DL-5-fluorotryptophan n-butyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: DL-5-fluorotryptophan n-butyl ester
• 英文别名: butyl 2-amino-3-(5-fluoro-1H-indol-3-yl)propanoate
• 化学式: C₁₅H₁₉FN₂O₂
• 分子量: 278.326
• InChiKey: WHQKGGCOUJUJNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  DL-5-fluorotryptophan n-butyl ester 、 N-(2-甲酰基-5,8-二氧代-5,8-二氢喹啉-7-基)乙酰胺 以 苯甲醚 为溶剂， 反应 5.0h， 以51%的产率得到butyl 1-(7-acetamido-5,8-dioxoquinolin-2-yl)-6-fluoro-9H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of antitumor activity of novel N-acyllavendamycin analogues and quinoline-5,8-diones

  摘要：

  A series of 7-N-acyllavendamycins with zero, one or two substituents at the C-2', C-3', and C-11' were synthesized through short and efficient methods. Pictet-Spengler condensation of 7-N-acylamino-2-formylquinoline-5,8-diones with tryptamine or tryptophans produced the desired lavendamycins. Screening data on a panel of three ras oncogene-transformed cell lines and the non-transformed parent cell line showed that a significant number of these analogues are potent antitumor agents and appear to be particularly active against K-ras transformed cells. Compared with the corresponding quinolinediones, these novel lavendamycins are much more inhibitory toward the transformed cells indicating that the P-carboline moiety of the lavendamycin analogues plays an important role in its potency and selective toxicity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.039
• 作为产物：
  描述：

  5-氟-DL-色氨酸 、 正丁醇 在 盐酸 作用下， 以 乙醚 为溶剂， 以88%的产率得到DL-5-fluorotryptophan n-butyl ester
  参考文献：
  名称：

  Synthesis and evaluation of antitumor activity of novel N-acyllavendamycin analogues and quinoline-5,8-diones

  摘要：

  A series of 7-N-acyllavendamycins with zero, one or two substituents at the C-2', C-3', and C-11' were synthesized through short and efficient methods. Pictet-Spengler condensation of 7-N-acylamino-2-formylquinoline-5,8-diones with tryptamine or tryptophans produced the desired lavendamycins. Screening data on a panel of three ras oncogene-transformed cell lines and the non-transformed parent cell line showed that a significant number of these analogues are potent antitumor agents and appear to be particularly active against K-ras transformed cells. Compared with the corresponding quinolinediones, these novel lavendamycins are much more inhibitory toward the transformed cells indicating that the P-carboline moiety of the lavendamycin analogues plays an important role in its potency and selective toxicity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.039

文献信息

• Synthesis and evaluation of antitumor activity of novel N-acyllavendamycin analogues and quinoline-5,8-diones
  作者：Mohammad Behforouz、Wen Cai、Farahnaz Mohammadi、Mark G. Stocksdale、Zhengxiang Gu、Mohammad Ahmadian、Darric E. Baty、Michele R. Etling、Charmaine H. Al-Anzi、Tyson M. Swiftney

  DOI：10.1016/j.bmc.2006.09.039

  日期：2007.1.1

  A series of 7-N-acyllavendamycins with zero, one or two substituents at the C-2', C-3', and C-11' were synthesized through short and efficient methods. Pictet-Spengler condensation of 7-N-acylamino-2-formylquinoline-5,8-diones with tryptamine or tryptophans produced the desired lavendamycins. Screening data on a panel of three ras oncogene-transformed cell lines and the non-transformed parent cell line showed that a significant number of these analogues are potent antitumor agents and appear to be particularly active against K-ras transformed cells. Compared with the corresponding quinolinediones, these novel lavendamycins are much more inhibitory toward the transformed cells indicating that the P-carboline moiety of the lavendamycin analogues plays an important role in its potency and selective toxicity. (c) 2006 Elsevier Ltd. All rights reserved.