American Journal of Interdisciplinary Research and Development ISSN Online: 2771-8948 Website: www.ajird.journalspark.org Volume 12, Jan., 2023 36 | P a g e STRUCTURAL ANALYSIS OF SUPRAMOLECULAR COMPLEXES OF SCHIFF BASES Khakberdiyev Shukhrat Mahramovich Mamatova Farangiz Qodir qizi Azizova Safina Isroiljon qizi Jizzakh Polytechnic Institute E-mail: h.shyxrat81@gmail.com Abstract Gossypol Schiff bases were synthesized and water-soluble supramolecular complexes of monoammonium salt of glycyrrhizic acid (MSGA) in a ratio of 1:4 were obtained, taking into account the insolubility of these substances in water. Some physico-chemical parameters of the complexes, their structure were estimated using IR-, UV-spectra and computer software. These quantum-chemical calculations were carried out in the ChemOffice program using the molecular mechanics (MM2) method with an empirical force field. Keywords: Gossypol, amino compound, Schiff's base, spectrum, polyphenol, triterpene, aldehyde, cotton plant, naphthalene, MSGA. Gossypol is found in different concentrations in different parts of the cotton plant. Gossypol, together with the diversity of its chemical structure and biological activity, is the main source for the creation of drugs against various viral diseases, colds, gastrointestinal ulcers and swellings. Some of Schiff's bases have strong interferon- inducing properties along with high biological activity, but gossypol derivatives are not soluble in water [1-2]. Taking into account the insolubility of Schiff bases in water, it is aimed to obtain their supramolecular complexes with the monoammonium salt of glycyrrhizic acid (MSGA) [3-4-5]. Molecules in these complexes are formed not by covalent bonds, but by hydrogen bonds. In most cases, covalent bonding is the major part of this process. MSGA is known to form clathrates with sparingly water-soluble drugs into a water- soluble form. MSGA is a major triterpene glycoside isolated from the root of the licorice plant and has a number of unique physicochemical properties, one of which is its solubilization property. Therefore, by forming supramolecular complexes with drugs, MSGA dramatically increases their solubility in water, reduces their toxicity, and at the same time provides an opportunity to maintain the effectiveness of action even in very small doses [6-7-8]. American Journal of Interdisciplinary Research and Development ISSN Online: 2771-8948 Website: www.ajird.journalspark.org Volume 12, Jan., 2023 37 | P a g e To obtain supramolecular complexes, 4 mol of MSGA was dissolved in 50 % С2Н5OН, 1 mol of Schiff's base was added to it, and the reaction was carried out at 50-60 0C for 6-8 hours with regular stirring. Ethyl alcohol was removed from the reaction mixture using a rotary evaporator, and the aqueous portion was lyophilized. Supramolecular complexes of thirty gossypol Schiff bases in 1:4 ratio were obtained. Some of their physico-chemical parameters were studied: Supramolecular complexes were obtained according to the following scheme: Table 1 Some physicochemical constants of water-soluble supramolecular complexes of Schiff bases with MSGA № Supramolecular complex M o l R a ti o Liquid 0S Rf R e a c ti o n y ie ld , in % Color 1 Di-(1-amino-2-bromoethane)gossypol + MSGA 1:4 211-212 0.421 0.282 91 yellow 2 Di-(2-amino-2-methylpropane)gossypol + MSGA 1:4 218-219 0.421 0.343 93 yellow 3 Di-(1-aminobutane)gossypol+MSGA 1:4 214-215 0.381 91 yellow 4 Di-(phenylhydrazine)gossypol+MSGA 1:4 189-190 0,702 90 yellow 5 Di-(2,4-dinitrophenylhydrazine)gossypol + MSGA 1:4 239-240 0,642 98 yellow 6 Di-(o-nitroaniline)gossypol+MSGA 1:4 212-213 0,463 98 yellow 7 Di-(4-amino-2-methylphenol)gossypol + MSGA 1:4 221-222 0,302 99 yellow 8 Di-(solicylamine) gossypol+MSGA 1:4 197-198 0,303 94 yellow 9 Di-(benzylamine)gossypol+MSGA 1:4 218-219 0.581 96 yellow American Journal of Interdisciplinary Research and Development ISSN Online: 2771-8948 Website: www.ajird.journalspark.org Volume 12, Jan., 2023 38 | P a g e Systems: 1) Hexane-acetone 1:1 2) Hexane-acetone 1.5:1 3) Benzene-acetone 2:1 When MSGA forms supramolecular complexes, the -OН and -СOOН groups in it form a hydrogen bond and allow joining. In addition, the hydrophobic part of GKMAT is affected by the hydrophobic parts of gossypol derivatives.When the UV and IR spectra of the obtained supramolecular complexes were analyzed, it was revealed that the signals in the spectrum of Schiff bases were broadened due to the hydrogen bonds in the complex compounds [9-10-11-12]. MSGA with di-(2,4-dinitrophenylhydrazine) gossypol When analyzing the IR spectrum of the supramolecular complex, we can see the change of the absorption maxima at 3091 cm-1 due to the valence vibrations of the new –N=СН– bond and the absorption maxima at 3450.98-2873.94 cm-1 due to the bonds in the MSGA supramolecular complex. Figure 1. IR spectrum of di-(2,4-dinitrophenylhydrazine)gossypol+ MSGA The UV spectrum of MSGA supramolecular complex with di-(2,4- dinitrophenylhydrazine)gossypol gave absorption maxima at 244.33-424.72 cm-1 for this substance [13-14-15-16]. 4000.0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400.0 60.0 62 64 66 68 70 72 74 76 78 80 82 84 86 88 90 92 94.0 cm-1 %T 3278.86 2947.30 1723.18 1616.30 1515.86 1422.94 1333.26 1215.98 1173.87 1057.36 981.29 839.32 689.24 2873.94 3450.98 1644.75 1591.60 1451.74 1390.20 1124.47 American Journal of Interdisciplinary Research and Development ISSN Online: 2771-8948 Website: www.ajird.journalspark.org Volume 12, Jan., 2023 39 | P a g e Figure 2. UV spectrum of di-(2,4-dinitrophenylhydrazine) gossypol+GKMAT When analyzing the IR-spectrum of the Schiff base formed by p-toluidine with gossypol, we can see the absorption maxima at 3240-3430 cm-1 belonging to the –NН2 group at 3091 cm-1 due to the valence vibrations of the new –N=СН– bond [17-18-19- 20]. When analyzing the IR-spectrum of the supramolecular complex with MSGA based on the obtained Schiff base, it was found that the absorption maxima at 3091 cm-1 were due to the valence vibrations of the new –N=СН– bond and at 3467.50-2920.22 cm-1 were due to hydrogen bonds. we can see absorption maxima [21-22-23]. Model of MSGA supramolecular complexes with gossypol derivatives based on computer calculation Figure 3. 1:4 with MSGA of gossypolidene benzylamine model of the supramolecular complex in proportion 200.0 250 300 350 400 450 500 550 600 650 700 750 800.0 0.00 0.2 0.4 0.6 0.8 1.0 1.2 1.4 1.6 1.8 2.0 2.2 2.4 2.6 2.8 3.0 3.2 3.4 3.60 nm A 424.72 244.33 American Journal of Interdisciplinary Research and Development ISSN Online: 2771-8948 Website: www.ajird.journalspark.org Volume 12, Jan., 2023 40 | P a g e USED LITERATURE 1. Hakberdiev, S. M., Talipov, S. A., Dalimov, D. N., & Ibragimov, B. T. (2013). 2, 2′- Bis {8-[(benzylamino) methylidene]-1, 6-dihydroxy-5-isopropyl-3- methylnaphthalen-7 (8H)-one}. Acta Crystallographica Section E: Structure Reports Online, 69(11), o1626-o1627. 2. Хакбердиев Ш. М., Тошов Х. С. Моделирование реакции конденсации госсипола с о-толуидином //ББК 74.58 G 54. – С. 257. 3. Khamza, Toshov, Khakberdiev Shukhrat, and Khaitbaev Alisher. "X-ray structural analysis of gossypol derivatives." Journal of Critical Reviews 7.11 (2020): 460- 463. 4. Хакбердиев, Ш. М. (2020). Бензиаминнинг госсиполли ҳосиласи синтези, тузилиши ва мис, никель, собалть тузлари билан металлокомплексларини олиш. Science and Education, 1(8), 16-21. 5. Хакбердиев, Ш. М. (2020). Турли тузилишли аминларнинг госсиполи ҳосилалари синтези ва биологик фаоллиги. Science and Education, 1(9). 6. Khakberdiyev, S. M. (2021). Study of the structure of supramolecular complexes of azomethine derivatives of gossipol. Science and Education, 2(1), 98-102. 7. Ҳамидов С. Х., Муллажонова З. С. Қ., Хакбердиев Ш. М. Кумушнинг госсиполли комплекси ва спектрал таҳлили //Science and Education. – 2021. – Т. 2. – №. 2. 8. Хақбердиев Ш. Янги шифф асослари ва уларнинг сувда эрувчан комплекслари тузилишини ўрганиш //Журнал естественных наук. – 2021. – Т. 1. – №. 2. 9. Хамидов, C. Ҳ., & Хакбердиев, Ш. М. (2021). Бирламчи алифатик аминларнинг госсиполли ҳосилалари синтези. Science and Education, 2(3), 113-118. 10. Муллажонова, З. С., Хамидов, C. Ҳ., & Хакбердиев, Ш. М. (2021). Турли усулларлар ёрдамида госсиполли комплекс таркибидан кумуш ионини аниқлаш. Science and Education, 2(3), 64-70. 11. Khaitbaev A. K., Khakberdiev S. М., Toshov K. S. Isolation of Gossypol from the Bark of Cotton Roots //Annals of the Romanian Society for Cell Biology. – 2021. – С. 1069-1073. 12. Хақбердиев Ш. Госсипол ҳосилалари, металлокомплекслари синтези қилиш ва кукунли дифрактометрда ўрганиш //Журнал естественных наук. – 2021. – Т. 1. – №. 2. 13. Хақбердиев Ш. Шифф асоси ва металлокомплексларининг термик анализи //Журнал естественных наук. – 2021. – Т. 1. – №. 3. American Journal of Interdisciplinary Research and Development ISSN Online: 2771-8948 Website: www.ajird.journalspark.org Volume 12, Jan., 2023 41 | P a g e 14. Хакбердиев Ш. Синтез, строение и получение супрамолекулярных комплексов ароматических аминов с госсиполом //Журнал естественных наук. – 2021. – Т. 1. – №. 4. 15. Хакбердиев Ш. М. и др. Синтез госсипольных производных орто, мета, пара толуидина и их строение //Science and Education. – 2021. – Т. 2. – №. 10. – С. 195-200. 16. Khakberdiev, Sh M., et al. "Synthesis and structure of gossypol azomethine derivatives." Young Scientist,(4) (2015): 42-44. 17. Хакбердиев Ш. М. и др. 3-аминопропанол-1 билан госсиполнинг турли комплекслари синтези ва макрофаглар миқдорига таъсири //Журнал естественных наук. – 2021. – Т. 1. – №. 1. 18. Хакбердиев, Ш. М. (2021). Госсиполнинг аминопиридинлар билан синтези ва уларнинг никел тузи металлокомплексларини олиш. Журнал естественных наук, 3(5), 10-15. 19. Хакбердиев, Ш., Қодир, Д., Маматова, Ф., & Муллажонова, З. (2022). Госсипол асосида ациклик аминобирикмаларнинг ҳосилалари синтези. Журнал естественных наук, 1(2 (7)), 12-16. 20. Mahramovich, K. S., Sattarovna, K. F., & Farangiz, M. (2022). Synthesis of Gossipy Products of Pyrimidine Bases and Getting Their Water-Solved Complexes. Eurasian Scientific Herald, 8, 118-121. 21. Mahramovich, K. S. (2022). Results of computer study of biological activity of gossipol products. Web of Scientist: International Scientific Research Journal, 3(6), 1373-1378. 22. Хакбердиев, Ш., Муллажонова, З., & Маматова, Ф. (2022). Адениннинг госсиполли ҳосиласи унинг металло ва супрамолекуляр комплексларини турли таҳлиллар асосида ўрганиш. Журнал естественных наук, 1(2 (7)), 288-293. 23. Khakberdiyev Shukhrat Mahramovich, & Mamatova Farangiz Qodir qizi. (2022). Synthesis of metallocomplexes of schiff bases and their structural analysis. World Bulletin of Public Health, 16, 173-177. Retrieved from.