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RU2586067C1

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[mishka]

Bis-(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propyl) selenide, having antioxidant and hypoglycemic activity.Ayzman, R. I.; Gaydarova, A. P.; Kandalintseva, N. V.; Koroshshenko, G. A.; Prosenko, A. E.; Kholshin, S. V.; Yagunov, S. E. (FGBOU VPO "Novosibirskii Gosudarstvennyi Pedagogicheskii Universitet", Russia; Nekommercheskoe Partnerstvo "Novosibirskii Institut Antioksidantov"). Russ. (2016), 13pp. CODEN:RUXXE7 RU 2586067 C1 20160610 Patent written in Russian. Application: RU 2015-114862 20150420. Priority: RU 2015-114862 20150420. CAN 165:31310 AN 2016:944323 CAPLUS

ABSTRACT
Selenium-contg. phenol compd. 4-HO-3,5-tBu2C6H2(CH2)3Se(CH2)3C6H2-3,5-tBu2-4-OH (1), useful as antioxidant, low-toxic and hypoglycemic agent for use in medicine, veterinary and exptl. biol., was prepd. by borohydride redn. of diselenide 4-HO-3,5-tBu2C6H2(CH2)3Se2(CH2)3C6H2-3,5-tBu2-4-OH (2). In an example, reaction of 5.95 mmol of selenium with 23-95 mmol of sodium sulfite in 20 mL of water at 100° for 10 h gave a transparent soln., which was reacted with 5.36 mmol of 4-(3-bromopropyl)-2,6-di-tert-butylphenol (3) in 20 mL of EtOH at reflux for 3 h gave the diselenide 2 with 72% yield. The diselenide 2 (3.06 mmol) was reacted with 6.43 mmol of the bromo-deriv. 3 and 12.24 mmol of NaBH4 in EtOH/THF (1:1 vol./vol.) at reflux for 3 h gave the invented compd. 1 with 83% yield. In another example, the compd. 1 caused no acute toxicity and mortality in mice at 5000 mg/kg peroral dose. The compd. 1 caused redn. of blood glucose in alloxan-induced rat diabetes model from 18.3 mmol/L to 3.7 mmol/L in 100 mg/kg peroral dose with 3.6 mmol/L control level, consequently increasing liver glycogen level from 457 mg/100 g to 1403 mg/100 g at control level of 889 ng/100 g.

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