epsilon-异紫红霉酮 | 21204-32-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 中文名称: epsilon-异紫红霉酮
• 英文名称: ε-iso-rhodomycinone
• 英文别名: ε-Isorhodomycinone；ε-Isorhodomycinon；(1R)-2c-ethyl-2t,4t,5,7,10,12-hexahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1r-carboxylic acid methyl ester；(1R)-2c-Aethyl-2t,4t,5,7,10,12-hexahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1r-carbonsaeure-methylester；ε-Iso-rhodomycinon；methyl (1R,2R,4S)-2-ethyl-2,4,5,7,10,12-hexahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate
• CAS: 21204-32-0
• 化学式: C₂₂H₂₀O₁₀
• 分子量: 444.395
• InChiKey: CIXXANXJCSBTFL-ACHUOPHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  182
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  epsilon-异紫红霉酮 在 sodium hydroxide 、 sodium tetrahydroborate 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 硼酸 、 nickel dichloride 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 、 丙酮 为溶剂， 反应 23.0h， 生成 7-O-(3-Amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-ε-isorhodomycinone
  参考文献：
  名称：

  Semisynthetic ε-isorhodomycins: Their synthesis using glycals and their structure-activity relationship

  摘要：

  Syntheses and structure-activity relationships of 7-O-(3-amino-2,3,6-trideoxy-a-L-lyxo- (18), -L-arabino- (20) and -L-ribo- hexopyranosyl)-epsilon-isorhodomycins (25) and their 3'-dimethylamino derivatives 22, 23 and 26 are described. Condensation (trimethylsilyl triflate, molecular sieves 4 A, 10:1 dichloromethane-acetone, -15 degrees) of epsilon-isorhodomycinone (epsilon-isoRMN, 6) with 1,5-anhydro-4-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxo- (5) -L-arabino- (9) or -L-ribo-hex-l-enitols (10) afforded mainly the 7-O-a-glycosyl-epsilon-isoRMNs 7, 11, and 12. Similar glycosylation of 6 with 1,5-anhydro-3-azido-4-O-p-nitrobenzoyl-2,3,6-trideoxy-L-arabino-hex-1-++ +enitol (15) yielded a-glycoside 16. Removal (M NaOH) of the p-nitrobenzoyl and trifluoroacetyl groups from 7, 11, and 12 gave the 7-O-(3-amino-2,3,6-trideoxy-a-L-hexopyranosyl)-epsilon-isoRMNs 18, 20, and 25. Reductive alkylation (CH2O, NaCNBH3) of these products afforded the 3'-N,N-dimethyl analogues 22, 23, and 26. The cytotoxic effect (IC50) of the semisynthetic epsilon-isorhodomycins was tested in vitro in leukemia cell line L1210.

  DOI：

  10.1016/0008-6215(90)84241-l

文献信息

• A short and efficient transformation of rhamnose into activated daunosamine, acosamine, ristosamine and epi-daunosamine derivatives, and synthesis of an anthracycline antibiotic acosaminyl-ε-iso-rhodomycinone
  作者：Bernd Renneberg、Yue-Ming Li、Hartmut Laatsch、Heinz-Herbert Fiebig

  DOI：10.1016/s0008-6215(00)00257-3

  日期：2000.12

  constituents of most anthracycline antitumour antibiotics. For an investigation of structure-activity relationships, the four diastereomeric amino sugars daunosamine, acosamine, ristosamine, and epi-daunosamine were synthesised in short and efficient routes starting from commercially available rhamnose. Several glycosyl donors were provided and their use was exemplified in the synthesis of acosaminyl-e

  3-氨基-2,3,6-三甲氧基己基吡喃糖是大多数蒽环类抗肿瘤抗生素的重要组成部分。为了研究结构-活性关系，从市售鼠李糖开始以短而有效的途径合成了四种非对映体氨基糖柔红胺，二十二胺，香豆胺和表柔红胺。提供了几种糖基供体，其用途在合成氨糖基-ε-异二十四烯酮中得到了例证。
• Semisynthetic ε-(iso)rhodomycins: a new glycosylation variant and modification reactions
  作者：Cenek Kolar、Günther Kneissl、Ursula Knödler、Konrad Dehmel

  DOI：10.1016/0008-6215(91)80147-f

  日期：1991.1

  Synthesis of 7-O-(3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)-e-(iso)rhodomycinones 16 and 17, and their 3'-morpholino derivatives are described. Glycosylation (trimethylsilyl triflate, 10:1 dichloro-methane-acetone, -35-degrees-) of 1-O-tert-butyldimethylsilyl-2,3,6-trideoxy-4-O-p-nitrobenzoyl-?? 3-trifluorace-tamido-beta-L-lyxo-hexopyranose (4) with e-rhodomycinone (e-RMN, 5) or e-isorhodomycinone (e-isoRMN, 6) afforded 7-O-alpha-glycosyl-e-RMN (9) and -e-isoRMN (12) in high yield. The glycosyl donors 2,3,6-trideoxy-4-O-p-nitrobenzoly-3-trifluoroacetamido-L-lyxo-hexopyranose (2) or its 1-O-trimethylsilylated alpha-anomer 3 were less suitable for the glycosylation of these aglycons. Saponification of 9 and 12 provided 16 and 17, respectively, which reacted with various 2,2'-oxydiacetaldehydes under conditions of reductive alkylation to give 3'-morpholinyl-e-(iso)rhodomycins.
• Synthesis and cytotoxic activity of new 4′-deoxy C-3′-homo anthracyclines
  作者：J.-P. Gesson、J.-C. Jacquesy、B. Renoux

  DOI：10.1016/s0040-4020(01)80827-9

  日期：1994.1

  Starting from (S)-propylene oxide, the protected C-3 homolog of 4-deoxy daunosamine 11 is prepared in 4 steps. Acid catalyzed glycosidation of anthracyclinones such as daunosamine, beta-rhodomycinone and epsilon-isorhodomycinone with 11 affords new analogs of anthracyclines demonstrating strong cytotoxicity against L1210 leukemia, A-549 and HT-29 tumor cells.
• Klaffke, Werner; Pudlo, Peter; Springer, Dirk, Liebigs Annalen der Chemie, 1991, # 6, p. 509 - 512
  作者：Klaffke, Werner、Pudlo, Peter、Springer, Dirk、Thiem, Joachim

  DOI：——

  日期：——
• KOLAR, CENEK;PAAL, MICHAEL;HERMENTIN, PETER;KRAEMER, HANS PETER
  作者：KOLAR, CENEK、PAAL, MICHAEL、HERMENTIN, PETER、KRAEMER, HANS PETER

  DOI：——

  日期：——