2-(4'-chlorobenzoyl)-3H-benzo[f]chromen-3-one | 74556-37-9

• 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: 2-(4'-chlorobenzoyl)-3H-benzo[f]chromen-3-one
• 英文别名: 2-(4-chlorobenzoyl)-3H-benzo[f]chromen-3-one；3-(4-chlorobenzoyl)-2H-benzo[f]chromen-2-one；2-(4-chloro-benzoyl)-benzo[f]chromen-3-one；2-(4-Chlorobenzoyl)-3H-naphtho[2,1-b]pyran-3-one；2-(4-chlorobenzoyl)benzo[f]chromen-3-one
• CAS: 74556-37-9
• 化学式: C₂₀H₁₁ClO₃
• 分子量: 334.759
• InChiKey: WGCXSENKCBICRU-UHFFFAOYSA-N

物化性质

• 熔点：
  >200 °C(Solv: ethanol (64-17-5))
• 沸点：
  569.5±50.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4'-chlorobenzoyl)-3H-benzo[f]chromen-3-one 在 sodium tetrahydroborate 作用下， 以 吡啶 为溶剂， 反应 2.0h， 以90%的产率得到2-(4'-chlorobenzoyl)-1,2-dihydro-benzo[f]chromen-3-one
  参考文献：
  名称：

  Novel Cambinol Analogs as Sirtuin Inhibitors: Synthesis, Biological Evaluation, and Rationalization of Activity

  摘要：

  The tenovins and cambinol are two classes of sirtuin inhibitor that exhibit antitumor activity in preclinical models. This report describes modifications to the core structure of cambinol, in particular by incorporation of substitutents at the N1-position, which lead to increased potency and modified selectivity. These improvements have been rationalized using molecular modeling techniques. The expected functional selectivity in cells was also observed for both a SIRT1 and a SIRT2 selective analog.

  DOI：

  10.1021/jm8014298
• 作为产物：
  描述：

  2-羟基-1-萘甲醛 、 (4-氯苯甲酰基)乙酸乙酯 在 哌啶 作用下， 以 乙醇 为溶剂， 以74%的产率得到2-(4'-chlorobenzoyl)-3H-benzo[f]chromen-3-one
  参考文献：
  名称：

  Novel Cambinol Analogs as Sirtuin Inhibitors: Synthesis, Biological Evaluation, and Rationalization of Activity

  摘要：

  The tenovins and cambinol are two classes of sirtuin inhibitor that exhibit antitumor activity in preclinical models. This report describes modifications to the core structure of cambinol, in particular by incorporation of substitutents at the N1-position, which lead to increased potency and modified selectivity. These improvements have been rationalized using molecular modeling techniques. The expected functional selectivity in cells was also observed for both a SIRT1 and a SIRT2 selective analog.

  DOI：

  10.1021/jm8014298

文献信息

• Facile Synthesis of 3-Thioxo-3H-benzo[f]chromen-2-yl methanone and 3H-Benzo[f]chromene-3-one Under Solvent Free Condition
  作者：Okram Mukherjee Singh、Nepram Sushuma Devi、Laishram Ronibala Devi、Ki-Bum Lim、Yong-Jin Yoon、Sang-Geyong Lee

  DOI：10.5012/bkcs.2011.32.1.175

  日期：2011.1.20

  reaction for the synthesis of coumarin involves the condensation of phenols with β-ketonic esters in the presence of variety of acidic condensing agents such as sul-furic acid, hydrochloric acid and phosphoric acid, phosphorous pentoxide, trifluoroacetic acid and Lewis acids such as ZnCl

  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。
• Condensation of α-Aroylketene Dithioacetals and 2-Hydroxyarylaldehydes Results in Facile Synthesis of a Combinatorial Library of 3-Aroylcoumarins
  作者：H. Surya Prakash Rao、S. Sivakumar

  DOI：10.1021/jo061372e

  日期：2006.11.1

  facile, convenient, efficient, and high yielding synthesis of a combinatorial library of 3-aroylcoumarins has been developed by the condensation of easily available α-aroylketene dithioacetals (AKDTAs) and 2-hydroxybenzaldehydes (salicylaldehydes)/2-hydroxy-1-naphthaldehyde in the presence of catalytic amount of piperidine in THF reflux. The condensation of ferrocene derived α-aroylketene dithioacetal

  通过将易得的α-芳基烯酮二硫缩醛（AKDTAs）与2-羟基苯甲醛（水杨醛）/ 2-羟基-1-萘醛缩合，已开发出一种简便，便捷，高效且高收率的3-aroyl香豆素组合文库的合成方法。在催化量的哌啶存在下于四氢呋喃回流中。二茂铁衍生的α-芳基烯酮二硫缩醛与2-羟基苯甲醛的香豆素缩合，安装在二茂铁平台上。
• Simplification of the tetracyclic SIRT1-selective inhibitor MC2141: Coumarin- and pyrimidine-based SIRT1/2 inhibitors with different selectivity profile
  作者：Dante Rotili、Vincenzo Carafa、Domenico Tarantino、Giorgia Botta、Angela Nebbioso、Lucia Altucci、Antonello Mai

  DOI：10.1016/j.bmc.2011.01.025

  日期：2011.6

  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.
• 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.
• Andreichikov, Yu. S.; Tokmakova, T. N., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 4, p. 796 - 800
  作者：Andreichikov, Yu. S.、Tokmakova, T. N.

  DOI：——

  日期：——