7-O-(4-O-p-Nitrobenzoyl-2,3,6-trideoxy-3-trifluoroacetylamido-α-L-arabino-hexopyranosyl)-ε-isorhodomycinone | 130320-86-4

• 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-(4-O-p-Nitrobenzoyl-2,3,6-trideoxy-3-trifluoroacetylamido-α-L-arabino-hexopyranosyl)-ε-isorhodomycinone
• 英文别名: 7-O-(2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-α-L-arabino-hexopyranosyl)-ε-iso-rhodomycinone；7-O-acosaminyl-ε-isorhodomycinone；methyl (1R,2R,4S)-2-ethyl-2,5,7,10,12-pentahydroxy-4-[(2R,4S,5R,6S)-6-methyl-5-(4-nitrobenzoyl)oxy-4-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]oxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate
• CAS: 130320-86-4
• 化学式: C₃₇H₃₃F₃N₂O₁₆
• 分子量: 818.668
• InChiKey: IRLFYKMDLLIFQA-XAOXUXBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  58
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  281
• 氢给体数：
  6
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  7-O-(4-O-p-Nitrobenzoyl-2,3,6-trideoxy-3-trifluoroacetylamido-α-L-arabino-hexopyranosyl)-ε-isorhodomycinone 在 sodium hydroxide 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.5h， 以72%的产率得到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
• 作为产物：
  描述：

  epsilon-异紫红霉酮 、 2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-(trifluoroacetamido)-L-arabino-hex-1-enitol 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 2.0h， 以76%的产率得到7-O-(4-O-p-Nitrobenzoyl-2,3,6-trideoxy-3-trifluoroacetylamido-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。
• KOLAR, CENEK;DEHMEL, KONRAD;KRAEMER, HANS-PETER, CARBOHYDR. RES., 201,(1990) N, C. 249-259
  作者：KOLAR, CENEK、DEHMEL, KONRAD、KRAEMER, HANS-PETER

  DOI：——

  日期：——
• Semisynthetic ε-isorhodomycins: Their synthesis using glycals and their structure-activity relationship
  作者：Cenek Kolar、Konrad Dehmel、Hans-Peter Kraemer

  DOI：10.1016/0008-6215(90)84241-l

  日期：1990.7

  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.