7-O-(3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)-ε-rhodomycinone | 76123-96-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 蒽环类药物
• 英文名称: 7-O-(3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)-ε-rhodomycinone
• 英文别名: 7-O-daunosaminyl-ε-rhodomycinone；daunosaminyl ε-rhodomycinone；Rhodomycin D；methyl (1R,2R,4S)-4-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate
• CAS: 76123-96-1
• 化学式: C₂₈H₃₁NO₁₁
• 分子量: 557.554
• InChiKey: CADJZGPRUYOSGU-QWWLYEKJSA-N

物化性质

• 熔点：
  164-166 °C
• 沸点：
  700.0±55.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  40
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  206
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2-(1-methoxy-2-oxoethoxy)propanal 、 7-O-(3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)-ε-rhodomycinone 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以77.7%的产率得到7-O-<2,3,6-Trideoxy-3-<6(S)-hydroxymethyl-2(S)-methoxymorpholin-4-yl>-α-L-lyxo-hexopyranosyl>-ε-rhodomycinone
  参考文献：
  名称：

  Semisynthetic ε-(iso)rhodomycins: a new glycosylation variant and modification reactions

  摘要：

  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.

  DOI：

  10.1016/0008-6215(91)80147-f
• 作为产物：
  描述：

  7-O-(2,3,6-Trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-α-L-lyxo-hexopyranosyl)-ε-rhodomycinone 在 sodium hydroxide 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.5h， 以73.6%的产率得到7-O-(3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)-ε-rhodomycinone
  参考文献：
  名称：

  Semisynthetic ε-(iso)rhodomycins: a new glycosylation variant and modification reactions

  摘要：

  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.

  DOI：

  10.1016/0008-6215(91)80147-f

文献信息

• The synthesis of daunosaminyl ε-rhodomycinone, daunosaminyl 10-epi-ε-rhodomycinone, daunosaminyl ε-pyrromycinone, and 10-descarbomethoxy-ε-pyrromycin
  作者：John M. Essery、Terrence W. Doyle

  DOI：10.1139/v80-295

  日期：1980.9.1

  The epimerisation at C10 of ε-rhodomycinone by aqueous alkali treatment of its 6,7-acetonide is described. Daunosaminyl ε-rhodomycinone and daunosaminyl 10-epi-ε-rhodomycinone were prepared and compared with regard to their antibacterial properties. Daunosaminyl ε-pyrromycinone and 10-descarbomethoxy-ε-pyrromycin were synthesized and their antitumor properties were compared with some naturally occurring glycosides of ε-pyrromycinone.

  通过对6,7-缩醛衍生物进行水性碱处理，描述了ε-罗多霉素酮C10的顺式异构化。制备了达诺霉胺基ε-罗多霉素酮和达诺霉胺基10-顺式异构体ε-罗多霉素酮，并比较了它们的抗菌性能。合成了达诺霉胺基ε-吡啶霉素酮和10-脱羧甲氧基-ε-吡啶霉素，并将它们的抗肿瘤性能与一些天然产生的ε-吡啶霉素酮糖苷进行了比较。
• Re-Exploring the Anthracycline Chemical Space for Better Anti-Cancer Compounds
  作者：Merle A. van Gelder、Sabina Y. van der Zanden、Merijn B. L. Vriends、Roos A. Wagensveld、Gijsbert A. van der Marel、Jeroen D. C. Codée、Herman S. Overkleeft、Dennis P. A. Wander、Jacques J. C. Neefjes

  DOI：10.1021/acs.jmedchem.3c00853

  日期：2023.8.24

  capacity to induce DNA- and chromatin damage. This coherent set of data allowed us to deduce a few guidelines on anthracycline design, as well as discover novel, highly potent anthracyclines that may be better tolerated by patients.

  蒽环类抗癌药物在临床上广泛用于治疗多种癌症。它们会产生 DNA 双链断裂，但最近引入染色质损伤的诱导作为抗癌活性的另一个主要决定因素。这两个事件的结合导致了所报告的副作用。虽然我们对蒽环类药物的结构-活性关系的了解有所提高，但许多结构变异仍然没有得到很好的探索。因此，我们在此报告了一组不同的蒽环类药物的制备方法，这些蒽环类药物在糖部分、胺烷基化模式、糖链和糖苷配基方面存在差异。我们评估了相关人类癌细胞系的体外细胞毒性，以及诱导 DNA 和染色质损伤的能力。这组连贯的数据使我们能够推断出一些关于蒽环类药物设计的指南，并发现患者可能更好耐受的新型高效蒽环类药物。
• KOLAR, CENEK;KNEISSL, GUNTHER;KNODLER, URSULA;DEHMEL, KONRAD, CARBOHYDR. RES., 209,(1991) C. 89-100
  作者：KOLAR, CENEK、KNEISSL, GUNTHER、KNODLER, URSULA、DEHMEL, KONRAD

  DOI：——

  日期：——
• 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.