5-fluoro-2-(4-hydroxyphenyl)benzothiazole | 880088-30-2

• 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: 5-fluoro-2-(4-hydroxyphenyl)benzothiazole
• 英文别名: 4-(5-fluoro-1,3-benzothiazol-2-yl)phenol
• CAS: 880088-30-2
• 化学式: C₁₃H₈FNOS
• mdl: MFCD11636983
• 分子量: 245.277
• InChiKey: FTDAZLXVIURESD-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：
  61.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-fluoro-2-(4-hydroxyphenyl)benzothiazole 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 水 、 乙腈 为溶剂， 反应 0.25h， 以44%的产率得到4-(5-fluorobenzo[d]thiazol-2-yl)-4-hydroxycyclohexa-2,5-dienone
  参考文献：
  名称：

  Antitumour properties of fluorinated benzothiazole-substituted hydroxycyclohexa-2,5-dienones (‘quinols’)

  摘要：

  The synthesis and in vitro antitumour evaluation of a new series of fluorinated benzothiazole-substituted 4-hydroxycyclohexa-2,5-dienones ('quinols') is described. The new compounds were found to be of comparable activity compared to the nonfluorinated precursor PMX 464, in terms of antiproliferative activity in sensitive human cancer cell lines (nanomolar GI(50) values) and inhibitory activity against the thioredoxin signalling system. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.072
• 作为产物：
  描述：

  对羟基苯甲醛 、 bis(2-amino-4-fluorophenyl)disulfide 在 对甲苯磺酸 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 72.0h， 生成 5-fluoro-2-(4-hydroxyphenyl)benzothiazole
  参考文献：
  名称：

  强效抗肿瘤药2-（3,4-二甲氧基苯基）-5-氟苯并噻唑的苯并噻唑，苯并恶唑和chromen-4-one类似物的合成和生物学特性（PMX 610，NSC 721648）。

  摘要：

  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。

  DOI：

  10.1021/jm800418z

文献信息

• 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
• 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。
• Antitumour properties of fluorinated benzothiazole-substituted hydroxycyclohexa-2,5-dienones (‘quinols’)
  作者：Cedric J. Lion、Charles S. Matthews、Geoffrey Wells、Tracey D. Bradshaw、Malcolm F.G. Stevens、Andrew D. Westwell

  DOI：10.1016/j.bmcl.2006.07.072

  日期：2006.10

  The synthesis and in vitro antitumour evaluation of a new series of fluorinated benzothiazole-substituted 4-hydroxycyclohexa-2,5-dienones ('quinols') is described. The new compounds were found to be of comparable activity compared to the nonfluorinated precursor PMX 464, in terms of antiproliferative activity in sensitive human cancer cell lines (nanomolar GI(50) values) and inhibitory activity against the thioredoxin signalling system. (c) 2006 Elsevier Ltd. All rights reserved.