4-(苯并[d]噻唑)-2-溴苯胺 | 178804-06-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 4-(苯并[d]噻唑)-2-溴苯胺
• 英文名称: 2-(4-amino-3-bromophenyl)benzothiazole
• 英文别名: 4-benzothiazol-2-yl-2-bromophenylamine；4-(1,3-benzothiazole-2-yl)-2-bromoaniline；4-(Benzo[d]thiazol-2-yl)-2-bromoaniline；4-(1,3-benzothiazol-2-yl)-2-bromoaniline
• CAS: 178804-06-3
• 化学式: C₁₃H₉BrN₂S
• mdl: MFCD00950806
• 分子量: 305.198
• InChiKey: PZNQWLHSPUPLEL-UHFFFAOYSA-N

物化性质

• 沸点：
  456.2±55.0 °C(Predicted)
• 密度：
  1.606±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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：

  4-(苯并[d]噻唑)-2-溴苯胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 6-(benzothiazol-2-yl)-3-methyl-2-thiomethyl-benzothiazolium tosylate
  参考文献：
  名称：

  Syntheses and DNA-binding studies of a series of unsymmetrical cyanine dyes: structural influence on the degree of minor groove binding to natural DNA

  摘要：

  Twelve crescent-shaped unsymmetrical dyes have been synthesized and their interactions with DNA have been investigated by spectroscopic methods. A new facile synthetic-route to this type of cyanine dyes has been developed, involving the preparation of 6-substituted 2-thiomethyl-benzothiazoles in good yields. The new dyes are analogues to the minor groove binding unsymmetrical cyanine dye, BEBO, recently reported by us. In this dye, the structure of the known intercalating cyanine dye BO was extended with a 6-methylbenzothiazole substituent. Herein we further investigate the role of the extending benzazole heterocycle, as well as of the pyridine or quinoline moiety of the cyanine chromophore, for the binding mode of these crescent-shaped dyes to calf thymus DNA. Flow LD and CD studies of the 12 dyes show that the extent of minor groove binding to mixed sequence DNA varies significantly between the dyes. We find that hydrophobicity and size are the crucial parameters for recognition of the minor groove. The relatively high fluorescence quantum yield of many of these cyanines bound to DNA, combined with their absorption at long wavelengths, may render them useful in biological applications. In particular, two of the benzoxazole containing dyes BOXTO and 2-BOXTO show a high degree of minor groove binding and quantum yields of 0.52 and 0.32, respectively, when bound to DNA. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.02.006
• 作为产物：
  描述：

  4-(2-苯并噻唑基)苯胺 在 溴 作用下， 以 二氯甲烷 为溶剂， 以79.1%的产率得到4-(苯并[d]噻唑)-2-溴苯胺
  参考文献：
  名称：

  2-arylbenzazole compounds

  摘要：

  本文披露了含有3'-取代基和4'-NR.sup.2 R.sup.6取代基的2-苯基苯并咪唑化合物，其中苯基中的R.sup.5和R.sup.6分别为氢或烷基，或者4'-NR.sup.5 R.sup.6取代基为N-酰基（或N-苯甲酰基）。还披露了以4'-N磺酸盐形式存在的2-苯基苯并咪唑化合物。这些化合物在肿瘤细胞中表现出显著的选择性细胞毒活性，并为选择性治疗多种癌症提供了潜在有用的化疗药物。

  公开号：

  US06034246A1

文献信息

• Synthesis of 2-(4-aminophenyl)benzothiazoles using MF resin supported H+ under solvent free conditions
  作者：Yingjie Lei、Xinshi Wu、Guochun Zhang、Cuiling Ai

  DOI：10.1134/s1070363215030251

  日期：2015.3

  A simple and convenient approach to 2-(4-aminophenyl)benzothiazole derivatives by condensation of o-aminothiophenol with (un)substituted p-aminobenzoic acid under the action of melamine formaldehyde resin (MFR) supported sulfuric acid under microwave irradiation (MW) and solvent-free conditions has been developed. Structures of the corresponding products were elucidated by IR, 1H NMR spectra, and elemental

  在三聚氰胺甲醛树脂（MFR）负载的硫酸作用下，邻位氨基硫酚与（未）取代的对氨基苯甲酸缩合，在微波辐射（MW）下，生成2-（4-氨基苯基）苯并噻唑衍生物的简便方法。已经开发出无溶剂条件。通过IR，1 H NMR光谱和元素分析来阐明相应产物的结构。该树脂可以容易地回收并再用于后续反应。
• 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。
• COMPOUND FOR TREATING OR PREVENTING BREAST CANCER
  申请人：Jiangsu Atom Bioscience And Pharmaceutical Co., Ltd

  公开号：EP3296294A1

  公开（公告）日：2018-03-21

  Disclosed are a class of compounds for treating or preventing breast cancer, in particular 2-phenyl benzoselenazole compounds, and a pharmaceutically acceptable salt thereof and an easily hydrolysable prodrug thereof. Further disclosed are a pharmaceutical composition containing these compounds and the use of such compounds for for treating or preventing breast cancer in mammals. The compounds of the present invention can effectively inhibit or reduce the growth or proliferation of mammalian breast cancer cells, and at the same time, such compounds do not inhibit the growth of partial test cells, apart from breast cancer cells in mammals, and have a good selectivity. Such compounds show a more obvious medicinal effect, and have high selectivivity, low toxicity and few side effects.

  公开了一类用于治疗或预防乳腺癌的化合物，特别是 2-苯基苯并硒唑化合物，及其药学上可接受的盐和易水解的原药。进一步公开的是含有这些化合物的药物组合物，以及这些化合物用于治疗或预防哺乳动物乳腺癌的用途。本发明的化合物可以有效地抑制或减少哺乳动物乳腺癌细胞的生长或增殖，同时，除了哺乳动物的乳腺癌细胞外，这类化合物不会抑制部分试验细胞的生长，具有良好的选择性。这类化合物的药效更明显，选择性高，毒性低，副作用小。
• Antitumor Benzothiazoles. 3. Synthesis of 2-(4-Aminophenyl)benzothiazoles and Evaluation of Their Activities against Breast Cancer Cell Lines <i>in </i><i>Vitro </i>and <i>in Vivo</i>
  作者：Dong-Fang Shi、Tracey D. Bradshaw、Samantha Wrigley、Carol J. McCall、Peter Lelieveld、Iduna Fichtner、Malcolm F. G. Stevens

  DOI：10.1021/jm9600959

  日期：1996.1.1

  A new series of 2-(4-aminophenyl)benzothiazoles substituted in the phenyl ring and benzothiazole moiety has been synthesized by simple, high-yielding routes. The parent molecule 5a shows potent inhibitory activity in vitro in the nanomolar range against a panel of human breast cancer cell lines, but is inactive (IC50 > 30 mu M) against other cell types: activity against the sensitive breast lines MCF-7 and MDA 468 is characterized by a biphasic dose-response relationship. Structure-activity relationships derived using these cell types has revealed that activity follows the heterocyclic sequence benzothiazole > benzoxazole much greater than benzimidazole and that 2-(4-aminophenyl)benzothiazoles bearing a 3'-methyl- 9a, 3'-bromo- 9c, 3'- iodo- 9f, and 3'-chloro-substituent 9i are especially potent and their activity extends to ovarian, lung, and renal cell lines. Four compounds have been evaluated in vivo against human mammary carcinoma models in nude mice. Compound 9a showed the most potent growth inhibition against the ER(+) (MCF-7 and BO) and ER(-) (MT-1 and MT-3) tumors. Our efforts to identify a pharmacological mechanism of action for these intriguing compounds have not, as yet, been successful.
• Antitumor Benzothiazoles. 7. Synthesis of 2-(4-Acylaminophenyl)benzothiazoles and Investigations into the Role of Acetylation in the Antitumor Activities of the Parent Amines
  作者：Mei-Sze Chua、Dong-Fang Shi、Samantha Wrigley、Tracey D. Bradshaw、Ian Hutchinson、P. Nicholas Shaw、David A. Barrett、Lesley A. Stanley、Malcolm F. G. Stevens

  DOI：10.1021/jm981076x

  日期：1999.2.1

  2-(4-Aminophenyl)benzothiazoles display potent and selective antitumor activity against inter alia breast, ovarian, colon, and renal cell lines, but their mechanism of action, though yet to be defined, may be novel. Metabolism is suspected to play a central role in the mode of action of these benzothiazoles since drug uptake and biotransformation were observed in sensitive cell lines (e.g., breast MCF-7 and MDA 468 cells) in vitro, whereas insensitive cell lines (e.g., prostate PC 3 cells) showed negligible uptake and biotransformation. N-Acyl derivatives of the arylamines have been synthesized, and in vitro studies confirm N-acetylation and oxidation as the main metabolic transformations of 2-(4-aminophenyl)benzothiazoles, with the predominant process being dictated by the nature of the 3'-substituent. The prototype amine 3 underwent mainly N-acetylation in vitro, while 3'-substituted analogues 4 and 5 were primarily oxidized. N-Acetylation of 4 to 11 exerts a drastic dyschemotherapeutic effect in vitro, but acetylation of the halogeno congeners 5-7 gave acetylamines 12-14 which substantially retain selective antitumor activity. In vivo pharmacokinetic studies in rats confirmed rapid and exclusive N-acetylation of the 3'-methyl analogue 4, but less acetylation with the 3'-chloro analogue 5. Distinct expression patterns of N-acetyltransferase NAT1 and NAT2 have been demonstrated in our panel of cell lines.