(1E,4E)-1,5-di(pyridin-2-yl)penta-1,4-dien-3-one | 26251-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (1E,4E)-1,5-di(pyridin-2-yl)penta-1,4-dien-3-one
• 英文别名: (1E,4E)-1,5-bis(2-pyridyl)penta-1,4-dien-3-one；(1E,4E)-1,5-dipyridin-2-ylpenta-1,4-dien-3-one
• CAS: 26251-49-0
• 化学式: C₁₅H₁₂N₂O
• 分子量: 236.273
• InChiKey: FIXSLRFECSIFLZ-FIFLTTCUSA-N

物化性质

• 熔点：
  155-158 °C
• 沸点：
  429.3±40.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吡啶-2-甲醛 在 sodium hydroxide 、 丙酮 作用下， 生成 (1E,4E)-1,5-di(pyridin-2-yl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Profft et al., Journal fur praktische Chemie (Leipzig 1954), 1955, vol. <4>2, p. 147,159

  摘要：

  DOI：

文献信息

• COMPOUNDS USEFUL AGAINST KINETOPLASTIDEAE PARASITES
  申请人：Davioud-Charvet Elisabeth

  公开号：US20120214996A1

  公开（公告）日：2012-08-23

  Dibenzylidene and heterobenzylideneacetone derivatives, related 4-piperidones, related 4-thiopyranones and the corresponding sulfinyl- and sulfonyl-analogues for their use for prophylaxis or treatment of trypanosomiasis and leishmaniasis.

  二苄基亚烷和杂二苄基亚烷乙酮衍生物，相关的4-哌啶酮，相关的4-噻opyranones以及相应的亚磺酰基和磺酰基类似物，用于预防或治疗锥虫病和利什曼病。
• Synthesis of the pyridinyl analogues of dibenzylideneacetone (pyr-dba) via an improved Claisen–Schmidt condensation, displaying diverse biological activities as curcumin analogues
  作者：Bin Cao、Yong Wang、Kan Ding、Nouri Neamati、Ya-Qiu Long

  DOI：10.1039/c1ob06773g

  日期：——

  An efficient and easy procedure to synthesize the pyridinyl analogues of dibenzylideneacetone (pyr-dba) was developed by the condensation of substituted nicotinaldehyde and acetone in the presence of K2CO3 in toluene-EtOH-H2O solvent system. Structurally diverse pyr-dba, including quinolinyl dba, can be prepared conveniently in moderate to excellent yields under mild conditions with this method. The resulting pyr-dba functioned as the enone analogs of curcumin and efficiently inhibited the activation of NF-κB and the growth of colorectal carcinoma HCT116 p53+/+ cells as well as the HIV-1 IN-LEDGF/p75 interaction.

  在甲苯-EtOH-H2O 溶剂体系中，在 K2CO3 的存在下，通过取代的烟醛和丙酮的缩合，开发了一种合成二亚苄基丙酮（pyr-dba）吡啶类似物的高效简便的方法。用这种方法可以在温和的条件下方便地制备出结构多样的吡咯-二巴（包括喹啉基二巴），收率从中等到极好。所制备的 pyr-dba 可作为姜黄素的烯酮类似物，有效抑制 NF-κB 的活化、结直肠癌 HCT116 p53+/+ 细胞的生长以及 HIV-1 IN-LEDGF/p75 的相互作用。
• Chemoselective Synthesis and Anti-Kinetoplastidal Properties of 2,6-Diaryl-4H-tetrahydro-thiopyran-4-one S-Oxides: Their Interplay in a Cascade of Redox Reactions from Diarylideneacetones
  作者：Thibault Gendron、Don Antoine Lanfranchi、Nicole I. Wenzel、Hripsimée Kessedjian、Beate Jannack、Louis Maes、Sandrine Cojean、Thomas J. J. Müller、Philippe M. Loiseau、Elisabeth Davioud-Charvet

  DOI：10.3390/molecules29071620

  日期：——

  methodologies were developed and generalized from diarylideneacetones and 2,6-diaryl-4H-tetrahydro-thiopyran-4-ones to allow the introduction of a wide substitution profile and to prepare the related S-oxides. The in vitro biological activity and selectivity of diarylideneacetones, 2,6-diaryl-4H-tetrahydro-thiopyran-4-ones, and their S-sulfoxide and sulfone metabolites were evaluated against Trypanosoma

  2,6-二芳基-4H-四氢-噻喃-4-酮和相应的亚砜和砜衍生物被设计为通过前药作用降低其母体抗动铂二亚芳基丙酮的主要毒性。从二亚芳基丙酮和2,6-二芳基-4H-四氢-噻喃-4-酮中开发并推广了新的非对映选择性方法，以允许引入广泛的取代谱并制备相关的S-氧化物。评估了二亚芳基丙酮、2,6-二芳基-4H-四氢-噻喃-4-酮及其 S-亚砜和砜代谢物对布氏锥虫、克氏锥虫和各种利什曼原虫的体外生物活性和选择性。及其针对人成纤维细胞 hMRC-5 的细胞毒性。数据显示，迈克尔受体位点暂时被掩盖的硫化物、亚砜和砜对哺乳动物细胞的毒性较小，而对布氏锥虫、克氏锥虫、婴儿乳杆菌和锥虫的抗锥虫效力得以维持。 L. donovani，从而证实了前药策略的有效性。其作用机制被认为是由于二亚芳基丙酮参与涉及锥硫酮系统的级联氧化还原反应。迈克尔将二硫醇加成到双键上，形成伸长的聚合物，后者在 S-氧化后，随后进行顺式消除
• 10.1039/d4dt00985a
  作者：Chandra, Anushri、Basu, Pousali、Raha, Shreya、Dhibar, Papu、Bhattacharya, Samaresh

  DOI：10.1039/d4dt00985a

  日期：——

  2′-bipyridine and phen = 1,10-phenanthroline). The crystal structure of [Ru(L3)2(bpy)] has been determined and the structure of [Ru(L2)2(phen)] has been optimized by the DFT method. The electronic spectra of the four [Ru(Ln)2(dmso)2] complexes and the two derivatives ([Ru(Ln)2(L′)]; n = 3, L′ = bpy; n = 2, L′ = phen), recorded in dichloromethane solutions, show intense absorptions spanning the visible and

  [Ru(dmso) 4 Cl 2 ]与四黄原酸钾盐(RO–C( S) S- ; R = Me、Et、 i Pr 和t Bu) 配体（表示为 L n ； n = 1–4）在热甲醇中提供一组 [Ru(L n ) 2 (dmso) 2 ] 类型的混合配体配合物。四种配合物的晶体结构均已测定，表明黄原酸配体与金属中心结合形成四元螯合物，dmso通过硫配位，互为顺式。借助DFT计算评估了这些配合物的顺式异构体和其他可能的反式异构体的相对热力学稳定性，这表明顺式异构体是更稳定的异构体。 [Ru(L n ) 2 (dmso) 2 ]配合物中的配位 dmso 可以通过螯合双齿配体（表示为 L'）轻松置换，以提供 [Ru(L n ) 2 (L')] 类型的配合物，正如通过分离两个这样的复合物所证明的，即。[Ru(L 3 ) 2 (bpy)]和[Ru(L 2 ) 2 (phen)]（bpy = 2,2′-联吡啶和phen
• Design, synthesis, and evaluation of novel heteroaromatic analogs of curcumin as anti-cancer agents
  作者：Nawras Samaan、Qiu Zhong、Jayjoel Fernandez、Guanglin Chen、Ali M. Hussain、Shilong Zheng、Guangdi Wang、Qiao-Hong Chen

  DOI：10.1016/j.ejmech.2014.01.041

  日期：2014.3

  To improve the potential of curcumin to treat advanced hormone-refractory prostate cancer, three series (A-C) of heteroaromatic analogs (thirty two compounds) with different monoketone linkers have been synthesized and evaluated for cytotoxicity against two human androgen-independent prostate cancer cell lines (PC-3 and DU-145). Among them, thirty analogs are more potent than curcumin against PC-3 cells, and twenty one analogs are more cytotoxic towards DU-145 cells relative to curcumin. The most potent compounds (44, 45, 51, and 52) also showed impressive cytotoxicity against three other metastatic cancer cell lines (MDA-MB-231, HeLa, and A549), with IC50 values ranging from 50 nM to 390 nM. All four most potent analogs exhibited no apparent cytotoxicity towards the MCF-10A normal mammary epithelial cells. Taken together, selective enhancement of cell death in prostate cancer cell lines and other aggressive cancer cell lines suggests that nitrogen-containing heteroaromatic rings are promising bio-isosteres of the substituted phenyl ring in curcumin. Published by Elsevier Masson SAS.