Marcellomycin → HCID 86736131, compound

HRID 972050Notes

Reaction equation

HRID 972050 reaction equation
CCC1C=CC2C(=CC3C(=O)C4C(=C(O)C=CC=4O)C(=O)C=3C=2O)C=1C(OC)=O.CC[C@]1(O)[C@H](C(OC)=O)C2C=C3C(=O)C4C(O)=CC=C(O)C=4C(=O)C3=C(O)C=2[C@@H](O[C@@H]2O[C@@H](C)[C@@H](O[C@@H]3O[C@@H](C)[C@@H](O)[C@@H](O)C3)[C@@H](N(C)C)C2)C1.[CH3:81][CH2:82][C@:83]1([OH:140])[C@H:105]([C:106]([O:108][CH3:109])=[O:107])[C:87]2[CH:88]=[C:89]3[C:101](=[O:102])[C:100]4[C:99]([OH:103])=[CH:98][CH:97]=[C:96]([OH:104])[C:95]=4[C:93](=[O:94])[C:90]3=[C:91]([OH:92])[C:86]=2[C@@H:85]([O:110][C@@H:111]2[O:116][C@@H:115]([CH3:117])[C@@H:114]([O:118][C@@H:119]3[O:124][C@@H:123]([CH3:125])[C@@H:122]([O:126][C@@H:127]4[O:132][C@@H:131]([CH3:133])[C@@H:130]([OH:134])[C@@H:129]([OH:135])[CH2:128]4)[C@@H:121]([OH:136])[CH2:120]3)[C@@H:113]([N:137]([CH3:139])[CH3:138])[CH2:112]2)[CH2:84]1.[CH3:141][CH2:142][C@:143]1([OH:200])[C@H:165]([C:166]([O:168][CH3:169])=[O:167])[C:147]2[CH:148]=[C:149]3[C:161](=[O:162])[C:160]4[C:159]([OH:163])=[CH:158][CH:157]=[C:156]([OH:164])[C:155]=4[C:153](=[O:154])[C:150]3=[C:151]([OH:152])[C:146]=2[C@@H:145]([O:170][C@@H:171]2[O:176][C@H:175]([CH3:177])[C@@H:174]([O:178][C@@H:179]3[O:184][C@H:183]([CH3:185])[C@@H:182]([O:186][C@@H:187]4[O:193][C@@H:192]([CH3:194])[C:190](=[O:191])[CH:189]=[C:188]4[NH2:195])[C@@H:181]([OH:196])[CH2:180]3)[C@@H:173]([N:197]([CH3:199])[CH3:198])[CH2:172]2)[CH2:144]1>>[CH3:141][CH2:142][C@:143]1([OH:200])[C@H:165]([C:166]([O:168][CH3:169])=[O:167])[C:147]2[CH:148]=[C:149]3[C:161](=[O:162])[C:160]4[C:159]([OH:163])=[CH:158][CH:157]=[C:156]([OH:164])[C:155]=4[C:153](=[O:154])[C:150]3=[C:151]([OH:152])[C:146]=2[C@@H:145]([O:170][C@@H:171]2[O:176][C@H:175]([CH3:177])[C@@H:174]([O:178][C@@H:179]3[O:184][C@H:183]([CH3:185])[C@@H:182]([O:186][C@@H:187]4[O:193][C@@H:192]([CH3:194])[C:190](=[O:191])[CH:189]=[C:188]4[NH2:195])[C@@H:181]([OH:196])[CH2:180]3)[C@@H:173]([N:197]([CH3:199])[CH3:198])[CH2:172]2)[CH2:144]1.[CH3:81][CH2:82][C@:83]1([OH:140])[C@H:105]([C:106]([O:108][CH3:109])=[O:107])[C:87]2[CH:88]=[C:89]3[C:101](=[O:102])[C:100]4[C:99]([OH:103])=[CH:98][CH:97]=[C:96]([OH:104])[C:95]=4[C:93](=[O:94])[C:90]3=[C:91]([OH:92])[C:86]=2[C@@H:85]([O:110][C@@H:111]2[O:116][C@@H:115]([CH3:117])[C@@H:114]([O:118][C@@H:119]3[O:124][C@@H:123]([CH3:125])[C@@H:122]([O:126][C@@H:127]4[O:132][C@@H:131]([CH3:133])[C@@H:130]([OH:134])[C@@H:129]([OH:135])[CH2:128]4)[C@@H:121]([OH:136])[CH2:120]3)[C@@H:113]([N:137]([CH3:139])[CH3:138])[CH2:112]2)[CH2:84]1

Participants

5

Reactant 4

HCID 107861MarcellomycinHCID 120369Methyl 2-ethyl-5,7,10-trihydroxy-6,11-dioxo-6,11-dihydrotetracene-1-carboxylateHCID 4455959563710-09-8HCID 44584031HCID 44584031, compound

Product 1

HCID 86736131HCID 86736131, compound

Procedure

The solids obtained were chromatographed on Brinkmann 60F254 silica gel thin layer plates using an 80:20 toluene:methanol solvent system. The first band to elute was shown by thin layer chromatography to be a complex inactive mixture. The second band gave a characteristic pinkish red zone at about Rf =0.75. This fraction was also inactive and was found to comprise mainly η-pyrromycinone. The third fraction to elute gave a single zone with Rf ~0.3. This was determined to be musettamycin and was highly active when tested on both the L1210 and P388 mouse leukemia systems. The final band to elute gave a zone of Rf ~0.3 and comprised mainly marcellomycin but also a minor proportion of rudolphomycin. This component exhibited high activity when tested on L1210 and P388 mouse leukemia systems.

Workup

  1. customThe solids obtained
  2. customwere chromatographed on Brinkmann 60F254 silica gel thin layer plates
  3. washThe first band to elute
  4. customThe second band gave a characteristic pinkish red zone at about Rf =0.75
  5. washThe third fraction to elute
  6. customgave a single zone with Rf ~0.3
  7. washThe final band to elute
  8. customgave a zone of Rf ~0.3

Sources & evidence

ORD record
ord-c81e579c3ace45618e84e4a75c6b2fa5
Source dataset
uspto-grants-1979_07
Patent number
US04162938

Reaction notes

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