1-(4-nitrophenyl)pentane-1,4-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-nitrophenyl)pentane-1,4-dione
• 化学式: C₁₁H₁₁NO₄
• 分子量: 221.213
• InChiKey: VRRFPGFRSOBAGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-nitrophenyl)pentane-1,4-dione 、 4-(2-苯并噻唑基)苯胺 在 potassium hydrogensulfate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以84%的产率得到2-(4-(2-methyl-5-(4-nitrophenyl)-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole
  参考文献：
  名称：

  Synthesis and study of benzothiazole conjugates in the control of cell proliferation by modulating Ras/MEK/ERK-dependent pathway in MCF-7 cells

  摘要：

  By applying a methodology, a series of benzothiazole-pyrrole based conjugates (4a-r) were synthesized and evaluated for their antiproliferative activity. Compounds such as 4a, 4c, 4e, 4g-j, 4m, 4n, 4o and 4r exhibited significant cytotoxic effect in the MCF-7 cell line. Cell cycle effects were examined for these conjugates at 2 mu M as well as 4 mu M concentrations and FACS analysis show an increase of G2/M phase cells with concomitant decrease of G1 phase cells thereby indicating G2/M cell cycle arrest by them. Interestingly 4o and 4r are effective in causing apoptosis in MCF-7 cells. Moreover, 4o showed down regulation of oncogenic expression of Ras and its downstream effector molecules such as MEK1, ERK1/2, p38 MAPK and VEGF. The apoptotic aspect of this conjugate is further evidenced by increased expression of caspase-9 in MCF-7 cells. Hence these small molecules have the potential to control both the cell proliferation as well as the invasion process in the highly malignant breast cancers. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.068
• 作为产物：
  描述：

  对硝基苯乙酮 在 溴苯 、 silver fluoride 、 三乙胺 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 36.17h， 生成 1-(4-nitrophenyl)pentane-1,4-dione
  参考文献：
  名称：

  硅基烯醇醚的银催化控制分子间交叉偶联：可扩展地获得 1,4-二酮

  摘要：

  公开了一种用于甲硅烷基烯醇化物的银催化受控分子间交叉偶联的方案。该协议显示出良好的官能团耐受性，并允许有效制备一系列合成有用的 1,4-二酮。初步的机理研究表明，该反应通过一个单电子过程进行，其中涉及自由基物质，其中 PhBr 充当氧化剂。

  DOI：

  10.1021/acs.orglett.2c01477

文献信息

• Synthesis of 1,4-Dicarbonyl Compounds from Silyl Enol Ethers and Bromocarbonyls, Catalyzed by an Organic Dye under Visible-Light Irradiation with Perfect Selectivity for the Halide Moiety over the Carbonyl Group
  作者：Naoto Esumi、Kensuke Suzuki、Yoshihiro Nishimoto、Makoto Yasuda

  DOI：10.1021/acs.orglett.6b02869

  日期：2016.11.4

  We report the visible-light-induced radical coupling reaction of silyl enol ethers with α-bromocarbonyl compounds to give 1,4-dicarbonyls. The reaction was effectively accelerated using an inexpensive organic dye (eosin Y) as a photoredox catalyst. 1,4-Dicarbonyl compounds alone were afforded, without the generation of carbonyl adducts of the α-halocarbonyls, which are usually generated in the presence

  我们报道了可见光诱导的甲硅烷基烯醇醚与α-溴羰基化合物的自由基偶联反应，得到1,4-二羰基。使用廉价的有机染料（曙红Y）作为光氧化还原催化剂可有效地促进反应。仅提供1，4-二羰基化合物，而没有生成α-卤代羰基的羰基加合物，α-卤代羰基的羰基加合物通常是在氟阴离子或路易斯酸的存在下生成的。将多种甲硅烷基烯醇醚，α-溴代酮，α-溴代酸酯和α-溴代酰胺应用于该系统以产生偶联化合物。
• Highly selective synthesis of 1-phenylpentane-1, 4-diones, and (<i>E</i>)-5-hydroxy-5-phenylpent-3-en-2-ones catalyzed by organophosphorus compounds
  作者：Qing Zhang、Yan-Fei Qiao、Min Huang、Hong-Dong Liang、Ru-Jin Zhou

  DOI：10.1002/hc.20568

  日期：——

  1-Phenylpentane-1, 4-diones, and (E)-5-hydroxy-5-phenylpent-3-en-2-ones were synthesized via organophosphine-catalyzed addition reaction of but-3-en-2-one with aldehydes. The features of the present protocols include high selectivity, operational simplicity, atom economy, and mild reaction conditions without transition metals. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 20:425–430, 2009; Published

  1-Phenylpentane-1, 4-diones 和 (E)-5-hydroxy-5-phenylpent-3-en-2-ones 是通过 but-3-en-2-one 与醛的有机膦催化加成反应合成的. 本协议的特点包括高选择性、操作简单、原子经济性和无过渡金属的温和反应条件。© 2010 Wiley Periodicals, Inc. 杂原子化学 20:425–430, 2009; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20568
• Synthesis of furans, pyrroles and pyridazines by a ruthenium-catalysed isomerisation of alkynediols and in situ cyclisation
  作者：Simon J. Pridmore、Paul A. Slatford、James E. Taylor、Michael K. Whittlesey、Jonathan M.J. Williams

  DOI：10.1016/j.tet.2009.06.108

  日期：2009.10

  Alkyne-1,4-diols are readily available substrates which are isomerised to 1,4-diketones using Ru(PPh3)(3)(CO)H-2/xantphos as a catalyst. In situ cyclisation into furans, pyrroles and pyridazines has been achieved under suitable conditions. (C) 2009 Elsevier Ltd. All rights reserved.
• 2,5-Disubstituted furans from 1,4-alkynediols
  作者：Simon J. Pridmore、Paul A. Slatford、Jonathan M.J. Williams

  DOI：10.1016/j.tetlet.2007.05.069

  日期：2007.7

  1-4-Alkynediols serve as readily available starting materials for isomerisation to 1,4-diketones, which can be converted in situ into the corresponding furans by acid-catalysed dehydration. A range of 2,5-disubstituted furans was prepared using the ruthenium-based catalyst Ru(PPh3)(3)(CO)H-2 with Xantphos at 1 mol % loading. (C) 2007 Published by Elsevier Ltd.
• Synthesis and study of benzothiazole conjugates in the control of cell proliferation by modulating Ras/MEK/ERK-dependent pathway in MCF-7 cells
  作者：Ahmed Kamal、Shaikh Faazil、M. Janaki Ramaiah、Md. Ashraf、M. Balakrishna、S.N.C.V.L. Pushpavalli、Nibedita Patel、Manika Pal-Bhadra

  DOI：10.1016/j.bmcl.2013.07.068

  日期：2013.10

  By applying a methodology, a series of benzothiazole-pyrrole based conjugates (4a-r) were synthesized and evaluated for their antiproliferative activity. Compounds such as 4a, 4c, 4e, 4g-j, 4m, 4n, 4o and 4r exhibited significant cytotoxic effect in the MCF-7 cell line. Cell cycle effects were examined for these conjugates at 2 mu M as well as 4 mu M concentrations and FACS analysis show an increase of G2/M phase cells with concomitant decrease of G1 phase cells thereby indicating G2/M cell cycle arrest by them. Interestingly 4o and 4r are effective in causing apoptosis in MCF-7 cells. Moreover, 4o showed down regulation of oncogenic expression of Ras and its downstream effector molecules such as MEK1, ERK1/2, p38 MAPK and VEGF. The apoptotic aspect of this conjugate is further evidenced by increased expression of caspase-9 in MCF-7 cells. Hence these small molecules have the potential to control both the cell proliferation as well as the invasion process in the highly malignant breast cancers. (C) 2013 Elsevier Ltd. All rights reserved.