4-Nitro-benzoic acid (2S,3S,4S,6R)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-6-[(1S,3S)-3,5,12-trihydroxy-3-(4-nitro-phenylcarbamoyloxymethyl)-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy]-tetrahydro-pyran-3-yl ester | 91593-28-1

• 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: 4-Nitro-benzoic acid (2S,3S,4S,6R)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-6-[(1S,3S)-3,5,12-trihydroxy-3-(4-nitro-phenylcarbamoyloxymethyl)-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy]-tetrahydro-pyran-3-yl ester
• CAS: 91593-28-1
• 化学式: C₄₁H₃₃F₃N₄O₁₆
• 分子量: 894.725
• InChiKey: XKQSXPGPGMRBTN-DFHOXQHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.08
• 重原子数：
  64.0
• 可旋转键数：
  10.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  293.3
• 氢给体数：
  5.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  4-Nitro-benzoic acid (2S,3S,4S,6R)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-6-[(1S,3S)-3,5,12-trihydroxy-3-(4-nitro-phenylcarbamoyloxymethyl)-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy]-tetrahydro-pyran-3-yl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.75h， 生成 (7S,9S)-7-<(3'-amino-2',3',6'-trideoxy-α-L-lyxohexopyranosyl)oxy>-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-<<<(4-nitrophenyl)carbamoyl>oxy>methyl>-5,12-naphthacenedione
  参考文献：
  名称：

  Synthesis and antitumor activity of 9-[(carbamoyloxy)alkyl]anthracyclines a novel class of anthracycline derivatives

  摘要：

  A number of 4-demethoxyanthracyclines having hydroxylalkyl functions at the 9-position have previously been synthesized and shown to have potent antitumor activity. A series of carbamate derivatives of these (hydroxyalkyl)anthracyclines have now been prepared, many of which possess considerably greater efficacy in an L-1210 leukemia test system than do the parent alcohols or the known anthracyclines daunorubicin (1), doxorubicin (2), and 4-demethoxydaunorubicin (3). Phenylcarbamate 8a was more active than methyl analogue 8b, while the 4'-deoxy and 4'-epi phenylcarbamates 17 and 18 showed particularly high efficacy at optimal dose levels similar to that of doxorubicin. Secondary carbamates were more potent, with the 13R isomer 23 having significantly higher efficacy than 13S analogue 24.

  DOI：

  10.1021/jm00171a011
• 作为产物：
  描述：

  [(1S,17S)-3,14-dihydroxy-5,12-dioxo-19-phenyl-18,20-dioxa-19-borapentacyclo[15.3.1.02,15.04,13.06,11]henicosa-2(15),3,6,8,10,13-hexaen-17-yl]methyl acetate 在 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 4-Nitro-benzoic acid (2S,3S,4S,6R)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-6-[(1S,3S)-3,5,12-trihydroxy-3-(4-nitro-phenylcarbamoyloxymethyl)-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy]-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis and antitumor activity of 9-[(carbamoyloxy)alkyl]anthracyclines a novel class of anthracycline derivatives

  摘要：

  A number of 4-demethoxyanthracyclines having hydroxylalkyl functions at the 9-position have previously been synthesized and shown to have potent antitumor activity. A series of carbamate derivatives of these (hydroxyalkyl)anthracyclines have now been prepared, many of which possess considerably greater efficacy in an L-1210 leukemia test system than do the parent alcohols or the known anthracyclines daunorubicin (1), doxorubicin (2), and 4-demethoxydaunorubicin (3). Phenylcarbamate 8a was more active than methyl analogue 8b, while the 4'-deoxy and 4'-epi phenylcarbamates 17 and 18 showed particularly high efficacy at optimal dose levels similar to that of doxorubicin. Secondary carbamates were more potent, with the 13R isomer 23 having significantly higher efficacy than 13S analogue 24.

  DOI：

  10.1021/jm00171a011