3-(acridin-9-yl)-1,1-dipropyl-thiourea | 215930-61-3

• 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: 3-(acridin-9-yl)-1,1-dipropyl-thiourea
• 英文别名: 3-Acridin-9-yl-1,1-dipropylthiourea
• CAS: 215930-61-3
• 化学式: C₂₀H₂₃N₃S
• 分子量: 337.489
• InChiKey: WBAQRULFRLUCQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  溴甲基乙酸酯 、 3-(acridin-9-yl)-1,1-dipropyl-thiourea 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到2'-dipropylamino-5'-methoxycarbonyl-spiro[dihydroacridine 9(10H),4'-thiazoline]
  参考文献：
  名称：

  A Simple Synthesis of 2′,5′-Disubstituted-Spiro [Dihydroacridine 9(10H), 4′-Thiazolines] by the Reaction of Corresponding 3-(Acridin-9-Yl)-Thioureas with Methyl Bromoacetate and Bromoacetonitrile

  摘要：

  A convenient method has been devised for the preparation of the spirodihydroacridinethiazolines 5a-j by the treatment of thioureas 3a-e with methyl bromoacetate and bromoacetonitrile via non-isolable isothioureas 4a-j and their subsequent cyclization with methanolic sodium methoxide.

  DOI：

  10.1080/00397919809458697
• 作为产物：
  描述：

  9-异硫氰酸酯吖啶 、 二正丙胺 以 乙醚 为溶剂， 以95%的产率得到3-(acridin-9-yl)-1,1-dipropyl-thiourea
  参考文献：
  名称：

  A Simple Synthesis of 2′,5′-Disubstituted-Spiro [Dihydroacridine 9(10H), 4′-Thiazolines] by the Reaction of Corresponding 3-(Acridin-9-Yl)-Thioureas with Methyl Bromoacetate and Bromoacetonitrile

  摘要：

  A convenient method has been devised for the preparation of the spirodihydroacridinethiazolines 5a-j by the treatment of thioureas 3a-e with methyl bromoacetate and bromoacetonitrile via non-isolable isothioureas 4a-j and their subsequent cyclization with methanolic sodium methoxide.

  DOI：

  10.1080/00397919809458697

文献信息

• Methylation of Acridin-9-ylthioureas. Structure, Fluorescence and Biological Properties of Products
  作者：Juraj Bernát、Eva Balentová、Pavol Kristian、Ján Imrich、Erik Sedlák、Ivan Danihel、Stanislav Böhm、Naďa Prónayová、Kalevi Pihlaja、Karel D. Klika

  DOI：10.1135/cccc20040833

  日期：——

  The structure, fluorescence, biological properties and S(N)-methylation reactions of ten 1,1-alkyl/aryl-disubstituted 3-(acridin-9-yl)thioureas 4 have been studied. Various reaction conditions allowed to obtain corresponding S-methyl 5 and S,N-dimethyl derivatives 6 in good yields. Structure and stereochemistry of the synthesized products are demonstrated by ab initio quantum chemical calculations and NMR techniques including PDQF-COSY, selective INEPT and NOE-difference experiments. Remarkable upfield ¹³C shifts of resonance signals of carbons C-4a, C-10a adjacent to acridine N-10 are characteristic of hydroiodides in contrast to free bases. Z configuration in isothioureas 7 with secondary amino rest in relation to E configuration of isothioureas with primary amino rest is discussed. Of the obtained products, some isothiourea salts 6 exhibit more than 2 orders of magnitude higher intensity of fluorescence, using 9-isothiocyanatoacridine as a standard. The obtained isothiourea hydroiodides 5 and dimethylisothiourea iodides 6 show remarkable biological activity against Mycobacterium tuberculosis.

  对十个1,1-烷基/芳基-二取代-3-(吖啶-9-基)硫脲的结构、荧光、生物活性和S(N)-甲基化反应进行了研究。各种反应条件使得可以很好地获得相应的S-甲基衍生物5和S,N-二甲基衍生物6。合成产物的结构和立体化学通过ab initio量子化学计算和NMR技术进行展示，包括PDQF-COSY、选择性INEPT和NOE差异实验。与自由碱相比，吖啶N-10相邻的碳C-4a、C-10a的共振信号显著上移是碘化物的特征。讨论了次级氨基取代的异硫脲7与初级氨基取代的异硫脲的Z构型与E构型的关系。在获得的产物中，一些异硫脲盐6的荧光强度比使用9-异硫氰酸吖啶作为标准时高2个数量级。获得的异硫脲碘化物5和二甲基异硫脲碘化物6对Mycobacterium tuberculosis显示出显著的生物活性。

• A Simple Synthesis of 2′,5′-Disubstituted-Spiro [Dihydroacridine 9(10H), 4′-Thiazolines] by the Reaction of Corresponding 3-(Acridin-9-Yl)-Thioureas with Methyl Bromoacetate and Bromoacetonitrile
  作者：Juraj Bernát、Igor Chomča、Pavol Kristian、Gundula Voss

  DOI：10.1080/00397919809458697

  日期：1998.11

  A convenient method has been devised for the preparation of the spirodihydroacridinethiazolines 5a-j by the treatment of thioureas 3a-e with methyl bromoacetate and bromoacetonitrile via non-isolable isothioureas 4a-j and their subsequent cyclization with methanolic sodium methoxide.