9-Isothiocyanato-4-methoxyacridine | 154389-38-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9-Isothiocyanato-4-methoxyacridine
• CAS: 154389-38-5
• 化学式: C₁₅H₁₀N₂OS
• 分子量: 266.323
• InChiKey: ACDFHWMFJZLDNL-UHFFFAOYSA-N

物化性质

• 沸点：
  481.1±15.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-双(3-氨基丙基)哌嗪 、 9-Isothiocyanato-4-methoxyacridine 以 四氢呋喃 为溶剂， 反应 6.0h， 以33%的产率得到1-(3-(4-(3-(4-methoxy-9-acridinylamine)methanethioamidopropyl)piperazin-1-yl)propyl)-3-(4-methoxyacridin-9-yl)thiourea
  参考文献：
  名称：

  Synthesis of Bis-acridine Derivatives Exhibiting Anticancer and Anti-inflammatory Activity

  摘要：

  A series of bis‐acridine derivatives 3a–j and 5a–j have been synthesized by condensation of 9‐chloro‐2,4‐(un)substituted acridines (1a–e) and 9‐isothiocyanato‐2,4‐(un)substituted acridines (4a–e) with diamine 2a and 2b, respectively. These bis‐acridines were evaluated in vitro for activity against a panel of human cancer cell lines of lung (NCI H‐522), ovary (PA1), breast (T47D), colon (HCT‐15), and liver (HepG2). Several bis‐acridines were found to possess good anticancer activity against various cancer cell lines. Of these, compound 3h exhibited good anticancer activity against all cancer cell lines tested except liver (HepG2) cell line. In addition to this, these compounds were screened for anti‐inflammatory activity at a dose of 50 mg/kg p.o. Compound 3g exhibited 41% anti‐inflammatory activity, which is better than most commonly used standard drug ibuprofen, which showed 39% anti‐inflammatory (at 50 mg/kg p. o.) activity.

  DOI：

  10.1002/jhet.985
• 作为产物：
  描述：

  9-chloro-4-methoxyacridine 、 silver thiocyanate 以 甲苯 为溶剂， 以62%的产率得到9-Isothiocyanato-4-methoxyacridine
  参考文献：
  名称：

  Fluorescence Reagents for Labelling of Biomolecules. Part I. Synthesis and Spectral Characterization of 2- and 4-Substituted 9-Isothiocyanatoacridines

  摘要：

  从相应的9-氯基蒽醌I-VII制备了9-异硫氰酸酯蒽醌VIII-XIV。给出了产物的红外线、1H NMR、13C NMR和荧光光谱。C-9 ipso碳原子的13C NMR化学位移呈现出与与C-2碳相连的取代基的Hammett常数相符合的趋势。这些取代基对C-NCS的化学位移的影响很小。研究了异硫氰酸酯VIII-XIV在介质pH值上的水解依赖性。发现9-异硫氰酸酯蒽醌在pH 7-10不会发生水解。与9-氨基蒽醌相比，确定了化合物VIII-XIV在pH 7.4下的相对荧光强度（F/F0）。没有发现荧光强度与取代基极性特征之间的直接关系。

  DOI：

  10.1135/cccc19940203

文献信息

• Fluorescence Reagents for Labelling of Biomolecules. Part I. Synthesis and Spectral Characterization of 2- and 4-Substituted 9-Isothiocyanatoacridines
  作者：Dana Mazagová、Danica Sabolová、Pavol Kristian、Ján Imrich、Marián Antalík、Dušan Podhradský

  DOI：10.1135/cccc19940203

  日期：——

  9-Isothiocyanatoacridines VIII - XIV were prepared from the corresponding 9-chloroacridines I - VII. The IR, ¹H NMR, ¹³C NMR and fluorescence spectra of the products are given. The ¹³C NMR chemical shifts of the C-9 ipso carbon atom exhibit a trend that is in accord with the Hammett constants of substituents bonded to the C-2 carbon. Effect of these substituents on the chemical shift of C-NCS was only small. The dependence of hydrolysis of isothiocyanates VIII - XIV on pH of the medium was studied. It was found that 9-isothiocyanatoacridines do not undergo hydrolysis at pH 7 - 10. The relative fluorescence intensities (F/F₀) of compounds VIII - XIV at pH 7.4 have been determined in comparison with that of 9-aminoacridine. No direct dependence between the fluorescence intensity and the polar character of substituents has been found.

  从相应的9-氯基蒽醌I-VII制备了9-异硫氰酸酯蒽醌VIII-XIV。给出了产物的红外线、1H NMR、13C NMR和荧光光谱。C-9 ipso碳原子的13C NMR化学位移呈现出与与C-2碳相连的取代基的Hammett常数相符合的趋势。这些取代基对C-NCS的化学位移的影响很小。研究了异硫氰酸酯VIII-XIV在介质pH值上的水解依赖性。发现9-异硫氰酸酯蒽醌在pH 7-10不会发生水解。与9-氨基蒽醌相比，确定了化合物VIII-XIV在pH 7.4下的相对荧光强度（F/F0）。没有发现荧光强度与取代基极性特征之间的直接关系。
• Fluorescence Reagents for Labelling of Biomolecules. Part III. Study of the Reactions of 2- and 4-Substituted 9-Isothiocyanatoacridines with Glycine
  作者：Danica Sabolová、Dana Mazagová、Pavol Kristian、Marián Antalík、Dušan Podhradský、Ján Imrich

  DOI：10.1135/cccc19941682

  日期：——

  Kinetics of nucleophilic addition reaction of 2- and 4-substituted 9-isothiocyanatoacridines I - VII with glycine in buffered aqueous dimethylformamide has been studied. The addition products, N-(9-acridinylthiocarbamoyl)glycines VIII - XIV, were characterized by IR, UV, ¹H NMR, mass and fluorescence spectra. Derivatives VIII, X and XII exhibited higher fluorescence intensity than the starting isothiocyanates; the highest fluorescence was found for the unsubstituted compound X. The reaction mechanism is discussed on the basis of properties of the reaction products and kinetic characteristics.

  研究了2-和4-取代的9-异硫氰酸基吖啶-在缓冲水合二甲基甲酰胺中与甘氨酸的亲核加成反应动力学。加成产物VIII-XIV为N-(9-吖啶基硫氨酰)甘氨酸，通过红外、紫外、¹H核磁共振、质谱和荧光光谱进行表征。衍生物VIII、X和XII的荧光强度高于起始异硫氰酸酯，其中无取代化合物X的荧光最强。根据反应产物的性质和动力学特征讨论了反应机理。
• Synthesis of acridinyl-thiazolino derivatives and their evaluation for anti-inflammatory, analgesic and kinase inhibition activities
  作者：Sham M. Sondhi、Nirupma Singh、Anand M. Lahoti、Kiran Bajaj、Ashok Kumar、Olivier Lozach、Laurent Meijer

  DOI：10.1016/j.bmc.2005.04.017

  日期：2005.7

  Variety of N-(4-phenyl-3-(2',3',4'(un) substituted phenyl)thiazol-2(3H)-ylidene)-2,4(un)substituted acridin-9-amine (4a-o) and 1-[(2,4-(un)substituted acridin-9-yl)-3-(4-phenyl-3-(2',3',4'(un)substituted phenyl)thiazol-2(3H)-ylidene)lisothiourea (5a-h) derivatives have been synthesized by condensation of 4-phenyl-3-(2',3',4'(un)substituted phenyl)thiazol-2(3H)-imine (3a-g) with 9-chloro-2,4-(un)substituted acridine (la-c) and 9-isothiocyanato-2,4-(un)substituted acridine (2a-d), respectively. All these compounds were characterized by correct H-1 NMR, FT-IR, MS and elemental analyses. These compounds were screened for antiinflammatory, analgesic and kinase (CDK1, CDK5 and GSK3) inhibition activities. Some compounds exhibited good anti-inflammatory (25-32%) and potent analgesic (50-75%) activities, at 50 mg/kg p.o. A compound, 4o (R-1 = H, R-2 = OCH3, R-3 = CH3, R-4 = CH3, R-5 = H) exhibited moderate CDK1 (IC50 = 8.5 mu M) inhibition activity. (c) 2005 Published by Elsevier Ltd.
• Synthesis of Bis-acridine Derivatives Exhibiting Anticancer and Anti-inflammatory Activity
  作者：Sham M. Sondhi、Sandeep Kumar、Reshma Rani、Ajanta Chakraborty、Partha Roy

  DOI：10.1002/jhet.985

  日期：2013.3

  A series of bis‐acridine derivatives 3a–j and 5a–j have been synthesized by condensation of 9‐chloro‐2,4‐(un)substituted acridines (1a–e) and 9‐isothiocyanato‐2,4‐(un)substituted acridines (4a–e) with diamine 2a and 2b, respectively. These bis‐acridines were evaluated in vitro for activity against a panel of human cancer cell lines of lung (NCI H‐522), ovary (PA1), breast (T47D), colon (HCT‐15), and liver (HepG2). Several bis‐acridines were found to possess good anticancer activity against various cancer cell lines. Of these, compound 3h exhibited good anticancer activity against all cancer cell lines tested except liver (HepG2) cell line. In addition to this, these compounds were screened for anti‐inflammatory activity at a dose of 50 mg/kg p.o. Compound 3g exhibited 41% anti‐inflammatory activity, which is better than most commonly used standard drug ibuprofen, which showed 39% anti‐inflammatory (at 50 mg/kg p. o.) activity.
• Dipole Moments of 2- and 4-Substituted 9-Isothiocyanatoacridines
  作者：Ivan Danihel、Gejza Suchár、Pavol Kristian、Stanislav Böhm

  DOI：10.1135/cccc19961615

  日期：——

  Dipole moments of a series of 2- and 4-substituted 9-isothiocyanatoacridines were determined and compared with the values calculated by vector addition using bond and group dipole moments. The results are discussed from the viewpoint of geometrical and conformational structures of the compounds investigated.

  一系列2-和4-取代的9-异硫氰酸基蒽啉的偶极矩已被测定，并与使用键和基团偶极矩进行向量相加计算的值进行比较。从所研究化合物的几何和构象结构的观点讨论了结果。