tert-butyl N-[(2R)-1-[3-[4-(3-aminopropylamino)butylamino]propylamino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamate | 330162-64-6

• 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: tert-butyl N-[(2R)-1-[3-[4-(3-aminopropylamino)butylamino]propylamino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamate
• CAS: 330162-64-6
• 化学式: C₂₆H₄₄N₆O₃
• 分子量: 488.674
• InChiKey: AEBQGYNUGHSBGZ-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  35
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  133
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2R)-1-[3-[4-(3-aminopropylamino)butylamino]propylamino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以94%的产率得到N¹-spermine D-tryptophanyl amide tetrahydrochloride
  参考文献：
  名称：

  Amino Acid/Spermine Conjugates:  Polyamine Amides as Potent Spermidine Uptake Inhibitors

  摘要：

  In this paper we describe the synthesis and characterization of a series of simple spermine/amino acid conjugates, some of which potently inhibit the uptake of spermidine into MDAMB-231 breast cancer cells. The presence of an amide in the functionalized polyamine appeared to add to the affinity for the polyamine transporter. The extensive biological characterization of an especially potent analogue from this series, the Lys-Spm conjugate (31), showed this molecule will be an extremely useful tool for use in polyamine research. It was shown that the use of 31 in combination with DFMO led to a cytostatic growth inhibition of a variety of cancer cells, even when used in the presence of an extracellular source of transportable spermidine. It was furthermore shown that this combination effectively reduced the cellular levels of putrescine and spermidine while not affecting the levels of spermine. These facts together with the nontoxic nature of 31 make it a novel lead for further anticancer development.

  DOI：

  10.1021/jm0101040
• 作为产物：
  描述：

  BOC-D-色氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 18.0h， 生成 tert-butyl N-[(2R)-1-[3-[4-(3-aminopropylamino)butylamino]propylamino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamate
  参考文献：
  名称：

  Amino Acid/Spermine Conjugates:  Polyamine Amides as Potent Spermidine Uptake Inhibitors

  摘要：

  In this paper we describe the synthesis and characterization of a series of simple spermine/amino acid conjugates, some of which potently inhibit the uptake of spermidine into MDAMB-231 breast cancer cells. The presence of an amide in the functionalized polyamine appeared to add to the affinity for the polyamine transporter. The extensive biological characterization of an especially potent analogue from this series, the Lys-Spm conjugate (31), showed this molecule will be an extremely useful tool for use in polyamine research. It was shown that the use of 31 in combination with DFMO led to a cytostatic growth inhibition of a variety of cancer cells, even when used in the presence of an extracellular source of transportable spermidine. It was furthermore shown that this combination effectively reduced the cellular levels of putrescine and spermidine while not affecting the levels of spermine. These facts together with the nontoxic nature of 31 make it a novel lead for further anticancer development.

  DOI：

  10.1021/jm0101040

文献信息

• Amino Acid/Spermine Conjugates:  Polyamine Amides as Potent Spermidine Uptake Inhibitors
  作者：Mark R. Burns、C. Lance Carlson、Scott M. Vanderwerf、Josh R. Ziemer、Reitha S. Weeks、Feng Cai、Heather K. Webb、Gerard F. Graminski

  DOI：10.1021/jm0101040

  日期：2001.10.1

  In this paper we describe the synthesis and characterization of a series of simple spermine/amino acid conjugates, some of which potently inhibit the uptake of spermidine into MDAMB-231 breast cancer cells. The presence of an amide in the functionalized polyamine appeared to add to the affinity for the polyamine transporter. The extensive biological characterization of an especially potent analogue from this series, the Lys-Spm conjugate (31), showed this molecule will be an extremely useful tool for use in polyamine research. It was shown that the use of 31 in combination with DFMO led to a cytostatic growth inhibition of a variety of cancer cells, even when used in the presence of an extracellular source of transportable spermidine. It was furthermore shown that this combination effectively reduced the cellular levels of putrescine and spermidine while not affecting the levels of spermine. These facts together with the nontoxic nature of 31 make it a novel lead for further anticancer development.