3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-(4-(methylthio)-phenyl)-10-p-tolyl-acridine-1,8-(2H,5H,9H,10H)-dione | 1228050-06-3

• 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: 3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-(4-(methylthio)-phenyl)-10-p-tolyl-acridine-1,8-(2H,5H,9H,10H)-dione
• 英文别名: 3,3,6,6-tetramethyl-10-(4-methylphenyl)-9-(4-methylsulfanylphenyl)-4,5,7,9-tetrahydro-2H-acridine-1,8-dione
• CAS: 1228050-06-3
• 化学式: C₃₁H₃₅NO₂S
• 分子量: 485.69
• InChiKey: MYOSQCRLRGHSNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙烷,三氯氟- 、 5,5-二甲基-1,3-环己二酮 、 4-(甲基巯基)苯甲醛 以 乙醇 为溶剂， 反应 3.58h， 以75%的产率得到3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-(4-(methylthio)-phenyl)-10-p-tolyl-acridine-1,8-(2H,5H,9H,10H)-dione
  参考文献：
  名称：

  一锅级联合成和S-甲基苯基取代a啶-1,8-二酮的抗炎和抗糖尿病活性的体外评估

  摘要：

  通过一锅级联法合成了各种S-甲基苯基取代的cr啶-1,8-二酮系列（4a–i），该方法涉及4-（甲硫基）苯甲醛和二甲酮与多种胺作为氮源在回流下的反应在乙醇中。所有合成的衍生物均通过光谱法表征。研究了所有合成化合物的抗炎和抗糖尿病功效的体外评估。抗炎结果表明化合物4c和4d它们表现出优异的活性，通过膜稳定作用的抑制百分比为80.58±0.42,81.72±1.72，通过白蛋白变性方法的抑制百分比为77.72±0.76,78.76±0.81，与浓度为100μg/ ml的标准双氯芬酸相当。此外，抗糖尿病试验显示，相对于其标准药物阿卡波糖，浓度为100μg/ ml的合成化合物具有中等活性。

  DOI：

  10.1111/cbdd.12973

文献信息

• Sulfuric acid-modified poly(vinylpyrrolidone) ((PVP–SO₃H)HSO₄): a new highly efficient, bio-degradable and reusable polymeric catalyst for the synthesis of acridinedione derivatives
  作者：Hamid Reza Safaei、Maryam Safaei、Mohsen Shekouhy

  DOI：10.1039/c4ra12219d

  日期：——

  The synthesis of a new biodegradable polymer catalyst and its efficiency for the synthesis of acridindiones.

  合成一种新的可生物降解聚合物催化剂及其在合成吖啶二酮中的效率。
• One-Pot Multi Component Synthesis of Xanthenediones and Acridinediones at Room Temperature
  作者：Hamid Reza Safaei、Abolfazl Eshghi Movahhed、Mansooreh Davoodi、Mohsen Shekouhy、Vahid Rahmanian、Maryam Safaei

  DOI：10.14233/ajchem.2013.13260

  日期：——

  A facile and efficient protocol for the synthesis of xanthenedione and acridinrdione derivatives has been developed via the one-pot condensation reaction between dimedone and aldehydes (for the synthesis of xanthenediones) and dimedone, aldehydes and primary amines (for the synthesis of acridinediones) in presence of the formic acid as solvent at room temperature. All the products were obtained in good to excellent yields and all reactions were completed in short times.

  在室温下，以甲酸为溶剂，通过二聚酮和醛类（用于合成呫吨二酮）以及二聚酮、醛类和伯胺（用于合成吖啶二酮）之间的一锅缩合反应，开发出了一种简便高效的合成呫吨二酮和吖啶二酮衍生物的方法。所有产物的收率都很高，甚至非常高，而且所有反应都在很短的时间内完成。
• Silica-bonded<i>S</i>-sulfonic acid as recyclable catalyst for the synthesis of 1,8-dioxo-decahydroacridines and 1,8-dioxo-octahydroxanthenes
  作者：Khodabakhsh Niknam、Farhad Panahi、Dariush Saberi、Molki Mohagheghnejad

  DOI：10.1002/jhet.303

  日期：——

  Abstract magnified image Silica‐bonded S‐sulfonic acid (SBSSA) has been found to be an efficient catalyst for the synthesis of 1,8‐dioxo‐decahydroacridines and 1,8‐dioxo‐octahydroxanthenes in excellent yields. The former have been synthesized from aromatic aldehydes, amines, and 5,5‐dimethyl‐1,3‐cyclohexanedione, whereas the latter from this mixture without amines. The method is an easy access to functionalized acridine and xanthene derivatives. The catalyst can be reused. J. Heterocyclic Chem., (2010).
• Sulfonated Polyethylene Glycol (PEG-SO₃H) as Eco-Friendly and Potent Water Soluble Solid Acid for Facile and Green Synthesis of 1,8-Dioxo-Octahydroxanthene and 1,8-Dioxo-Decahydroacridine Derivatives
  作者：Alireza Hasaninejad、Mohsen Shekouhy、Marzieh Miar、Somayeh Firoozi

  DOI：10.1080/15533174.2014.900799

  日期：2016.1.2

  In this work, a green, simple, and highly efficient procedure for the preparation of 1,8-dioxo-octahydroxanthene and 1,8-dioxo-decahydroacridine derivatives (as biologically active heterocycles, fluorescence materials and Pharmaceutical compounds) is described. Sulfonated polyethylene glycol (PEG-SO3H) has been used as an efficient and reusable catalyst for the one-pot multi component domino condensation reaction of dimedone and an aromatic aldehyde without/and a primary amine. The reactions were completed at 80 degrees C in water as green solvent. Using this procedure, all the products were obtained in good to excellent yields. The catalyst has been recovered and reused several times without any lose of reactivity.
• One-pot cascade synthesis and in vitro evaluation of anti-inflammatory and antidiabetic activities of S-methylphenyl substituted acridine-1,8-diones
  作者：Lavanya Mallu、Dhakshanamurthy Thirumalai、Indira Viswambaran Asharani

  DOI：10.1111/cbdd.12973

  日期：2017.10

  investigated. The anti-inflammatory results infer that the compounds 4c and 4d are showing excellent activity with an inhibition percentage of 80.58 ± 0.42, 81.72 ± 1.72 by membrane stabilization and 77.72 ± 0.76, 78.76 ± 0.81 by albumin denaturation methods, which is comparable with the standard diclofenac at a concentration of 100 μg/ml. Further, the antidiabetic assay revealed the moderate activity for the

  通过一锅级联法合成了各种S-甲基苯基取代的cr啶-1,8-二酮系列（4a–i），该方法涉及4-（甲硫基）苯甲醛和二甲酮与多种胺作为氮源在回流下的反应在乙醇中。所有合成的衍生物均通过光谱法表征。研究了所有合成化合物的抗炎和抗糖尿病功效的体外评估。抗炎结果表明化合物4c和4d它们表现出优异的活性，通过膜稳定作用的抑制百分比为80.58±0.42,81.72±1.72，通过白蛋白变性方法的抑制百分比为77.72±0.76,78.76±0.81，与浓度为100μg/ ml的标准双氯芬酸相当。此外，抗糖尿病试验显示，相对于其标准药物阿卡波糖，浓度为100μg/ ml的合成化合物具有中等活性。