9-isothiocyanato-1,2,3,4-tetrahydroacridine | 113105-99-0

• 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-1,2,3,4-tetrahydroacridine
• CAS: 113105-99-0
• 化学式: C₁₄H₁₂N₂S
• 分子量: 240.329
• InChiKey: OKPMIDOMSBJNDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  9-isothiocyanato-1,2,3,4-tetrahydroacridine 在 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 1.0h， 生成 2-<(1,2,3,4-tetrahydroacridin-9-yl)imino>-3-benzyl-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Synthesis of Acetylcholinesterase Inhibitors on the Basis of 9-Isothiocyanato-1,2,3,4-tetrahydroacridine: 2-[(1,2,3,4-Tetrahydroacridin-9-yl)imino]-3-substituted 1,3-Thiazolidin-4-ones

  摘要：

  The synthesis of 2-[(1,2,3,4-tetrahydroacridin-9-yl)imino]-3-substituted 1,3-thiazolidin-4-ones (5a-e) via cyclization of N-(1,2,3,4-tetrahydroacridin-9-yl)-S-methoxycarbonylmethyl-N'-substituted isothiourea hydrobromides was elaborated. As a synthon, 9-isothiocyanato-1,2,3,4-tetrahydroacridine, an analogue of tacrine, was used. The reaction represents a simple way for the preparation of new cholinergic compounds.

  DOI：

  10.3987/com-98-s16
• 作为产物：
  描述：

  邻氨基苯甲酸甲酯 在 四磷十氧化物 、 N,N-二甲基环己胺 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 9-isothiocyanato-1,2,3,4-tetrahydroacridine
  参考文献：
  名称：

  In vitro investigating of anticancer activity of new 7-MEOTA-tacrine heterodimers

  摘要：

  A combination of biochemical, biophysical and biological techniques was used to study calf thymus DNA interaction with newly synthesized 7-MEOTA-tacrine thiourea 12-17 and urea heterodimers 18-22, and to measure interference with type I and II topoisomerases. Their biological profile was also inspected in vitro on the HL-60 cell line using different flow cytometric techniques (cell cycle distribution, detection of mitochondrial membrane potential dissipation, and analysis of metabolic activity/viability). The compounds exhibited a profound inhibitory effect on topoisomerase activity (e.g. compound 22 inhibited type I topoisomerase at 1 mu M concentration). The treatment of HL-60 cells with the studied compounds showed inhibition of cell growth especially with hybrids containing thiourea (14-17) and urea moieties (21 and 22). Moreover, treatment of human dermal fibroblasts with the studied compounds did not indicate significant cytotoxicity. The observed results suggest beneficial selectivity of the heterodimers as potential drugs to target cancer cells.

  DOI：

  10.1080/14756366.2019.1593159

文献信息

• Asthana, Pratibha; Prasad, Mohan; Rastogi, Shri Nivas, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, p. 330 - 334
  作者：Asthana, Pratibha、Prasad, Mohan、Rastogi, Shri Nivas

  DOI：——

  日期：——
• Synthesis and Biological Evaluation of Novel Tacrine Derivatives and Tacrine–Coumarin Hybrids as Cholinesterase Inhibitors
  作者：Slavka Hamulakova、Ladislav Janovec、Martina Hrabinova、Katarina Spilovska、Jan Korabecny、Pavol Kristian、Kamil Kuca、Jan Imrich

  DOI：10.1021/jm5008648

  日期：2014.8.28

  A series of novel tacrine derivatives and tacrine-coumarin heterodimers were designed, synthesized, and biologically evaluated for their potential inhibitory effect on both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). Of these compounds, tacrine-coumarin heterodimer 7c and tacrine derivative 6b were found to be the most potent inhibitors of human AChE (hAChE), demonstrating IC50 values of 0.0154 and 0.0263 μM. Ligands 6b, 6c, and 7c exhibited the highest levels of inhibitory activity against human BuChE (hBuChE), demonstrating IC50 values that range from 0.228 to 0.328 μM. Docking studies were performed in order to predict the binding modes of compounds 6b and 7c with hAChE/hBuChE.
• Synthesis, Structure, and Cholinergic Effect of Novel Neuroprotective Compounds Bearing the Tacrine Pharmacophore
  作者：Pavol Kristian、Slávka Hamul'aková、Daniel Jun、Kamil Kuca、Ján Imrich、Ivan Danihel、Stanislav Böhm、Karel D. Klika

  DOI：10.3987/com-08-s(n)83

  日期：——
• ASTHANA, PRATIBHA;PRASAD, MOHAN;RASTOGI, SHRI NIVAS, INDIAN J. CHEM., 26,(1987) N 4, 330-334
  作者：ASTHANA, PRATIBHA、PRASAD, MOHAN、RASTOGI, SHRI NIVAS

  DOI：——

  日期：——