1-(2-chloroethylamino)-9,10-anthraquinone | 3591-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-(2-chloroethylamino)-9,10-anthraquinone
• 英文别名: 1-(2-chloro-ethylamino)-anthraquinone；1-(2-Chlor-aethylamino)-anthrachinon；1-<2-Chlor-ethylamino>-anthrachinon；1-(2-chloroethylamino)anthracene-9,10-dione
• CAS: 3591-06-8
• 化学式: C₁₆H₁₂ClNO₂
• 分子量: 285.73
• InChiKey: JZRLOMSNDJNWAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-chloroethylamino)-9,10-anthraquinone 在 potassium carbonate 作用下， 以 硝基苯 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(9,10-dioxo-9,10-dihydroanthracen-1-ylamino)ethyl furan-2-carboxylate
  参考文献：
  名称：

  Transformation of 1-(acyl)(2-haloethyl)amino-9,10-anthraquinones into 1-(2-acyloxyethylamino)-9,10-anthraquinones

  摘要：

  Acylation of 1-(2-haloethylamino)-9,10-anthraquinones gave 1-[(2-haloethyl)(aroyl, hetaroyl, or acetyl)amino]-9,10-anthraquinones which were converted into the corresponding 1-[2-(aroyloxy, hetaroyloxy, or acetoxy)ethylamino]-9,10-anthraquinone on keeping in dimethylformamide. According to the experimental data (including those obtained by kinetic study), the transformation involves intramolecular migration of the acyl group through aziridinium or oxazolidinium intermediates.

  DOI：

  10.1134/s1070428006100125
• 作为产物：
  描述：

  溶剂红L-B 在 吡啶 、 苯磺酰氯 作用下， 反应 0.33h， 以95%的产率得到1-(2-chloroethylamino)-9,10-anthraquinone
  参考文献：
  名称：

  Transformation of 1-(acyl)(2-haloethyl)amino-9,10-anthraquinones into 1-(2-acyloxyethylamino)-9,10-anthraquinones

  摘要：

  Acylation of 1-(2-haloethylamino)-9,10-anthraquinones gave 1-[(2-haloethyl)(aroyl, hetaroyl, or acetyl)amino]-9,10-anthraquinones which were converted into the corresponding 1-[2-(aroyloxy, hetaroyloxy, or acetoxy)ethylamino]-9,10-anthraquinone on keeping in dimethylformamide. According to the experimental data (including those obtained by kinetic study), the transformation involves intramolecular migration of the acyl group through aziridinium or oxazolidinium intermediates.

  DOI：

  10.1134/s1070428006100125

文献信息

• DE646786
  申请人：——

  公开号：——

  公开（公告）日：——
• Potent cytotoxicity and inhibition of pan-cell cycle progression by an alkylating anthraquinone
  申请人：Epenetos Antoniou Agamemnon

  公开号：US20070208085A1

  公开（公告）日：2007-09-06

  The present invention generally relates to chemotherapeutic treatment of proliferative disorders, such as cancer. The invention more specifically relates to inhibition of pan-cell cycle progression with alkylating anthraquinones, which may inhibit mitotic commitment, lead to limited expression of G2 arrest and force cells to enter polyploidy via an aberrant mitosis. The methods of the invention are particularly useful in the treatment of chemotherapy-resistant cancers.
• [EN] ALCHEMIX FOR THE TREATMENT OF CANCER<br/>[FR] ALCHEMIX DANS LE TRAITEMENT DU CANCER
  申请人：SOMANTA LTD

  公开号：WO2007083114A1

  公开（公告）日：2007-07-26

  [EN] The present invention generally relates to chemotherapeutic treatment of proliferative disorders, such as cancer. The invention more specifically relates to inhibition of pan-cell cycle progression with alkylating anthraquinones, which may inhibit mitotic commitment, lead to limited expression of G2 arrest and force cells to enter polyploidy via an aberrant mitosis. The methods of the invention are particularly useful in the treatment of chemotherapy-resistant cancers.
  [FR] La présente invention concerne de façon générale un traitement par chimiothérapie de troubles prolifératifs, tels que les cancers. La présente invention concerne de façon plus spécifique l'inhibition de la progression de l'ensemble du cycle cellulaire par des anthraquinones alkylantes, ce qui peut inhiber la tendance à la mitose, mener à une expression limitée d'arrêt en G2 et contraindre les cellules à entrer en phase polyploïde via une mitose aberrante. Les méthodes selon l'invention peuvent en particulier être employées dans le traitement de cancers résistant aux chimiothérapies.
• [EN] N-OXIDES OF CYTOTOXIC ANTHRAQUINONES AS HYPOXIA-TARGETING PRODRUGS IN CANCER TREATMENT<br/>[FR] N-OXYDES D'ANTHRAQUINONES CYTOTOXIQUES COMME PRO-MÉDICAMENTS CIBLANT L'HYPOXIE DANS LE TRAITEMENT DU CANCER
  申请人：SOMANTA LTD

  公开号：WO2008062252A1

  公开（公告）日：2008-05-29

  [EN] The present invention generally relates to chemotherapeutic treatment of cancer. The invention more specifically provides novel DNA-directed N-oxide derivatives of chloroethylaminoanthraquinones and their precursor hydroxylated compounds, which display cytotoxic activity despite an absence of alkylating capability. The compounds of the invention further are inactive until reduced in a hypoxic environment.
  [FR] La présente invention concerne de manière générale un traitement chimiothérapique du cancer. L'invention concerne plus spécifiquement de nouveaux dérivés N-oxydes de chloroéthylaminoanthraquinones dirigés vers l'ADN et leurs composés hydroxylés précurseurs, qui présentent une activité cytotoxique malgré une absence de capacité alkylante. Les composés selon l'invention sont en outre inactifs jusqu'à ce qu'ils soient réduits dans un environnement hypoxique.