Marcellomycin → HCID 86736131, Verbindung

HRID 972050Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 972050
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

Komponenten

5

Edukt 4

HCID 107861MarcellomycinHCID 120369Methyl 2-ethyl-5,7,10-trihydroxy-6,11-dioxo-6,11-dihydrotetracene-1-carboxylateHCID 44559595MusettamycinHCID 44584031HCID 44584031, Verbindung

Produkt 1

HCID 86736131HCID 86736131, Verbindung

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c81e579c3ace45618e84e4a75c6b2fa5
Quelldatensatz
uspto-grants-1979_07
Patentnummer
US04162938

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