(1S,2S,5R,6S,12R,14S)-5-(benzotriazol-2-ylmethyl)-9,14-dimethyl-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradec-9-en-4-one | 1449759-48-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2S,5R,6S,12R,14S)-5-(benzotriazol-2-ylmethyl)-9,14-dimethyl-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradec-9-en-4-one
• CAS: 1449759-48-1
• 化学式: C₂₁H₂₃N₃O₃
• 分子量: 365.432
• InChiKey: NWHOPSDXTYXADU-PNLNEYCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  69.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  T406石油添加剂 、 ludartin 以 乙腈 为溶剂， 以75%的产率得到(1S,2S,5R,6S,12R,14S)-5-(benzotriazol-2-ylmethyl)-9,14-dimethyl-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradec-9-en-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of amino analogs of Ludartin: Potent and selective cytotoxic agents

  摘要：

  Diverse amino analogs of Ludartin, a cytotoxic guaianolide and a position isomer of an anticancer drug, Arglabin were prepared through Michael type addition at its highly active alpha-methylene-gamma-lactone motif. The semisynthetic derivatives were subjected to sulphorhodamine B cytotoxicity assay against a panel of four different human cancer cell lines viz. lung (A-549), leukemia (THP-1), prostate (PC-3) and colon (HCT-116) to look into structure-activity relationship. Few of the analogs displayed potent selective cytotoxicity compared to the parent molecule-Ludartin (1). (11R)-13-(Diethyl amine)-11,13-dihydroludartin (6) and (11R)-13-(piperidine)-11,13-dihydroludartin (10) showed almost same cytotoxicity against leukemia cell lines (THP-1) as that of parent molecule-Ludartin, but were More active against colon (HCT-116) cancer cells. (11R)-13-(Morpholine)-11,13-dihydroludartin (11) displayed selectively better cytotoxicity against Leukemia cancer cells (THP-1) exhibiting IC50 of 2.8 mu M. (11R)-13-(6-Nitroindazole)-11,13-dihydroludartin (17) was four times more potent than Ludartin with selective cytotoxic effects against prostate cancer cells (2.2 mu M) while as (11R)-13-(6-nitroindazole)-11,13-dihydroludartin (18) exhibited three-fold selective cytotoxicity for Lung (A-549) cancer cell lines exhibiting IC50 of 2.6 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.068

文献信息

• Synthesis and biological evaluation of amino analogs of Ludartin: Potent and selective cytotoxic agents
  作者：Shabir H. Lone、Khursheed A. Bhat、Shakeel-u-Rehman、Rabiya Majeed、Abid Hamid、Mohd A. Khuroo

  DOI：10.1016/j.bmcl.2013.06.068

  日期：2013.9

  Diverse amino analogs of Ludartin, a cytotoxic guaianolide and a position isomer of an anticancer drug, Arglabin were prepared through Michael type addition at its highly active alpha-methylene-gamma-lactone motif. The semisynthetic derivatives were subjected to sulphorhodamine B cytotoxicity assay against a panel of four different human cancer cell lines viz. lung (A-549), leukemia (THP-1), prostate (PC-3) and colon (HCT-116) to look into structure-activity relationship. Few of the analogs displayed potent selective cytotoxicity compared to the parent molecule-Ludartin (1). (11R)-13-(Diethyl amine)-11,13-dihydroludartin (6) and (11R)-13-(piperidine)-11,13-dihydroludartin (10) showed almost same cytotoxicity against leukemia cell lines (THP-1) as that of parent molecule-Ludartin, but were More active against colon (HCT-116) cancer cells. (11R)-13-(Morpholine)-11,13-dihydroludartin (11) displayed selectively better cytotoxicity against Leukemia cancer cells (THP-1) exhibiting IC50 of 2.8 mu M. (11R)-13-(6-Nitroindazole)-11,13-dihydroludartin (17) was four times more potent than Ludartin with selective cytotoxic effects against prostate cancer cells (2.2 mu M) while as (11R)-13-(6-nitroindazole)-11,13-dihydroludartin (18) exhibited three-fold selective cytotoxicity for Lung (A-549) cancer cell lines exhibiting IC50 of 2.6 mu M. (C) 2013 Elsevier Ltd. All rights reserved.