Antitumor and antibacterial substituted disulfide derivatives prepared from compounds possessing a methlytrithio group

A process for producing a substituted disulfide of formula Q--Sp--SS--W from a compound of formula CH.sub.3 SSS--W and designated as LL-E33288.alpha..sub.1 -Br, .alpha..sub.1 -I, .alpha..sub.2 -Br, .alpha..sub.2 -I, .alpha..sub.3 -Br, .alpha..sub.3 -I, .alpha..sub.4 -Br, .beta..sub.1 -Br, .beta..sub.1 -I, .beta..sub.2 -Br, .beta..sub.2 -I, .gamma..sub.1 -Br, .gamma..sub.1 -I, .delta..sub.1 I, the iodo or bromo pseudoaglycones, their dihydro or N-acyl counterparts, BBM-1675, FR-900405, FR-900406, PD114759, PD 115028, CL-1577A, CL-1577B, CL-1577D, CL-1577E, CL-1724, or their N-acetyl counterparts, wherein ##STR16## R.sub.5 is CH.sub.3, C.sub.2 H.sub.5, or (CH.sub.3).sub.2 CH;

• R.sub.8 is OH and R.sub.9 is H, or R.sub.8 and R.sub.9 together is a carbonyl group;
• X is an iodine or bromine atom;
• R.sub.5 is a hydrogen or the group RCO, wherein R is hydrogen or a branched or unbranched alkyl (C.sub.1 -C.sub.10) or alkylene (C.sub.1 -C.sub.10) group, a C.sub.6 -C.sub.11 aryl group, or C.sub.6 -C.sub.11 aryl-alkyl (C.sub.1 -C.sub.5) group or 2- or 3-furyl, 2- or 3-thienyl, 2- or 3-(N-methylpyrrolyl), 2-, 3-, or 4-pyridyl, 2-, 4-, or 5-(N-methylimidazolyl), 2-, 4- or 5-oxazolyl, 2-, 4-, 5- or 6-pyrimidinyl, 2-, 3-, 4-, 5-, 6-, 7- or 8-quinolyl, or 1-, 3-, 4-, 5-, 6-, 7- or 8-isoquinolyl heterocycles wherein the aryl groups are optionally substituted by one or more hydroxy, amino, carboxy, halo, nitro, lower (C.sub.1 -C.sub.3) alkoxy, or lower (C.sub.1 -C.sub.5) thioalkoxy groups;
• Sp is straight or branched-chain divalent or trivalent (C.sub.1 -C.sub.18) radicals, divalent or trivalent C.sub.6 -C.sub.11 aryl or heteroaryl radicals, divalent or trivalent (C.sub.3 -C.sub.18) cycloalkyl radicals, divalent or trivalent aryl- or heteroaryl-alkyl (C.sub.4 -C.sub.18) radicals, divalent or trivalent cycloalkyl-alkyl (C.sub.4 -C.sub.18) radicals, or divalent or trivalent (C.sub.2 -C.sub.18) unsaturated alkyl radicals wherein heteroaryl is furyl, thienyl, N-methylpyrrolyl, pyridyl, N-methylimidazolyl, oxazolyl, pyrimidinyl, quinolyl, isoquinolyl, N-methylcarbazolyl, aminocourmarinyl, or phenazinyl;
• and wherein if Sp is a trivalent radical, it can be additionally substituted by amino, C.sub.1 -C.sub.10 alkylamino, C.sub.6 -C.sub.11 arylamino, heteroarylamino, carboxyl, lower alkoxy, hydroxy, thiol, or lower alkylthio groups;
• Q is hydrogen, halogen, amino, C.sub.1 -C.sub.10 alkylamino, C.sub.1 -C.sub.10 dialkylamino, piperidino, pyrrolidino, piperazine, carboxyl, carboxaldehyde, lower alkoxy, hydroxy, thiol, lower alkyldicarboxyl, --CONHNH.sub.2, --NHCONHNH.sub.2, --CSNHNH.sub.2, --NHCSNHNH.sub.2, or --ONH.sub.2 ;
• with the proviso that when Sp is ethylidine, Q cannot be hydrogen;
• which comprises reacting a methyl trisulfide antitumor antibiotic from those of the above with Q--Sp--SH, wherein Q and Sp are as hereinabove defined, in acetonitrile or a combination of acetonitrile and tetrahydrofuran or acetonitrile and dimethylformamide, at a temperature of between -20.degree. to about +40.degree. C., for a period of from one hour to six days.