2-(3-fluoro-4-hydroxyphenyl)benzothiazole | 920520-37-2

• 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-(3-fluoro-4-hydroxyphenyl)benzothiazole
• 英文别名: 4-(1,3-Benzothiazol-2(3H)-ylidene)-2-fluorocyclohexa-2,5-dien-1-one；4-(1,3-benzothiazol-2-yl)-2-fluorophenol
• CAS: 920520-37-2
• 化学式: C₁₃H₈FNOS
• 分子量: 245.277
• InChiKey: BKTFPKDWBGTAPI-UHFFFAOYSA-N

物化性质

• 熔点：
  222-223 °C
• 沸点：
  405.9±55.0 °C(Predicted)
• 密度：
  1.408±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

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：
  61.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-fluoro-4-hydroxyphenyl)benzothiazole 在 四氯化碳 、 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 25.52h， 生成 4-(benzothiazol-2-yl)-2-fluorophenyl dihydrogen phosphate
  参考文献：
  名称：

  Synthesis of 2-arylbenzothiazole derivatives and their application in bacterial detection

  摘要：

  A series of 2-arylbenzothiazole derivatives have been prepared as fluorogenic enzyme substrates in order to detect aminopeptidase, esterase, phosphatase and beta-galactosidase activity in clinically important Gram-negative and Gram-positive bacteria. Substrates were incorporated into an agar-based culture medium and this allowed growth of intensely fluorescent bacterial colonies based on hydrolysis by specific enzymes. Substrate 20 targeted L-alanine aminopeptidase activity and was hydrolysed exclusively by a range of Gram-negative bacteria and inhibited the growth of a range of Gram-positive bacteria. Substrate 19a targeted beta-alanyl aminopeptidase activity and generated fluorescent colonies of selected Gram-negative species including Pseudomonas aeruginosa. Substrate 21b targeted C8-esterase activity and resulted in strongly fluorescent colonies of selected species known to harbour such enzyme activity (e. g., Salmonella and Pseudomonas). Most Gram-negative species produced colonies with an intense blue fluorescence due to hydrolysis of phosphatase substrates 24a-c and substrate 24c was also hydrolysed by strains of Staphylococcus aureus. Compounds 26b and 26c targeted beta-galactosidase activity and generated strongly fluorescent colonies with coliform bacteria that produced this enzyme (e. g., Escherichia coli). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.013
• 作为产物：
  描述：

  2-(3-fluoro-4-methoxyphenyl)-2,3-dihydrobenzo[d]thiazole 在 吡啶溴化氢盐 、 四氯苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 20.5h， 生成 2-(3-fluoro-4-hydroxyphenyl)benzothiazole
  参考文献：
  名称：

  Synthesis of 2-arylbenzothiazole derivatives and their application in bacterial detection

  摘要：

  A series of 2-arylbenzothiazole derivatives have been prepared as fluorogenic enzyme substrates in order to detect aminopeptidase, esterase, phosphatase and beta-galactosidase activity in clinically important Gram-negative and Gram-positive bacteria. Substrates were incorporated into an agar-based culture medium and this allowed growth of intensely fluorescent bacterial colonies based on hydrolysis by specific enzymes. Substrate 20 targeted L-alanine aminopeptidase activity and was hydrolysed exclusively by a range of Gram-negative bacteria and inhibited the growth of a range of Gram-positive bacteria. Substrate 19a targeted beta-alanyl aminopeptidase activity and generated fluorescent colonies of selected Gram-negative species including Pseudomonas aeruginosa. Substrate 21b targeted C8-esterase activity and resulted in strongly fluorescent colonies of selected species known to harbour such enzyme activity (e. g., Salmonella and Pseudomonas). Most Gram-negative species produced colonies with an intense blue fluorescence due to hydrolysis of phosphatase substrates 24a-c and substrate 24c was also hydrolysed by strains of Staphylococcus aureus. Compounds 26b and 26c targeted beta-galactosidase activity and generated strongly fluorescent colonies with coliform bacteria that produced this enzyme (e. g., Escherichia coli). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.013

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。
• Synthesis, Antiproliferative Evaluation and QSAR Analysis of Novel Halogen- and Amidino-Substituted Benzothiazoles and Benzimidazoles
  作者：Valentina Rep Kaulić、Livio Racané、Marijana Leventić、Domagoj Šubarić、Vesna Rastija、Ljubica Glavaš-Obrovac、Silvana Raić-Malić

  DOI：10.3390/ijms232415843

  日期：——

  HuT78 cells with IC50 < 10 µM. Moreover, compounds 45c and 46c containing the methoxy group at the phenoxy unit were not toxic to normal BJ cells. Of all the tested compounds, benzimidazole 45a with the unsubstituted phenoxy central core showed the most pronounced cell growth inhibition on THP1 cells in the nanomolar range (IC50 = 0.8 µM; SI = 70). QSAR models of antiproliferative activity for benzazoles

  6-卤素取代的苯并噻唑的合成是通过 4-羟基苯甲醛和 2-氨基苯硫酚缩合，然后用适当的卤化物进行 O-烷基化，而 6-脒基取代的苯并噻唑是通过 5-脒基-2-氨基苯硫酚和相应的缩合合成的苯甲醛。虽然来自未取代和卤素取代的苯并噻唑系列的大多数化合物对测试的肿瘤细胞系显示出边缘抗增殖活性，但脒基苯并唑表现出更强的抑制活性。一般来说，咪唑基苯并噻唑显示出明显的非选择性活性，但 36c 除外，它对 HuT78 细胞具有强烈的抑制作用 (IC50 = 1.6 µM)，而对正常 BJ 细胞没有不利的细胞毒性 (IC50 >100 µM)。与苯并噻唑相比，含有 1,2,3-三唑环的苯并咪唑结构类似物 45a-45c 和 46c 对 HuT78 细胞表现出显着和选择性的抗增殖活性，IC50 < 10 µM。此外，在苯氧基单元上含有甲氧基的化合物 45c 和 46c 对正常 BJ 细胞没有毒性。在所有测试的
• Benzothiazole derivatives as histone deacetylase inhibitors for the treatment of autosomal dominant polycystic kidney disease
  作者：Xudong Cao、Zhiyuan Fan、Lingfang Xu、Wenchao Zhao、Haoran Zhang、Yunfang Yang、Ying Ren、Yuxian Xiao、Nan Zhou、Long Yin、Xueyan Zhou、Xu Zhu、Dong Guo

  DOI：10.1016/j.ejmech.2024.116428

  日期：2024.5

  Recent evidence suggests that histone deacetylases (HDACs) are important regulators of autosomal dominant polycystic kidney disease (ADPKD). In the present study, a series of benzothiazole-bearing compounds were designed and synthesized as potential HDAC inhibitors. Given the multiple participation of HDACs in ADPKD cyst progression, we embarked on a targeted screen using HeLa nuclear extracts to identify

  最近的证据表明组蛋白脱乙酰酶 (HDAC) 是常染色体显性多囊肾病 (ADPKD) 的重要调节因子。在本研究中，设计并合成了一系列含有苯并噻唑的化合物作为潜在的 HDAC 抑制剂。鉴于 HDAC 在 ADPKD 囊肿进展中的多重参与，我们开始使用 HeLa 核提取物进行靶向筛选，以鉴定有效的泛 HDAC 抑制剂。复合物成为最有效的候选者。随后的药理学表征表明，该化合物可有效抑制多种 HDAC，尤其是 HDAC1、HDAC2 和 HDAC6 (IC < 150 nM)，对 HDAC6 显示出特别高的敏感性 (IC = 11 nM)。所选化合物可显着阻止囊肿模型中囊肿的形成和扩张，并能有效减少胚胎肾囊肿模型和 ADPKD 小鼠模型中的囊肿生长。我们的结果提供了令人信服的证据，证明该化合物是一种用于治疗 ADPKD 的新型 HDAC 抑制剂。
• 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.