3-(2-thienylbenzoyl)-2H-benzo[f]chromen-2-one | 86548-42-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 3-(2-thienylbenzoyl)-2H-benzo[f]chromen-2-one
• 英文别名: 2-(thiophen-2-carbonyl)-3H-benzo[f]chromen-3-one；2-(thiophene-2-carbonyl)-benzo[f]chromen-3-one；2-(Thiophen-2-carbonyl)-benzo[f]chromen-3-on；2-(thiophene-2-carbonyl)benzo[f]chromen-3-one
• CAS: 86548-42-7
• 化学式: C₁₈H₁₀O₃S
• 分子量: 306.342
• InChiKey: YIPFBJUAKGJYHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.28
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(2-thienylbenzoyl)-2H-benzo[f]chromen-2-one 在 吡啶 、 sodium tetrahydroborate 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 5-[(2-hydroxynaphthalen-1-yl)methyl]-6-(thiophen-2-yl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one
  参考文献：
  名称：

  Simplification of the tetracyclic SIRT1-selective inhibitor MC2141: Coumarin- and pyrimidine-based SIRT1/2 inhibitors with different selectivity profile

  摘要：

  In this report we describe the synthesis and biological characterization of two series of sirtuins' inhibitors (SIRTi), designed as simplification products of the previously reported SIRT1-selective inhibitor MC2141 (4). In the first series (5a-t) we report a number of 2-substituted-1,2-dihydrobenzo[f] chromen-3-ones with a marked selectivity for the inhibition of SIRT2 over SIRT1. Some of such derivatives showed also high pro-apoptotic (5i and 5l) and/or cytodifferentiating (5d, 5i, and 5o) properties in a human leukemia cell line (U937). The second group of SIRTi (6a-q) is characterized by some analogues of cambinol (3), a well known SIRTi active against the Burkitt lymphoma. Such compounds, differently from the unselective prototype, are endowed with a selective inhibition of SIRT1 over SIRT2, and, in some cases (6j, 6k, and 6q), are more efficient than 3 to induce apoptosis in U937 cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.025
• 作为产物：
  描述：

  3,3-bis(methylthio)-1-(thiophen-2-yl)prop-2-en-1-one 、 2-羟基-1-萘甲醛 在 copper(II) choride dihydrate 作用下， 反应 0.17h， 以85%的产率得到3-(2-thienylbenzoyl)-2H-benzo[f]chromen-2-one
  参考文献：
  名称：

  Facile Synthesis of 3-Thioxo-3H-benzo[f]chromen-2-yl methanone and 3H-Benzo[f]chromene-3-one Under Solvent Free Condition

  摘要：

  在无溶剂条件下，在一定量的 $CuCl_2$ 催化剂存在下，通过缩合现成的 $\beta$ 二硫代氧化物和 S,S-缩醛与 2- 羟基-1-萘甲醛，开发出了一种简单、方便、高效和高产的香豆素组合库合成方法。

  DOI：

  10.5012/bkcs.2011.32.1.175

文献信息

• Buu-Hoi et al., Journal of the Chemical Society, 1957, p. 2593,2596
  作者：Buu-Hoi et al.

  DOI：——

  日期：——
• Synthesis of functionalized benzo[f]2H-chromenes and evaluation of their antimicrobial activities
  作者：Irom Harimala Chanu、Laishram Ronibala Devi、Nonibala Khumanthem、N. Irabanta Singh、Dalip Kumar、Okram Mukherjee Singh

  DOI：10.1134/s1068162017020054

  日期：2017.3

  Knoevenagel cyclocondensations of alpha-hydroxy naphthaldehyde with beta-oxodithioesters and ketene dithioacetals yielded 2H-benzo[f]chromene-2-thiones and 2H-benzo[f]chromen-2-ones, respectively, in high yields. The newly synthesized compounds were evaluated for antifungal and antibacterial activities. Among them, compounds (2-furyl)(3-thioxo-3H-benzo[f]chromen-2-yl)methanone and phenyl(3-oxo-3H-benzo[f]chromen-2-yl)methanone exhibited excellent antifungal activity against tested fungi Curvularia lunata and Fusarium moniliforme. The highest antibacterial activity against the tested bacteria Escherichia coli and Staphylococcus aureus was observed for (4-chlorophenyl)(3-oxo-3H-benzo[f]chromen-2-yl)methanone. The results of antimicrobial screening demonstrate that (2-furyl)(3-thioxo-3H-benzo[f]chromen-2-yl)methanone, phenyl(3-oxo-3H-benzo[f]chromen-2-yl)methanone, and (4-chlorophenyl)(3-oxo-3H-benzo[f]chromen-2-yl)methanone are promising as antimicrobial drugs.