13-[(4-tert-butylphenyl)methyl]-7,19-difluoro-3-[(2R,3R,4S,5S,6S)-6-(fluoromethyl)-3,4,5-trihydroxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione | 406722-15-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 13-[(4-tert-butylphenyl)methyl]-7,19-difluoro-3-[(2R,3R,4S,5S,6S)-6-(fluoromethyl)-3,4,5-trihydroxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione
• CAS: 406722-15-4
• 化学式: C₃₇H₃₂F₃N₃O₆
• 分子量: 671.673
• InChiKey: BDPCQHVDHIUFHF-OFWRJWMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  49
• 可旋转键数：
  5
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  128
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  13-[(4-tert-butylphenyl)methyl]-7,19-difluoro-3-[(2R,3R,4S,5S,6S)-6-(fluoromethyl)-3,4,5-trihydroxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 3,8-Difluoro-11-((2R,3R,4S,5S,6S)-6-fluoromethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yl)-11,12-dihydro-11,12-diaza-indeno[2,1-a]fluorene-5,6-dicarboxylic acid
  参考文献：
  名称：

  Discovery of a Fluoroindolo[2,3-a]carbazole Clinical Candidate with Broad Spectrum Antitumor Activity in Preclinical Tumor Models Superior to the Marketed Oncology Drug, CPT-11

  摘要：

  A series of fluoroglycosylated fluoroindolocarbazoles was examined with respect to their topoisomerase I activity, cytotoxicity, and selectivity. The lead clinical candidate from this series, BMS-250749, displays broad spectrum antitumor activity superior to CPT-11 against some preclinical xenograft models, including curative antitumor activity against Lewis lung carcinoma.

  DOI：

  10.1021/jm049090z
• 作为产物：
  描述：

  13-[(4-Tert-butylphenyl)methyl]-7,19-difluoro-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione 在 palladium dihydroxide 偶氮二甲酸二异丙酯 、 三苯基膦 、 环己烯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 13-[(4-tert-butylphenyl)methyl]-7,19-difluoro-3-[(2R,3R,4S,5S,6S)-6-(fluoromethyl)-3,4,5-trihydroxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione
  参考文献：
  名称：

  Discovery of a Fluoroindolo[2,3-a]carbazole Clinical Candidate with Broad Spectrum Antitumor Activity in Preclinical Tumor Models Superior to the Marketed Oncology Drug, CPT-11

  摘要：

  A series of fluoroglycosylated fluoroindolocarbazoles was examined with respect to their topoisomerase I activity, cytotoxicity, and selectivity. The lead clinical candidate from this series, BMS-250749, displays broad spectrum antitumor activity superior to CPT-11 against some preclinical xenograft models, including curative antitumor activity against Lewis lung carcinoma.

  DOI：

  10.1021/jm049090z

文献信息

• Discovery of a Fluoroindolo[2,3-<i>a</i>]carbazole Clinical Candidate with Broad Spectrum Antitumor Activity in Preclinical Tumor Models Superior to the Marketed Oncology Drug, CPT-11
  作者：Mark G. Saulnier、Balu N. Balasubramanian、Byron H. Long、David B. Frennesson、Edward Ruediger、Kurt Zimmermann、Jeffrey T. Eummer、Denis R. St. Laurent、Karen M. Stoffan、B. Narasimhulu Naidu、Mikael Mahler、Francis Beaulieu、Carol Bachand、Frank Y. Lee、Craig R. Fairchild、Linda K. Stadnick、William C. Rose、Carola Solomon、Henry Wong、Alain Martel、John J. Wright、Robert Kramer、David R. Langley、Dolatrai M. Vyas

  DOI：10.1021/jm049090z

  日期：2005.4.1

  A series of fluoroglycosylated fluoroindolocarbazoles was examined with respect to their topoisomerase I activity, cytotoxicity, and selectivity. The lead clinical candidate from this series, BMS-250749, displays broad spectrum antitumor activity superior to CPT-11 against some preclinical xenograft models, including curative antitumor activity against Lewis lung carcinoma.