БИОЛОГИЧЕСКИ АКТИВНЫЕ СИНТЕТИЧЕСКИЕ ОРГАНИЧЕСКИЕ КРАСИТЕЛИ
Аннотация
Для цитирования:
Кузнецов Д.Н., Кобраков К.И., Ручкина А.Г., Станкевич Г.С. Биологически активные синтетические органические красители. Изв. вузов. Химия и хим. технология. 2017. Т. 60. Вып. 1. С. 4-33.
Настоящий обзор построен на публикациях, найденных с помощью базы данных CAS (Chemical Abstracts Service), доступной через STN (The Scientific and Technical Information Network) по биоцидным красителям или соединениям, которые могут быть отнесены к ним по химическому строению. Систематизация проведена по особенностям строения хромофорной системы красителя. Особое внимание уделяется зависимости «строение – свойство» в ряду структурно подобных соединений. В обзоре не рассматриваются биоцидные свойства красителей, выделенных из природного сырья.
Литература
Stepanov B.I. Introduction to the chemistry and technology of organic dyes. М.: Khimiya. 1984. 349 p. (in Russian).
Gordon P.F., Gregory P. Organic chemistry in colour. M.: Mir. 1987. 344 p. (in Russian).
Beck J.W., Saavedra D., Antett G. J., Tejeiro В. The treatment of pinworm infections in Humans (Enterobiasis) with Pyrvinium Chloride and Pyrvinium Pamoate. Am. J. Trop. Med. Hyg. 1959. V. 8. N 3. P. 349-352.
Dugan B.J., Henrie R.N., Rosen D.S., Shulman I., Shunxiang Zhang, Y Larry Zhang, Zydowsky T.M. Pat. WO 2004010761, English. Pesticidal cyanine dye deri-vatives. Publ. 02.05.2004.
Parke Davis & co Pat. FR 1448707, France. Procédé de préparation d'un composé du 2,4,5-trichlorophénol. Publ. 18.03.1966.
Rosen D., Zhang L., Henrie R. Pat. WO 2004010761, English. Pesticidal cyanine dye derivatives. Publ. 02.05.2004.
Yuzo Seto Pat. US 3245874, United States. Cyanine dyes as an agricultural bactericide. Publ. 12.04.1966.
Panea Ioan, Chiorean Vasile Pat. RO 75092, Romania. Colorants 4-oxo-4H-l-benzopyrano-3-dimethylecianiques non-simetriques et procede d'obtenir Publ. 30.09.1980.
Nakagawa Yoshinori, Yoshino Sueo, Kusakari Youichi Pat. JP 60202817, Japanese. Agent for treatment of cultured fish. Publ. 14.10.1985.
Khalil Z.H., Koraiem A.I.M., El-Maghraby M.A., Abu-El-Hamd R.M. Synthesis, spectral behaviour and biological activity of benzoxazonyl(quinoxalonyl)-benzfurano-(indolo)-quinoline apocyanine dyes. J. Chem. Tech. Biotechnol. 1986. V. 36. N 3. P. 379–388. DOI: 10.1002/ jctb.280360808.
El-Maghraby M.A., Khalafallah A.K., Hassan M.E., Soleiman H.A. Synthesis and biological activity of pyra-zolo[3,4–d]-8-amino-1-azaquinoxaline dimethine cyanine dyes. J. Chin. Chem. Soc. 1988. V. 35. N 1. P. 53-56. DOI: 10.1002/jccs.198800008.
Shindy H.A., Koraiem A.I.M., Khalafallah A.K., Solei-man H.A. New cyanine dyes from 4, 9-dioxopiperi-dino-[2,3-g]-1,2,3,4,6,7,8,9-octahydroquinolinoquinone. Indian J. Chem. 2001. 40B. P. 426-429.
Koraiem A.I.M., Khalafallah A.K., Soleiman H.A. Synthesis and spectral behaviour of some novel biheterocyclic metal complexes cyanine dyes. Asw. Sc. Tech. Bull. 2002. V. 21. P. 36-47.
Shindy H.A., El-Maghraby M.A., Eissa F.M. Synthesis, photosensitization and antimicrobial activity of certain oxadiazine cyanine dyes. Dyes and Pigments. 2006. V. 70. N 2. P. 110-116. DOI: 10.1016/j.dyepig.2005.04.003.
Jha B.N., Jha R.K., D. Kumari Jha, Jhad S.N. Synthesis, visible absorption, photosensitisation and antimicrobial activity of some butadienochromophoric chain-substituted asymmetric cyanines. Dyes and Pigments. 1990. V. 13. N 2. P. 135-154. DOI: 10.1016/0143-7208(90)80028-N.
Abd El-Ala R.M., Koraierm A.I.M. Synthesis, absorption spectra studies and biological activity of some novel conjugated dyes. J. Chin. Chem. Soc. 2000. V. 47. P. 389-395. DOI: 10.1002/jctb.280360808.
Abd El-Aala R.M., Younis M. Synthesis and antimicrobial activity of certain novel monomethine cyanine dyes. Dyes and Pigments. 2004. V. 60. N 3. P. 205–214. DOI: 10.1016/ S0143-7208(03)00131-1.
Chang E., Congdon E.E., Honson N.S., Duff K.E, Kuret J. Structure-activity relationship of cyanine tau aggregation inhibitors. J. Med. Chem. 2009. V. 52. N 11. P. 3539–3547. DOI: 10.1021/jm900116d.
Melnikov N.N. Pesticides. Chemistry, technology and applications. М.: Khimiya. 1987. 712 p. (in Russian).
Safonova T.S. Ways of development of the chemistry of drugs. М.: Znanie. 1978. 64 p. (in Russian).
Awad I.M.A. Synthesis of some new azosulphonamides based on salicylic acid and thiosalicylic acid, and having antibacterial and antifungal activity. Dyes and Pigments. 1991. V. 17. N 2. P. 123-139. DOI: 10.1016/0143-7208(91)87026-J.
Hafez A.A., Awad I.M.A. Azo-dyes related to 5-sulpho-nylpiperidino-and/or morpholino-8-quinolinol. Dyes and Pigments. 1992. V. 20. N 3. P. 197-209. DOI: 10.1016/0143- 7208(92)80045-O.
Awad I.M.A. Synthesis and application of novel sulpha drugs based on quinoxaline-2-one and/or quinoxaline-2-thione. J. Chem. Tech. Biotechnol. 1992. V. 53. N 3. P. 227–236.
DU PONT Pat. GB 442884, English. Azo compounds and their application and compositions containing the same. Publ. 17.02.1936.
Carboni R.A. Pat. US 2904544, United States. Polynuclear nitrogen containing compounds and process of making same. Publ. 15.09.1959.
Shen Liu, Jiang Ma, Defeng Zhao Synthesis and characterization of cationic monoazo dyes incorporating quaternary ammonium salts. Dyes and Pigments. 2007. V. 75. N 2. P. 255-262. DOI: 10.1016/j.dyepig.2006.05.004.
Bhat K.L., Mendel Trachtman, Bhat C.W. N-hydroxy-monomethoxy-4-aminoazobenzenes: a computational study. Dyes and Pigments. 2001. V. 48. N 3. P. 197-207. DOI: 10.1016/S0143-7208(00)00104-2.
Bhat K.L., Mendel Trachtman, Bhat C.W. Mutagenicity of aminoazobenzene dyes and related structures: a QSAR/QPAR investigation. Dyes and Pigments. 2002. V. 55. N 1. P. 35–52. DOI: 10.1016/S0143-7208(02)00070-0.
Ushkarov V.I., Kobrakov K.I., Alafinov A.I., Shevelev S.A., Shakhnes A.H. Methyl phloroglucinol - accessible intermediate for the synthesis of azo dyes. Khimicheskaya Tekhnologiya. 2006. N 8. P. 5-8 (in Russian).
Ushkarov V.I., Kobrakov K.I., Alafinov A.I., Stankevich G.S., Shevelev S.A., Shakhnes A.Kh. Methylphloroglucinol-based dyes for chemical fibres. Fibre Chem. 2006. V. 38. N 3. P. 188-190. DOI: 10.1007/s10692-006-0067-3.
Alafinov A.I., Kobrakov K.I., Kuznetsov D.N., Dmitri-eva M.B. Synthesis of new azoderivatives of methylphloro-glucinol - potential dyes and pigments for textile materials. Butlerov. soobshch. 2013. V. 33. N 3. P. 93-99. (in Russian).
Kozlova S.E. Research in the field of imparting antimicrobial properties to woolen materials. Dissertation for candidate degree on chemical sciences. M.: MTI. 1972. 311 p. (in Russian).
Gorbatscheva I.N., Kozinda Z.J., Suvorova E.G., Tscher-tov V.A., Dvoskin S.I., Podgaevskaja T.A., Skvirenko A.B. Pat. DE 3009522, German. Antimikrobielle eigenschaften aufweisende azofarbstoffe. Publ. 25.09.1980.
Pat. FR 2436161, France. Halogen-containing azo dyes. Publ. 11.04.1980.
Grukova O.P., Kobrakov K.I., Stankevich G.S., Shakhnes A.H., Shevelev A.S. Synthesis of azo dyes based on 2,4,6-trinitrotoluene and 1,3,5-trinitrobenzene. Khimiches-kaya Tekhnologiya. 2003. N 7. P. 12-13 (in Russian).
Kobrakov K.I., Stankevich G.S., Neborako O.Yu., Grukova O.P. The search for effective new dyes for chemical fibres. Fibre Chem. 2005. V. 37. N 2. P. 84-88. DOI: 10.1007/s10692-005-0059-8.
Somari Giri, Awadhesh Kumar Mishra. Fungicidal and molluscicidal activity of some 3-substituted 4-hydroxy-coumarin derivatives. J. Agric. Food Chem. 1904. V. 32. N 4. P. 759-762. DOI: 10.1021/jf00124a014.
Sudhir Kumar P., Ghosh G., Rout S.K., Paul D. Synthesis and antimicrobial evaluation of some novel 4-hydroxy coumarin derivatives bearing azo moiety. Rasayan J. Chem. 2013. V. 6. N 2. P.147-152.
Sharma Pratibha, Pritmani Shreeya Synthesis, characterization and antimicrobial studies of some novel 3-arylazo-7 - hydroxy-4-methylcoumarins. Indian J.Chem. 1999. V. 38B. P. 1139-1142.
Kryštof V., Cankař P., Fryšová I., Slouka J., Kontopidis G., Džubák P., Hajdúch M., Srovnal J., AzevedoJr W.F., Orság M., Paprskářová M., Rolík J., Látr A., Fischer P.M., Strnad M. 4-Arylazo-3,5-diamino-1H-pyrazole CDK inhibitors: SAR study, crystal structure in complex with CDK2, selectivity, and cellular effects. J. Med. Chem. 2006. V. 49. N 22. P. 6500–6509. DOI: 10.1021/jm0605740.
Helal M.H., Elgemeie G.H., Masoud D.M. Preparation and characterisation of novel methylsulfanylpyrazolopyrimidines as heterocyclic dyes from ketene dithioacetals. Pigment & Resin Technology. 2007. V. 36. N 5. P. 306-311. DOI: 10.1108/03699420710820423.
Karci Fikret, Demircali Aykut Synthesis of disazo pyrazolo[1,5-a]pyrimidines. Dyes and Pigments. 2007. V. 74. N 2. P. 288-297. DOI: 10.1016/j.dyepig.2006.02.007.
Tsai Pi Chen, Wang Ing Jing A facile synthesis of some new pyrazolo[1,5-a]pyrimidine heterocyclic disazo dyes and an evaluation of their solvatochromic behavior. Dyes and Pigments. 2007. V. 74. N 3. P. 578-584. DOI: 10.1016/j.dyepig.2006.03.022.
Fathy N.M., El-Said M.K., El-Bazza Z.E., Faddah L.M. Behavior of 3,5-diaminopyrazoles towards activated double bond systems: novel synthesis of pyrazolo[1,5-a]pyrimidi-nes. Egyptian J.Pharm. Sci. 1992. V. 33. P. 1-9.
Hassan Alaa A., Ibrahim Yusria R., Mohamed Nasr K., Mourad Aboul-Fetouh E. Reaction of tetracyanoethylene with arylazoaminopyrazoles via charge-transfer complexation. J. fuer Praktische Chemie (Leipzig). 1990. V. 332. N 6. P. 1049-1053.
Elnagdi Mohamed Hilmy, Kandeel Ezzat Mohamed, Zayed Ezzat Mohamed, Kandil Zaghloul Elshahat Pyrimidine derivatives and related compounds VI. A novel synthesis of 3,5-diacetamidopyrazole and of 2-aminopyrazolo [1,5-α] pyrimidines. J. Heterocyc. Chem. 1977. V. 14. N 1. P. 155-157. DOI: 10.1002/jhet.5570140132.
Fikret Karcı, Nesrin Sёener, Mustafa Yamaз, Izzet Sёener, Aykut Demirзalı The synthesis, antimicrobial activity and absorption characteristics of some novel heterocyclic disazo dyes. Dyes and Pigments. 2009. V. 80. N 1.
P. 47–52. DOI: 10.1016/j.dyepig.2008.05.001.
Amin S.A., Abdou L.A., Kamel H. Relation between the rotproofing properties and chemical structure of some reactive compounds and their chromophorie derivatives. Textile res. j. 1974. V. 44. N 8. P. 568-573.
Toshkhodzhaev N.A., Kobrakov K.I., Shvekhgeiymer G.A., Balabanova L.V. Synthesis and properties of some dyes based on 6-substituted 2,3,5-trichloropyridine. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 1993. V. 36. N 3. P. 97-101 (in Russian).
Kobrakov K.I., Kondratkov V.T., Stankevich G.S., Dmitrieva M.B. Protection of textile materials made of different types of fibres from biodeterioration with special dyes. Fibre Chem. 1999. V. 31. N 4. P. 291-294. DOI: 10.1007/BF02358335.
Sun Yuyu Pat. US 20090074821, United States. Colorants based n-halamines compositions and method of making and using. Publ. 19.03.2009.
Sun Yuyu, Luo Jie Pat. WO 2009039180, English. Colorants based n-halamines compositions and method of making and using. Publ. 26.03.2009.
Rybina I.I. Synthesis and study of properties of derivatives of 3,5-dichloropyridyl-2-hydrazine. Candidate dissertation for chemical sciences. Moscow. MSTU. 2001. 158 p. (in Russian).
Bocharnikova V.A., Pavlov I.V., Stankevich G.S., Kobra-kov K.I., Bogza S.L., Dmitrieva M.B. Pyrazole-containing dyes: synthesis, features of structure and properties. Presentations of Fourth Congress of chemists-textile-workers and colourers. М.: МТI. 2002. P. 43-44 (in Russian).
Rizk H.F., Ibrahim S.A., El-Borai M.A. Synthesis, fastness properties, color assessment and antimicrobial activity of some azo reactive dyes having pyrazole moiety. Dyes and Pigments. 2015. V. 112. P. 86–92. DOI: 10.1016/j.dyepig.2014.06.026.
Feoktistov M.K., Stankevich G.S., Kobrakov K.I., Dmitrieva M.B., Brodsky I.I., Begunov R.S. Synthesis and study of properties of azo dyes containing biophore groups. Izv. Vyssh. Uchebn. Zaved. Tekhnol. Text. Indus. 2007. N 3. P. 65-67 (in Russian).
Kobrakov K.I., Feoktistov M.K., Stankevich G.S., Zvolinskii V.I., Bormasheva K.M., Moiseev I.K., Orlov V.Yu., Begunov R.S., Yakovleva O.Yu. New pyrazole-containing azo dyes for polycaproamide: synthesis and properties. Fibre Chem. 2009. V. 41. N 2. P 73-79. DOI: 10.1007/s10692-009-9150-x.
Shvekhgeimer M.-G. A., Kondrashova N.N. Synthesis of azo compounds containing the nucleus of 4-quinolinecarbo-xylic acid. Doklady Chemistry. 2003. V. 391. N 1. P. 181-184. DOI: 10.1023/A:1024790613111.
Kuznetsov D.N., Agapov G.A., Glotova M.O., Ruchkina A.G., Kobrakov K.I., Alexanyan K.G., Dmitrieva M.B. Design, synthesis and properties of new fungicides azo dyes for polycaproamide. Butlerov. soobshch. 2012. V. 30. N 4. P. 44-50.
Rozova Z.S. Waterproof-putrid impregnation dyeing. Text. Indus. 1941. V. 1. P. 20-21 (in Russian).
Samsona S.A. The substituents for the antiseptic impregnation. Text. Indus. 1943. V. 3. P. 15-17 (in Russian).
Maltseva T.A. Development of methods for the preparation of modified cellulosic fibers and fabrics that have antimicrobial properties. Dissertation for candidate degree on chemical sciences. M.: MTI. 1965. 286 p. (in Russian).
Kozinda Z.Yu. Research on modification of the protein fibers. Dissertation for candidate degree on chemical sciences. M.: MTI. 1965. 170 p. (in Russian).
Khazanov G.I. Improving finishing technology of technical felts using in the press section of a paper machine. Dissertation for candidate degree on chemical sciences. M.: MTI. 1987. 189 p. (in Russian).
Dyson G., Mei P. Chemical synthetic drugs. M.: Mir. 1964. 289 p. (in Russian).
Toyoshima Satoru, Watanabe Masayasu, Yamada Masayuki Pat. JP 2005009065, Japanese. Bactericidal/anti-bacterial textile product and method for manufacturing the same. Publ. 13. 01.2005.
Balabanova M., Popova L., Tchipeva R. Dyes in dermatology. Disease-A-Month. 2004. V. 50. N 6. P. 270-279.
Orosa G., Cserharti T. Use of principal component analysis and a spectral mapping technique for the evaluation of the antifungal activity of anthracene-based synthetic dyes. SAR and QSAR in Environmental Research. 2009. V. 20. P. 379–391.
Browning C.H., Gilmour W. Proceedings of the pathological society of Great Britain and Ireland. J. Pathol. Bacteriol. 1913. V. 18. N 1. P. 114–148.
Venkataraman K. The Chemistry of synthetic dyes. V. 4. L.: Khimiya. 1975. 488 p. (in Russian).
Sabnis R.W. Handbook of biological dyes and stains. Synthesis and industrial applications. New York: Wiley. 2010. 521 p.
Krylov Yu.F., Bobyrev V.M. Pharmacology. М.: VUNMTs. 1999. 352 p. (in Russian).
Khomyakov K.P., Virnik A.D., Rogovin Z.A. The prolongation of the action of pharmaceutical preparations by mixing or combining them with polymers. Russ. Chem. Rev. 1964. 33 (9). P. 462–467. DOI: 10.1070/RC1964v033n09ABEH001468.
Snezhko D.L., Virnik A.D., Pestereva G.D., Rogovin Z.A. Investigation of the effect of bond type between antimicrobial agents and modified cellulose macromolecule on the antimicrobial properties of fabric. Izv. Vyssh. Uchebn. Zaved. Tekhnol. Text. Indus. 1968. N 6. P. 92-95 (in Russian).
Belikov V.G. Tutorial pharmaceutical chemistry. M.: Meditsyna. 1979. 328 p. (in Russian).
Wainwright M. Phenothiazinium photosensitisers: V. Photobactericidal activities of chromophore-methylated phenothiazinium salts. Dyes and Pigments. 2007. V. 73. N 1. P. 7-12. DOI: 10.1016/j.dyepig.2005.10.001.
Gorman S.A., Bell A.L., Roberts J.G.D., Brown S.B. The synthesis and properties of unsymmetrical 3,7-diamino-phenothiazin-5-ium iodide salts: Potential photosensitisers for photodynamic therapy. Dyes and Pigments. 2006. V. 71. N 3 P. 153-160. DOI: 10.1016/j.dyepig.2005.06.011.
Hanna M.A., Girges M.M., Gawinecki R. Cationic azomethine disperse dyes: Synthesis, antifungal activity and tinctorial properties of N-arylideneamino p-substituted pyridinium salts as possible dyes for synthetic fibres. J. Chem. Tech. Biotechnol. 1991. V. 52. N 4. P. 559-570. DOI: 10.1002/jctb.280520413.
Rongchun Li, Zhanyong Guo, Pingan Jiang. Synthesis, characterization, and antifungal activity of novel quaternary chitosan derivatives. Carbohydrate Research. 2010. V. 345. N 13. P. 1896-1900. DOI: 10.1016/j.carres.2010.05.029.
Gilbert Ian, Sellarajah Shane Pat. WO 2005085189А2, English. Compounds. Publ. 15.09.2005.
Minghua Ma, Yuyu Sun, Gang Sun Antimicrobial cationic dyes: part 1: synthesis and characterization. Dyes and Pigments. 2003. V. 58. N 1. P. 27–35. DOI: 10.1016/S0143-7208(03)00025-1.
Minghua Ma, Gang Sun Antimicrobial cationic dyes. Part 3: simultaneous dyeing and antimicrobial finishing of acrylic fabrics. Dyes and Pigments. 2005. V. 66. N 1. P. 33-41. DOI: 10.1016/j.dyepig.2004.09.001.
Randall D.I. Pat. US 2619492, United States. Soluble onium salts of halogenmethylated dibenzanthronyls. Publ. 25.11.1952.
Elton Cole John Pat. US 2061186, United States. Fluorine containing vat dyes. Publ. 06.12.1933.
Spesia M.B., Durantini E.N. Synthesis and antibacterial photosensitizing properties of a novel tricationic subphthalocyanine derivative. Dyes and Pigments. 2008. V. 77. N 1. P. 229-237. DOI: 10.1016/j.dyepig.2007.05.008.
Fasiulla M.H., Moinuddin Khan, Harish M.N.K., Keshavayya J., Venugopala Reddy K.R. Venugopala Reddy Synthesis, spectral, magnetic and antifungal studies on symmetrically substituted metal(II)octaiminophthalocyanine pigments. Dyes and Pigments. 2008. V. 76. N 2. P. 557-563. DOI: 10.1016/j.dyepig.2006.11.007.
Moinuddin Khan, Fasiulla M.H., Keshavayya J., Venu-gopala Reddy K.R. Synthesis, structural investigations and biological studies on symmetrically substituted 3,3′,3",3"′-tetra-methoxyphenylimino phthalocyanine complexes. Russ. J. Inorg. Chem. 2008. V. 53. N 1 P. 68-77. DOI: 10.1134/ S0036023608010117.
Moinuddin Khan M.H., Venugopala Reddy K.R., Keshavayya J., Fasiulla M.H., Raghavendra S. Synthesis, characterizations and biological studies of symmetrically substituted 2, 9, 16, 23-tetra-hydroxyphenylimino phthalocyanine complexes. Green Chemistry Letters and Reviews. 2009.
V. 2. N 2. P. 77-85. DOI: 10.1080/17518250903042414.