2a-f. The acid dissociation constants for the series prepared were determined and correlated by the Hammett equation. The results of such correlation together with the spectral data indicated that the studied compounds exist predominantly in the hydrazone keto structure, (D) as the Z-configuration. The dyes were applied to polyester fabrics, affording orange-yellow shades and assessments of their dyeing performance are considered. Further, the compounds 4a-f were screened for their antimicrobial activity against various microorganisms.
 Keywords
Azo-hydrazone tautomerism;Disperse dyes;
 Language
English
 Cited by
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 References
1.
Ozdemir, A.; Turan-Zitouni, G.; AslmKaplanclkll, Z.; Revial, G.; Demirci, F.; Iscan, G. J Enzyme Inhib Med Chem. 2010, 25, 565. crossref(new window)

2.
Kucukguzel, S. G.; Rollas, S. Farmaco 2002, 57, 583. crossref(new window)

3.
Kucukguzel, S. G.; Rollas, S.; Erdeniz, H.; Kiraz, M.; Cevdet Ekinci, A.; Vidin, A. Eur. J. Med. Chem. 2000, 35, 761. crossref(new window)

4.
Khalil, N. S. Carbohydr. Res. 2009, 344, 1654. crossref(new window)

5.
El-Kashef, H. S.; Abd-Alla, M. A.; Bayoumib, B. E.; El-Timawy, A. M. J. Chem. Technol. Biotechnol. 1983, 33A, 294.

6.
Tantawy, A.; Eisa, H.; Ismail, A.; El-Kerdawy, M. Alex J Pharm Sci. 1988, 11, 113.

7.
Goda, F. E.; Maarouf, A. R.; El-Bendary, E. R. Saudi Pharm J. 2003, 11, 111.

8.
Ibrahim, S. A.; El-Gahami, M. A.; Khafagi, Z. A.; El-Gyar, S. A. J. Inorg. Biochem. 1991, 43, 1. crossref(new window)

9.
Sugiura, S.; Ohno, S.; Ohtani, O.; Izumi, K.; Kitamikado, T.; Asai, H.; Kato, K.; Hori, M.; Fujimura, H. J. Med. Chem. 1977, 20, 80. crossref(new window)

10.
Takeo, S.; Ei-ichi, Y.; Yoshio, O.; Teruo, A.; Kazuo, H. Bull. Chem. Soc. Jap. 1965, 38, 1049. crossref(new window)

11.
Khalifa, H.; Issa, Y. M. Egypt. J. Chem. 1974, 17, 581.

12.
Azarifar, D.; Shaebanzadeh, M. Molecules 2002, 7, 885. crossref(new window)

13.
Karci, F.; Ertan, N. Dyes Pigm. 2002, 55, 99. crossref(new window)

14.
Ho, Y. W. Dyes Pigm. 2005, 64, 223. crossref(new window)

15.
Colotta, V.; Cecchi, L.; Melani, F.; Palazzino, G.; Fillacchioni, G. Tetrahedron Lett. 1987, 28, 5165. crossref(new window)

16.
Strakova, I.; Strakovs, A.; Petrova, M.; Belyakov, S. Chem. Heterocycl. Compd. 2009, 45, 1319. crossref(new window)

17.
Morita, H.; Harada, K.; Okamoto, Y.; Takagi, K. J. Heterocyclic Chem. 1999, 36, 767. crossref(new window)

18.
Froggett, J. A.; Hockley, M. H.; Titman, R. B. J. Chem. Res. Synop. 1997, 1, 30.

19.
Heubner, C. F.; Link, K. P. J. Am. Chem. Soc. 1945, 67, 102. crossref(new window)

20.
Metwally, M. A.; Abdel-Latif, E.; Khalil, A. M.; Amer, F. A.; Kaupp, G. Dyes Pigm. 2004, 60, 181.

21.
Metwally, M. A.; Khalifa, M. E.; Amer, F. A. Dyes Pigm. 2007, 76, 379. crossref(new window)

22.
Fadda, A. A.; Metwally, M. A.; Khalil, A. M. Indian J. Fibre Text. Res. 1983, 8, 82.

23.
Abdel-Latif, E.; Metwally, M. A.; Amer, F. A.; Khalifa, M. E. Pigm Resin Technol. 2009, 38, 105. crossref(new window)

24.
Jung, J. C.; Jung, Y. J.; Park, O. S. Synth. Commun. 2001, 31, 1195. crossref(new window)

25.
Shawali, A. S.; Harb, N. M. S.; Badahdah, K. O. J. Heterocycl. Chem. 1985, 22, 1397. crossref(new window)

26.
Yazdanbakhsh, M. R.; Ghanadzadeh, A.; Moradi, E. J. Mol. Liq. 2007, 136, 165. crossref(new window)

27.
VanUitert, L. G.; Haas, C. G. J. Am. Chem. Soc 1953, 75, 451. crossref(new window)

28.
Albert, A.; Serjeant, E. P. The Determination of Ionization Constant of Acid; Chapman and Hall Ltd.: London, 1971; p 9.

29.
Gans, P.; Sabatini, A.; Vacca, A. Inorg. Chim. Acta 1976, 18, 237. crossref(new window)

30.
Anonymous. Standard Methods for the Determination of the Color Fastness of Textiles and Leather, 5th ed.; Bradford: The Society of Dyers and Colorists: England, 1990; p 619.

31.
Shamroukh, A. H.; Zaki, M. E. A.; Morsy, E. M. H.; Abdel-Motti, F. M.; Abdel-Megeid, F. M. E. Arch. Pharm. 2007, 340, 345. crossref(new window)

32.
Yasuda, H. Bull. Chem. Soc. Jap. 1967, 40, 1239. crossref(new window)

33.
Malik, W. U.; Garg, H. G.; Arora, V. J. Pharm. Sci. 1971, 60, 1738. crossref(new window)

34.
Garg, H. G.; Arora, V. J. Pharm. Sci. 1972, 61, 130. crossref(new window)

35.
Gillam, A. E.; Stern, E. S. An Introduction to Electronic Absorption Spectroscopy in Organic Chemistry; Edward Arnold Ltd.: London, 1960; p 271.

36.
Yasuda, H.; Nidokawa, H. J. Org. Chem. 1966, 31, 1722. crossref(new window)

37.
Jones, R.; Ryan, A. J.; Sternhell, S.; Wright, S. E. Tetrahedron 1963, 19, 1497. crossref(new window)

38.
Salman, A.; Ates, O.; NesrinCesur, N.; Otuk, G. Arch. Pharm. 1991, 324, 55. crossref(new window)

39.
Yagi, Y. Bull. Chem. Soc. Jap. 1963, 36, 487. crossref(new window)

40.
Yao, H. C. J. Org. Chem. 1964, 29, 2959. crossref(new window)

41.
Russell, P. E. J. Am. Chem. Soc. 1953, 75, 5315. crossref(new window)

42.
Randall, H. M; Fuson, N.; Fowler, R. G.; Dangl, J. R. Infrared Determination of Organic Compounds; D.Van Nostrand Co. Inc.: New York, 1949; p 222.

43.
Gagnon, P. E.; Boivin, J. L.; MacDonald, B. R; Yaffe, L. Can. J. Chem. 1954, 32, 823. crossref(new window)

44.
Colthup, N. B. J. Opt. Soc. Am. A 1950, 40, 397. crossref(new window)

45.
Saito, Y.; Kim, B.; Machida, K.; Uno, T. Bull. Chem. Soc. Jap. 1974, 47, 2111. crossref(new window)

46.
Kelemen, J.; Moss, S.; Sauter, H.; Winkler, T. Dyes Pigm. 1982, 3, 27. crossref(new window)

47.
Lestina, G. J.; Regan, T. H. J. Org. Chem. 1969, 34, 1685. crossref(new window)

48.
Yoder, C. H.; Barth, R. C.; Richter, W. M.; Snavely, F. A. J. Org. Chem. 1972, 37, 4121. crossref(new window)

49.
Snavely, F. A.; Yoder, C. H. J. Org. Chem. 1968, 33, 513. crossref(new window)

50.
Johnson, C. D. The Hammett Equation; Cambridge University press: U.K., 1973; p 1.

51.
Humffray, A. A.; Ryan, J. J. J. Chem. Soc. B 1969, 1138. crossref(new window)

52.
Shawali, A. S.; Rizk, M. S.; Abdelhamid, A. O.; Abdallah, M. A.; Parkanyi, C.;Wojciechowska, M. E. Heterocycles 1983, 320, 2211.

53.
Hassaneen, H. M. Synth. Commun. 2007, 37, 3579. crossref(new window)

54.
Kuzueva, O. G.; Burgart, Y.V.; Saloutin, V. I. Russ. Chem. Bull. 1998, 47, 673. crossref(new window)

55.
Mitchell, A.; Nonhebel, D. C. Tetrahedron 1979, 35, 2013. crossref(new window)

56.
SDL. Atlas Ltd. P.O. Box 162; Crown Royal; Shawcross St.; Stockport SK1 3JW.

57.
Gordon, P. F.; Gregory, P. Organic Chemistry in Color; Springer-Verlag: Berlin, 1983; p 289.

58.
Muller, C. Recent Developments in the Chemistry of Disperse Dyes and their Intermediate; American Dyestuff reporter: 1970; p 37.