2-(4-amino-3-fluorophenyl)benzothiazole | 343975-63-3

• 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-amino-3-fluorophenyl)benzothiazole
• 英文别名: 4-benzothiazol-2-yl-2-fluoro-phenylamine；4-benzothiazol-2-yl-2-fluorophenylamine；Benzenamine, 4-(2-benzothiazolyl)-2-fluoro-；4-(1,3-benzothiazol-2-yl)-2-fluoroaniline
• CAS: 343975-63-3
• 化学式: C₁₃H₉FN₂S
• 分子量: 244.292
• InChiKey: YPMSJWNNIBRQDS-UHFFFAOYSA-N

物化性质

• 熔点：
  160-161 °C
• 沸点：
  413.7±55.0 °C(Predicted)
• 密度：
  1.372±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  4

反应信息

• 作为反应物：
  描述：

  4-氯噻吩并[3,2-d]嘧啶 、 2-(4-amino-3-fluorophenyl)benzothiazole 以 乙二醇 为溶剂， 反应 3.0h， 生成 (4-benzothiazol-2-yl-2-fluoro-phenyl)-thieno[3,2-d]pyrimidin-4-yl-amine
  参考文献：
  名称：

  N-substituted 2′-(aminoaryl)benzothiazoles as kinase inhibitors: Hit identification and scaffold hopping

  摘要：

  Starting with a hit from vHTS attained by a docking procedure of virtual compounds into ATP pockets of different kinases applying the 4SCan (R) technology, variations of the adenine mimic resulted in the identification of promising scaffolds, giving rise to in vitro IC50 values in the nanomolar range on different kinases down to 63 nM. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.054
• 作为产物：
  描述：

  3-氟-4-氨基苯甲酸 、 2-氨基苯硫醇 在 PPA 作用下， 生成 2-(4-amino-3-fluorophenyl)benzothiazole
  参考文献：
  名称：

  N-substituted 2′-(aminoaryl)benzothiazoles as kinase inhibitors: Hit identification and scaffold hopping

  摘要：

  Starting with a hit from vHTS attained by a docking procedure of virtual compounds into ATP pockets of different kinases applying the 4SCan (R) technology, variations of the adenine mimic resulted in the identification of promising scaffolds, giving rise to in vitro IC50 values in the nanomolar range on different kinases down to 63 nM. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.054

文献信息

• 2-arylbenzothiazole analogues and uses thereof
  申请人：Ehlert Jan

  公开号：US20070021446A1

  公开（公告）日：2007-01-25

  The present invention relates to compounds of the general formula (I) and salts, prodrugs, and stereoisomers thereof, wherein Y independently represents S, O, NR 2 , SO, SO 2 ; A independently represents a fife- or six-membered aromatic carbocycle or heterocycle and wherein R 1 to R 20 in formula (I) represent independently of each other a variety of different substituents comprising alkyl, aryl, aralkyl, alkylaryl, heteroaryl groups and monofunctional moieties.

  本发明涉及一般式(I)的化合物及其盐、前药和立体异构体，其中Y独立表示S、O、NR2、SO、SO2；A独立表示五元或六元芳香碳环或杂环，式(I)中的R1至R20独立地表示各种不同取代基，包括烷基、芳基、芳基烷基、烷基芳基、杂芳基团和单官能团。
• 2-Arylbenzothiazole analogues and uses thereof in the treatment of cancer
  申请人：4SC AG

  公开号：EP1746096A1

  公开（公告）日：2007-01-24

  The present invention relates to anticancer compounds of the general formula (I) and salts and physiologically functional derivatives thereof, wherein Y independently represents S, O, NR2, SO, SO2; A independently represents a five- or six-membered aromatic carbocycle or heterocycle and wherein R1 in formula (I) represents one of the heteroaryl groups defined in the claims.

  本发明涉及一般式（I）的抗癌化合物及其盐和生理功能衍生物，其中Y独立表示S、O、NR2、SO、SO2；A独立表示五元或六元芳香碳环或杂环，式（I）中的R1表示权利要求中定义的杂芳基中的一个。
• Substituted 2-arylbenzothiazoles as kinase inhibitors: Hit-to-lead optimization
  作者：Stefan Tasler、Oliver Müller、Tanja Wieber、Thomas Herz、Stefano Pegoraro、Wael Saeb、Martin Lang、Rolf Krauss、Frank Totzke、Ute Zirrgiebel、Jan E. Ehlert、Michael H.G. Kubbutat、Christoph Schächtele

  DOI：10.1016/j.bmc.2009.07.047

  日期：2009.9

  Based on an (aminoaryl)benzothiazole quinazoline hit structure for kinase inhibition, a systematic optimization program resulted in a lead structure allowing for inhibitory activities in cellular phosphorylation assays in the low nanomolar range. (C) 2009 Elsevier Ltd. All rights reserved.
• Antitumor Benzothiazoles. 14. Synthesis and in Vitro Biological Properties of Fluorinated 2-(4-Aminophenyl)benzothiazoles
  作者：Ian Hutchinson、Mei-Sze Chua、Helen L. Browne、Valentina Trapani、Tracey D. Bradshaw、Andrew D. Westwell、Malcolm F. G. Stevens

  DOI：10.1021/jm001104n

  日期：2001.4.1

  Synthetic routes to a series of mono- and difluorinated 2-(4-amino-3-substituted-phenyl)benzothiazoles have been devised. Whereas mixtures of regioisomeric 5- and 7-fluorobenzothiazoles were formed from the established Jacobsen cyclization of precursor 3-fluorothiobenzanilides, two modifications to this general process have allowed the synthesis of pure samples of these target compounds. Fluorinated 2-(4-aminophenyl)benzothiazoles were potently cytotoxic (GI(50) < 1 nM) in vitro in sensitive human breast MCF-7 (ER+) and MDA 468 (ER-) cell lines but inactive (GI(50) > 10 muM) against PC 3 prostate, nonmalignant HBL 100 breast, and HCT 116 colon cells. The biphasic dose-response relationship characteristically shown by the benzothiazole series against sensitive cell lines was exhibited by the 4- and 6-fluorobenzothiazoles (10b,d) but not by the 5- and 7-fluoro-benzothiazoles (10h,i). The most potent broad spectrum agent in the NCI cell panel was 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole (10h) which, unlike the g-fluoro isomer (10d), produces no exportable metabolites in the presence of sensitive MCF-7 cells. Induction of cytochrome P450 CYP1A1, a crucial event in determining the antitumor specificity of this series of benzothiazoles, was not compromised. 10h is currently the focus of pharmaceutical and preclinical development.
• Metabolically Stabilized Benzothiazoles for Imaging of Amyloid Plaques
  作者：Gjermund Henriksen、Andrea I. Hauser、Andrew D. Westwell、Behrooz H. Yousefi、Markus Schwaiger、Alexander Drzezga、Hans-Jürgen Wester

  DOI：10.1021/jm061466g

  日期：2007.3.1

  Six new N-C-11-labeled aminophenylbenzothiazoles substituted with fluorine in different positions have been synthesized and evaluated as amyloid-beta binding ligands. Our structure-property relationship studies show that the substitution pattern of the phenyl ring and the benzothiazole moiety has an influence on the metabolic stability, which in turn has an effect on the brain uptake kinetics. Two lead compounds have been identified with improved physicochemical characteristics for A beta-plaque imaging in vivo.