7-O-<3,4,6-tri-O-acetyl-2-deoxy-2-<(trifluoroacetyl)amino>-β-D-glucosyl>-9-deacetyl-9-(2,2-dimethyl-4-methoxydioxolan-4-yl)daunomycinone | 79974-26-8

• 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-<3,4,6-tri-O-acetyl-2-deoxy-2-<(trifluoroacetyl)amino>-β-D-glucosyl>-9-deacetyl-9-(2,2-dimethyl-4-methoxydioxolan-4-yl)daunomycinone
• CAS: 79974-26-8
• 化学式: C₃₉H₄₂F₃NO₁₈
• 分子量: 869.754
• InChiKey: UCLLCIVAJKIOBT-XAPQPUJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  61.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  258.21
• 氢给体数：
  4.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  7-O-<3,4,6-tri-O-acetyl-2-deoxy-2-<(trifluoroacetyl)amino>-β-D-glucosyl>-9-deacetyl-9-(2,2-dimethyl-4-methoxydioxolan-4-yl)daunomycinone 在 盐酸 、 sodium hydroxide 作用下， 生成 3-Glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-tetracenyl 2-amino-2-deoxy-beta-D-glucopyranoside
  参考文献：
  名称：

  Adriamycin analogs. 1. Preparation and antitumor evaluation of 7-O-(.beta.-D-glucosaminyl)daunomycinone and 7-O-(.beta.-D-glucosaminyl)adriamycinone and their N-trifluoroacetyl derivatives

  摘要：

  The title compounds were prepared by Koenigs-Knorr condensation of 3,4,6-tri-O-acetyl-2-deoxy-2-[(trifluoroacetyl)amino]-alpha-D-glucopyranosyl bromide with daunomycinone or a side-chain protected adraimycinone, followed by selective hydrolysis of blocking groups. Despite poor complexation with DNA and weak growth-inhibitory properties in vitro, the glucosaminyl analogues of the antitumor antibiotics daunorubicin and adriamycin, at their optimal (highest nontoxic) doses, exhibited antileukemic activity equivalent to that of adriamycin against a usually drug-refractory mouse leukemia model system (L1210) in vivo. These findings, together with other data from these laboratories, continue to support the hypothesis that the mechanism of action of adriamycin and related agents cannot be due exclusively to DNA binding, as has earlier been believed.

  DOI：

  10.1021/jm00343a005
• 作为产物：
  描述：

  9-deacetyl-9-(2,2-dimethyl-4-methoxydioxolan-4-yl)daunomycinone 、 3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucospyranosyl bromide 在 3 A molecular sieve 、 mercury dibromide 、 mercury(II) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以69.4%的产率得到7-O-<3,4,6-tri-O-acetyl-2-deoxy-2-<(trifluoroacetyl)amino>-β-D-glucosyl>-9-deacetyl-9-(2,2-dimethyl-4-methoxydioxolan-4-yl)daunomycinone
  参考文献：
  名称：

  Adriamycin analogs. 1. Preparation and antitumor evaluation of 7-O-(.beta.-D-glucosaminyl)daunomycinone and 7-O-(.beta.-D-glucosaminyl)adriamycinone and their N-trifluoroacetyl derivatives

  摘要：

  The title compounds were prepared by Koenigs-Knorr condensation of 3,4,6-tri-O-acetyl-2-deoxy-2-[(trifluoroacetyl)amino]-alpha-D-glucopyranosyl bromide with daunomycinone or a side-chain protected adraimycinone, followed by selective hydrolysis of blocking groups. Despite poor complexation with DNA and weak growth-inhibitory properties in vitro, the glucosaminyl analogues of the antitumor antibiotics daunorubicin and adriamycin, at their optimal (highest nontoxic) doses, exhibited antileukemic activity equivalent to that of adriamycin against a usually drug-refractory mouse leukemia model system (L1210) in vivo. These findings, together with other data from these laboratories, continue to support the hypothesis that the mechanism of action of adriamycin and related agents cannot be due exclusively to DNA binding, as has earlier been believed.

  DOI：

  10.1021/jm00343a005