8-(trifluoromethyl)benzo[f][1,2,3,4,5]pentathiepin-6-amine | 1092771-94-2

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 8-(trifluoromethyl)benzo[f][1,2,3,4,5]pentathiepin-6-amine
• 英文别名: 8-(trifluoromethyl)-1,2,3,4,5-benzopentathiepin-6-amine；8-(trifluoromethyl)benzo[f][1-5]pentathiepin-6-amine；8-(trifluoromethyl)-1,2,3,4,5-benzopentathiepine-6-amine
• CAS: 1092771-94-2
• 化学式: C₇H₄F₃NS₅
• 分子量: 319.441
• InChiKey: YKFGOBADMHOIFW-UHFFFAOYSA-N

物化性质

• 沸点：
  470.7±55.0 °C(Predicted)
• 密度：
  1.706±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  8-(trifluoromethyl)benzo[f][1,2,3,4,5]pentathiepin-6-amine 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 122.5h， 生成 2,2,2-trifluoro-N-(6-(trifluoromethyl)benzo[d][1,3]dithiol-4-yl)acetamide
  参考文献：
  名称：

  取代的苯并五硫平-6-胺的抗菌活性。

  摘要：

  合成了许多取代的不带有多硫环的苯并戊并噻吩-6-胺及其类似物，并在体外评估了其对一组参考细菌和真菌菌株的抗菌活性。三氟乙酰胺14表现出对金黄色葡萄球菌（MRSA株）的高抗菌活性，MIC为4μg/ mL，比参考药物阿莫西林的活性高四倍。该化合物还对白色念珠菌具有最强的活性（MIC为1μgml-1），而含有吗啉取代基的酰胺17对新型隐球菌具有最强的活性（MIC为2μgml-1）。这些化合物没有溶血活性，细胞毒性低。用1，3-二硫代噻吩-2-酮或1，3-二硫代戊环部分取代戊硫平环导致抗微生物活性的丧失。

  DOI：

  10.1038/s41429-019-0191-y
• 作为产物：
  描述：

  4-氯-3,5-二硝基三氟甲苯 在 sodium hydrogen sulfide 作用下， 以 二甲基亚砜 为溶剂， 生成 8-(trifluoromethyl)benzo[f][1,2,3,4,5]pentathiepin-6-amine
  参考文献：
  名称：

  8-（三氟甲基）-1,2,3,4,5-苯并戊硫平-6-胺及其盐酸盐的镇痛活性

  摘要：

  8-（三氟甲基）-1，2，3，4，5-苯并戊硫平-6-胺1a及其盐酸盐在乙酸诱发的扭体试验中显示出明显的镇痛活性，化合物1a的ED 50为0.66mg / kg。在热板疼痛试验中，在盐酸盐1a * HCl中发现了可靠的镇痛活性，而游离碱1a被证明是无活性的。根据纳洛酮试验的结果，在两种试验中化合物1a * HCl的镇痛作用均由阿片体能系统介导。游离碱1a及其盐酸盐均未显示抗炎活性。CF3基团被氟原子取代导致乙酸诱导的扭体试验中止痛活性完全丧失。

  DOI：

  10.2174/157018012800389296

文献信息

• Synthesis of 6-Aminobenzopentathiepines by Reactions of 4-Nitrobenzodithiol- 2-ones with NaHS
  作者：Tatyana M. Khomenko、Dina V. Korchagina、Nina I. Komarova、Konstantin P. Volcho、Nariman F. Salakhutdinov

  DOI：10.2174/157017811795038331

  日期：2011.3.1

  The reactions of benzodithiol-2-ones containing a 4-nitro group with NaHS led to mixtures of 6- aminobenzopentathiepines and 4-nitrobenzotrithiols. The product ratio and yields depend on the substituent in the aromatic ring. Based on the yields of benzopentathiepines, the following series of substituent efficiency can be inferred: CF3 F, Cl CN. Aminobenzopentathiepines are probably formed via the intermediate benzotrithiols; the transformation apparently starts with the reduction of the nitro group.

  含有4- nitro基的苯二硫酮与NaHS反应，生成了6-氨基苯五硫啶和4-硝基苯三硫醇的混合物。产物的比例和产率取决于芳香环中的取代基。根据苯五硫啶的产率，可以推断出以下取代基效能的系列：CF3 > F > Cl > CN。氨基苯五硫啶可能是通过中间体苯三硫醇形成的；该转化显然是从硝基的还原开始的。
• Synthesis of benzopentathiepin analogs and their evaluation as inhibitors of the phosphatase STEP
  作者：Tyler D. Baguley、Angus C. Nairn、Paul J. Lombroso、Jonathan A. Ellman

  DOI：10.1016/j.bmcl.2015.01.020

  日期：2015.3

  Striatal-enriched protein tyrosine phosphatase (STEP) is a brain specific protein tyrosine phosphatase that has been implicated in many neurodegenerative diseases, such as Alzheimer's disease. We recently reported the benzopentathiepin TC-2153 as a potent inhibitor of STEP in vitro, cells and animals. Herein, we report the synthesis and evaluation of TC-2153 analogs in order to define what structural features are important for inhibition and to identify positions tolerant of substitution for further study. The trifluoromethyl substitution is beneficial for inhibitor potency, and the amine is tolerant of acylation, and thus provides a convenient handle for introducing additional functionality such as reporter groups. (C) 2015 Elsevier Ltd. All rights reserved.
• Cytotoxic and cancer preventive activity of benzotrithioles and benzotrithiole oxides, synthetic analogues of varacins
  作者：Alexandra S. Kuzmich、Tatyana M. Khomenko、Sergey N. Fedorov、Tatyana N. Makarieva、Larisa K. Shubina、Nina I. Komarova、Dina V. Korchagina、Tatyana V. Rybalova、Konstantin P. Volcho、Nariman F. Salakhutdinov

  DOI：10.1007/s00044-016-1759-8

  日期：2017.2

  The cytotoxic and cancer preventive activities of synthetic analogs of natural varacins with polysulfide groups were studied. Presence of a sulfoxide group was found to have no significant effect on the cytotoxicity of these compounds. At the same time, this group is important for inhibition of colony formation of tumor cells treated with tumor promoter thus demonstrating cancer preventive activity. The most promising compound appears to be a synthetic varacin C analog, sulfoxide 10a, which exhibits the cancer preventive activity at dose into 100 times lower than its cytotoxic concentrations.
• [EN] APPLICATION OF 8-(TRIFLUOROMETHYL)BENZO[F][1,2,3,4,5]PENTATHIEPINE-6-AMINE AS AN ANTIDEPRESSANT<br/>[FR] UTILISATION DE 8-(TRIFLUORMÉTHYL)BENZO[F][1,2,3,4,5]PENTATHIÉPINE-6-AMINE EN TANT QUE ANTIDÉPRESSEUR<br/>[RU] ПРИМЕНЕНИЕ 8-(ТРИФТОРМЕТИЛ)БЕНЗО[f][1,2,3,4,5]ПЕНТАТИЕПИН-6-АМИНА В КАЧЕСТВЕ АНТИДЕПРЕССАНТА
  申请人：OBSHESTVO S OGRANICHENNOI OTVETSTVENNOSTJU INNOVATIVE PHARMACOLOGY RES IPHAR

  公开号：WO2015160281A1

  公开（公告）日：2015-10-22

  Изобретение относится к области медицины, а именно, к лекарственным средствам, обладающим антидепрессантной активностью. Предложено применение 8-(трифторметил)бензо[f][1,2,3,4,5]пентатиепин-6-амина формулы (I) в качестве антидепрессанта. Средство обладает высокой активностью, низкой токсичностью, может быть использовано в медицине.
• Antimicrobial Activity of Substituted Benzopentathiepin-6-amines
  作者：Tatyana M. Khomenko、Dina V. Korchagina、Dmitry S. Baev、Pavel M. Vassiliev、Konstantin P. Volcho、Nariman F. Salakhutdinov

  DOI：10.1038/s41429-019-0191-y

  日期：2019.8

  number of substituted benzopentathiepin-6-amines and their analogues without a polysulfur ring were synthesized and evaluated in vitro for antimicrobial activity against a panel of reference bacterial and fungal strains. Trifluoroacetamide 14 demonstrated high antibacterial activity against Staphylococcus aureus (MRSA strain) with a MIC of 4 μg/mL, which was four-fold higher than the activity of a reference

  合成了许多取代的不带有多硫环的苯并戊并噻吩-6-胺及其类似物，并在体外评估了其对一组参考细菌和真菌菌株的抗菌活性。三氟乙酰胺14表现出对金黄色葡萄球菌（MRSA株）的高抗菌活性，MIC为4μg/ mL，比参考药物阿莫西林的活性高四倍。该化合物还对白色念珠菌具有最强的活性（MIC为1μgml-1），而含有吗啉取代基的酰胺17对新型隐球菌具有最强的活性（MIC为2μgml-1）。这些化合物没有溶血活性，细胞毒性低。用1，3-二硫代噻吩-2-酮或1，3-二硫代戊环部分取代戊硫平环导致抗微生物活性的丧失。