4-(4-methoxyphenyl)thiazole-2(3H)-thione | 2104-05-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-methoxyphenyl)thiazole-2(3H)-thione
• 英文别名: 4-(p-Methoxy-phenyl)-Δ⁴-thiazolin-2-thion；4-(4-methoxy-phenyl)-3H-thiazole-2-thione；4-(4-Methoxy-phenyl)-3H-thiazol-2-thion；4-(4-Methoxyphenyl)-1,3-thiazole-2-thiol；4-(4-methoxyphenyl)-3H-1,3-thiazole-2-thione
• CAS: 2104-05-4
• 化学式: C₁₀H₉NOS₂
• 分子量: 223.32
• InChiKey: HHKFGXNOUWCQEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-methoxyphenyl)thiazole-2(3H)-thione 在 potassium carbonate 、 肼 作用下， 生成 <4-(4'-methoxyphenyl)thiazol-ylthio>acetic acid hydrazide
  参考文献：
  名称：

  方便合成3-（噻唑-2'-基硫基）-2h-1-苯并吡喃-2-酮的新途径

  摘要：

  通过使（噻唑-2-基硫基）乙酸酰肼与2-羟基苯甲醛反应，然后在PPA存在下环化形成的N-亚苄基衍生物，来制备不同的噻唑基硫香豆素。

  DOI：

  10.1016/s0040-4020(01)90053-5
• 作为产物：
  描述：

  4-羟基-2-氯苯乙酮 在 乙醇 、 苯 作用下， 生成 4-(4-methoxyphenyl)thiazole-2(3H)-thione
  参考文献：
  名称：

  The Syntheses of 2-Thio-4-arylthiazolines

  摘要：

  DOI：

  10.1021/ja01876a055

文献信息

• Synthesis of 4- and 5-arylthiazolinethiones as inhibitors of indoleamine 2,3-dioxygenase
  作者：Monaem Balti、Aurélie Plas、Céline Meinguet、Marie Haufroid、Quentin Thémans、Mohamed Lotfi Efrit、Johan Wouters、Steve Lanners

  DOI：10.1016/j.bmcl.2016.06.052

  日期：2017.8

  ring within pocket A of the enzyme. On this basis, chemical modifications were proposed to increase inhibition activity. Synthetic routes had to be adapted and optimized to yield the desired substituted 4- and 5-arylthiazolinethiones. Their biological evaluation shows that 5-aryl regioisomers are systematically less potent than the corresponding 4-aryl analogs. Substitution on the phenyl ring does not

  4-苯基噻唑啉硫酮对人 IDO1 的对接研究表明，环外硫原子与血红素铁的络合进一步被酶口袋 A 内苯环的疏水相互作用增强。在此基础上，提出了化学修饰以增加抑制活性。合成路线必须进行调整和优化以产生所需的取代 4-和 5-芳基噻唑啉硫酮。他们的生物学评估表明，5-芳基区域异构体的效力低于相应的 4-芳基类似物。除 4-Br 和 4-Cl 衍生物外，苯环上的取代不会显着增加抑制效力。
• 2-[3H-THIAZOL-2-YLIDINEMETHYL]PYRIDINES AND RELATED COMPOUNDS AND THEIR USE
  申请人：Brown Robert

  公开号：US20090247579A1

  公开（公告）日：2009-10-01

  The present invention pertains to certain 2-[3H-thiazol-2-ylidinemethyl]pyridine compounds and analogs thereof, which, inter alia, inhibit cell proliferation, treat cancer, etc., and more specifically to compounds of the following formula, wherein R A1 , R A2 , R A3 , R A4 , R B1 , R B2 , R NA , R NB , and X − are as defined herein: 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, to inhibit cell proliferation, and in the treatment of proliferative conditions such as cancer, etc.

  本发明涉及某些2-[3H-噻唑-2-基亚甲基]吡啶化合物及其类似物，其中包括抑制细胞增殖、治疗癌症等作用，更具体地涉及以下式的化合物，其中R A1 、R A2 、R A3 、R A4 、R B1 、R B2 、R NA 、R NB 和X − 如本文所定义： 本发明还涉及包含这种化合物的药物组合物，以及在体外和体内使用这种化合物和组合物来抑制细胞增殖，并用于治疗癌症等增生性疾病。
• Synthesis of novel azabicyclo derivatives containing a thiazole moiety and their biological activity against pine-wood nematodes
  作者：Hui Li、Aoyun Lu、Yanqiu Zhang、Yanqing Peng、Gonghua Song

  DOI：10.1080/10426507.2019.1700260

  日期：2020.5.3

  Abstract To explore a new skeleton with nematicidal activity, a series of novel azabicyclo derivatives containing a thiazole moiety were designed, synthesized and evaluated for their nematicidal activities. The bioassay results against pine-wood nematodes (Bursaphelenchus xylophilus) showed that most of the title compounds displayed nematicidal activity at a concentration of 40 mg/L. Especially, the title

  摘要 为了探索具有杀线虫活性的新骨架，设计、合成了一系列含有噻唑部分的新型氮杂双环衍生物并评价了它们的杀线虫活性。针对松材线虫 (Bursaphelenchus xylophilus) 的生物测定结果表明，大多数标题化合物在 40 mg/L 的浓度下显示出杀线虫活性。特别是，标题化合物 2-((8-methyl-8-azabicyclo[3.2.1]octan-3-yl)oxy)-4-(4-chlorophenyl)thiazole (7e), 2-((8-methyl-8 -氮杂双环[3.2.1]辛基-3-基)硫基)-4-苯基噻唑(10a)和2-((8-甲基-8-氮杂双环[3.2.1]辛基-3-基)硫基)-4- (4-氯苯基)噻唑 (10e) 对松材线虫的死亡率超过 90%。图形概要
• An approach to the synthesis of 4-aryl and 5-aryl substituted thiazole-2(3H)-thiones employing flow processing
  作者：Monaem Balti、Shelli A. Miller、Mohamed Lotfi Efrit、Nicholas E. Leadbeater

  DOI：10.1039/c6ra15488c

  日期：——

  A method for the preparation of 4-aryl and 5-aryl substituted thiazole-2(3H)-thiones is described. Flow processing is employed as a tool, and supported acids and bases used to facilitate both the synthetic strategy and product isolation. The methodology is applicable to a range of substrates.

  描述了一种制备4-芳基和5-芳基取代的噻唑-2（3H）-硫酮的方法。流动加工被用作工具，并且负载的酸和碱用于促进合成策略和产物分离。该方法适用于多种基材。
• S-Alkylation en s�rie h�t�rocyclique par catalyse par transfert de phase: thioalkyl-2-thiazoles, thioalkyl-2-?-4-thiazolines et thioalkyl-2-benzothiazoles
  作者：Henri J. M. Dou、Parina Hassanaly、Jacky Kister、Gaston Vernin、Jacques Metzger

  DOI：10.1002/hlca.19780610842

  日期：1978.12.13

  S-Alkylation in heterocyclic serie by phase transfer catalysis: 2-alkylthiothiazoles, 2-alkylthio-Δ-4-thiazolines and 2-alkylthiobenzothiazoles

  相转移催化在杂环系列中的S-烷基化：2-烷硫基噻唑，2-烷硫基-Δ-4-噻唑啉和2-烷硫基苯并噻唑