4-(3-hydroxy-4-methoxyphenyl)-3-butene-2-one | 77334-11-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-(3-hydroxy-4-methoxyphenyl)-3-butene-2-one
• 英文别名: 4-(3-hydroxy-4-methoxyphenyl)-but-3-en-2-one；4-(3-Hydroxy-4-methoxyphenyl)-3-buten-2-one；4-(4-methoxy-3-hydroxyphenyl)-3-buten-2-one；4-(3-hydroxy-4-methoxyphenyl)but-3-en-2-one
• CAS: 77334-11-3
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: BWJQTZKTOVCXOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3-hydroxy-4-methoxyphenyl)-3-butene-2-one 在 silica gel supported copper(II) bromide 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 生成 bromomethyl 3-hydroxy-4-methoxystyryl ketone
  参考文献：
  名称：

  4-Amino-2-arylamino-5-indoloyl/cinnamoythiazoles, analogs of topsentin-class of marine alkaloids, induce apoptosis in HeLa cells

  摘要：

  Marine organisms provide several biologically active compounds that include alkaloids with high cytotoxic activity but only a few of them have so far reached clinical stage, due partly to their limited supply and complex structural features. In an attempt to develop novel anticancer compounds, we have now synthesized diaminoindoloylthiazoles (4a-c; DIT1-3) and diaminocinnamoylthiazoles (5a,b; DCT1-2) as analogs based on a topsentin scaffold and investigated the cytotoxic and apoptotic activities of these compounds in HeLa cells. The results suggest that diaminoindoloylthiazoles (DIT1-3) inhibit cell growth and among these, DIT3 is the most cytotoxic against HeLa cells (IC50 1 mu M). The diaminocinnamoylthiazoles DCT1 and DCT2, which can be viewed as curcumin-diaminothiazole hybrids, also inhibited cell growth but at relatively higher concentrations with IC50 values of 60 and 30 mu M, respectively. These compounds induced apoptosis through the intrinsic pathway by reducing the mitochondrial membrane potential and activating caspases, 9 and 3, but not caspase 8. Among the marine alkaloid analogs tested in this study, DIT1-3 are very effective in inducing apoptosis of HeLa cells followed by DCT2 and DCT1. The treated cells were arrested in G(2)/M phase followed by accumulation of the cells in the Sub G(0) phase. The curcumin-diaminothiazole hybrid DCT1 had the maximum effect in downregulating TNF-induced NF-kappa B activation among the compounds tested in this study. Thus, we demonstrate that diaminoindoloylthiazoles and diaminocinnamoylthiazoles induce apoptosis, regulate cell cycle and NF-kappa B signaling and thus show promising anticancer effects that warrant further investigation. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.032
• 作为产物：
  描述：

  异香兰素 、 丙酮 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 4-(3-hydroxy-4-methoxyphenyl)-3-butene-2-one
  参考文献：
  名称：

  新型5-Methyl-7-Phenyl-3H-Thiazolo[4,5-b]Pyridin-2-Ones的合成及生物活性评价

  摘要：

  设计、合成了一系列 5-methyl-7-phenyl-3 H - thiazolo[4,5 - b ]pyridin-2-ones，并通过光谱数据对其进行了表征。筛选了目标化合物对一些病原菌和真菌的抗菌活性，其中大部分表现出中等活性，尤其是化合物3g，对铜绿假单胞菌和大肠杆菌显示出有效的抑制作用，MIC值为0.21 μM。活性噻唑并吡啶衍生物3c、3f和3g使用 MTT 测定筛选了它们对 HaCat、Balb/c 3T3 细胞的细胞毒性作用，结果显示出有希望的结果。化合物3c、3f和3g 的计算机模拟评估还揭示了合适的类药物参数和 ADME 特性。最活跃的化合物3g的结合相互作用是通过分子对接对 MurD 和 DNA 促旋酶进行的，与参考药物环丙沙星相比具有结合能和抑制常数。测试的噻唑并[4,5- b ]吡啶为进一步开发新的合成抗菌剂提供了令人兴奋的背景。

  DOI：

  10.3390/scipharm89040052

文献信息

• Catalytic asymmetric synthesis of chiral phenols in ethanol with recyclable rhodium catalyst
  作者：Jian Yao、Na Liu、Long Yin、Junhao Xing、Tao Lu、Xiaowei Dou

  DOI：10.1039/c9gc02420d

  日期：——

  A general method to access diverse chiral phenols by rhodium-catalyzed asymmetric conjugate arylation using hydroxylated arylboronic acids in ethanol was developed. Recycling of the rhodium catalyst by flash chromatography on silica gel was feasible in this system. The synthetic utility of the strategy was demonstrated by efficient synthesis of chiral drug tolterodine.

  建立了在乙醇中使用羟基化的芳基硼酸通过铑催化的不对称共轭芳基化反应获得各种手性酚的通用方法。在该系统中通过快速色谱法在硅胶上回收铑催化剂是可行的。通过手性药物托特罗定的有效合成证明了该策略的合成效用。
• Rapid access to α-carbolines via a one-pot tandem reaction of α,β-unsaturated ketones with 2-nitrophenylacetonitrile and the anti-proliferative activities of the products
  作者：Xiaofei Zhang、Qian He、Haoyue Xiang、Shanshan Song、Zehong Miao、Chunhao Yang

  DOI：10.1039/c3ob41921e

  日期：——

  An effective and convenient method has been developed for the preparation of 2 or 2,4-substituted α-carbolines via a one-pot tandem reaction of α,β-unsaturated ketones with 2-nitrophenylacetonitrile in the presence of zinc dust, acetic acid and triethylamine. This protocol presents a simple, rapid and pot/step economical strategy for preparing biologically interesting α-carbolines with moderate anti-tumor activities.

  在锌粉、乙酸和三乙胺存在下，通过δ,δ²-不饱和酮与 2-硝基苯乙腈的单锅串联反应，开发出了一种有效而方便的方法来制备 2 或 2,4 取代的δ-羰基化合物。该方案提供了一种简单、快速、经济的锅/步反应策略，可用于制备具有适度抗肿瘤活性的具有生物学意义的δ-羰基化合物。
• Synthesis and characterization of 2-(4-aryl-3-cyano-6-methylpyridin-2(1H)-ylidene)malononitriles
  作者：Ivan N. Bardasov、Anastasiya U. Alekseeva、Sergey S. Chunikhin、Maria A. Shishlikova、Oleg V. Ershov

  DOI：10.1016/j.tetlet.2019.03.054

  日期：2019.4

  The synthesis of pyridine derivatives containing a buta-1,3-diene-1,1,3-tricarbonitrile fragment via the base-promoted reaction of benzalacetones and malononitrile dimer with subsequent oxidation is described. The influence of the substituents on the spectral-luminescent and electrochemical properties was also investigated.

  含有丁-1,3-二烯-1,1,3- tricarbonitrile片段吡啶衍生物的合成通过benzalacetones并与随后的氧化丙二腈二聚物的碱促进的反应进行说明。还研究了取代基对光谱发光和电化学性质的影响。
• Discovery of diarylheptanoids that activate α7 nAchR-JAK2-STAT3 signaling in macrophages with anti-inflammatory activity in vitro and in vivo
  作者：Yuan Lin、Kanjana Wongkrajang、Xiaofei Shen、Ping Wang、Zongyuan Zhou、Thipphawan Chuprajob、Nilubon Sornkaew、Na Yang、Lijuan Yang、Xiaoxia Lu、Ratchanaporn Chokchaisiri、Apichart Suksamrarn、Guolin Zhang、Fei Wang

  DOI：10.1016/j.bmc.2022.116811

  日期：2022.7

  anti-inflammatory properties. However, the possible mechanism of diarylheptanoids has rarely been investigated. In this study, we isolated and synthesized 49 diarylheptanoids and analogues and evaluated their anti-inflammatory activities. Among them, compounds 28 and 40 markedly blocked lipopolysaccharide (LPS)-induced production of nitric oxide (NO), interleukin-1β (IL-1β) and interleukin-6 in murine RAW264.7 cells

  脓毒症等急性炎症性疾病是危及生命的疾病。调节 α7 烟碱型乙酰胆碱受体 (α7 nAchR) 介导的信号传导可能是治疗败血症的有希望的策略。早就发现二芳基庚烷具有抗炎特性。然而，很少研究二芳基庚烷的可能机制。在这项研究中，我们分离并合成了 49 种二芳基庚烷和类似物，并评估了它们的抗炎活性。其中，化合物28和40显着阻断了脂多糖 (LPS) 诱导的小鼠 RAW264.7 细胞中一氧化氮 (NO)、白细胞介素 1β (IL-1β) 和白细胞介素 6 的产生。此外，化合物28和40还有效减弱 LPS 诱导的脓毒症、急性肺损伤和体内细胞因子释放。从机制上讲，化合物28和40显着诱导 janus 激酶 2/信号转导和转录激活因子 3 (JAK2/STAT3) 信号传导和核因子-κB (NF-κB) 通路的抑制。此外，阻断 α7 nAchR 可以有效地消除化合物28和40介导的 JAK2-STAT3
• Synthesis and Biological Activity Evaluation of Novel 5-Methyl-7-phenyl-3H-thiazolo[4,5-b]pyridin-2-ones
  作者：Andrii Lozynskyi、Yulian Konechnyi、Julia Senkiv、Ihor Yushyn、Dmytro Khyluk、Olexandr Karpenko、Yulia Shepeta、Roman Lesyk

  DOI：10.3390/scipharm89040052

  日期：——

  coli with MIC value of 0.21 μM. The active thiazolopyridine derivatives 3c, 3f, and 3g were screened for their cytotoxicity effects on HaCat, Balb/c 3T3 cells using MTT assay, which revealed promising results. In silico assessment for compounds 3c, 3f, and 3g also revealed suitable drug-like parameters and ADME properties. The binding interactions of the most active compound 3g were performed through

  设计、合成了一系列 5-methyl-7-phenyl-3 H - thiazolo[4,5 - b ]pyridin-2-ones，并通过光谱数据对其进行了表征。筛选了目标化合物对一些病原菌和真菌的抗菌活性，其中大部分表现出中等活性，尤其是化合物3g，对铜绿假单胞菌和大肠杆菌显示出有效的抑制作用，MIC值为0.21 μM。活性噻唑并吡啶衍生物3c、3f和3g使用 MTT 测定筛选了它们对 HaCat、Balb/c 3T3 细胞的细胞毒性作用，结果显示出有希望的结果。化合物3c、3f和3g 的计算机模拟评估还揭示了合适的类药物参数和 ADME 特性。最活跃的化合物3g的结合相互作用是通过分子对接对 MurD 和 DNA 促旋酶进行的，与参考药物环丙沙星相比具有结合能和抑制常数。测试的噻唑并[4,5- b ]吡啶为进一步开发新的合成抗菌剂提供了令人兴奋的背景。