benzocycloheptenone thiosemicarbazone

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: benzocycloheptenone thiosemicarbazone
• 英文别名: 1-benzosuberone thiosemicarbazone；(6,7,8,9-Tetrahydrobenzo[7]annulen-5-ylideneamino)thiourea
• 化学式: C₁₂H₁₅N₃S
• mdl: MFCD21102039
• 分子量: 233.337
• InChiKey: HOKJJMKQHAEGNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-溴苯乙酮 、 benzocycloheptenone thiosemicarbazone 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以90%的产率得到N-(4-phenylthiazol-2-yl)-N'-(6,7,8,9-tetrahydrobenzocyclohepten-5-ylidene)hydrazine
  参考文献：
  名称：

  Novel anti-tubercular and antibacterial based benzosuberone-thiazole moieties: Synthesis, molecular docking analysis, DNA gyrase supercoiling and ATPase activity

  摘要：

  Herein, molecular hybridization strategy was utilized in the design of new benzosuberone-thiazole derivatives. The structures of the synthesized hybrids were determined on the basis of elemental and spectral analyses. These compounds were evaluated for their antibacterial activities against five bronchitis causing bacteria in addition to their anti-tubercular activities. Most compounds revealed promising activities. Amongst active compounds, benzosuberone-dithiazole derivatives 22a and 28 with MIC value = 1.95 µg/ml against H. influenza, M. pneumonia, and B. pertussis displayed four times the activity of ciprofloxacin (MIC = 7.81 µg/ml) against H. influenza, twice the activity of ciprofloxacin (MIC = 3.9 µg/ml) against M. pneumonia and were equipotent to ciprofloxacin against B. pertussis (MIC = 1.95 µg/ml). Additionally, benzosuberone-dithiazole derivatives 22a and 27 were the most promising anti-tubercular among the tested compounds with MIC values of 0.12 and 0.24 µg/ml, respectively against sensitive M. tuberculosis in addition to high activity against resistant strain of M. tuberculosis (MIC = 0.98 and 1.95 µg/ml, respectively) compared to isoniazid (MIC = 0.12 µg/ml against sensitive M. tuberculosis and no activity against resistant M. tuberculosis). Cytotoxicity study of the active dithiazole derivatives 22a, 27 and 28 against normal human lung cells (WI-38) indicated their high safety profile as showed from their high IC₅₀ values (IC₅₀ = 107, 74.8, and 117 µM, respectively). Furthermore, DNA gyrase supercoiling and ATPase activity assays showed that 22a, 27 and 28 have the potential to inhibit DNA gyrase at low micromolar levels (IC₅₀ = 3.29-15.64 µM). Molecular docking analysis was also carried out to understand the binding profiles of the synthesized compounds into the ATPase binding sites of bacterial and mycobacterial DNA gyraseB.

  DOI：

  10.1016/j.bioorg.2020.104316
• 作为产物：
  描述：

  氨基硫脲 、 1-苯并环庚酮 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以49%的产率得到benzocycloheptenone thiosemicarbazone
  参考文献：
  名称：

  组织蛋白酶L的小分子抑制剂结合功能化的环稠合的分子框架

  摘要：

  组织蛋白酶L是在多种恶性肿瘤中上调的半胱氨酸蛋白酶，在癌细胞的侵袭和迁移中起重要作用。它是开发小分子抑制剂的有吸引力的目标，小分子抑制剂可能被证明是限制或阻止癌症转移的治疗剂是有益的。我们之前已经确定了一系列结构上不同的基于硫半脲酮的抑制剂，这些抑制剂结合了二苯甲酮和硫代苯并二氢吡喃酮分子支架。本文中，我们报告了这项工作的重要扩展，旨在探索具有氮原子掺入（基于二氢喹啉）和碳原子排他性（基于四氢萘）的稠合芳基-烷基环分子系统。此外，类似物还包含氧气（基于苯并二氢吡喃酮），硫（基于硫代苯并二氢吡喃酮），亚砜，抗组织蛋白酶L时，其活性最强的化合物（7-溴二氢喹啉硫代半碳zone酮48）为50 <500 nM），IC 50  = 164 nM。所评估的所有化合物均不作为组织蛋白酶B抑制剂而处于非活性状态（IC 50 > 10,000 nM），因此，对于该组织中最活跃的组织蛋白酶L抑制剂，其选择性（

  DOI：

  10.1016/j.bmcl.2012.12.025

文献信息

• Hydrazonoyl Halides as Precursors for Synthesis of Novel Bioactive Thiazole and Formazan Derivatives
  作者：Thoraya A. Farghaly、Eman M.H. Abbas

  DOI：10.3184/174751912x13491094428620

  日期：2012.11

  prepared by reaction of hydrazonoyl chlorides with a thiosemicarbazone derivative. The tautomeric structures of the products were studied using electronic absorption and NMR spectroscopy. The site-selectivities of the reactions of hydrazonoyl halides with benzocyclohepten-5-one hydrazone were also investigated. In addition, the antimicrobial activity of some of the products was evaluated. Many derivatives

  新系列取代的 4-甲基-5-(芳基偶氮)-2-[N'-(6,7,8,9-四氢-苯并环庚烯-5-亚基)-肼]-噻唑和 5-(芳基偶氮)- 2-[N'-(6,7,8,9-四氢-苯并环庚烯-5-亚基)-肼基]-噻唑-4-酮通过腙酰氯与缩氨基硫脲衍生物反应制备。使用电子吸收和核磁共振光谱研究了产物的互变异构结构。还研究了腙酰卤与苯并环庚烯-5-酮腙反应的位点选择性。此外，还评估了一些产品的抗菌活性。许多衍生物对抗菌和抗真菌物种具有有希望的活性。
• Evaluation of the semicarbazones, thiosemicarbazones and bis-carbohydrazones of some aryl alicycylic ketones for anticonvulsant and other biological propertie
  作者：JR Dimmock、SN Pandeya、JW Quail、U Pugazhenthi、TM Allen、GY Kao、J Balzarini、E DeClercq

  DOI：10.1016/0223-5234(96)88238-9

  日期：——

  A number of aryl alicyclic ketones were converted to their corresponding semicarbazones, thiosemicarbazones and bis-carbohydrazones. Anticonvulsant activity was displayed by most of the compounds in the maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) screens when given intraperitoneally to mice. However, on oral administration to rats, a marked selective activity in the MES screen only was noted. X-ray crystallography on five semicarbazones was undertaken in order to find correlations between the shapes of these molecules and anticonvulsant properties. The thiosemicarbazones displayed greater cytotoxicity to P388D1 and L1210 cells than the semicarbazones while a number of human tumors and different viruses were, in general, insensitive to representative compounds.