Detail of "4233-33-4"

Reference

25-Dehydrovitamin D3 derivatives as neoplasm inhibitors

25-Dehydrovitamin D3 derivatives as neoplasm inhibitors. (Teijin Ltd., Japan). Jpn. Kokai Tokkyo Koho JP 60067422 A2 17 Apr 1985 Showa, 6 pp. (Japanese). (Japan). CODEN: JKXXAF. CLASS: ICM: A61K031-59. ICS: A61K031-59. APPLICATION: JP 83-174356 22 Sep 1983. DOCUMENT TYPE: Patent CA Section: 63 (Pharmaceuticals) Section cross-reference(s): 1, 18, 24, 25, 32 25-Dehydrovitamin D3 derivs. I (R = H or OH; A = carbonyl or hydroxymethylene) are neoplasm inhibitors. Thus, 24-oxo-5a,8a-(4-phenyl-1,2-urazolo)cholest-6-ene-1a,3b-diol [96862-44-1] was prepd. by the treatment of 24-oxocholesta-5,7-diene-1a-,3b-diol [70834-97-8] with 4-phenyl-1,2,4-triazoline-3,5-dione [4233-33-4]. 24-Oxo-25-dehydro-1a-hydroxyvitamin D3 [95420-03-4] was dissolved in coconut oil (7 mg/mL) and encapsulated with a soln. consisting of gelatin, glycerin, Et 4-hydroxybenzoate, and H2O. I pharmacol. studies were described.

Synthesis and biologic activity of a C-ring analog of vitamin D3: biologic and protein binding properties of 11a-hydroxyvitamin D3

Synthesis and biologic activity of a C-ring analog of vitamin D3: biologic and protein binding properties of 11a-hydroxyvitamin D3. Revelle, Larry; Solan, Vishnu; Londowski, James; Bollman, Susan; Kumar, Rajiv (Dep. Med., Mayo Clinic and Found., Rochester, MN 55905, USA). Biochemistry, 23(9), 1983-7 (English) 1984. CODEN: BICHAW. ISSN: 0006-2960. DOCUMENT TYPE: Journal CA Section: 32 (Steroids) Section cross-reference(s): 6 Dehydrogenation of cholesta-5,7-dien-3b-ol acetate by Hg(OAc)2 gave triene I. Protection of the 5,7-diene in I with a 4-phenyl-1,2,4-triazoline-3,5-dione Diels-Alder adduct and then oxidn.In this article, certain chemicals are used. Some of their cas registry numbers are 89321-97-1 and 4233-33-4 of the unprotected 9(11)-olefin gave epoxide II. Reverse Diels-Alder and reductive ring opening of II gave cholesta-5,7-diene-3b,11a-diol (III). Photolysis of III to the previtamin followed by thermal rearrangement gave 11a-hydroxyvitamin D3 (IV). IV increased Ca transport at 500 pmol/rat but failed to increase bone Ca mobilization at 50,000 pmol/rat. IV was slightly less efficient than 25-hydroxyvitamin D3, 24(R),25-dihydrovitamin D3, and 25(S),26-dihydroxyvitamin D3 in displacing radiolabeled 25-hydroxyvitamin D3 from rat plasma vitamin D binding protein. However, IV had greater binding efficiency than 1a-hydroxyvitamin D3, 1,25-dihydroxyvitamin D3, and vitamin D3 under these same conditions. IV had approx. the same efficiency as vitamin D3 in displacing radiolabeled 1,25-dihydroxyvitamin D3 from a chick intestinal cytosol receptor but was less effective than 25-hydroxyvitamin D3, 24(R),25-dihydroxyvitamin D3, 25(S),26-dihydroxyvitamin D3, 1a-hydroxyvitamin D3, and 1,25-dihydroxyvitamin D3. Thus, introduction of an 11a-hydroxyl group into the C-ring of vitamin D3 results in a vitamin analog with moderate vitamin D3 agonist activity in the intestine but no activity with respect to bone Ca mobilization at the levels tested. IV does not have improved binding affinity to the intestinal cytosol receptor when compared to vitamin D3 but has significantly greater binding affinity to plasma vitamin D binding protein than vitamin D3 or 1a-hydroxyvitamin D3, suggesting that an extra hydroxyl group sufficiently removed from the 3b-hydroxyl is important in the binding of vitamin D analogs to vitamin D binding protein. .