Synthesis of Bis(Isoxazol-4-Ylmethylsulfanyl)Alkanes and Some Metal Complexes as a Hepatoprotective Agents

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Akhmetova Vnira Rakhimovna; Galimova Rozalia Akramovna; Akhmadiev Nail Salavatovich; Galimova Albina Midkhatovna; Khisamutdinov Ravil Akhmetzyanovich; Nurtdinova Galiya Maratovna; Agletdinov Eduard Feliksovich; Kataev Valery Alekseevich

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Journal: Advanced Pharmaceutical Bulletin Year:2018 | Volume:8 | Issue:2 Page(s): 267-275

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Title

Synthesis of Bis(Isoxazol-4-Ylmethylsulfanyl)Alkanes and Some Metal Complexes as a Hepatoprotective Agents

Author(s)

Keywords

Metal-organic frameworks

Isoxazoles

Hepatoprotector

In vivo

Liver

Hepatitis

Abstract

Purpose: This research is devoted to designing the synthesis of sulfanyl-substituted 3, 5-dimethylIsoxazoles, which contain structural analogues of the SAM drug in the molecule. SAM (S-adenosyl-L-methionine), formed in the biosynthetic process, is used as an effective hepatoprotective drug. Complexation and hepatoprotective properties of the combinatorial series of bis(isoxazolylsulfanyl)ethane have been studied. Methods: Bis(isoxazol-4-ylmethylsulfanyl)alkanes were synthesized using the one-pot method. The structures of compounds were established by one-dimensional (1H, 13C) and two-dimensional (COSY, HCQS, HMBC) NMR spectroscopy, mass-spectrometry and Xray diffraction. The biological activity of the combinatorial series of sulfanyl derivatives of diketones, azoles and their metal complexes has been studied by In vivo method. Simulation of the animal associated processes was carried out in accordance with the principles of bioethics. Screening studies of hepatoprotective activity were carried out in a model of acute CC14 intoxication after a single injection intraperitoneally as a 50% solution in olive oil. The pharmacologically known hepatoprotective drug SAM served as a control. Results: Two-step synthesis of novel α , ω-bis(isoxazol-4-ylmethylsulfanyl)alkanes was carried out via the multicomponent reaction between 2, 4-pentandione, CH2O and α , ω-dithiols, then the resulting α , ω-bis(1, 3-diketone-2-ylmethylsulfanyl)alkanes were transformed by hydroxyl amine to obtain bis-isoxasole derivatives. Promising precursor 1, 2-bis(isoxazol-4-ylmethylsulfanyl)ethane was converted to metal complexes by interaction with PdCl2 or CuCl. The obtained compounds were found to be practically nontoxic compounds (1001 – 3000 mg/kg) according to the classification of K. K. Sidorov, but copper complex refers to low-toxic compounds substances (165 mg/kg). Compounds of sulfanyl ethane series demonstrate hepatoprotective activity. Conclusion: Palladium(II) complex being almost non-toxic possesses hepatoprotective activity comparable to the drug like SAM.

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APA: Copy

Akhmetova, Vnira Rakhimovna, Galimova, Rozalia Akramovna, Akhmadiev, Nail Salavatovich, Galimova, Albina Midkhatovna, Khisamutdinov, Ravil Akhmetzyanovich, Nurtdinova, Galiya Maratovna, Agletdinov, Eduard Feliksovich, & Kataev, Valery Alekseevich. (2018). Synthesis of Bis(Isoxazol-4-Ylmethylsulfanyl)Alkanes and Some Metal Complexes as a Hepatoprotective Agents. ADVANCED PHARMACEUTICAL BULLETIN, 8(2), 267-275. SID. https://sid.ir/paper/753815/en

Vancouver: Copy

Akhmetova Vnira Rakhimovna, Galimova Rozalia Akramovna, Akhmadiev Nail Salavatovich, Galimova Albina Midkhatovna, Khisamutdinov Ravil Akhmetzyanovich, Nurtdinova Galiya Maratovna, Agletdinov Eduard Feliksovich, Kataev Valery Alekseevich. Synthesis of Bis(Isoxazol-4-Ylmethylsulfanyl)Alkanes and Some Metal Complexes as a Hepatoprotective Agents. ADVANCED PHARMACEUTICAL BULLETIN[Internet]. 2018;8(2):267-275. Available from: https://sid.ir/paper/753815/en

IEEE: Copy

Vnira Rakhimovna Akhmetova, Rozalia Akramovna Galimova, Nail Salavatovich Akhmadiev, Albina Midkhatovna Galimova, Ravil Akhmetzyanovich Khisamutdinov, Galiya Maratovna Nurtdinova, Eduard Feliksovich Agletdinov, and Valery Alekseevich Kataev, “Synthesis of Bis(Isoxazol-4-Ylmethylsulfanyl)Alkanes and Some Metal Complexes as a Hepatoprotective Agents,” ADVANCED PHARMACEUTICAL BULLETIN, vol. 8, no. 2, pp. 267–275, 2018, [Online]. Available: https://sid.ir/paper/753815/en

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