Acetic Acid → 98328-00-8

HRID 1737076Notes

Reaction equation

[CH3:1][C:2]1[C:6]2[C:7]34[C:12](=[CH:13][C:14](=[O:15])[C:5]=2[NH:4][CH:3]=1)[N:11]([C:16]([C:18]1[NH:26][C:25]2[C:20](=[C:21]5[CH2:32][CH2:31][N:30]([C:33]([C:35]6[NH:43][C:42]7[C:37](=[C:38]8[CH2:49][CH2:48][N:47]([C:50]([NH2:52])=[O:51])[C:39]8=[C:40]([OH:46])[C:41]=7[O:44][CH3:45])[CH:36]=6)=[O:34])[C:22]5=[C:23]([OH:29])[C:24]=2[O:27][CH3:28])[CH:19]=1)=[O:17])[CH2:10][CH:9]3[CH2:8]4.[C:53]([OH:56])(=[O:55])[CH3:54]>>[C:53]([O:56][CH2:8][CH:9]1[CH2:10][N:11]([C:16]([C:18]2[NH:26][C:25]3[C:24]([O:27][CH3:28])=[C:23]([OH:29])[C:22]4[N:30]([C:33]([C:35]5[NH:43][C:42]6[C:41]([O:44][CH3:45])=[C:40]([OH:46])[C:39]7[N:47]([C:50]([NH2:52])=[O:51])[CH2:48][CH2:49][C:38]=7[C:37]=6[CH:36]=5)=[O:34])[CH2:31][CH2:32][C:21]=4[C:20]=3[CH:19]=2)=[O:17])[C:12]2[CH:13]=[C:14]([OH:15])[C:5]3[NH:4][CH:3]=[C:2]([CH3:1])[C:6]=3[C:7]1=2)(=[O:55])[CH3:54]

Participants

Reactant 2

HCID 176Acetic Acid2×

HCID 73240CC-1065

Product 1

HCID 16366898328-00-8

Procedure

In The Journal of Antibiotics, 1985, 38, 746, D. G. Martin et al reported that acetic acid adds across the spirocyclopropylcyclohexadienyl (SCPCH) system of CC-1065 to produce the phenolic, acetic acid product (AAP), 7-[[7-[[1-[(acetyloxy)methyl]-1,6-dihydro-5-hydroxy-8-methylbenzo[1,2-b:4,3-b']dipyrrol-3(2H)-yl]carbonyl]-1,6-dihydro-4-hydroxy-5-methoxybenzo[1,2-b:4,3-b']-dipyrrol-3(2H)-yl]carbonyl]-1,6-dihydro-4-hydroxy-5-methoxy-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxamide. AAP was tested in vitro and in vivo and found to be less potent than CC-1065 by a factor of 103 to 104 depending upon the particular test system and therefore tended to divert attention from adducts of the SCPCH system as useful antitumor agents or as prodrugs to CC-1065 analogs.

Sources & evidence

ORD record: ord-3b71cf52d4b341f2b4b29a7bc27c147f
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05541339

Reaction notes

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