4-methyl-9-isothiocyanatoacridine | 24628-53-3

• 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: 4-methyl-9-isothiocyanatoacridine
• 英文别名: 9-isothiocyanato-4-methylacridine；9-isothiocyanato-4-methyl-acridine；4-Methyl-9-isothiocyanatoacridin
• CAS: 24628-53-3
• 化学式: C₁₅H₁₀N₂S
• 分子量: 250.324
• InChiKey: RKBURDRRANWKCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyl-9-isothiocyanatoacridine 以 乙醚 、 二氯甲烷 为溶剂， 生成 3-(4-methylacridin-9-yl)-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  Reaction of O-Alkyl-N-substituted Iminothiocarbonates with Bromoacetyl Bromide. A General Method for the Synthesis of 3-Substituted 1,3-Thiazolidine-2,4-diones

  摘要：

  通过溴乙酰溴与甲基-O-取代亚硫代碳酸亚胺钠盐的反应，可以得到3-取代-1,3-噻唑啉-2,4-二酮，产率高且纯度高，这代表了一种新的通用制备方法。合成产物的结构已通过1H NMR、13C NMR、IR和质谱以及独立合成进行了确认。

  DOI：

  10.1135/cccc19960432
• 作为产物：
  描述：

  4-methyl-9-chloroacridine 、 silver thiocyanate 以 甲苯 为溶剂， 以82%的产率得到4-methyl-9-isothiocyanatoacridine
  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 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。
• 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。
• Sondhi, Sham M.; Johar, Monika; Singhal, Nidhi, Monatshefte fur Chemie, 2000, vol. 131, # 5, p. 511 - 520
  作者：Sondhi, Sham M.、Johar, Monika、Singhal, Nidhi、Dastidar, Sunanda G.、Shukla, Rakesh、Raghubir, Ram

  DOI：——

  日期：——
• Vlassa, M.; Kezdi, Maria; Bogdan, M., Journal fur praktische Chemie (Leipzig 1954), 1985, vol. 327, # 6, p. 1007 - 1010
  作者：Vlassa, M.、Kezdi, Maria、Bogdan, M.

  DOI：——

  日期：——
• Synthesis, anti-inflammatory and anticancer activity evaluation of some novel acridine derivatives
  作者：Sham M. Sondhi、Jaiveer Singh、Reshma Rani、P.P. Gupta、S.K. Agrawal、A.K. Saxena

  DOI：10.1016/j.ejmech.2009.10.042

  日期：2010.2

  Condensation of 9-chloro-2,4-(un)substituted acridines (la-c) with various amines (2a-e) and 9-isothiocyanato-2,4-(un)substituted acridines (4a,b) with different amines (2a,b,d,e) gave condensed products 3a-o and 5a-g respectively. Compounds 3a-o and Sa-g were screened for anti-inflammatory activity at a dose of 50 mg/kg p.o. Compound 3e exhibited 41.17% 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. Anticancer activity evaluation of compounds 3a-o and Sa-g was carried out against a small panel of human cancer cell lines and compounds 3g, 3m and 5g exhibited good anticancer activity against breast (MCF-7), liver (HEP-2), colon (COLO-205, 502713, HCT-15), lung (A-549) and neuroblastoma (IMR-32) cancer cell lines at a concentration of 1 x 10(-5) M. (C) 2009 Elsevier Masson SAS. All rights reserved.