4-bromo-4'-demethylepipodophyllotoxin derivatives

Details 4-bromo-4'-demethylepipodophyllotoxin derivatives 4-bromo-4'-demethylepipodophyllotoxin derivatives

1989-09-19

1991-10-29

Brown, Johnnie R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 172, 536 175, 536 176, 536 179, 536 181, 549298, C07H 1104, C07H 1500

Patent

active

050617915

ABSTRACT:
Preparation of 4-bromo-4'-demethylepipodophyllotoxin by reacting podophyllotoxin with hydrogen bromide at about -20.degree. C. New antitumor compounds of the formula: ##STR1## wherein R is A--(CH.sub.2).sub.n [A(CH.sub.2).sub.n ].sub.m (CHAH).sub.p --Q or ##STR2## each A, independently, is O, S, SO or SO.sub.2 ; n is an integer from 1 to 6, except when n and p, taken together, are zero, then n is 2 to 6; n is 0, 1, or 2; p is 0, 1, or 2; Q is H, alkyl from 1 to 6 carbon atoms which may be substituted with an NR.sub.1 R.sub.2 group wherein each R.sub.1 and R.sub.2, independently, is selected from the group of H, alkyl containing 1 to 6 carbon atoms which may be substituted with OH, alkanoyl containing 1 to 6 carbon atoms, or R.sub.1 and R.sub.2 are interconnected and together with the N to which they are connected form an N heterocyclic ring of 5 to 6 carbon atoms; R.sub.3 is hydrogen, and R.sub.4 is an alkyl, alkenyl, cycloalkyl, 2-furyl, 2-thienyl, aryl, aralkyl, and aralkenyl, wherein the aromatic ring may optionally be substituted, preferentially by one or more of hydroxyl, alkyl, alkoxy, nitro, or halogen radicals. R.sub.3 and R.sub.4 together with the carbon atom to which they are attached may form a saturated cycloaliphatic ring having 5 or 6 carbon atoms; each X and Y, individually, is OH or NR.sub.6 R.sub.7 wherein R.sub.6 and R.sub.7, independently, is H, alkyl containing 1 to 6 carbon atoms or one of R.sub.6 and R.sub.7 is acyl; and Z is ##STR3## Novel process for the preparation of the novel compounds or analogs thereof having advantageous stereoselection using alkyltin thiolates, preferably with selected solvents.

REFERENCES:
patent: 3524844 (1970-08-01), Keller-Juslen et al.
patent: 4556654 (1985-12-01), Showalter et al.
patent: 4564675 (1986-01-01), Kurabayashi et al.
patent: 4604390 (1986-08-01), Elslager et al.
patent: 4609644 (1986-09-01), Nemec
patent: 4912204 (1990-03-01), Ohnuma et al.
Synthesis and Biological Evaluation of Antitumor Analogues of Podophyllotoxin and .alpha.-Peltatin (1986) Lee Scott Thurston-pp. 42, 45, 46.
Studies on Lignan Lactone Antitumor Agents, I, Saito et al., Chem. Pharm. Bull. 34(9), 3733-3740 (1986).
Studies on Lignan Lactone Antitumor Agents, II, Saito et al., Chem. Pharm. Bull. 34(9), 3741-3746 (1986).
Derwent Abstract No. 89-153953/21 for J0 1093-589-A.
Journal of Natural Products, Kuo-Hsiung Lee et al., vol. 52, No. 3, pp. 606-613, May-Jun. 1989.
Studies on Lignan Lactone Antitumor Agents. V. Saito et al., Bull. Chem. Soc. Jpn., vol. 61, No. 2, 2493-2497 (1988).
Derwent Abstract No. 88-068417/10 for J6 3023-884-A.

Affiliated with

Also associated with

Rating

4-bromo-4'-demethylepipodophyllotoxin derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with 4-bromo-4'-demethylepipodophyllotoxin derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 4-bromo-4'-demethylepipodophyllotoxin derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1401459