2,7-diaminomitosene 1-(9-β-D-ribofuranosyl-6-mercaptopurine) | 132019-19-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2,7-diaminomitosene 1-(9-β-D-ribofuranosyl-6-mercaptopurine)
• 英文别名: [2,6-diamino-3-[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]sulfanyl-7-methyl-5,8-dioxo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-4-yl]methyl carbamate
• CAS: 132019-19-3
• 化学式: C₂₄H₂₆N₈O₈S
• 分子量: 586.585
• InChiKey: WZFLLCWDBLPXTQ-LVUCLCPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  282
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  6-疏基嘌呤核苷 、 mitomycin C 在 palladium on activated charcoal 水 作用下， 以 水 为溶剂， 反应 0.5h， 以43%的产率得到2,7-diaminomitosene 1-(9-β-D-ribofuranosyl-6-mercaptopurine)
  参考文献：
  名称：

  Additional nucleotide derivatives of mitosenes. Synthesis and activity against parental and multidrug resistant L1210 leukemia

  摘要：

  Cytidine 5'-monophosphate and 5'-ara-CMP conjugates of 2,7-diaminomitosene, with the phosphate groups linked to C-1, were prepared by treating mitomycin C with the appropriate nucleotides. 5'-UMP conjugates were prepared from mitomycin A, 7 (M-83), and 8 (BMY-25282) by similar procedures. A conjugate could not be prepared from mitomycin C and 6-MPRP, but a sulfur-linked derivative was made with 6-MP ribonucleoside. The corresponding 1-hydroxy-2-aminomitosenes were prepared from the parent mitomycin analogues for structure-activity comparisons. All compounds were tested against L1210 murine leukemia in the MTT tetrazolium dye assay. In general, the conjugates were less potent than the parent mitomycins; however 5'-ara-CMP conjugate 14 derived from mitomycin C was more potent than the parent compound or any mitomycin tested except mitomycin A. It also was more potent than ara-C. This result establishes the value of this approach to prodrugs, at least in cell culture. Against a multidrug-resistant L1210 cell line, all of the conjugates derived from mitomycin C were more potent than the parent compound. 6-Mercaptopurine ribonucleoside conjugate 15 was more active against the resistant cells than it was against the parental cell line.

  DOI：

  10.1021/jm00111a004

文献信息

• IYENGAR, BHASHYAM S.;DORR, ROBERT T.;REMERS, WILLIAM A., J. MED. CHEM., 34,(1991) N, C. 1947-1951
  作者：IYENGAR, BHASHYAM S.、DORR, ROBERT T.、REMERS, WILLIAM A.

  DOI：——

  日期：——