2-溴-4-(4-甲基苯基)噻唑 | 101862-33-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-溴-4-(4-甲基苯基)噻唑
• 英文名称: 2-bromo-4-p-tolyl-thiazole
• 英文别名: 2-bromo-4-(4-methylphenyl)-1,3-thiazole；2-Brom-4-p-tolyl-thiazol；2-Bromo-4-(p-tolyl)thiazole
• CAS: 101862-33-3
• 化学式: C₁₀H₈BrNS
• 分子量: 254.15
• InChiKey: GVZVUOXJUMFTQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  artemisinin 、 2-溴-4-(4-甲基苯基)噻唑 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.66h， 生成
  参考文献：
  名称：

  Thiazole, Oxadiazole, and Carboxamide Derivatives of Artemisinin are Highly Selective and Potent Inhibitors of Toxoplasma gondii

  摘要：

  We have prepared 23 new dehydroartemisinin (DART) trioxane derivatives (11 thiazoles, 2 oxadiazoles, and 10 carboxamides) and have screened them for in vitro activity in the Toxoplasma lytic cycle. Fifteen (65%) of the derivatives were noncytotoxic to host cells (TD50 >= 320 mu M). Eight thiazole derivatives and two carboxamide derivatives displayed effective inhibition of Toxoplasma growth (IC50 = 0.25-0.42 mu M), comparable in potency to artemether (IC50 = 0.31 mu M) and > 100 times more inhibitory than the currently employed front-line drug trimethoprim (IC50 = 46 mu M). The thiazoles as a group were more effective than the other derivatives at inhibiting growth of extracellular as well as intracellular parasites. Unexpectedly, two thiazole trioxanes (5 and 6) were parasiticidal; both inhibited parasite replication irreversibly after parasite exposure to 10 mu M of drug for 24 h, whereas the standard trioxane drugs artemisinin and artemether were not parasiticidal. Some of the new derivatives of artemisinin described here represent effective anti-Toxoplasma trioxanes as well as molecular probes for elucidating the mechanism of action of the DART class of artemisinin derivatives.

  DOI：

  10.1021/jm901857d
• 作为产物：
  描述：

  4-甲基苯乙酮硫氰酸酯 在 氢溴酸 作用下， 以 乙醚 为溶剂， 生成 2-溴-4-(4-甲基苯基)噻唑
  参考文献：
  名称：

  Ralhan,N.K. et al., Journal of the Indian Chemical Society, 1960, vol. 37, p. 773 - 774

  摘要：

  DOI：

文献信息

• 5-HYDROXYPYRIMIDINE-4-CARBOXAMIDE COMPOUND
  申请人：Kuribayashi Takeshi

  公开号：US20110112103A1

  公开（公告）日：2011-05-12

  The present invention provides compounds which promote erythropoietin production. Compounds represented by the following general formula (1) or pharmacologically acceptable salts thereof are provided: [wherein, R 1 represents a group —X-Q 1 , X-Q 1 -Y-Q 2 or X-Q 1 -Y-Q 2 -Z-Q 3 , X represents a single bond, —CH 2 — or the like, Q 1 represents a monocyclic or bicyclic heterocyclic group which may have substituent(s), Y represents a single bond, —CH 2 —, or the like, Q 2 represents a monocyclic or bicyclic hydrocarbon ring group which may have substituent(s) or a monocyclic or bicyclic heterocyclic group which may have substituent(s), Z represents a single bond, —CR 11 R 12 — or the like, R 11 and R 12 each independently represents a hydrogen atom, a halogen atom or the like, Q 3 represents a phenyl group which may have substituent(s), a C 3 -C 7 cycloalkyl group which may have substituent(s), a C 3 -C 7 cycloalkenyl group which may have substituent(s) or a monocyclic or bicyclic heterocyclic group which may have substituent(s), R 2 represents a C 1 -C 3 alkyl group or the like, and R 3 represents a hydrogen atom or a methyl group].

  本发明提供促进促红细胞生成素产生的化合物。提供以下一般式（1）表示的化合物或其药理学上可接受的盐： [其中，R 1 表示一个基团-X-Q 1 ，X-Q 1 -Y-Q 2 或X-Q 1 -Y-Q 2 -Z-Q 3 ，X表示一个单键，-CH 2 -或类似物，Q 1 表示可能具有取代基的单环或双环杂环基团，Y表示一个单键，-CH 2 -或类似物，Q 2 表示可能具有取代基的单环或双环碳氢环基团或可能具有取代基的单环或双环杂环基团，Z表示一个单键，-CR 11 R 12 -或类似物，R 11 和R 12 各自独立地表示氢原子、卤素原子或类似物，Q 3 表示可能具有取代基的苯基团，可能具有取代基的C 3 -C 7 环烷基团，可能具有取代基的C 3 -C 7 环烯基团或可能具有取代基的单环或双环杂环基团，R 2 表示C 1 -C 3 烷基团或类似物，R 3 表示氢原子或甲基基团]。
• Thiopegan derivatives—XXI
  作者：G.M. Sharma、H.S. Sachdev、N.K. Ralhan、H. Singh、G. Sarjit Sandhu、K. Gandhi、K.S. Narang

  DOI：10.1016/0040-4020(61)80007-0

  日期：1961.1

  Reactions between α-haloketones and o-carbethoxy phenyl thiourea have been discussed; a mechanism for the observed exclusive formation of 9:10-thiopega-2:10-diene-4-ones in the case of α-haloalkaryl ketones has been advanced and a number of intermediates isolated in case of chloro acetone.

  讨论了α-卤代酮与邻-甲乙氧基苯基硫脲之间的反应。已经提出了在α-卤代烷芳基酮的情况下观察到的9：10-thiopega-2：10-二烯-4-酮的排他性形成的机理，并且在氯丙酮的情况下，分离了许多中间体。
• Ralhan,N.K. et al., Journal of the Indian Chemical Society, 1960, vol. 37, p. 773 - 774
  作者：Ralhan,N.K. et al.

  DOI：——

  日期：——
• Thiazole, Oxadiazole, and Carboxamide Derivatives of Artemisinin are Highly Selective and Potent Inhibitors of <i>Toxoplasma gondii</i>
  作者：Christopher P. Hencken、Lorraine Jones-Brando、Claudia Bordón、Remo Stohler、Bryan T. Mott、Robert Yolken、Gary H. Posner、Lauren E. Woodard

  DOI：10.1021/jm901857d

  日期：2010.5.13

  We have prepared 23 new dehydroartemisinin (DART) trioxane derivatives (11 thiazoles, 2 oxadiazoles, and 10 carboxamides) and have screened them for in vitro activity in the Toxoplasma lytic cycle. Fifteen (65%) of the derivatives were noncytotoxic to host cells (TD50 >= 320 mu M). Eight thiazole derivatives and two carboxamide derivatives displayed effective inhibition of Toxoplasma growth (IC50 = 0.25-0.42 mu M), comparable in potency to artemether (IC50 = 0.31 mu M) and > 100 times more inhibitory than the currently employed front-line drug trimethoprim (IC50 = 46 mu M). The thiazoles as a group were more effective than the other derivatives at inhibiting growth of extracellular as well as intracellular parasites. Unexpectedly, two thiazole trioxanes (5 and 6) were parasiticidal; both inhibited parasite replication irreversibly after parasite exposure to 10 mu M of drug for 24 h, whereas the standard trioxane drugs artemisinin and artemether were not parasiticidal. Some of the new derivatives of artemisinin described here represent effective anti-Toxoplasma trioxanes as well as molecular probes for elucidating the mechanism of action of the DART class of artemisinin derivatives.