2,2'-diselenobisnicotinic acid | 41323-11-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,2'-diselenobisnicotinic acid
• 英文别名: 2,2′-diselanediyldinicotinic acid；2-[(3-Carboxypyridin-2-yl)diselanyl]pyridine-3-carboxylic acid
• CAS: 41323-11-9
• 化学式: C₁₂H₈N₂O₄Se₂
• 分子量: 402.127
• InChiKey: JMKNVMYDHDSJGG-UHFFFAOYSA-N

物化性质

• 沸点：
  649.1±65.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.85
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2'-diselenobisnicotinic acid 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 ethyl 2-(chloroseleno)nicotinate
  参考文献：
  名称：

  [EN] PHARMACEUTICAL FORMULATIONS
  [FR] FORMULATIONS PHARMACEUTIQUES

  摘要：

  本文披露了谷胱甘肽与异硒唑或异硫唑衍生物（例如ebselen或ebsulfur衍生物）结合治疗糖尿病、狼疮或其他慢性炎症性疾病的方法。谷胱甘肽最好以快速释放口服制剂的形式提供，以便在回肠的第一部分中吸收谷胱甘肽。异硒唑或异硫唑衍生物最好以延迟释放制剂的形式提供，以避免重叠的高肠内浓度。这些可以在同一单位剂量形式中提供。

  公开号：

  WO2017091737A1
• 作为产物：
  描述：

  2-氯烟酸 在 selenium 、 sodium tetrahydroborate 、 sodium 作用下， 以 乙醇 为溶剂， 以28%的产率得到2,2'-diselenobisnicotinic acid
  参考文献：
  名称：

  In situ formation and solid-state oxidation of a triselenane NSeN-pincer MOF

  摘要：

  在Co²⁺或Ni²⁺存在下，对2-硒代烟酸进行控制部分分解，导致基于三硒烷配体（RSeSeSeR）以NSeN夹持器形式配位到M²⁺中心的一种不寻常的MOF的原位形成。

  DOI：

  10.1039/c9cc07851g

文献信息

• Oxidative addition reactions of nicotinamide based organoselenium compounds on [M(PPh3)4] (M=Pd or Pt): An insight study for the formation of several isolable products
  作者：Rohit Singh Chauhan、C. Parashiva Prabhu、Prasad P. Phadnis、G. Kedarnath、James A. Golen、Arnold L. Rheingold、Vimal K. Jain

  DOI：10.1016/j.jorganchem.2012.09.012

  日期：2013.1

  addition reactions of [2-NC5H3(3-COR)Se]2 (R = NH2, NHPh, or NHpym (pym = pyrimidine)) with [M(PPh3)4] (M = Pd, Pt) in benzene afforded complexes of the type, [Mη2-SeC5H3(3-COR)N}SeC5H3(3-COR)N}(PPh3)] (1) (M = Pt, Pd; R = NH2, NHPh, or NHpym). A similar reaction with [2-NC5H3(3-COOH)Se]2 gave an insoluble product which after extraction with dichloromethane gave [M(Cl)SeC5H3(3-COOH)N}(PPh3)2] (2). Compound

  [2-NC 5 H 3（3-COR）Se] 2（R = NH 2，NHPh或NHpym（pym =嘧啶））与[M（PPh 3）4 ]（M = Pd，Pt ）中的类型的苯，得到配合物，[M η 2 -sec 5 ħ 3（3-COR）N} 秒5 ħ 3（3-COR）N}（PPH 3）]（1）（M =铂，Pd； R = NH 2，NHPh或NHpym）。与[2-NC 5 H 3（3-COOH）Se] 2的相似反应产生不溶产物，其在用二氯甲烷萃取后得到[M（Cl）SeC 5H 3（3-COOH）N}（PPh 3）2 ]（2）。化合物2，在甲醇溶液转化成二聚离子络合物，但在CH长时间站立2氯2或三氯甲烷3被转换成[M（Cl）的η 2 -sec 5 ħ 3（3-COOH）N}（ PPh 3）]。用[2-NC 5 H 3（3-CONHPh）SeI处理[M（PPh 3）4 ]最初产生了预期的氧化加成产物[M（I）SeC
• Design, synthesis and cytotoxic activity of vitamin E bearing selenium compounds against human breast cancer cell line (MCF-7)
  作者：Shams H. Abdel-Hafez、Ahmed B. Abdelwahab、Gilbert Kirsch

  DOI：10.1080/10426507.2017.1333505

  日期：2017.10.3

  vitamin E/selenated pyridine, vitamin E/selenated pyridazine, vitamin E/selenated coumarine and vitamin E/selenated nicotine moieties were synthesized and their cytotoxic activity is investigated using the human breast cancer cell line. The newly synthesized compounds were characterized using spectroscopic tools (IR, 1H NMR, 13C NMR, and mass spectroscopy) as well as microanalysis. Our study reveals

  图形摘要摘要合成了一系列新的维生素 E/硒化吡啶、维生素 E/硒化哒嗪、维生素 E/硒化香豆素和维生素 E/硒化尼古丁部分，并使用人乳腺癌细胞系研究了它们的细胞毒活性。使用光谱工具（IR、1H NMR、13C NMR 和质谱）以及微量分析对新合成的化合物进行了表征。我们的研究表明，复合维生素 E/硒化尼古丁部分比其他合成化合物具有最高的细胞毒性作用。
• Azaanalogues of ebselen as antimicrobial and antiviral agents: synthesis and properties
  作者：H. Wójtowicz、K. Kloc、I. Maliszewska、J. Młochowski、M. Piętka、E. Piasecki

  DOI：10.1016/j.farmac.2004.07.003

  日期：2004.11

  The different analogues of ebselen-unsubstituted benzisoselenazol-3(2H)-one (2a) 2-pyridylbenzisoselenazol-3(2H)-ones (2b-h) and 7-azabenzisoselenazol-3(2H)-ones (3a-j) were designed as new selenium-containing antiviral and antimicrobial agents and synthesized. Some of them were found in the antiviral assay in vitro to be strong inhibitors of cythopatic activity of herpes simplex virus type 1--HSV-1

  依伯硒烯未取代的苯并异硒唑-3（2H）-一个（2a）2-吡啶基苯并聚硒氮唑-3（2H）-一个（2b-h）和7-氮杂苯并石墨烯-3（2H）-一个（3a-j）的不同类似物是设计作为新型的含硒抗病毒和抗菌剂并合成。在体外抗病毒测定中发现其中一些是1型单纯疱疹病毒HSV-1（化合物2a，b，f，h，3a-j）和脑心肌炎病毒EMCCV（化合物2a，h，3a-f，k，l）。发现化合物2a，h和3a-e，j在体外对革兰氏阳性细菌（金黄色葡萄球菌和芽孢杆菌）具有明显的活性，其中一些抑制病原酵母（白色念珠菌）（3a，b）和丝状真菌（3a-e，f）。
• Design and Synthesis of DiselenoBisBenzamides (DISeBAs) as Nucleocapsid Protein 7 (NCp7) Inhibitors with anti-HIV Activity
  作者：Luca Sancineto、Alice Mariotti、Luana Bagnoli、Francesca Marini、Jenny Desantis、Nunzio Iraci、Claudio Santi、Christophe Pannecouque、Oriana Tabarrini

  DOI：10.1021/acs.jmedchem.5b01183

  日期：2015.12.24

  The interest in the synthesis of Se-containing compounds is growing with the discovery of derivatives exhibiting various biological activities. In this manuscript, we have identified a series of 2,2'-diselenobisbenzamides (DISeBAs) as novel HIV retroviral nucleocapsid protein 7 (NCp7) inhibitors. Because of its pleiotropic functions in the whole viral life cycle and its mutation intolerant nature, NCp7 represents a target of great interest which is not reached by any anti-HIV agent in clinical use. Using the diselenobisbenzoic scaffold, amino acid, and benzenesulfonamide derivatives were prepared and biologically profiled against different models of HIV infection. The incorporation of amino acids such as glycine and glutamate into DISeBAs 7 and 8 resulted in selective anti-HIV activity against both acutely and chronically infected cells as well as an interesting virucidal effect. DISeBAs demonstrated broad antiretroviral activity, encompassing HIV-1 drug-resistant strains including clinical isolates, as well as simian immunodeficiency virus (SW). Time of addition experiments, along with the observed dose dependent inhibition of the Gag precursor proper processing, confirmed that their mechanism of action is based on NCp7 inhibition.
• Synthesis of 7-Azabenzisoselenazol- 3(2H)-ones: A New Group of Selenium Containing Antimicrobials
  作者：Krystian Kloc、Irena Maliszewska、Jacek Młochowski

  DOI：10.1081/scc-120025191

  日期：2003.11

  A convenient, general method for synthesis of various 2-substituted 7-azabenzisoselenazol-3(2H)-ones having pyridine ring condensed with selenazolone moiety is presented. It is based on the conversion of 2-chloronicotinic acid into 2-(chloroseleno)nicotinic acid chloride and its reaction with primary amines. The title compounds were found in the antimicrobial assay in vitro to be highly active against broad spectrum of bacteria and fungi.