3-(4-methoxybenzoyl)-8-methoxy-2H-chromene-2-thione | 1228956-76-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-methoxybenzoyl)-8-methoxy-2H-chromene-2-thione
• 英文别名: 3(4-methoxybenzoyl)-8-methoxy-2H-chromene-2-thione；(4-Methoxyphenyl)-(8-methoxy-2-sulfanylidenechromen-3-yl)methanone
• CAS: 1228956-76-0
• 化学式: C₁₈H₁₄O₄S
• 分子量: 326.373
• InChiKey: XWZIZCMDNDUDSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  76.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对甲氧基苯乙酮 在 indium(III) chloride 、 sodium hydride 、 尿素 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.0h， 生成 3-(4-methoxybenzoyl)-8-methoxy-2H-chromene-2-thione
  参考文献：
  名称：

  在无溶剂条件下通过InCl 3催化的β-氧二硫代酯环化反应制得高度官能化的2 H-苯二甲基-2-硫酮的简便方法

  摘要：

  通过β-氧代二硫代酯与水杨醛/α-的缩合反应，开发出了一种方便的一锅合成3-芳酰基/杂芳酰基-2 H-亚甲基-2-硫酮和苯并[ f ] 2 H-亚甲基-2-硫酮的方法。在无溶剂条件下在三氯化铟存在下生成羟基萘醛。该反应操作简便，易于扩展，可快速进入差异取代的亚甲基-2-硫酮骨架。

  DOI：

  10.1016/j.tet.2010.11.055

文献信息

• An expedient route to highly functionalized 2H-chromene-2-thiones via ring annulation of β-oxodithioesters catalyzed by InCl3 under solvent-free conditions
  作者：Rajiv Kumar Verma、Girijesh K. Verma、Keshav Raghuvanshi、Maya Shankar Singh

  DOI：10.1016/j.tet.2010.11.055

  日期：2011.1

  A convenient and one-pot synthesis of 3-aroyl/heteroaroyl-2H-chromene-2-thiones and benzo[f]2H-chromene-2-thiones has been developed by the condensation of β-oxodithioesters and salicylaldehydes/α-hydroxynaphthaldehydes in the presence of indium trichloride under solvent-free conditions. The reaction is operationally facile, readily scalable, and offers rapid entry into differentially substituted chromene-2-thione

  通过β-氧代二硫代酯与水杨醛/α-的缩合反应，开发出了一种方便的一锅合成3-芳酰基/杂芳酰基-2 H-亚甲基-2-硫酮和苯并[ f ] 2 H-亚甲基-2-硫酮的方法。在无溶剂条件下在三氯化铟存在下生成羟基萘醛。该反应操作简便，易于扩展，可快速进入差异取代的亚甲基-2-硫酮骨架。
• Novel 3-alkanoyl/aroyl/heteroaroyl-2H-chromene-2-thiones: Synthesis and evaluation of their antioxidant activities
  作者：Okram Mukherjee Singh、Nepram Sushuma Devi、Dhanaraj Singh Thokchom、Gurumayum Jitendra Sharma

  DOI：10.1016/j.ejmech.2010.01.070

  日期：2010.6

  A facile, convenient and high yielding synthesis of a combinatorial library of 3-alkanoyl/aroyl/heteroaroyl-2H-chromene-2-thiones has been developed by the condensation of easily accessible beta-oxodithioesters and salicylaldehyde/substituted 2-hydroxybenzaldehydes under solvent-free conditions. The assessment of radical scavenging capacity of the compounds towards the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) was measured and these compounds were found to scavenge DPPH free radical efficiently. Five selected compounds were able to protect curcumin from the attack of sulfur free radical generated by radiolysis of glutathione (GSH). The newly synthesized compounds exhibited profound antioxidant activities Five of them rendered comparatively high antioxidant capacity.
• Devi, Nepram Sushuma; Singh, Thokchom Prasanta; Khumanthem, Nonibala, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 9, p. 1224 - 1231
  作者：Devi, Nepram Sushuma、Singh, Thokchom Prasanta、Khumanthem, Nonibala、Singh, Okram Mukherjee

  DOI：——

  日期：——
• Molecular Docking and in Vitro Antileishmanial Evaluation of Chromene-2-thione Analogues
  作者：Rajiv Kumar Verma、Vijay Kumar Prajapati、Girijesh Kumar Verma、Deblina Chakraborty、Shyam Sundar、Madhukar Rai、Vikash Kumar Dubey、Maya Shankar Singh

  DOI：10.1021/ml200280r

  日期：2012.3.8

  Leishmaniases are an epidemic in various countries, and the parasite is developing resistance against available drugs. Thus, development of new drugs against Leishmania is an open area of investigation for synthetic organic chemists. To meet this challenge, a series of chromene-2-thione derivatives have been synthesized and docked into the active site of trypanothione reductase (TryR) enzyme required for redox balance of the parasite. These were screened on promastigote, axenic amastigote, and intracellular amastigote stages of Leishmania donovani and found to show high levels of antileishmanial activity together with minimal toxicity to human peripheral blood mononuclear cells. Compounds 3b and 3k were found to be the most active among the tested compounds. Although the compounds show moderate antileishmanial activity, they identify a chemical space to design and develop drugs based on these chromene-2-thione derivatives against the Leishmania parasite.