(2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal | 717920-70-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal
• 英文别名: (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine 2-carboxaldehyde diethylthioacetal；(2S)-N-[4-hydroxy-5-methoxy-2-nitrobenzoyl]-4-fluoropyrrolidine-2-carboxaldehyde-diethylthioacetal；[(2S,4S)-2-[bis(ethylsulfanyl)methyl]-4-fluoropyrrolidin-1-yl]-(4-hydroxy-5-methoxy-2-nitrophenyl)methanone
• CAS: 717920-70-2
• 化学式: C₁₇H₂₃FN₂O₅S₂
• 分子量: 418.51
• InChiKey: QGCXNRHBANUIBO-GWCFXTLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  146
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal 在 potassium carbonate 、 tin(ll) chloride 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 4.0h， 生成 1,1'-{[(propane-1,3-diyl)dioxy]bis[(2-amino-5-methoxy-1,4-phenylene)carbonyl]}bis[4-fluoropyrrolidine-2-carboxaldehyde diethylthioacetal]
  参考文献：
  名称：

  The effect of C2-fluoro group on the biological activity of DC-81 and its dimers

  摘要：

  C2-Fluoro substituted pyrrolobenzodiazepines (PBDs) have been synthesized that exhibit potential anticancer activity in a number of human tumour cell lines. These C2-fluoro substituted PBDs also exhibit significant DNA-binding ability. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.063
• 作为产物：
  描述：

  methyl (2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxylate 在 三甲基氯硅烷 、 三氟化硼乙醚 、 二异丁基氢化铝 、 乙硫醇 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 36.75h， 生成 (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal
  参考文献：
  名称：

  The effect of C2-fluoro group on the biological activity of DC-81 and its dimers

  摘要：

  C2-Fluoro substituted pyrrolobenzodiazepines (PBDs) have been synthesized that exhibit potential anticancer activity in a number of human tumour cell lines. These C2-fluoro substituted PBDs also exhibit significant DNA-binding ability. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.063

文献信息

• Synthesis and biological evaluation of anilino substituted pyrimidine linked pyrrolobenzodiazepines as potential anticancer agents
  作者：Ahmed Kamal、J. Surendranadha Reddy、M. Janaki Ramaiah、E. Vijaya Bharathi、D. Dastagiri、M. Kashi Reddy、S.N.C.V.L. Pushpavalli、Manika Pal-Bhadra

  DOI：10.1016/j.bmcl.2010.06.147

  日期：2010.9

  A series of new anilino substituted pyrimidine linked pyrrolo[2,1-c][1,4]benzodiazepine (PBD) conjugates were prepared and evaluated for their anticancer activity. The effects of four promising PBD conjugates on cell cycle of cancerous cell line A375 were investigated. These compounds showed the characteristic features of apoptosis like enhancement in the levels of p53, release of cytochrome c, and

  制备了一系列新的苯胺基取代的嘧啶连接的吡咯并[2,1- c ] [1,4]苯并二氮杂（PBD）缀合物，并评估了其抗癌活性。研究了四种有前景的PBD缀合物对癌细胞系A375的细胞周期的影响。这些化合物显示出凋亡的特征，例如p53水平的增强，细胞色素c的释放以及PARP的裂解。
• [EN] C2-FLUORO PYRROLO[2,1-c][1,4]BENZODIAZEPINE DIMERS<br/>[FR] DIMERES DE C2-FLUORO PYRROLO[2,1-C][1,4]BENZODIAZEPINE
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2005063758A1

  公开（公告）日：2005-07-14

  The present invention relates to novel 2-fluoro-pyrrolo[2,1-c][1,4]benzodiazepine dimers of formula (IX) where n is 3 to 10 useful as antitumour agents and to a process for the preparation thereof.

  本发明涉及一种新型2-氟吡咯并[2,1-c][1,4]苯二氮平二聚体，其化学式为(IX)，其中n为3至10，可用作抗肿瘤药物，并提供其制备方法。
• C2-fluoro pyrrolo [2,1-c][1,4]benzodiazepine dimers
  申请人：Kamal Ahmed

  公开号：US20050222131A1

  公开（公告）日：2005-10-06

  The present invention relates to novel 2-fluoro-pyrrolo[2,1-c][1,4]benzodiazepine dimers useful as antitumour agents and to a process for the preparation thereof

  本发明涉及一种新型2-氟吡咯并[2,1-c][1,4]苯二氮平二聚体，可用作抗肿瘤剂，并提供其制备方法。
• US7189710B2
  申请人：——

  公开号：US7189710B2

  公开（公告）日：2007-03-13
• The effect of C2-fluoro group on the biological activity of DC-81 and its dimers
  作者：Ahmed Kamal、P.S.M.M. Reddy、D. Rajasekhar Reddy

  DOI：10.1016/j.bmcl.2004.02.063

  日期：2004.5

  C2-Fluoro substituted pyrrolobenzodiazepines (PBDs) have been synthesized that exhibit potential anticancer activity in a number of human tumour cell lines. These C2-fluoro substituted PBDs also exhibit significant DNA-binding ability. (C) 2004 Elsevier Ltd. All rights reserved.