N-deacetyl-N-(N-trifluoroacetyl-(R)-methylglicyl)thiocolchicine

• 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: N-deacetyl-N-(N-trifluoroacetyl-(R)-methylglicyl)thiocolchicine
• 英文别名: (2R)-2-[(2,2,2-trifluoroacetyl)amino]-N-[(7S)-1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]propanamide
• 化学式: C₂₅H₂₇F₃N₂O₆S
• 分子量: 540.56
• InChiKey: BGUKTNNLDZYXPV-WBMJQRKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-deacetyl-N-(N-trifluoroacetyl-(R)-methylglicyl)thiocolchicine 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 5.0h， 生成 (2R)-2-amino-N-[(7S)-1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]propanamide
  参考文献：
  名称：

  N-Deacetyl-N-aminoacylthiocolchicine Derivatives:  Synthesis and Biological Evaluation on MDR-Positive and MDR-Negative Human Cancer Cell Lines

  摘要：

  A new series of N-deacetyl-N-(N-trifluoroacetylaminoacyl)thiocolchicine derivatives 9-15 have been synthesized starting from the corresponding N-deacetylthiocolchicine (3) and the N-trifluoroacetylamino acids 5-8 which were used as a racemic mixture. The trifluoroacetyl protecting group has been removed easily, giving the corresponding N-deacetyl-N-aminoacylthiocolchicines 16-22. Optical pure compounds 9-22 were isolated from the diastereoisomeric mixture or were prepared starting from compound 3 and an optical pure amino acid derivative; the configuration of each compound was assigned unequivocally. The diastereoisomeric couples of amino acids synthesized were tested, and their antiproliferative activity on MDR-positive and MDR-negative human cancer cell lines was evaluated.

  DOI：

  10.1021/jm981134e
• 作为产物：
  描述：

  trifluoroacetyl-DL-alanine 、 (7S)-7-氨基-1,2,3-三甲氧基-10-甲硫基-6,7-二氢-5H-苯并[g]庚搭烯-9-酮 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-deacetyl-N-(N-trifluoroacetyl-(S)-methylglicyl)thiocolchicine 、 N-deacetyl-N-(N-trifluoroacetyl-(R)-methylglicyl)thiocolchicine
  参考文献：
  名称：

  N-Deacetyl-N-aminoacylthiocolchicine Derivatives:  Synthesis and Biological Evaluation on MDR-Positive and MDR-Negative Human Cancer Cell Lines

  摘要：

  A new series of N-deacetyl-N-(N-trifluoroacetylaminoacyl)thiocolchicine derivatives 9-15 have been synthesized starting from the corresponding N-deacetylthiocolchicine (3) and the N-trifluoroacetylamino acids 5-8 which were used as a racemic mixture. The trifluoroacetyl protecting group has been removed easily, giving the corresponding N-deacetyl-N-aminoacylthiocolchicines 16-22. Optical pure compounds 9-22 were isolated from the diastereoisomeric mixture or were prepared starting from compound 3 and an optical pure amino acid derivative; the configuration of each compound was assigned unequivocally. The diastereoisomeric couples of amino acids synthesized were tested, and their antiproliferative activity on MDR-positive and MDR-negative human cancer cell lines was evaluated.

  DOI：

  10.1021/jm981134e

文献信息

• <i>N</i>-Deacetyl-<i>N</i>-aminoacylthiocolchicine Derivatives:  Synthesis and Biological Evaluation on MDR-Positive and MDR-Negative Human Cancer Cell Lines
  作者：Maria Luisa Gelmi、Sabrina Mottadelli、Donato Pocar、Antonella Riva、Ezio Bombardelli、Rosa De Vincenzo、Giovanni Scambia

  DOI：10.1021/jm981134e

  日期：1999.12.1

  A new series of N-deacetyl-N-(N-trifluoroacetylaminoacyl)thiocolchicine derivatives 9-15 have been synthesized starting from the corresponding N-deacetylthiocolchicine (3) and the N-trifluoroacetylamino acids 5-8 which were used as a racemic mixture. The trifluoroacetyl protecting group has been removed easily, giving the corresponding N-deacetyl-N-aminoacylthiocolchicines 16-22. Optical pure compounds 9-22 were isolated from the diastereoisomeric mixture or were prepared starting from compound 3 and an optical pure amino acid derivative; the configuration of each compound was assigned unequivocally. The diastereoisomeric couples of amino acids synthesized were tested, and their antiproliferative activity on MDR-positive and MDR-negative human cancer cell lines was evaluated.