5-chloro-2-(2-hydroxyethyl)-7-[(2,4, 6-trimethylphenyl)methoxy]anthra-[1,9-cd]pyrazol-6(2H)-one | 156498-26-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 5-chloro-2-(2-hydroxyethyl)-7-[(2,4, 6-trimethylphenyl)methoxy]anthra-[1,9-cd]pyrazol-6(2H)-one
• 英文别名: 10-chloro-14-(2-hydroxyethyl)-6-[(2,4,6-trimethylphenyl)methoxy]-14,15-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2(7),3,5,9,11,13(16)-heptaen-8-one
• CAS: 156498-26-9
• 化学式: C₂₆H₂₃ClN₂O₃
• 分子量: 446.933
• InChiKey: YWXMAPHODUCTHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-chloro-2-(2-hydroxyethyl)-7-[(2,4, 6-trimethylphenyl)methoxy]anthra-[1,9-cd]pyrazol-6(2H)-one 在 吡啶 、 盐酸 、 二苯基膦叠氮化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.5h， 生成 5-[(2-aminoethyl)amino]-2-(2-azidoethyl)-7-hydroxyanthra[1,9-cd]pyrazol-6(2H)-one
  参考文献：
  名称：

  Synthesis of Losoxantrone Metabolites Isolated from Human Urine

  摘要：

  The first regiospecific synthesis of the monoacid metabolites (2) and (3) of losoxantrone is reported. In addition, synthesis of the diacid metabolite (4) via two different routes is also described. The chemical structures of these metabolites as well as their intermediates have been fully characterized.

  DOI：

  10.3987/com-99-8641
• 作为产物：
  描述：

  1,4-二氯-5-羟基蒽-9,10-二酮 在 caesium carbonate 、 N,N-二异丙基乙胺 作用下， 生成 5-chloro-2-(2-hydroxyethyl)-7-[(2,4, 6-trimethylphenyl)methoxy]anthra-[1,9-cd]pyrazol-6(2H)-one
  参考文献：
  名称：

  Reversal of the regioselectivity of anthrapyrazole formation. A new synthesis of losoxantrone (DUP941)

  摘要：

  Losoxantrone, a potent anticancer agent, has been efficiently synthesized in a 6 step process from 5-hydroxy-1,4-dichloroanthracene-9,10-dione.

  DOI：

  10.1016/s0040-4039(00)73069-3

文献信息

• Intermediates for the synthesis of anthrapyrazolone anticancer agents
  申请人：The Du Pont Merck Pharmaceutical Company

  公开号：US05393886A1

  公开（公告）日：1995-02-28

  This invention relates to compounds, including 5-chloro-2-[2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-7-[2,4,6-trimethylphen yl)methoxy]anthra[1,9-cd]pyrazol-6(2H)-one and analogs thereof, which are useful as intermediates for the synthesis of anthrapyrazolone anticancer agents, including losoxantrone. This invention also relates to methods for the synthesis of anthrapyrazolone anticancer agents, including losoxantrone.

  本发明涉及化合物，包括5-氯-2-[2-[[(4-甲基苯基)磺酰氧]乙基]-7-[2,4,6-三甲基苯基)甲氧基]蒽[1,9-cd]吡唑-6(2H)-酮及其类似物，其可用作合成蒽吡唑酮抗癌药物，包括洛索昔诺的中间体。本发明还涉及合成蒽吡唑酮抗癌药物，包括洛索昔诺的方法。
• Method for the synthesis of anthrapyrazolones
  申请人：The DuPont Merck Pharmaceutical Company

  公开号：US05618944A1

  公开（公告）日：1997-04-08

  This invention relates to compounds, including 5-chloro-2-[2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-7-[2,4,6-trimethylphen yl)methoxy]anthra[1,9-cd]pyrazol-6(2H)-one and analogs thereof, which are useful as intermediates for the synthesis of anthrapyrazolone anticancer agents, including losoxantrone. This invention also relates to methods for the synthesis of anthrapyrazolone anticancer agents, including losoxantrone.

  本发明涉及一种化合物，包括5-氯-2-[2-[[(4-甲基苯基)磺酰氧]乙基]-7-[2,4,6-三甲基苯基)甲氧基]蒽[1,9-cd]吡唑-6(2H)-酮及其类似物，这些化合物可用作合成蒽吡唑酮类抗癌药物，包括洛索昔非洛的中间体。本发明还涉及合成蒽吡唑酮类抗癌药物，包括洛索昔非洛的方法。
• INTERMEDIATES AND METHODS FOR THE SYNTHESIS OF ANTHRAPYRAZOLONE ANTICANCER AGENTS
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0700390B1

  公开（公告）日：1998-11-18
• US5393886A
  申请人：——

  公开号：US5393886A

  公开（公告）日：1995-02-28
• [EN] INTERMEDIATES AND METHODS FOR THE SYNTHESIS OF ANTHRAPYRAZOLONE ANTICANCER AGENTS<br/>[FR] INTERMEDIAIRES ET PROCEDES DE SYNTHESE D'AGENTS ANTICANCER D'ANTHRAPYRAZOLONE
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：WO1994025441A1

  公开（公告）日：1994-11-10

  (EN) This invention relates to compounds, including 5-chloro-2-[2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-7-[2,4,6-trimethylphenyl)methoxy]anthra[1,9-cd]pyrazol-6(2H)-one and analogs thereof, which are useful as intermediates for the synthesis of anthrapyrazolone anticancer agents, including losoxantrone. This invention also relates to methods for the synthesis of anthrapyrazolone anticancer agents, including losoxantrone.(FR) L'invention concerne des composés, y compris 5-chloro-2-[2-[[(4-méthylphényl)sulfonyl]oxy]éthyl]-7-[2,4,6-triméthylphényl)méthoxy)anthra[1,9-cd]pyrazol-6(2H)-one et leurs analogues, présentant une efficacité en tant qu'intermédiaires de synthèse d'agents anticancer d'anthrapyrazolone, y compris losoxantrone. L'invention concerne également des procédés de synthèse d'agents anticancer d'anthrapyrazolone, y compris losoxantrone.