1-(4-chlorophenyl)-2-(4-methoxyphenoxy)ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-chlorophenyl)-2-(4-methoxyphenoxy)ethanone
• 英文别名: 1-(4-chlorophenyl)-2-(4-methoxyphenoxy)ethan-1-one；1-(4-chlorophenyl)-2-(4-methoxyphenoxy)ethyl-1-one；(4-methoxyphenoxymethyl)-(4-chlorophenyl)-ketone
• 化学式: C₁₅H₁₃ClO₃
• mdl: MFCD03361477
• 分子量: 276.719
• InChiKey: COELUAJXEMZWBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-2-(4-methoxyphenoxy)ethanone 在 氢溴酸 、 乙酸酐 作用下， 以 甲苯 为溶剂， 反应 10.0h， 生成 3-(4-chlorophenyl)benzofuran-5-ol
  参考文献：
  名称：

  Discovery of 4,6-bis(benzyloxy)-3-phenylbenzofuran as a novel Pin1 inhibitor to suppress hepatocellular carcinoma via upregulating microRNA biogenesis

  摘要：

  Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (Pin1) participates in diverse cancer-associated signaling pathways, playing an oncogenic role in multiple human cancers, including hepatocellular carcinoma (HCC). Our recent works clarify that Pin1 modulates miRNAs biogenesis by interacting with ERK-phosphorylated exportin-5 (XPO5) and changing XPO5 conformation, giving a potential target for HCC treatment. Herein, we discover 4,6-bis(benzyloxy)-3-phenylbenzofuran (TAB29) as a novel Pin1 inhibitor that targets Pin1 PPIase domain. TAB29 potently inhibits Pin1 activity with the IC50 value of 874 nM and displays an excellent selectivity toward Pin1 in vitro. Cell-based biological evaluation reveals that TAB29 significantly suppresses cell proliferation of HCC cells through restoring the nucleus-to-cytoplasm export of XPO5 and upregulating mature miRNAs expression. Collectively, this work provides a promising small molecule lead compound for Pin1 inhibition, highlighting the therapeutic potential of miRNA-based treatment for human cancers.

  DOI：

  10.1016/j.bmc.2019.04.028
• 作为产物：
  描述：

  4-甲氧基苯酚 、 2'-溴-4-氯苯乙酮 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 1-(4-chlorophenyl)-2-(4-methoxyphenoxy)ethanone
  参考文献：
  名称：

  使用木质素模型和 2-氨基苄醇环化合成 3-氧代喹啉

  摘要：

  苯氧基苯乙酮通常用作化学转化的 β-O-4' 木质素模型。在此，证明了 2-氨基苄醇和苯氧基苯乙酮之间的铱催化脱氢环化可制备有价值的 3-氧代喹啉衍生物，这些衍生物很难使用以前的方法制备。这种操作简单的反应可以耐受多种底物，并能够成功地进行克级制备。

  DOI：

  10.1021/acs.joc.2c02455

文献信息

• 一种C-3位氧取代的咪唑杂环化合物的制备 方法
  申请人：杭州师范大学

  公开号：CN106946875B

  公开（公告）日：2019-05-17

  本发明涉及一种如式(1)或式(2)或式(3)所示的化合物的合成方法，具体为将邻氨基氮杂环化合物、2‑氧基苯乙酮衍生物、过渡金属盐催化剂置于有机溶剂中，于含氧氛围下加热反应，反应结束后，反应液经后处理得到式(1)或式(2)或式(3)所示的化合物；所述2‑氨基杂环化合物为2‑氨基吡啶类化合物或2‑氨基苯并[d]噻唑类化合物或1‑氨基异喹啉。本发明合成方法，操作简单，反应条件温和，副产物仅为水，反应收率高，最高达到了97％，合成的两种杂环类化合物都具有药理性，可作为药物的重要前体。
• Preparation of leukotriene B4 inhibitory active 2- and 3-(2-aminothiazol-4-yl)benzo[b]furan derivatives and their growth inhibitory activity on human pancreatic cancer cells
  作者：Mari Kuramoto、Yoko Sakata、Kumi Terai、Ikuo Kawasaki、Jun-ichi Kunitomo、Takahiro Ohishi、Takehiko Yokomizo、Seiichi Takeda、Shuichi Tanaka、Yoshitaka Ohishi

  DOI：10.1039/b803313g

  日期：——

  A series of 2-(2-aminothiazol-4-yl)benzo[b]furan and 3-(2-aminothiazol-4-yl)benzo[b]furan derivatives were prepared, and their leukotriene B4 inhibitory activity and growth inhibitory activity in cancer cell lines were evaluated. Several compounds showed strong inhibition of calcium mobilization in CHO cells overexpressing human BLT1 and BLT2 receptors and growth inhibition to human pancreatic cancer cells MIA PaCa-2. 3-(4-Chlorophenyl)-2-[5-formyl-2-[(dimethylamino)methyleneamino]thiazol-4-yl]-5-methoxybenzo[b]furan 8b showed the most potent and selective inhibition for the human BLT2receptor, and its IC50 value was smaller than that of the selected positive control compound, ZK-158252. 3-(4-Chlorophenyl)-2-[2-[(dimethylamino)methyleneamino]-5-(2-hydroxyethyliminomethyl)thiazol-4-yl]-5-methoxybenzo[b]furan 9a displayed growth inhibitory activity towards MIA PaCa-2.

  一系列2-(2-氨基噻唑-4-基)苯并[b]呋喃和3-(2-氨基噻唑-4-基)苯并[b]呋喃衍生物被合成，并评估了它们对白三烯B4的抑制活性及对癌细胞系的生长抑制活性。几个化合物在过表达人类BLT1和BLT2受体的CHO细胞中显示出对钙动员的强抑制作用，并对人类胰腺癌细胞MIA PaCa-2表现出生长抑制。3-(4-氯苯基)-2-[5-甲酰基-2-[(二甲氨基)亚甲基氨基]噻唑-4-基]-5-甲氧基苯并[b]呋喃8b对人类BLT2受体显示出最强且选择性的抑制，其IC50值小于选定的阳性对照化合物ZK-158252。3-(4-氯苯基)-2-[2-[(二甲氨基)亚甲基氨基]-5-(2-羟基乙基亚氨基甲基)噻唑-4-基]-5-甲氧基苯并[b]呋喃9a对MIA PaCa-2显示出生长抑制活性。
• Natural tanshinone-like heterocyclic-fused ortho-quinones from regioselective Diels–Alder reaction: Synthesis and cytotoxicity evaluation
  作者：Yu-Dong Shen、Yuan-Xin Tian、Xian-Zhang Bu、Lian-Quan Gu

  DOI：10.1016/j.ejmech.2009.04.016

  日期：2009.10

  oxoheterocyclic-fused ortho-quinone derivatives were synthesized from readily available benzofuranol and N-substituted dienes via IBX oxidation–cycloaddition–aromatization procedure. The regiospecific Diels–Alder cycloaddition reactions of N-dienes were achieved efficiently with a variety of dienophiles. It is found that the amide moiety in the molecular could be preserved or eliminated by control of the aromatization

  通过IBX氧化-环加成-芳构化方法，从容易获得的苯并呋喃醇和N-取代的二烯中合成了一系列新的天然丹参酮样氧杂环稠合的邻醌衍生物。N-二烯的区域特异性Diels–Alder环加成反应可通过多种亲双烯体有效实现。发现通过控制芳构化条件可以保留或消除分子中的酰胺部分。选定的氧杂环稠合的邻醌以及几种硫杂环稠合的邻醌我们评估了之前获得的对苯二酚对不同癌细胞系的细胞毒性，并讨论了结构-活性关系（SAR）。
• Preparation of 3-(4-chlorophenyl)-2-(2-aminothiazol-4-yl)-5-methoxybenzo[b]furan derivatives and their leukotriene B4 inhibitory activity
  作者：Yoko Sakata、Mari Kuramoto、Kumiko Ando、Mami Yamaguchi、Ikuo Kawasaki、Jun-ichi Kunitomo、Takehiko Yokomizo、Yoshitaka Ohishi

  DOI：10.1039/b711391a

  日期：——

  A series of 3-(4-chlorophenyl)-2-(2-aminothiazol-4-yl)benzo[b]furan derivatives 6–10 were prepared and their leukotriene B4 inhibitory activity was evaluated. We found that several compounds showed strong inhibition of calcium mobilization in CHO cells overexpressing human BLT1 and BLT2 receptors. Among them, 3-(4-chlorophenyl)-2-[5-formyl-2-[(dimethylamino)methyleneamino]thiazol-4-yl]-5-methoxybenzo[b]furan9b showed the most potent and selective inhibition for the human BLT2 receptor, and its IC50 value was smaller than that of the selected positive control compound, ZK-158252.

  我们制备了一系列 3-(4-氯苯基)-2-(2-氨基噻唑-4-基)苯并[b]呋喃衍生物 6-10 并评估了它们的白三烯 B4 抑制活性。我们发现，在过表达人 BLT1 和 BLT2 受体的 CHO 细胞中，有几种化合物对钙动员有很强的抑制作用。其中，3-(4-氯苯基)-2-[5-甲酰基-2-[(二甲基氨基)亚甲基氨基]噻唑-4-基]-5-甲氧基苯并[b]呋喃9b对人BLT2受体的抑制作用最强，且选择性最强，其IC50值小于所选的阳性对照化合物ZK-158252。
• Ketones
  申请人：Barton John Peter

  公开号：US20050272036A1

  公开（公告）日：2005-12-08

  Compounds of formula (I): wherein variable groups are as defined within; for use in the inhibition of 11βHSD1 are described.

  描述了式(I)的化合物：其中变量基团如定义的那样；用于抑制11βHSD1。