6-ethoxy-2-(4-hydroxyphenyl)benzothiazole

• 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: 6-ethoxy-2-(4-hydroxyphenyl)benzothiazole
• 英文别名: 4-(6-ethoxybenzothiazol-2-yl)phenol；4-(6-ethoxy-1,3-benzothiazol-2-yl)phenol
• 化学式: C₁₅H₁₃NO₂S
• 分子量: 271.34
• InChiKey: JULMDIZRXYUITQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  70.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  bis(2-amino-5-ethoxyphenyl)disulfide 、 对羟基苯甲醛 在 sodium metabisulfite 作用下， 以 二甲基亚砜 为溶剂， 以91%的产率得到6-ethoxy-2-(4-hydroxyphenyl)benzothiazole
  参考文献：
  名称：

  苯并噻唑环上取代的与生物有关的2-苯基苯并噻唑的有效合成途径

  摘要：

  某些在苯并噻唑环上含有取代基的2-苯基苯并噻唑具有重要的生物学特性，但是迄今为止描述的2-苯基苯并噻唑的大多数合成方法都集中在它们的未取代环对应物上。在这里，我们描述了一种新的简洁有效的合成路线，该路线是由廉价的且无毒的无机氧化剂偏亚硫酸氢钠在DMSO中于120°C促进的，是由取代的2-氨基硫代苯酚二硫化物与苯甲醛的反应以高收率获得生物相关的2-苯基苯并噻唑的新方法。我们的新方法可耐受苯并噻唑和苯环上的一系列取代基，并且无需柱色谱即可有效获得取代的2-苯基苯并噻唑。

  DOI：

  10.1016/j.tet.2011.08.004

文献信息

• An efficient synthetic route to biologically relevant 2-phenylbenzothiazoles substituted on the benzothiazole ring
  作者：Ashley A. Weekes、Mark C. Bagley、Andrew D. Westwell

  DOI：10.1016/j.tet.2011.08.004

  日期：2011.10

  focus on their unsubstituted ring counterparts. Here we describe a new concise and efficient synthetic route to biologically relevant 2-phenylbenzothiazoles in high yield from the reaction of substituted 2-aminothiophenol disulfides and benzaldehydes, promoted by the inexpensive and non-toxic inorganic oxidant sodium metabisulfite in DMSO at 120 °C. Our new method is tolerant of a range of substituents

  某些在苯并噻唑环上含有取代基的2-苯基苯并噻唑具有重要的生物学特性，但是迄今为止描述的2-苯基苯并噻唑的大多数合成方法都集中在它们的未取代环对应物上。在这里，我们描述了一种新的简洁有效的合成路线，该路线是由廉价的且无毒的无机氧化剂偏亚硫酸氢钠在DMSO中于120°C促进的，是由取代的2-氨基硫代苯酚二硫化物与苯甲醛的反应以高收率获得生物相关的2-苯基苯并噻唑的新方法。我们的新方法可耐受苯并噻唑和苯环上的一系列取代基，并且无需柱色谱即可有效获得取代的2-苯基苯并噻唑。
• Synthesis and Biological Properties of Benzothiazole, Benzoxazole, and Chromen-4-one Analogues of the Potent Antitumor Agent 2-(3,4-Dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648)
  作者：Stefania Aiello、Geoffrey Wells、Erica L. Stone、Hachemi Kadri、Rana Bazzi、David R. Bell、Malcolm F. G. Stevens、Charles S. Matthews、Tracey D. Bradshaw、Andrew D. Westwell

  DOI：10.1021/jm800418z

  日期：2008.8.1

  New fluorinated 2-aryl-benzothiazoles, -benzoxazoles, and -chromen-4-ones have been synthesized and their activity against MCF-7 and MDA 468 breast cancer cell lines compared with the potent antitumor benzothiazole 5. Analogues such as 9a, b and 12a, d yielded submicromolar GI50 values in both cell lines; however, none of the new compounds approached 5 in terms of antitumor potency. For 5, binding

  已经合成了新的氟化的2-芳基-苯并噻唑，-苯并恶唑和-铬-4-酮，与有效的抗肿瘤苯并噻唑5相比，它们对MCF-7和MDA 468乳腺癌细胞系具有活性。 12a，d在两种细胞系中产生亚微摩尔GI 50值；然而，就抗肿瘤效力而言，新化合物均未达到5。对于5，似乎必须结合芳基烃受体，但不足以抑制生长。
• 2-Arylbenzothiazole derivatives
  申请人：Stevens Francis G. Malcolm

  公开号：US20060063816A1

  公开（公告）日：2006-03-23

  A compound of general structure I, wherein the compound is optionally in the form of an N-oxide or S-oxide or prodrug form and/or pharmaceutically acceptable salt thereof wherein: each of R 1 to R 9 is independently selected from hydrogen, hydroxyl, alkoxy, halo, mesyl, CX 3 (X=halo), —O(CH 2 )nNYZ—, substituted or unsubstituted lower alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl or heteroaryl, and substituted or unsubstituted aralkyl or heteroaralkyl; optionally R 6 and R 7 together form a dioxymethylene (—OCH 2 O—) unit and wherein n is 1 to 3 and Y and Z are independently selected from any of the following: C 1 -C 6 straight chain, branched or cyclic substituted or unsubstituted alkyl group, Y and Z can be taken together to form a cyclic alkyl or hetereoalkyl group wherein in addition to N the hetereoalkyl group comprises a heteroatom selected from N, O or S.

  通用结构I的化合物，其中该化合物可以是N-氧化物或S-氧化物或前药形式和/或其药用可接受盐形式，其中：R1至R9中的每一个独立地选择自氢、羟基、烷氧基、卤素、甲磺基、CX3（X=卤素）、—O(CH2)nNYZ—、取代或未取代的较低烷基、取代或未取代的杂烷基、取代或未取代的芳基或杂芳基，以及取代或未取代的芳基或杂芳基；可选地，R6和R7一起形成二氧亚甲基（—OCH2O—）单元，其中n为1至3，Y和Z分别选择自以下任一：C1-C6直链、支链或环状取代或未取代的烷基，Y和Z可以一起形成环状烷基或杂环烷基，其中除N外，杂环烷基还包括从N、O或S中选择的杂原子。
• US7384966B2
  申请人：——

  公开号：US7384966B2

  公开（公告）日：2008-06-10
• Convenient Synthesis of Substituted 2-Phenylbenzothiazoles Using Solid-Supported Triphenylphosphine
  作者：Ashley A. Weekes、Jan Frydrych、Andrew D. Westwell

  DOI：10.1080/00397911.2012.730648

  日期：2013.10.2

  We report an improved procedure using solid-supported triphenylphosphine for the concise synthesis of biologically relevant 2-phenylbenzothiazoles featuring a variety of substituents on both the benzothiazole and phenyl rings. Substituted 2-phenylbenzothiazoles were synthesized by heating equimolar quantities of 2-aminothiophenol disulfides with benzaldehydes and p-toluenesulfonic acid in the presence of polymer-supported triphenylphosphine in dimethylformamide/toluene. Appealing features of this new method include simple isolation of product (removal of phosphine oxide by-product by filtration), avoidance of column chromatography, and good yields of substituted 2-phenylbenzothiazole products. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.