Anthracycline Chemistry and Biology I: Biological Occurence by Hartmut Laatsch, Serge Fotso (auth.), Karsten Krohn (eds.)

By Hartmut Laatsch, Serge Fotso (auth.), Karsten Krohn (eds.)

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Fotso 38a 38b 38c 38d 38e 38f 38g 38h 38i 38j 38k 38l R1 R2 R3 Me Me Me Me H H eNgm Rha Me Me Me Me H H H H H H H 3-mRha DauA1 DauA2 NfDau NfDau COMe Et Me COCH2 OH COMe Me Me Me COMe COMe COMe CH(OH)Me for the first time in 1964 [60] and 1967 [61] by Farmitalia (now Pfizer) from a mutant strain of Streptomyces peuceticus, and approved by the FDA in 1974 for commercial use. Daunomycin (1a) was initially reported to exhibit strong activity against a variety of experimental tumors. Nowadays it is mostly used against acute leukemia.

48 H. Laatsch · S. Fotso Dihydrocinerubin-A β-Pyrromycin RDC MA-144-G2 Spartanamicin B; cinerubin A Taurimycin A 1-Hydroxyauramycin A Rudolfomycin; rudolphomycin Rhodirubin A; trypanomycin A2 Rhodirubin B; marcellomycin M2 Cinerubin R Nocardicyclin A Nocardicyclin B Nothramicin YL-01641P-A1 YL-01641P-A2 1,4,11-Trihydroxyanthracyclines α2-Rhodomycinone Alldimycin C; alpharubicin I α2-Rhodomycinone RDC 1-Hydroxyserirubicin Alldimycin A; violamycin A2 Alldimycin B; α2-rhodomycin-Roa2 α2-Rhodomycin A Violamycin B2 δ-Rhodomycinone 191 192 193 194 195 196 197 198 199 200 201 202 203 204 205 206 207 208 209 210 211 212 213 214 Name Fo no Table 5 (continued) OH OH OH OH OH OH OH OH OH H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H R6 OH OH OH OH OH OH OH OH OH H H H H H H H H H OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OMe OH OMe OH R2 R3 R4 OH H OH H OH H OH H OH H OH H OH H OH H OH H OH H OMe H OMe H OMe H OH H OH H R1 OH OH OH Roa-dFuc=CinA Roa Roa Roa-dFuc-CinA Roa-dFuc-Rho OH Roa-dFuc-Ami Roa-dFuc-CinA Roa-dFuc-d-CinA Roa-dFuc-CinA Roa-dFuc-CinA Roa-dFuc-CinA Roa-dFuc-Rdm Roa-dFuc-Rho Roa-Rho2 Roa-Rho-Acu B AB B 2,4-dRha 2,4-dRha R7 α H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H αOMe αOMe OMe H H R7 β R8 Et Et Et Et Et Et Et Et Et Et Et Et Et Et Me Et Et Et Et Me Me Me Me/OAc Me R9 OH Roa Roa-dFuc-CinA Roa-dFuc=CinA OH Roa OH OH COOMe COOMe OH COOMe COOMe COOMe COOMe COOMe COOMe COOMe COOMe CO CO OH S2 S2 R10 OH OH OH OH OH OH OH OH OH H H H H H H H H H H H H H H H [16, 17, 173] [80] [90] [107] [80] [80] [91] [78, 214, 215] [12, 13, 16, 17, 152] [94] [76, 77] [94] [169, 170] [168] [27, 28] [166] [94] [91, 171] [164, 172] [54] [54] [54] [115] [115] R11 Refs.

They are 1,6,11-trihydroxyanthracycline derivatives. While nogalamine is 1,2-connected with the chromophore in 42 and 43, the five respinomycins A1 , A2 , B, C, and D (44a–e) from Streptomyces xanthocidicus and Streptomyces sp. RK-483 [87, 88] are 4,6-dihydroxyanthracycline 44a 44b 44c 44d 44e R1 R2 R3 Avi-Vin Avi-Vin H H Dec-Vin Me Me H Me Me O-Vin H O-Vin O-Vin O-Vin Naturally Occurring Anthracyclines 31 derivatives and surprise by a 3,4-attached nogalamine and additional methoxy groups at C-8; stereochemical details are still unknown.

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