4-(5-fluorobenzo[d]thiazol-2-yl)-4-hydroxycyclohexa-2,5-dienone | 485843-31-0

• 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: 4-(5-fluorobenzo[d]thiazol-2-yl)-4-hydroxycyclohexa-2,5-dienone
• 英文别名: 4-(5-Fluoro-1,3-benzothiazol-2-yl)-4-hydroxycyclohexa-2,5-dien-1-one
• CAS: 485843-31-0
• 化学式: C₁₃H₈FNO₂S
• 分子量: 261.276
• InChiKey: XKPRKDMDJWBRLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  O-acetyl-N-(4-(5-fluorobenzo[d]thiazol-2-yl)phenyl)hydroxylamine 以 aq. phosphate buffer 、 乙腈 为溶剂， 生成 4-(5-fluorobenzo[d]thiazol-2-yl)-4-hydroxycyclohexa-2,5-dienone
  参考文献：
  名称：

  来自抗肿瘤 2-(4-氨基苯基)苯并噻唑的环取代 4-(苯并噻唑-2-基)苯基硝基离子的化学

  摘要：

  2-(4-氨基苯基)苯并噻唑的环取代衍生物1a , 1b – g正在开发中作为抗肿瘤剂。一种衍生物1f已作为前药2f Phortress (NSC 710305)进入 1 期临床试验。这些胺被 CYP450 1A1 激活，显然转化为羟胺8a - g，它们很可能被代谢成酯，这些酯电离成负责细胞损伤的氮烯离子。之前我们展示了9a，即8a的乙酸酯，产生长寿命 (530 ns) 氮鎓离子11a在水中水解或光解。在这项研究中，叠氮化物捕集显示，图9b -克生成11B -克通过限速N-O heterolysis。根据叠氮化物/溶剂选择性估计的离子寿命范围为 250 到 1150 ns，11a和11f 的寿命相同。胺的生物活性的差异可能不是由于阳离子化学的差异，而是由于单个胺的代谢活化/失活的差异。与氮烯离子不同，酯的寿命强烈依赖于 3'-Me 取代基。含有 3'-Me 的酯 ( 9b , 9f , 9g)

  DOI：

  10.1021/jo400826f

文献信息

• 4-Aryl quinols and analogs thereof as therapeutic agents
  申请人：——

  公开号：US20040220236A1

  公开（公告）日：2004-11-04

  The present invention pertains to compounds of the formula (I) which are, inter alia, antiprolilferative agents, anticancer agents, anitimycohacterial agents, antituberculosis agents, and/or thioredoxin/thioredoxin reductase inhibitor: wherein: Q is ═O or ═N—S(═O) 2 —R Q ; R Q is -II or optionally substituted C 1-7 alkyl, C 3-20 heterocyclyl, or C 5-20 aryl; Ar is optionally substituted C 5-20 aryl; R O is an oxy substituent; the bond marked &agr; is a single bond or a double bond; the bond marked &bgr; is a single bond or a double bond; R 3 and R 5 are each independently ring substituents; R 2 and R 6 are each independently ring substituents; and pharmaceutically acceptable salts, esters, amides, solvates, hydrates, and protected forms thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, for example, in the treatment of proliferative conditions, (e.g., cancer), mycobacterial infections (e.g., tuberculosis), and/or conditions mediated by thioredoxin/thioredoxin reductase. 1

  本发明涉及化合物的公式（I），其是抗增殖剂，抗癌剂，抗结核菌剂，抗结核病剂和/或硫氧还蛋白/硫氧还蛋白还原酶抑制剂，其中：Q是═O或═N-S（═O）2-RQ; RQ是-II或可选取代的C1-7烷基，C3-20杂环基或C5-20芳基; Ar是可选取代的C5-20芳基; RO是氧代取代基; 标记为&agr;的键是单键或双键; 标记为&bgr;的键是单键或双键; R3和R5各自独立地是环取代基; R2和R6各自独立地是环取代基; 以及其药学上可接受的盐，酯，酰胺，溶剂化合物，水合物和保护形式。本发明还涉及包含这种化合物的制药组合物，以及这种化合物和组合物的使用，无论是体外还是体内，例如，用于治疗增殖性疾病（例如癌症），结核菌感染（例如结核病）和/或由硫氧还蛋白/硫氧还蛋白还原酶介导的疾病。
• 4-aryl quinols and analogs thereof as therapeutic agents
  申请人：Stevens Francis Graham Malcolm

  公开号：US20060287396A1

  公开（公告）日：2006-12-21

  The present invention pertains to compounds of the following formula, which are, inter alia, antiproliferative agents, anticancer agents, antimycobacterial agents, antituberculosis agents, and/or thioredoxin/thioredoxin reductase inhibitors: wherein: Q is ═O or ═N—S(═O) 2 —R Q ; R Q is —H or optionally substituted C 1-7 alkyl, C 3-20 heterocyclyl, or C 5-20 aryl; Ar is optionally substituted C 5-20 aryl; R O is an oxy substituent; the bond marked α is a single bond or a double bond; the bond marked β is a single bond or a double bond; R 3 and R 5 are each independently ring substituents; R 2 and R 6 are each independently ring substituents; and pharmaceutically acceptable salts, esters, amides, solvates, hydrates, and protected forms thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, for example, in the treatment of proliferative conditions, (e.g., cancer), mycobacterial infections (e.g., tuberculosis), and/or conditions mediated by thioredoxin/thioredoxin reductase.

  本发明涉及以下式的化合物，它们是抗增殖剂、抗癌剂、抗分枝杆菌剂、抗结核菌剂和/或硫氧还蛋白/硫氧还蛋白还原酶抑制剂，其中：Q为═O或═N—S(═O)2—RQ；RQ为—H或可选取代的C1-7烷基、C3-20杂环基或C5-20芳基；Ar为可选取代的C5-20芳基；RO为氧代取代基；标记为α的键为单键或双键；标记为β的键为单键或双键；R3和R5各自独立地为环取代基；R2和R6各自独立地为环取代基；以及其药学上可接受的盐、酯、酰胺、溶剂化合物、水合物和保护形式。本发明还涉及包括这样的化合物的制药组合物，以及这样的化合物和组合物的使用，无论是体外还是体内，例如在治疗增殖性疾病（例如癌症）、分枝杆菌感染（例如结核病）和/或由硫氧还蛋白/硫氧还蛋白还原酶介导的疾病中。
• 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.
• 4-ARYL QUINOLS AND ANALOGS THEREOF AS THERAPEUTIC AGENTS
  申请人：Cancer Research Technology Limited

  公开号：EP1404659A1

  公开（公告）日：2004-04-07
• US7144893B2
  申请人：——

  公开号：US7144893B2

  公开（公告）日：2006-12-05