1R,3R-1-(3,5-dimethoxy-4-hydroxyphenyl)-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline | 157636-86-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1R,3R-1-(3,5-dimethoxy-4-hydroxyphenyl)-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline
• 英文别名: 1R,3R-1-(3-5-dimethoxy-4-hydroxyphenyl)-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline；methyl (1R,3R)-1-(4-hydroxy-3,5-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 157636-86-7
• 化学式: C₂₁H₂₂N₂O₅
• 分子量: 382.416
• InChiKey: JRMLIGDEWFBNFA-CRAIPNDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  92.8
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1R,3R-1-(3,5-dimethoxy-4-hydroxyphenyl)-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 8.0h， 生成 (3aR,10R)-10-(4-Hydroxy-3,5-dimethoxy-phenyl)-3a,4,9,10-tetrahydro-3H-2-oxa-9,10a-diaza-cyclopenta[b]fluoren-1-one
  参考文献：
  名称：

  Structure-activity relationship for DNA topoisomerase II-induced DNA cleavage by azatoxin analogues

  摘要：

  Eighteen analogues of the nonintercalative DNA topoisomerase II (topo II)-active epipodophyllotoxin-ellipticine hybrid, azatoxin, were synthesized and evaluated for their ability to induce topo II-mediated DNA strand breaks in vitro. In general, the SAR profile of the azatoxins showed more homology with that of the epipodophyllotoxins than with the ellipticines. Of the compounds studied, only fluoro substitution at the 8-, 9, and 10-positions of azatoxins enhanced activity, with 9-fluoroazatoxin being the most active compound in this series. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00113-2
• 作为产物：
  描述：

  D-色氨酸甲酯 在 sodium sulfate 、 三氟乙酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 72.0h， 生成 1R,3R-1-(3,5-dimethoxy-4-hydroxyphenyl)-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline
  参考文献：
  名称：

  Structure-activity relationship for DNA topoisomerase II-induced DNA cleavage by azatoxin analogues

  摘要：

  Eighteen analogues of the nonintercalative DNA topoisomerase II (topo II)-active epipodophyllotoxin-ellipticine hybrid, azatoxin, were synthesized and evaluated for their ability to induce topo II-mediated DNA strand breaks in vitro. In general, the SAR profile of the azatoxins showed more homology with that of the epipodophyllotoxins than with the ellipticines. Of the compounds studied, only fluoro substitution at the 8-, 9, and 10-positions of azatoxins enhanced activity, with 9-fluoroazatoxin being the most active compound in this series. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00113-2

文献信息

• US5606060A
  申请人：——

  公开号：US5606060A

  公开（公告）日：1997-02-25
• US5747520A
  申请人：——

  公开号：US5747520A

  公开（公告）日：1998-05-05
• Structure-activity relationship for DNA topoisomerase II-induced DNA cleavage by azatoxin analogues
  作者：Jose S. Madalengoitia、Jetze J. Tepe、Karl A. Werbovetz、Erich K. Lehnert、Timothy L. Macdonald

  DOI：10.1016/s0968-0896(97)00113-2

  日期：1997.9

  Eighteen analogues of the nonintercalative DNA topoisomerase II (topo II)-active epipodophyllotoxin-ellipticine hybrid, azatoxin, were synthesized and evaluated for their ability to induce topo II-mediated DNA strand breaks in vitro. In general, the SAR profile of the azatoxins showed more homology with that of the epipodophyllotoxins than with the ellipticines. Of the compounds studied, only fluoro substitution at the 8-, 9, and 10-positions of azatoxins enhanced activity, with 9-fluoroazatoxin being the most active compound in this series. (C) 1997 Elsevier Science Ltd.