Reference

Mode of action of butylated hydroxyanisole (BHA) and other phenols in preventing loss of 11b-hydroxylase activity in cultured bovine adrenocortical cells

Mode of action of butylated hydroxyanisole (BHA) and other phenols in preventing loss of 11b-hydroxylase activity in cultured bovine adrenocortical cells. Hornsby, Peter J.; Aldern, Kathy A.; Harris, Sandra E. (Sch. Med., Univ. California, La Jolla, CA 92093, USA). Biochem. Pharmacol., 34(6), 865-72 (English) 1985. CODEN: BCPCA6. ISSN: 0006-2952. DOCUMENT TYPE: Journal CA Section: 1 (Pharmacology) Section cross-reference(s): 2 The protective effects of several phenolic analogs of butylated hydroxyanisole (BHA) against loss of enzymic activity of 11b-hydroxylase [9029-66-7] in the presence of pseudosubstrates were studied in cultured bovine adrenocortical cells. The protective effects of these phenolic analogs of BHA in this system were compared to the activities of DMSO [67-68-5] and metyrapone [54-36-4].Several substances are used for example 9029-66-7 which is its cas registry number. When cultured adrenocortical cells were incubated with 50 mM cortisol [50-23-7] for 24 h, phenol [108-95-2] itself was about equipotent with BHA [25013-16-5] in preventing loss of enzymic activity. Addn. of Me, methoxy, and benzyl groups to phenol did not diminish protective activity of the compd., but addn. of one and particularly two tert-Bu groups greatly diminished activity. Thus, BHT (2,6-di-t-butyl-4-methylphenol) [128-37-0] was inactive, in contrast to BHA. The hydroxy group of phenol was essential since benzene [71-43-2] and fluorobenzene [462-06-6] were inactive. Compds. with multiple hydroxyl groups were not as active as phenol itself, with the exception of catechol [120-80-9]. No products of phenol formed during incubations of cells with cortisol were detected by HPLC. Estd. EC50 values for protection of 11b-hydroxylase by phenols were about 100 mM, whereas the EC50 values for DMSO and metyrapone were 10 mM and 300 nM resp. On a semilogarithmic plot, the dose-response curves for all these compds. were approx.There are some reagents like 9029-66-7 is used in this study. parallel. To aid in detg. the mechanism of protection of 11b-hydroxylase, phenols and DMSO were tested for prevention of loss of 11b-hydroxylase activity at 3 different O concns. (2, 5, and 19% O). Lowering the O concn. itself resulted in a small diminution of the loss of 11b-hydroxylase. Phenols and DMSO were more effective at low O and less effective in air. Because the cytochrome P 450 inhibitor metyrapone was found previously to be very effective in protecting 11b-hydroxylase against loss of activity, it was examd. whether phenols and DMSO may act by directly inhibiting 11b-hydroxylase activity. In a 1-h incubation with cells, BHA, phenol, and DMSO all inhibited 11b-hydroxylase, but at concns. that ranged from 4- to >100-fold higher than those required for protection. In contrast, for metyrapone, the EC50 values for protection and inhibition were very similar. Thus, it is unlikely that phenols act simply as inhibitors but may need to bind close to the active site of the enzyme. The obsd. synergism with lowered O suggests an involvement, in the loss of 11b-hydroxylase activity, of O-centered radicals that may be reactants for protective phenols. ..

4-Hydroxybenzophenones

4-Hydroxybenzophenones. Colquhoun, Howard Matthew (Imperial Chemical Industries PLC, UK). Eur. Pat. Appl. EP 128693 A2 19 Dec 1984, 15 pp. DESIGNATED STATES: R: AT, BE, CH, DE, FR, GB, IT, LI, NL, SE. (English). (European Patent Organization). CODEN: EPXXDW. CLASS: IC: C07C045-46; C07C049-83; C07C049-84; C08G063-06. APPLICATION: EP 84-303587 25 May 1984. PRIORITY: GB 83-15610 7 Jun 1983. DOCUMENT TYPE: Patent CA Section: 35 (Chemistry of Synthetic High Polymers) Section cross-reference(s): 25 4-Hydroxybenzophenone derivs., useful in the manuf. of polyoxyphenylene ketones, are prepd. by polymn. of 4-hydroxybenzoic acid (I) [99-96-7] in the presence of carbonyl halides, thionyl halides, or CF3CO2H [76-05-1] and reaction of the poly(4-hydroxybenzoyl) intermediate with arom. compds. bearing strongly electroneg. substituents and, optionally, 1-4 substituents that are not strongly electroneg., in the presence of Lewis acids. Thus, DMF contg. 65 g SOCl2 was added over 30 min. to 400 mL stirred PhF [462-06-6] contg. 69 g I at 60° and stirred 2 h at 85°. This suspension was added over 30 min to a stirred suspension of 100 mL PhF and 166 g AlCl3 at 65° and stirred 18 h at 85° to give 94% 4-fluoro-4'-hydroxybenzophenone (II) [25913-05-7].Several substances are used for example 99-96-7 which is its cas registry number. The content of 2-fluoro-4'-hydroxy isomer was reduced from 1.3 to 0.2% by 2 successive treatments with aq. NaOH and aq. HCl and recrystn. Purified II was polymd. (43.34 g) by 10.Chemical with cas number 99-96-7 also plays role.56 g Na2CO3 and 0.28 g K2CO3 in 93 g Ph2SO2 for 35 min at 175°, 40 min at 175-225°, 20 min at 225°, 55 min at 225-260°, 30 min at 260-300°, 25 min at 300-335°, and 35 min at 335° to give polymer [27400-53-9] with melt viscosity 0.31 kN-s/m2 at 400° and shear rate 1000 s-1, which could be compression-molded at 400° to a tough film. ..