(2R)-2-amino-4-methylsulfanyl-1-[4-(4-nitrophenyl)piperazin-1-yl]butan-1-one | 1308814-05-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (2R)-2-amino-4-methylsulfanyl-1-[4-(4-nitrophenyl)piperazin-1-yl]butan-1-one
• CAS: 1308814-05-2
• 化学式: C₁₅H₂₂N₄O₃S
• 分子量: 338.431
• InChiKey: CZDAVCOJNFBMKS-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R)-2-amino-4-methylsulfanyl-1-[4-(4-nitrophenyl)piperazin-1-yl]butan-1-one 、 4'-demethyl-4-deoxypodophyllotoxin 4'-(p-nitrophenyl) carbonate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 [4-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-2,6-dimethoxyphenyl] N-[(2R)-4-methylsulfanyl-1-[4-(4-nitrophenyl)piperazin-1-yl]-1-oxobutan-2-yl]carbamate
  参考文献：
  名称：

  Synthesis and biological evaluation of derivatives of 4-deoxypodophyllotoxin as antitumor agents

  摘要：

  In an attempt to generate compounds with superior bioactivity and reduced toxicity, a series of derivatives of deoxypodophyllotoxin were synthesized by reacting 4'-demethyl-4-deoxypodophyllotoxin with substituted piperazines or their amino acid amides. The cytotoxic activity of these compounds against three human cancer cell lines was evaluated. We found that p-nitrophenylpiperazine substitution (Compound 8b) led to an increase in the potency of the compound. Compound 8b exhibited the most potent cytotoxicity against A-549, HeLa and SiHa cells (IC50 values were 0.102, 0.180 and 0.0195 mu M, respectively). In addition, flow cytometric analysis showed that 8b induced cell cycle arrest in the G1 phase accompanied by apoptosis in A-549 cells. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.06.004
• 作为产物：
  描述：

  N-Boc-D-蛋氨酸 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (2R)-2-amino-4-methylsulfanyl-1-[4-(4-nitrophenyl)piperazin-1-yl]butan-1-one
  参考文献：
  名称：

  Synthesis and biological evaluation of derivatives of 4-deoxypodophyllotoxin as antitumor agents

  摘要：

  In an attempt to generate compounds with superior bioactivity and reduced toxicity, a series of derivatives of deoxypodophyllotoxin were synthesized by reacting 4'-demethyl-4-deoxypodophyllotoxin with substituted piperazines or their amino acid amides. The cytotoxic activity of these compounds against three human cancer cell lines was evaluated. We found that p-nitrophenylpiperazine substitution (Compound 8b) led to an increase in the potency of the compound. Compound 8b exhibited the most potent cytotoxicity against A-549, HeLa and SiHa cells (IC50 values were 0.102, 0.180 and 0.0195 mu M, respectively). In addition, flow cytometric analysis showed that 8b induced cell cycle arrest in the G1 phase accompanied by apoptosis in A-549 cells. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.06.004

文献信息

• Synthesis and evaluation of the apoptosis inducing and CT DNA interaction properties of a series of 4β-carbamoyl 4′-O-demethylepipodophyllotoxins
  作者：Chun-Yan Sang、Jian-Fei Liu、Wen-Wen Qin、Jie Zhao、Lin Hui、Yong-Xin Jin、Shi-Wu Chen

  DOI：10.1016/j.ejmech.2013.09.053

  日期：2013.12

  A series of carbamate derivatives of 4'-demethylepipodophyllotoxin have been synthesized, and their cytotoxicities against several human cancer cell lines, including HeLa, A549, HCT-8, and HL-60 cells, evaluated. Some of these compounds exhibited higher levels of cytotoxicity than the anticancer drug etoposide. 4 beta-4'-Demethylepipodophyllotoxin 1-(4-nitrophenyl) piperazinyl carbamate (19) was found to be the most potent compound of those synthesized in the current study, and induced cell cycle arrest in the G2/M phase in HeLa cells, which was accompanied by apoptosis. Furthermore, this compound activated the expression of Bax, p53 and caspase-3 in HeLa cells, leading to changes in the conformation of calf thymus DNA from the B-form to a more compact C-form. (C) 2013 Elsevier Masson SAS. All rights reserved.