2-(4-aminophenyl)-4-chlorobenzothiazole | 1073610-49-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(4-aminophenyl)-4-chlorobenzothiazole
• 英文别名: 4-(4-chloro-1,3-benzothiazole-2-yl)aniline；[4-(4-Chloro-1,3-benzothiazol-2-yl)phenyl]amine；4-(4-chloro-1,3-benzothiazol-2-yl)aniline
• CAS: 1073610-49-7
• 化学式: C₁₃H₉ClN₂S
• 分子量: 260.747
• InChiKey: MFTJXHQJSNXKMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-aminophenyl)-4-chlorobenzothiazole 、 鬼臼毒素 以75%的产率得到4β-[4-(4-chloro-1,3-benzothiazole-2-yl)anilino]-4-desoxypodophyllotoxin
  参考文献：
  名称：

  NOVEL 4BETA-AMINO PODOPHYLLOTOXIN CONGENERS AS POTENTIAL ANTICANCER AGENTS AND A PROCESS FOR THE PREPARATION THEREOF

  摘要：

  本发明提供了一类新的4β-[4″-(1″,3″-苯并噻唑-2″-基)苯胺基]翠榆毒素类似物，其结构式如下所示（4）。其中R=H或CH3；R1=H、卤素、CH3；R2=H、卤素、OCH3。本发明还提供了一种制备新的4β-[4″-(1″,3″-苯并噻唑-2″-基)苯胺基]翠榆毒素类似物作为有效抗癌剂的方法。更具体地，它提供了一种制备翠榆毒素的4β-[4″-(1″,3″-苯并噻唑-2″-基)苯胺基]衍生物的方法。合成新翠榆毒素类似物作为抗癌剂的方法产生了翠榆毒素的新颖和立体选择性衍生物，其中这些类似物的合成关键步骤是通过对C-4β-碘中间体的直接亲核取代。4β-碘翠榆毒素与取代或未取代的4-(1,3-苯并噻唑-2-基)苯胺以立体选择性的方式反应，从而得到4β-[4″-(1″,3″-苯并噻唑-2″-基)苯胺基]翠榆毒素衍生物。

  公开号：

  US20080275248A1
• 作为产物：
  描述：

  2-氨基-3-氯苯硫酚 、 对氨基苯甲酸 在 polyphosphoric acid 作用下， 反应 3.0h， 生成 2-(4-aminophenyl)-4-chlorobenzothiazole
  参考文献：
  名称：

  An efficient one-pot synthesis of benzothiazolo-4β-anilino-podophyllotoxin congeners: DNA topoisomerase-II inhibition and anticancer activity

  摘要：

  An efficient one-pot iodination methodology for the synthesis of benzothiazolo-4 beta-anilino-podophyllotoxin (5a-h) and benzothiazolo-4 beta-anilino-4-O-demethylepipodophyllotoxin (6a-h) congeners has been successfully developed by using zirconium tetrachloride/sodium iodide. Interestingly, this protocol demonstrates enhancement of stereoselectivity apart from the improvement in the yields in comparison to previous methods reported for such related podophyllotoxin derivatives. These compounds have been designed and synthesized using association strategy by coupling of 4 beta-podophyllotoxin and 4 beta-demethylepipodophyllotoxin with a variety of substituted aminoaryl benzothiazoles. Some of the representative compounds have been evaluated for their cytotoxicity against selected human cancer cell lines and DNA topoisomerase-II inhibition activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.002

文献信息

• An efficient one-pot synthesis of benzothiazolo-4β-anilino-podophyllotoxin congeners: DNA topoisomerase-II inhibition and anticancer activity
  作者：Ahmed Kamal、B. Ashwini Kumar、Paidakula Suresh、Nagula Shankaraiah、M. Shiva Kumar

  DOI：10.1016/j.bmcl.2010.11.002

  日期：2011.1

  An efficient one-pot iodination methodology for the synthesis of benzothiazolo-4 beta-anilino-podophyllotoxin (5a-h) and benzothiazolo-4 beta-anilino-4-O-demethylepipodophyllotoxin (6a-h) congeners has been successfully developed by using zirconium tetrachloride/sodium iodide. Interestingly, this protocol demonstrates enhancement of stereoselectivity apart from the improvement in the yields in comparison to previous methods reported for such related podophyllotoxin derivatives. These compounds have been designed and synthesized using association strategy by coupling of 4 beta-podophyllotoxin and 4 beta-demethylepipodophyllotoxin with a variety of substituted aminoaryl benzothiazoles. Some of the representative compounds have been evaluated for their cytotoxicity against selected human cancer cell lines and DNA topoisomerase-II inhibition activity. (C) 2010 Elsevier Ltd. All rights reserved.
• NOVEL 4BETA-AMINO PODOPHYLLOTOXIN CONGENERS AS POTENTIAL ANTICANCER AGENTS AND A PROCESS FOR THE PREPARATION THEREOF
  申请人：Ahmed Kamal

  公开号：US20080275248A1

  公开（公告）日：2008-11-06

  The present invention provides new class of 4β-[4″-(1″,3″-benzothiazole-2″-yl)anilino]podophyllotoxin analogues having the structural formula as follows (4). Where R═H or CH 3 ; R 1 ═H, halogen, CH 3 and R 2 ═H, halogen, OCH 3 . The present invention also provides a process for the preparation of new 4β-[4″-(1″, 3″-benzothiazole-2″-yl)anilino]podophyllotoxin analogues as useful anticancer agents. More particularly, it provides a process for the preparation of 4β-[4″-(1″,3″-benzothiazole-2″-yl)anilino] derivatives of podophyllotoxin. The process for the synthesis of new podophyllotoxin analogues as anticancer agents produces the novel and stereo-selective derivatives of the podophyllotoxin in good yields, where in the key step for the synthesis of these analogues is by direct nucleophilic substitution of C-4β-iodo intermediates. The 4β-iodopodophyllotoxin, which has been reacted with substituted or unsubstituted 4-(1,3-benzothiazole-2-yl)aniline in a stereo-selective manner to afford the 4β-[4″-(1″,3″-benzothiazole-2″-yl)anilino] derivatives of podophyllotoxin.

  本发明提供了一类新的4β-[4″-(1″,3″-苯并噻唑-2″-基)苯胺基]翠榆毒素类似物，其结构式如下所示（4）。其中R=H或CH3；R1=H、卤素、CH3；R2=H、卤素、OCH3。本发明还提供了一种制备新的4β-[4″-(1″,3″-苯并噻唑-2″-基)苯胺基]翠榆毒素类似物作为有效抗癌剂的方法。更具体地，它提供了一种制备翠榆毒素的4β-[4″-(1″,3″-苯并噻唑-2″-基)苯胺基]衍生物的方法。合成新翠榆毒素类似物作为抗癌剂的方法产生了翠榆毒素的新颖和立体选择性衍生物，其中这些类似物的合成关键步骤是通过对C-4β-碘中间体的直接亲核取代。4β-碘翠榆毒素与取代或未取代的4-(1,3-苯并噻唑-2-基)苯胺以立体选择性的方式反应，从而得到4β-[4″-(1″,3″-苯并噻唑-2″-基)苯胺基]翠榆毒素衍生物。