7,9-Bis-O-(4-O-p-nitrobenzoyl-2,3,6-trideoxy-3-trifluoroacetylamido-α-L-lyxo-hexopyranosyl)-ε-isorhodomycinone | 130223-42-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 7,9-Bis-O-(4-O-p-nitrobenzoyl-2,3,6-trideoxy-3-trifluoroacetylamido-α-L-lyxo-hexopyranosyl)-ε-isorhodomycinone
• 英文别名: 7,9-Bis-O-(2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-α-L-lyxo-hexopyranosyl)-ε-isorhodomycinone；methyl (1R,2R,4S)-2-ethyl-5,7,10,12-tetrahydroxy-2,4-bis[[(2S,4S,5S,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: 130223-42-6
• 化学式: C₅₂H₄₆F₆N₄O₂₂
• 分子量: 1192.94
• InChiKey: GFYFCLNHUMZCBE-YVXHUMCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  84.0
• 可旋转键数：
  14.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  375.36
• 氢给体数：
  6.0
• 氢受体数：
  22.0

反应信息

• 作为产物：
  描述：

  epsilon-异紫红霉酮 、 1-O-tert-butyldimethylsilyl 4-O-p-nitrobenzoyl-2,3,6-trideoxy-3-trifluoroacetamido-β-L-lyxo-hexopyranoside 生成 7,9-Bis-O-(4-O-p-nitrobenzoyl-2,3,6-trideoxy-3-trifluoroacetylamido-α-L-lyxo-hexopyranosyl)-ε-isorhodomycinone
  参考文献：
  名称：

  KOLAR, CENEK;KNEISSL, GUNTHER;KNODLER, URSULA;DEHMEL, KONRAD, CARBOHYDR. RES., 209,(1991) C. 89-100

  摘要：

  DOI：

文献信息

• 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.
• 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.
• 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：——