2-chloro-3,5-dinitro-N-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]benzamide | 680199-30-8

• 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-chloro-3,5-dinitro-N-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]benzamide
• 英文别名: 2-chloro-3,5-DINITRO-N-[2-(TETRAHYDRO-2H-PYRAN-2-yloxy) ethyl] benzamide；2-chloro-3,5-dinitro-N-[2-(oxan-2-yloxy)ethyl]benzamide
• CAS: 680199-30-8
• 化学式: C₁₄H₁₆ClN₃O₇
• 分子量: 373.75
• InChiKey: OAZVGZCFPYNGEO-UHFFFAOYSA-N

物化性质

• 沸点：
  505.2±50.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-chloro-3,5-dinitro-N-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]benzamide 在 三乙胺 、 lithium chloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 2-[N-(2-chloroethyl)-2,4-dinitro-6-({[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]amino}carbonyl)anilino]ethyl methanesulfonate
  参考文献：
  名称：

  Synthesis of asymmetric halomesylate mustards with aziridineethanol/alkali metal halides: application to an improved synthesis of the hypoxia prodrug PR-104

  摘要：

  Aromatic asymmetric halomesylate mustards are efficiently prepared by reaction of activated aromatic chlorides with aziridine-ethanol/alkali metal halides, followed by mesylation of the haloalcohol. The reaction conditions are sufficiently mild to be compatible with a range of different substituents and protecting groups, including carboxylate and phosphate esters, and have been used in an improved synthesis of the anticancer bromomesylate mustard PR-104, now in clinical trials. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.044
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 2-chloro-3,5-dinitro-N-(2-hydroxyethyl)benzamide 在 对甲苯磺酸 作用下， 反应 2.0h， 以100%的产率得到2-chloro-3,5-dinitro-N-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]benzamide
  参考文献：
  名称：

  [EN] NITROANILINE-BASED ALKYLATING AGENTS AND THEIR USE AS PRODRUGS
  [FR] AGENTS D'ALKYLATION A BASE DE NITROANILINE ET LEUR UTILISATION EN TANT QUE PROMEDICAMENTS

  摘要：

  基于硝基苯胺的不对称芥末化合物，其通用公式为（I），以及它们的制备方法和使用方法，作为基因依赖性酶前药治疗（GDEPT）和与硝基还原酶酶结合的细胞消融治疗的药物，以及作为缺氧选择性细胞毒素和抗癌药物的使用方法。

  公开号：

  WO2004033415A1

文献信息

• Nitroaniline-based alkylating agents and their use as prodrugs
  申请人：Denny Alexander William

  公开号：US20050256191A1

  公开（公告）日：2005-11-17

  Nitroaniline-based unsymmetrical mustards of the general formula (I) are provided, together with methods of preparation and methods for their use as prodrugs for gene-dependent enzyme prodrug therapy (GDEPT) and cell ablation therapy in conjunction with nitroreductase enzymes as hypoxia selective cytotoxins and as anticancer agents.

  提供了基于硝基苯胺的不对称芥子气的一般式（I），以及其制备方法和用作基因依赖性酶前药治疗（GDEPT）和细胞消融治疗的前药的方法，与硝酸还原酶酶一起使用作为缺氧选择性细胞毒素和抗癌剂。
• 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。
• Nitrophenyl mustard and nitrophenylaziridine alcohols and their corresponding phosphates and their use as targeted cytotoxic agents
  申请人：Auckland Uniservices Limited

  公开号：US07629332B2

  公开（公告）日：2009-12-08

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

  本发明涉及一种新型的硝基苯基芥和硝基苯基环丙烷醇，以及它们对应的磷酸酯，它们作为靶向细胞毒性药物的用途；作为低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治疗（GPEPT）和抗体定向酶前药治疗（ADEPT）。
• WO2008/30112
  申请人：——

  公开号：——

  公开（公告）日：——