4-aminophenylselenocyanate | 10336-11-5

• 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-aminophenylselenocyanate
• 英文别名: 4-selenocyanatoaniline；4-Amino-phenylselenocyanat；(4-aminophenyl) selenocyanate
• CAS: 10336-11-5
• 化学式: C₇H₆N₂Se
• 分子量: 197.098
• InChiKey: UMRQUSGJQJGLNV-UHFFFAOYSA-N

物化性质

• 熔点：
  93.5 °C
• 沸点：
  324.6±44.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.08
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-aminophenylselenocyanate 在 sodium tetrahydroborate 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 N,N'-(diselanediyldibenzene-4,1-diyl)dithiophene-2-sulfonamide
  参考文献：
  名称：

  Novel hybrid selenosulfonamides as potent antileishmanial agents

  摘要：

  Diselenide and sulfonamide derivatives have recently attracted considerable interest as leishmanicidal agents in drug discovery. In this study, a novel series of sixteen hybrid selenosulfonamides has been synthesized and screened for their in vitro activity against Leishmania infantum intracellular amastigotes and THP-1 cells. These assays revealed that most of the compounds exhibited antileishmanial activity in the low micromolar range and led us to identify three lead compounds (derivatives 2, 7 and 14) with IC50 values ranging from 0.83 to 1.47 mu M and selectivity indexes (SI) over 17, much higher than those observed for the reference drugs miltefosine and edelfosine. When evaluated against intracellular amastigotes, hybrid compound 7 emerged as the most active compound (IC50 = 2.8 mu M), showing higher activity and much less toxicity against THP-1 cells than edelfosine. These compounds could potentially serve as templates for future drug-optimization and drug-development efforts for their use as therapeutic agents in developing countries. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.030
• 作为产物：
  描述：

  potassium selenocyanate 、 磺胺 以 水 为溶剂， 反应 4.0h， 以25%的产率得到4-aminophenylselenocyanate
  参考文献：
  名称：

  Frolov, A. N.; Smirnov, E. V.; Kul'bitskaya, O. V., Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, p. 1963 - 1969

  摘要：

  DOI：

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。
• Using fluoroform for constructing aromatic and heterocyclic trifluoromethylselenyl compounds
  作者：Cheryl Aharon、Shlomo Rozen

  DOI：10.1016/j.jfluchem.2021.109866

  日期：2021.10

  trifluoromethyl moiety was reacted with aromatic and heterocyclic selenium cyanide derivatives to form the corresponding trifluoromethylselenium compounds. Selenium cyanides were made with 1,3-dicyanotriselenide prepared in situ from malononitrile and selenium dioxide. The electrophilicity of the reagent (δ+SeCN) was enough to attack aniline derivatives at the para position, but with other aromatics it

  根据文献程序使用氟仿制备CuCF 3。该亲核三氟甲基部分与芳族和杂环氰化硒衍生物反应形成相应的三氟甲基硒化合物。氰化硒由丙二腈和二氧化硒原位制备的 1,3-二氰化硒制成。试剂 ( δ+ SeCN)的亲电性足以攻击对位的苯胺衍生物，但对于其他芳烃，使用相应的硼酸是有利的，因为该部分很容易被氰酸硒部分取代。
• Pre-clinical evidences of the antileishmanial effects of diselenides and selenocyanates
  作者：Pablo Garnica、Mikel Etxebeste-Mitxeltorena、Daniel Plano、Esther Moreno、Socorro Espuelas、Juan Antonio Palop、Antonio Jiménez-Ruiz、Carmen Sanmartín

  DOI：10.1016/j.bmcl.2020.127371

  日期：2020.9

  wide chemical space was assessed for in vitro leishmanicidal activities against Leishmania infantum amastigotes. The cytotoxicity of those compounds was also evaluated on human THP-1 cells. Interestingly most tested derivatives were active in the low micromolar range and seven of them (A.I.3, A.I.7, B.I.1, B.I.2, C.I.7 C.I.8 and C.II.8) stood out for selectivity indexes higher than the ones exhibited by

  一系列的31硒化合物覆盖面广化学品空间被评定为体外leishmanicidal对活动婴儿利什曼原虫无鞭毛体。还评估了这些化合物对人THP-1细胞的细胞毒性。有趣的是，大多数经过测试的衍生物在低微摩尔范围内均具有活性，其中有七个（AI3，AI7，BI1，BI2，CI7，CI8和C.II.8）。）的选择性指数高于参考化合物米替福星和依德福星所显示的那些。对这些先导化合物进行了抗感染巨噬细胞的评估，并测定了其锥虫硫醚还原酶（TryR）的抑制能力，以进一步接近其引起其作用的机理。其中指出了经二硒化物测试的结构降低感染率的能力。前导化合物中的三种有效地抑制了TryR，因此该酶可能与这些化合物引起其杀菌作用的作用机理有关。
• Synthesis and X-ray Structural Characterization of Di-<i>p</i>-aminobenzenediselenide [<i>p</i>-H₂NC₆H₄Se]₂and its Mercury(II) Derivatives
  作者：Fabrício Bublitz、Melina de Azevedo Mello、Daniele Cocco Durigon、Bárbara Tirloni、Ernesto Schulz Lang

  DOI：10.1002/zaac.201400327

  日期：2014.10

  A synthetic route to obtain [p-H2NC6H4Se]2 (1) in good yield was developed, and the crystal structure of the product was characterized for the first time. The synthesis and structure of the mercury(II) derivative [Hg(SeC6H4NH2)2] (2) was also investigated and is reported herein. The versatile coordination chemistry of [Hg(SeC6H4NH2)2] with halides of the same metal and PCy3 allows the synthesis of

  开发了以良好收率获得[p-H2NC6H4Se]2(1)的合成路线，并首次表征了产物的晶体结构。汞 (II) 衍生物 [Hg(SeC6H4NH2)2] (2) 的合成和结构也进行了研究并在本文中进行了报道。[Hg(SeC6H4NH2)2] 与相同金属的卤化物和 PCy3 的多功能配位化学允许合成 [Hg(X)(SeC6H4NH2)(PCy3)] (X = Cl, Br, I) (3–5) . 产物 1、3-5 以结晶形式分离，并通过 X 射线结构分析表征。
• N-Selenocyanato-Dibenzenesulfonimide: A New Electrophilic Selenocyanation Reagent
  作者：Zhi-Min Chen、Deng Zhu、Ai-Hui Ye

  DOI：10.1055/a-1493-6885

  日期：2021.10

  A new electrophilic selenocyanation reagent N-seleno­cyanato-dibenzenesulfonimide was readily prepared in two steps from commercially available dibenzenesulfonimide for the first time. A variety of electrophilic selenocyanato reactions of nucleophiles have been achieved using it as selenocyanato source under mild and simple conditions. Numerous SeCN-containing compounds were obtained in moderate to

  一种新的亲电子硒氰化试剂N-硒代氰基-二苯磺酰亚胺很容易分两次从市售二苯磺酰亚胺中制备。使用它作为温和简单条件下的硒氰酸根源，已经实现了亲核试剂的各种亲电子硒酸氰酸根反应。以中等至极好的收率获得了许多含SeCN的化合物。同时，还开发了路易斯酸介导的烯烃与酚的串联硒代氰化/环化反应，该反应提供了以中等至良好收率形成各种含SeCN的苯并二氢呋喃和二氢苯并呋喃的简单方法。