2-[(2-chloroethyl)-2,4-dinitro-6-[[[2-(phosphonooxy)ethyl]amino]-carbonyl]anilino]ethyl methanesulfonate | 851627-58-2

• 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: 2-[(2-chloroethyl)-2,4-dinitro-6-[[[2-(phosphonooxy)ethyl]amino]-carbonyl]anilino]ethyl methanesulfonate
• 英文别名: 2-[N-(2-chloroethyl)-2,4-dinitro-6-(2-phosphonooxyethylcarbamoyl)anilino]ethyl methanesulfonate
• CAS: 851627-58-2
• 化学式: C₁₄H₂₀ClN₄O₁₂PS
• 分子量: 534.825
• InChiKey: GWNWCTIJYAYOLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  243
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  2-[N-(2-chloroethyl)-2-(6-tert-butoxy-8,8-dimethyl-6-oxido-5,7-dioxa-2-aza-6-phosphanon-1-anoyl)-4,6-dinitroanilino]ethyl methanesulfonate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以68%的产率得到2-[(2-chloroethyl)-2,4-dinitro-6-[[[2-(phosphonooxy)ethyl]amino]-carbonyl]anilino]ethyl methanesulfonate
  参考文献：
  名称：

  WO2008/30112

  摘要：

  公开号：

文献信息

• Novel nitrophenyl mustard and nitrophenylaziridine alcohols and their corresponding phosphates and their use as targeted cytotoxic agents
  申请人：Denny William Alexander

  公开号：US20100010094A1

  公开（公告）日：2010-01-14

  The present invention relates to novel nitrophenyl mustard and nitrophenylaziridine alcohols, to their corresponding phosphates, to their use as targeted cytotoxic agents; as bioreductive drugs in hypoxic tumours, and to their use in cell ablation, including gene-directed enzyme-prodrug therapy (GDEPT) and antibody-directed enzyme-prodrug therapy (ADEPT), in conjunction with nitroreductase enzymes.

  本发明涉及新型的硝基苯基芥和硝基苯基环氧丙烷醇，它们对应的磷酸盐，以及它们作为靶向细胞毒性药物的使用；作为缺氧肿瘤中的生物还原药物，并结合硝酸还原酶酶使用于细胞消融，包括基因定向酶前药物治疗（GDEPT）和抗体定向酶前药物治疗（ADEPT）。
• Processes of preparing asymmetric dinitrobenzamide mustard compounds, intermediate compounds useful therein and products obtained therefrom
  申请人：Atwell Graham John

  公开号：US20100121091A1

  公开（公告）日：2010-05-13

  The invention relates to methods of preparing compounds of formula (II) wherein Z represents —OR 1 or N(R 2 )R 2a —, where R 1 is lower alkylene (C 1 -C 6 ), R 2 is lower alkyl or H and R 2a is lower alkylene (C 1 -C 6 ) or H; Q is absent when R 2a is H and is otherwise selected from the group consisting of H, —OH and protected forms of —OH; one of X and Y is halogen and the other is —OSO 2 R 3 , where R 3 is selected from the group consisting of lower alkyl (C 1 -C 6 ), phenyl and CH 2 phenyl. The method comprises the steps of: (a) reacting a compound of formula (I) with aziridineethanol or a 2-[(2-haloethyl)amino]ethanol in the presence of a metal halide, to form a compound of the formula (III) wherein one of X and E is halogen and the other is hydroxy, and (b) reacting the compound of formula (III) with an alkyl- or arylsulfonyl halide or alkyl- or arylsulfonyl anhydride to obtain a compound of the formula (II). The invention also relates to methods of preparing compounds of formula (IV) from the compounds of formula (II) so obtained, and to novel compounds of formula (IIb) useful as intermediates in these methods.

  本发明涉及制备式（II）化合物的方法，其中Z代表—OR1或N（R2）R2a—，其中R1为低碳链（C1-C6），R2为低碳基或H，R2a为低碳链（C1-C6）或H；当R2a为H时，Q不存在，否则Q选择自羟基（—OH）和保护的羟基形式；X和Y中的一个是卤素，另一个是—OSO2R3，其中R3选择自低碳基（C1-C6）、苯基和CH2苯基。该方法包括以下步骤：（a）在金属卤化物的存在下，将式（I）化合物与环氧丙胺乙醇或2-[(2-卤基乙基)氨基]乙醇反应，形成式（III）化合物，其中X和E中的一个是卤素，另一个是羟基，（b）将式（III）化合物与烷基或芳基磺酰卤或烷基或芳基磺酰酐反应，得到式（II）化合物。本发明还涉及从所得到的式（II）化合物制备式（IV）化合物的方法，以及作为这些方法中间体的新型式（IIb）化合物。
• PROCESSES OF PREPARING ASYMMETRIC DINITROBENZAMIDE MUSTARD COMPOUNDS, INTERMEDIATE COMPOUNDS USEFUL THEREIN AND PRODUCTS OBTAINED THEREFROM
  申请人：AUCKLAND UNISERVICES LIMITED

  公开号：EP2059499A1

  公开（公告）日：2009-05-20
• US7629332B2
  申请人：——

  公开号：US7629332B2

  公开（公告）日：2009-12-08
• [EN] PROCESSES OF PREPARING ASYMMETRIC DINITROBENZAMIDE MUSTARD COMPOUNDS, INTERMEDIATE COMPOUNDS USEFUL THEREIN AND PRODUCTS OBTAINED THEREFROM<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS ASYMÉTRIQUES À BASE DE MOUTARDE DE DINITROBENZAMIDE, COMPOSES INTERMÉDIAIRES UTILES DANS DE TELLS PROCÉDÉS ET PRODUITS OBTENUS À PARTIR DESDITS PROCÉDÉS
  申请人：AUCKLAND UNISERVICES LTD

  公开号：WO2008030112A1

  公开（公告）日：2008-03-13

  [EN] The invention relates to methods of preparing compounds of formula (II) wherein Z represents -OR¹ or -N(R²)R^2a-, where R¹ is lower alkylene (C₁-C₆), R² is lower alkyl or H and R^2a is lower alkylene (C₁-C₆) or H;Q is absent when R^2a is H and is otherwise selected from the group consisting of H, -OH and protected forms of -OH; one of X and Y is halogen and the other is -OSO₂R³, where R³ is selected from the group consisting of lower alkyl (C₁-C₆), phenyl and CH₂phenyl. The method comprises the steps of: (a) reacting a compound of formula (I) with aziridineethanol or a 2-[(2-haloethyl)amino]ethanol in the presence of a metal halide, to form a compound of the formula (III) wherein one of X and E is halogen and the other is hydroxy, and (b) reacting the compound of formula (III) with an alkyl- or arylsulfonyl halide or alkyl- or arylsulfonyl anhydride to obtain a compound of the formula (II). The invention also relates to methods of preparing compounds of formula (IV) from the compounds of formula (II) so obtained, and to novel compounds of formula (IIb) useful as intermediates in these methods.
  [FR] La présente invention concerne des procédés de préparation de formule (II)dans laquelle: Z représente -OR¹ ou -N(R₂)R^2a-,où R¹ représente un alkylène inférieur (C₁-C₆), R² représente alkyle inférieur ou H et R^2a représente alkylène inférieur (C₁-C₆)ou H; Q est absent lorsque R^2a est H et sinon est choisi parmi le groupe constitué de H, -OH et des formes protégées de -OH; un entre X et Y est halogène et l'autre est -OSO₂R³, où R³ est choisi parmi le groupe constitué d'alkyle inférieur (C₁-C₆),phényle et CH₂phényle. Le procédé comprend les étapes suivantes : (a) la réaction d'un composé de formule (I) avec de l'aziridineéthanol ou un 2-[(2-haloéthyl)amino]éthanol en présence d'un halogènure métallique pour former un composé de formule (III) dans laquelle : un entre X et E est halogène et l'autre est hydroxy, et (b) la réaction du composé de formule (III) avec un halogénure d'alkyl-ou d'arylsulfonyle ou un anhydride d'alkyl- ou d'arylsulfonyle pour obtenir un composé de formule (II). L'invention concerne également des procédés de préparation de formule (IV) à partir des composés de formule (II) ainsi obtenus, et de nouveaux composés de formule (IIb) utiles en tant qu'intermédiaires dans ces procédés.