4-(4-氯苯基)-4-噻唑啉-2-硫酮 | 2104-00-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(4-氯苯基)-4-噻唑啉-2-硫酮
• 中文别名: 4-(4-氯苯基)-1,3-噻唑-2-硫醇；4-(4-氯苯基)-2(3h)-噻唑硫酮
• 英文名称: 4-(p-chlorophenyl)-2-mercaptothiazole
• 英文别名: 4-(4-chlorophenyl)-3H-1,3-thiazole-2-thione
• CAS: 2104-00-9
• 化学式: C₉H₆ClNS₂
• mdl: MFCD01995690
• 分子量: 227.738
• InChiKey: LXFBSCKJEIVRGP-UHFFFAOYSA-N

物化性质

• 密度：
  1.49

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  4-(4-氯苯基)-4-噻唑啉-2-硫酮 在 palladium on activated charcoal MOPS buffer 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 19.0h， 生成 (4R,5S,6S)-3-[4-(4-Chloro-phenyl)-thiazol-2-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological properties of a new series of anti-MRSA β-lactams; 2-(thiazol-2-ylthio)carbapenems

  摘要：

  A series of 1 beta-methylcarbapenems containing variously C-2 substituted thiazol-2-ylthio groups were synthesized, and their in vitro anti-MRSA activity was examined. Among them, 1 beta-methyl-2-(4-arylthiazol-2-ylthio) carbapenems exhibited superior anti-MRSA activity. Introduction of a cationic moiety in the C-2 side chain not only reduced the binding to HSA but also increased the stability against DHP-I, without affecting the anti-MRSA, activity. It was also found that the distance between the cationic moiety and the carbapenem skeleton was related to the strength of HSA binding and the stability against DHP-I. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00273-8
• 作为产物：
  描述：

  对氯苯乙酮 以 乙醇 、 乙腈 为溶剂， 反应 7.0h， 生成 4-(4-氯苯基)-4-噻唑啉-2-硫酮
  参考文献：
  名称：

  通过[羟基（甲苯磺酰氧基）碘]苯简便合成噻唑-2（3H）-硫酮

  摘要：

  摘要 通过使用 [羟基（甲苯磺酰氧基）碘] 苯对酮（1）进行高价碘氧化，然后用反应混合物处理，实现了噻唑-2（3H）-硫酮（4）的一锅简便合成。二硫代氨基甲酸盐 (3)。中间体 α-甲苯磺酰氧基酮 (2) 也已被分离并转化为目标化合物。

  DOI：

  10.1081/scc-200025631

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
• Heteroaryl-substituted carboxamides and use thereof for the stimulation of the expression of NO synthase
  申请人：sanofi-aventis

  公开号：EP1939181A1

  公开（公告）日：2008-07-02

  The present invention relates to heteroaryl-substituted carboxamides of the formula I, in which Het, A, X, R1, R2 and R3 have the meanings indicated in the claims, which modulate the transcription of endothelial nitric oxide (NO) synthase and are valuable pharmacologically active compounds. Specifically, the compounds of the formula I upregulate the expression of the enzyme endothelial NO synthase and can be applied in conditions in which an increased expression of said enzyme or an increased NO level or the normalization of a decreased NO level is desired. The invention further relates to processes for the preparation of compounds of the formula I, to pharmaceutical compositions comprising them, and to the use of compounds of the formula I for the manufacture of a medicament for the stimulation of the expression of endothelial NO synthase or for the treatment of various diseases including cardiovascular disorders such as atherosclerosis, thrombosis, coronary artery disease, hypertension and cardiac insufficiency, for example.

  本发明涉及公式I的杂环取代羧酰胺，其中Het、A、X、R1、R2和R3具有索引中指示的含义，这些化合物调节内皮一氧化氮（NO）合酶的转录，并且是有价值的药理活性化合物。具体地，公式I的化合物上调内皮一氧化氮合酶酶的表达，并可应用于需要增加该酶的表达或增加NO水平或正常化降低的NO水平的情况。该发明还涉及公式I化合物的制备方法，包括它们的药物组合物，以及公式I化合物用于制造刺激内皮一氧化氮合酶表达或治疗各种疾病的药物的用途，包括心血管疾病，如动脉粥样硬化、血栓形成、冠状动脉疾病、高血压和心脏功能不全等。
• Hypervalent Iodine in Organic Synthesis: One Pot Facile Syntheses of α-Thiocyanatoacetophenones, 2-Hydroxy-, and 2-Mercapto-4-arylthiazoles Using [Hydroxy(tosyloxy)iodo]benzene
  作者：Om Prakash、Neena Saini

  DOI：10.1080/00397919308011236

  日期：1993.5

  Abstract Hypervalent iodine oxidation of acetophenones (1a-1e) with [hydroxy(tosyloxy)iodo]benzene, followed by treatment with potassium thiocyanate offers a new facile synthesis of corresponding α-thiocyanatoacetophenones (3a-3e). Cyclization of 3a-3e, thus generated in situ, using AcOH/H2O and H2NC(S)NH2/HCl provides one pot facile syntheses of 2-hydroxy-, and 2-mercapto-4-arylthiazoles (4 & 5) respectively

  摘要 用 [羟基（甲苯磺酰氧基）碘] 苯对苯乙酮 (1a-1e) 进行高价碘氧化，然后用硫氰酸钾处理，为相应的 α-硫氰酸根合苯乙酮 (3a-3e) 提供了一种新的简便合成方法。使用 AcOH/H2O 和 H2NC(S)NH2/HCl 原位生成的 3a-3e 环化分别提供了 2-羟基-和 2-巯基-4-芳基噻唑（4 和 5）的一锅简便合成。