2,5-Cyclohexadien-1-one, 4-(2-benzothiazolyl)-4-propoxy- | 265312-18-3

• 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: 2,5-Cyclohexadien-1-one, 4-(2-benzothiazolyl)-4-propoxy-
• 英文别名: 4-(1,3-benzothiazol-2-yl)-4-propoxycyclohexa-2,5-dien-1-one
• CAS: 265312-18-3
• 化学式: C₁₆H₁₅NO₂S
• 分子量: 285.367
• InChiKey: ZTNISCNCNSHFFC-UHFFFAOYSA-N

物化性质

• 沸点：
  459.1±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丙醇 、 4-(1,3-苯并噻唑-2-基)苯酚 在 碘苯二乙酸 作用下， 以35%的产率得到2,5-Cyclohexadien-1-one, 4-(2-benzothiazolyl)-4-propoxy-
  参考文献：
  名称：

  抗肿瘤苯并噻唑。第10部分：苯并噻唑取代的喹诺酮衍生物的合成和抗肿瘤活性。

  摘要：

  通过高价碘介导的羟基化2-苯基苯并噻唑的氧化，报道了一系列新的抗肿瘤剂苯并噻唑取代的喹诺醚和酯的合成。发现该产物在体外对人结肠和乳腺癌细胞系有活性，IC50值在纳摩尔范围内。

  DOI：

  10.1016/s0960-894x(00)00027-5

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。
• 4-ARYL QUINOLS AND ANALOGS THEREOF AS THERAPEUTIC AGENTS
  申请人：Cancer Research Technology Limited

  公开号：EP1404659B1

  公开（公告）日：2010-02-10
• US7144893B2
  申请人：——

  公开号：US7144893B2

  公开（公告）日：2006-12-05
• Antitumour benzothiazoles. Part 10: The synthesis and antitumour activity of benzothiazole substituted quinol derivatives
  作者：Geoffrey Wells、Tracey D. Bradshaw、Patrizia Diana、Angela Seaton、Dong-Fang Shi、Andrew D. Westwell、Malcolm F.G. Stevens

  DOI：10.1016/s0960-894x(00)00027-5

  日期：2000.3

  The synthesis of a series of new antitumour agents, the benzothiazole substituted quinol ethers and esters, is reported via the hypervalent iodine mediated oxidation of hydroxylated 2-phenylbenzothiazoles. The products were found to be active in vitro against human colon and breast cancer cell lines with IC50 values in the nanomolar range.

  通过高价碘介导的羟基化2-苯基苯并噻唑的氧化，报道了一系列新的抗肿瘤剂苯并噻唑取代的喹诺醚和酯的合成。发现该产物在体外对人结肠和乳腺癌细胞系有活性，IC50值在纳摩尔范围内。