4-Methoxy-benzoyl isoselenocyanate | 184647-55-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Methoxy-benzoyl isoselenocyanate
• CAS: 184647-55-0
• 化学式: C₉H₇NO₂Se
• 分子量: 240.12
• InChiKey: ZTTGHJQPRLAFAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  五氟化(4-氨苯基)硫 、 4-Methoxy-benzoyl isoselenocyanate 以 丙酮 为溶剂， 以0.7 g的产率得到4-methoxy-N-[(4-(pentafluorosulfanyl)phenyl)carbamoselenoyl]benzamide
  参考文献：
  名称：

  硒脲化学的新见解：各种衍生物的合成和单晶结构研究†

  摘要：

  在室温下，使苯甲酰氯与KSeCN在丙酮中反应，然后用4-溴苯胺原位处理，以93％的收率得到N -（（4-溴苯基）氨基甲硒烯酰基）苯甲酰胺。对于4-甲氧基苯甲酰氯和4-五氟硫烷基苯胺观察到相同的反应，导致N-（（4-五氟硫烷基苯基）氨基甲硒烯酰基）-4-甲氧基苯甲酰胺，产率为76％。有趣的是，在相同条件下，4-甲氧基苯甲酰氯和4-溴苯胺产生了意想不到的2-（（4-溴苯基）氨基）-2-甲基丙烷和6-溴-2,2,4-三甲基-1,2 -二氢喹啉，产率分别为45％和52％。此外，4-硝基苯甲酰氯与4-五氟硫烷基苯胺的等效反应以19％的产率得到另外的3-（4-硝基苯甲酰基）亚氨基-5-（4-（五氟硫烷基）苯氨基）-1，2，4-二硒唑，其产率为19％。预期的4-硝基-N -（（4-（五氟硫烷基）苯基）氨基甲硒烯酰基）苯甲酰胺，产率为79％。此外，从氮的反应中获得了一系列的五元硒杂环-酰基硒脲与各种苯甲酰

  DOI：

  10.1039/c9nj01059a
• 作为产物：
  描述：

  potassium selenocyanate 、 对甲氧基苯甲酰氯 以 丙酮 为溶剂， 反应 0.25h， 生成 4-Methoxy-benzoyl isoselenocyanate
  参考文献：
  名称：

  Synthesis and Structure of Thia and Selena Heterocycles Containing Cycloamidine Substructures

  摘要：

  双芳基咪唑氯化物与酰基硒脲的环化反应导致了具有异构二烯结构的1,3-硒杂唑烷的构建。双芳基咪唑氯化物的另一反应（肼水解）导致了Δ2-1,2-二氮烯的形成，我们之前已表明其是环转化反应的反应性前体，能够生成不寻常的杂环。我们现在证明这些Δ2-1,2-二氮烯与各种异硫氰酸酯或异硒氰酸酯的反应为高度取代的1,3,4-硫或硒二氮烯的合成提供了高效途径。这些新颖衍生物的结构通过NMR质谱、元素分析和X射线结构分析得到了确认。详尽的多维77Se NMR实验以及密度泛函理论（DFT）计算展示了这些化合物的结构特征。

  DOI：

  10.1055/s-2007-983834

文献信息

• Combined Acylselenourea–Diselenide Structures: New Potent and Selective Antitumoral Agents as Autophagy Activators
  作者：Pablo Garnica、Ignacio Encío、Daniel Plano、Juan A. Palop、Carmen Sanmartín

  DOI：10.1021/acsmedchemlett.7b00482

  日期：2018.4.12

  clear gap situated phenyl substitution over heterocyclic moieties in terms of selectivity. Among carbocyclic compounds, derivatives 2 and 7 significantly inhibited cell growth of breast adenocarcinoma cells with GI50 values of 1.30 and 0.15 nM, respectively, with selectivity indexes 12 and 121 times higher than those obtained for doxorubicin. Preliminary mechanistic studies indicated that compounds 2 and

  按照基于片段的药物策略，已经设计了一系列16种新的二硒化物-酰基硒脲脲偶联物。针对六种人类癌细胞系和两种非恶性衍生细胞系，评估了化合物的体外细胞毒性潜力，旨在确定其效能和选择性。在至少四个癌细胞系中，有九种衍生物在10μM以下显示GI 50值。就选择性而言，明显的缺口位于苯基取代杂环部分上。在碳环化合物中，衍生物2和7具有GI 50显着抑制乳腺癌细胞的生长选择性分别为1.30和0.15 nM，选择性指数比对阿霉素的选择性指数高12和121倍。初步的机理研究表明，化合物2和7会诱导细胞周期停滞和自噬依赖性细胞死亡，这可以通过用渥曼青霉素或氯喹预处理阻止细胞死亡来证明，并通过MCF-7细胞中标志Beclin1和LC3B的上调来证实。
• The Preparation of Acylselenourea and Selenocarbamate Using Isoselenocyanate
  作者：Mamoru Koketsu、Yusuke Yamamura、Hiroshi Aoki、Hideharu Ishihara

  DOI：10.1080/10426500600862894

  日期：2006.12.1

  Acyl isoselenocyanates were prepared by a reaction of acyl chloride with KSeCN. The acyl isoselenocyanates formed in situ were ready for further reaction without concentration. N-Acyl selenoureas were obtained by a reaction of acyl isoselenocyanates with amines. The reaction of acyl isoselenocyanates with nucleophiles gave the corresponding selenocarbamate. All the compounds were well characterized

  酰基异硒氰酸酯是通过酰氯与 KSeCN 反应制备的。原位形成的酰基异硒氰酸酯无需浓缩即可用于进一步反应。N-酰基硒脲是通过酰基异硒氰酸酯与胺的反应获得的。酰基异硒氰酸酯与亲核试剂反应得到相应的硒代氨基甲酸酯。通过使用光谱数据，如 13C 和 77Se NMR 和 X 射线衍射，对所有化合物进行了很好的表征。
• Ferrocene incorporated selenoureas as anticancer agents
  作者：Raja Azadar Hussain、Amin Badshah、John M. Pezzuto、Nadeem Ahmed、Tamara P. Kondratyuk、Eun-Jung Park

  DOI：10.1016/j.jphotobiol.2015.04.024

  日期：2015.7

  For a compound to be a best chemopreventive agent it should be a descent DNA binder and at the same time should be active against any of the three stages of carcinogenesis i.e. cancer initiation, cancer propagation and tumor growth. Most of the problems associated with chemotherapy can be overcome if the chemopreventive agent is active against all the three stages of cancer development. Cancer may be initiated by higher concentration of free radicals, inflammating agents and phase I enzymes (Cytochrome P450) in the body. Cancer propagation can be very efficiently controlled by inducing the phase II enzymes (glutathione S-transferases (GSTs), UDP-glucuronosyl transferases, and quinone reductases) in the body and cancer termination depends on the killing of the faulty cells i.e. cytotoxic actions. This article reports comprehensively the comparative DNA binding studies (with, cyclic voltammetry, UV-vis spectroscopy and viscometry), antioxidant activities (DPPH scavenging), anti-inflammatory activities (nitrite inhibition), phase I enzyme inhibition activities (aromatase inhibition), phase II enzyme induction studies (quinone reductase induction) and cytotoxic studies against neuroblastoma (MYCN2 and SK-N-SH), liver cancer (Hepa 1c1c7) and breast cancer (MCF-7) of seventeen ferrocene incorporated selenoureas. (C) 2015 Elsevier B.V. All rights reserved.
• Synthesis, characterization and biological applications of selenoureas having ferrocene and substituted benzoyl functionalities
  作者：Raja Azadar Hussain、Amin Badshah、Nadeem Ahmed、John M. Pezzuto、Tammara P. Kondratyuk、Eun-Jung Park、Iqtadar Hussain

  DOI：10.1016/j.poly.2019.05.027

  日期：2019.9

  In this article we have comprehensively reported the synthesis, complete chemical characterization (FTIR, multinuclear NMR, single crystal XRD, CHNS, AAS) and biological applications of seventeen ferrocene incorporated selenoureas. Biological applications include comparative DNA binding studies (with, cyclic voltammetry), antioxidant activities (DPPH (2,2-diphenyl-1-picrylhydrazyl) scavenging), anti-inflammatory activities (nitrite inhibition), phase I enzyme inhibition activities (aromatase inhibition), phase II enzyme induction studies (quinone reductase induction) and cytotoxic studies against neuroblastoma (MYCN2 and SK-N-SH), liver cancer (Hepa 1c1c7) breast cancer (MCF-7) and human cervical carcinoma HeLa cells (ATCC (R) CCL-2). All the compounds showed decent structure dependent biological applications. (C) 2019 Elsevier Ltd. All rights reserved.
• Synthesis of Selenosemicarbazides and 1,2,4-Triazoles
  作者：Mamoru Koketsu、Yusuke Yamamura、Hideharu Ishihara

  DOI：10.3987/com-06-10725

  日期：——

  Acyl isoselenocyanates (1) were prepared from KSeCN and acyl chlorides in situ. Reactions of the acyl isoselenocyanates (1) with phenylhydrazine gave 2-phenyl-1,2-dihydro-3H-1,2,4-triazole-3-selones (2) and selenosemicarbazides (3). The obtained selenosemicarbazides (3) were refluxed in the presence of triethylamine in THF and trapped with alkyl halides to obtain the corresponding 3-alkylseleno-1-phenyl-1H-1,2,4-triazoles (5) in moderate yields.