4-硝基-N-(4-(三氟甲基)苯基)苯并硫代酰胺 | 1034681-37-2

• 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-硝基-N-(4-(三氟甲基)苯基)苯并硫代酰胺
• 英文名称: N-(4-trifluoromethylphenyl)-4-nitrothiobenzamide
• 英文别名: 4-nitro-N-(4-(trifluoromethyl)phenyl)benzothioamide；4-nitro-N-[4-(trifluoromethyl)phenyl]benzenecarbothioamide
• CAS: 1034681-37-2
• 化学式: C₁₄H₉F₃N₂O₂S
• 分子量: 326.299
• InChiKey: VNVHFGDUXJROEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-硝基-N-(4-(三氟甲基)苯基)苯并硫代酰胺 在 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 水 为溶剂， 生成 2-(4-nitrophenyl)-6-trifluoromethyl-benzothiazole
  参考文献：
  名称：

  Design, synthesis and antimetastatic evaluation of 1-benzothiazolylphenylbenzotriazoles for photodynamic therapy in oral cancer cells

  摘要：

  我们设计并合成了一系列新的1-苯并噻唑基苯基三唑类化合物 9a–p 并研究了它们在口腔癌细胞Ca9-22中通过UVA诱导的光敏作用参与的抗转移机制。

  DOI：

  10.1039/c6md00034g
• 作为产物：
  描述：

  N-(phenyl)-3-methyl-4-nitrothiobenzamide 以71%的产率得到4-硝基-N-(4-(三氟甲基)苯基)苯并硫代酰胺
  参考文献：
  名称：

  SYNTHESIS OF 2-(4-AMINOPHENYL) BENZOTHIAZOLE DERIVATIVES AND USE THEREOF

  摘要：

  本发明提供了一种制备6式化合物的方法，包括：(a) 将1式化合物与2式化合物反应以形成3式化合物，其中2式化合物的X为Cl或OH；(b) 用Lawesson试剂处理3式化合物以形成4式化合物；(c) 将4式化合物与氰化亚铁钾反应以生成5式化合物；(d) 用活性炭上的钯进行5式化合物的硝基团的催化还原，生成6式化合物，其中1-6式中的R1为H、C1-10烷基、C1-10烷氧基或C1-10卤代烷基，1-6式中的R2为H或C1-10烷基。本发明还提供了一种对患有至少一种肿瘤的患者进行光动力疗法的方法，包括以下步骤：向患者投药物学可接受的载体中的6式化合物（其中R1和R2如上所定义）；等待足够的时间以使给药的化合物被目标组织（至少一种肿瘤）吸收；照射患者身体含有目标组织的区域；从而抑制肿瘤的生长。

  公开号：

  US20120215154A1

文献信息

• Synthesis, and biological evaluation of 2-(4-aminophenyl)benzothiazole derivatives as photosensitizing agents
  作者：Wan-Ping Hu、Yin-Kai Chen、Chao-Cheng Liao、Hsin-Su Yu、Yi-Min Tsai、Shu-Mei Huang、Feng-Yuan Tsai、Ho-Chuan Shen、Long-Sen Chang、Jeh-Jeng Wang

  DOI：10.1016/j.bmc.2010.04.082

  日期：2010.8

  Photodynamic therapy (PDT) employing exogenous photosensitizers is currently being approved for treatment of basal cell carcinoma (BCC). 2-(4-Aminophenyl)benzothiazoles (6) consist of chromophoric structure and absorb light in the UVA (315–400 nm). These results encouraged us to design and synthesize a diversity of 2-phenylbenzothiazoles (6). Studies on the apoptotic mechanism involved in photosensitive effects

  使用外源光敏剂的光动力疗法（PDT）目前已被批准用于治疗基底细胞癌（BCC）。2-（4-氨基苯基）苯并噻唑（6）由发色结构组成，可吸收UVA（315-400 nm）中的光。这些结果鼓励我们设计和合成各种2-苯基苯并噻唑（6）。在本文中研究了UVC激活的6在BCC细胞中诱导的光敏效应所涉及的凋亡机制。用6 -UVA处理的细胞显示出一些凋亡特征，包括亚G1群体的增加，膜联蛋白V结合的显着增加以及caspase-3的激活。6-UVA诱导线粒体膜电位（Δ降低ψ公吨），并通过增强的ROS产生和胞外信号调节激酶（ERK）和p38 MAPK表达的促进磷酸ATP。这些结果表明6- UVA在涉及ERK和p38活化的线粒体过程中引起光敏作用，并最终导致BCC细胞凋亡。
• Synthesis of Sulfur−Sulfur Bond Formation from Thioamides Promoted by 2,3-Dichloro-5,6-dicyanobenzoquinone
  作者：Wei-Sheng Lo、Wan-Ping Hu、Hsiao-Ping Lo、Chung-Yu Chen、Chai-Lin Kao、Jaya Kishore Vandavasi、Jeh-Jeng Wang

  DOI：10.1021/ol102455x

  日期：2010.12.3

  A mild and efficient synthesis of sulfur-sulfur bond formation from thioformanilides with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) is described. Functionality on the aromatic ring plays a key role in the formation of a sulfur-sulfur bond.
• Synthesis and biological evaluation of thiobenzanilides as anticancer agents
  作者：Wan-Ping Hu、Hsin-Su Yu、Yan-Ren Chen、Yi-Min Tsai、Yin-Kai Chen、Chao-Cheng Liao、Long-Sen Chang、Jeh-Jeng Wang

  DOI：10.1016/j.bmc.2008.03.003

  日期：2008.5

  A series of novel thiobenzanilides is described. These compounds have been previously found to show strong biological activity such as antimycotic and antifungal actions. This is the first demonstration on the mechanism of the anticancer effect of thiobenzanilide agents (4a-c) on human melanoma A375 cells. The cytotoxic studies of compounds 4a-c on human melanoma A375 cells indicate thiobenzanilides induced higher cytotoxicity than nitrobenzanilides (3a-c). In addition, DNA flow cytometric analysis shows that 4a-c displays a significant G2/M phase arrest, which progresses to early apoptosis as detected by flow cytometry after double-staining with annexin V and propidium iodide (PI). Because cellular apoptosis is often preceded by the disruption of mitochondrial function, the assessment of mitochondrial function in 4a-c-treated cells is worthy of investigation. Our data revealed that treatment of A375 cells with 4a-c resulted in the loss of mitochondrial membrane potential (Delta Psi(mt)), a reduction of ATP synthesis, increased reactive oxygen species (ROS) generation, and activation of caspase-3. Thus, we suggest that 4a-c agents are potent inducers of cell apoptosis in A375 cells. (C) 2008 Elsevier Ltd. All rights reserved.
• SYNTHESIS OF 2-(4-AMINOPHENYL)BENZOTHIAZOLE DERIVATIVES AND USE THEREOF
  申请人：KAOHSIUNG MEDICAL UNIVERSITY

  公开号：US20140046290A1

  公开（公告）日：2014-02-13

  The present invention provides a photodynamic therapy to a patient having at least one tumor comprising the steps of: administering a compound of formula 6 (wherein R 1 and R 2 are defined as the above) in a pharmaceutically acceptable carrier to the patient; waiting for a sufficient time to allow the administered compound to be taken up by a target tissue having the at least one tumor; and irradiating a region of the patient containing the target tissue, wherein growth of the tumor is inhibited.
• US8592603B2
  申请人：——

  公开号：US8592603B2

  公开（公告）日：2013-11-26