1–(2,4-difluoro-6-hydroxyphenyl)ethan-1-one | 1356999-25-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1–(2,4-difluoro-6-hydroxyphenyl)ethan-1-one
• 英文别名: 1-(2,4-Difluoro-6-hydroxyphenyl)ethanone
• CAS: 1356999-25-1
• 化学式: C₈H₆F₂O₂
• mdl: MFCD18910100
• 分子量: 172.131
• InChiKey: SEZJLXWFVFPASJ-UHFFFAOYSA-N

物化性质

• 沸点：
  235.5±35.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H312,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  1–(2,4-difluoro-6-hydroxyphenyl)ethan-1-one 在 碘 、 barium(II) hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 13.0h， 生成 5,7-difluoro-2-(4-methoxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  类黄酮IP6K2抑制剂的合成及生物学评价

  摘要：

  摘要 肌醇多磷酸盐 (IPs) 是一组肌醇代谢物，可作为外部信号线索的第二信使。它们发挥着多种生理作用，例如胰岛素释放、端粒长度维持、细胞代谢和衰老。肌醇六磷酸激酶 2 (IP6K2) 是产生 5-二磷酸肌醇 1,2,3,4,6-五磷酸 (5-IP7) 的关键酶，它影响葡萄糖诱导的胞吐作用的早期阶段。因此，IP6Ks 的调控可能成为治疗糖尿病和肥胖等疾病的一种有前途的策略。在这项研究中，我们设计、合成和评估了基于类黄酮的化合物作为 IP6K2 的新抑制剂。构效关系研究确定化合物20s是最有效的 IP6K2 抑制剂，IC 为50值为 0.55 μM，使其比槲皮素强 5 倍，槲皮素是已报道的基于类黄酮的 IP6K2 抑制剂。化合物20s对 IP6K2 的抑制效力高于 IP6K1 和 IP6K3。化合物20s可用作命中化合物，用于 IP6K2 抑制剂的进一步结构修饰。

  DOI：

  10.1080/14756366.2023.2193866
• 作为产物：
  描述：

  3,5-二氟苯酚 在 吡啶 、 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 1–(2,4-difluoro-6-hydroxyphenyl)ethan-1-one
  参考文献：
  名称：

  卤化罗卡格酯衍生物：针对戊型肝炎病毒和新兴病毒的泛抗病毒药物

  摘要：

  据报道，属于黄黄素类天然产物的卤代罗卡格酯衍生物库的合成，其中西维甾醇是最突出的例子。确定了它们对多种致病病毒的抗病毒活性和细胞毒性，包括戊型肝炎、基孔肯雅热、裂谷热病毒和 SARS-CoV-2。在4'、6和8位上引入卤素取代基对罗卡格拉特的抗病毒活性有显着影响，其中一些甚至比CR-31-B和西维甾醇显示出增强的活性。

  DOI：

  10.1021/acs.jmedchem.3c01357

文献信息

• Discovery of novel 2-(3-phenylpiperazin-1-yl)-pyrimidin-4-ones as glycogen synthase kinase-3β inhibitors
  作者：Yoshihiro Usui、Fumiaki Uehara、Shinsuke Hiki、Kazutoshi Watanabe、Hiroshi Tanaka、Aya Shouda、Satoshi Yokoshima、Keiichi Aritomo、Takashi Adachi、Kenji Fukunaga、Shinji Sunada、Mika Nabeno、Ken-Ichi Saito、Jun-ichi Eguchi、Keiji Yamagami、Shouichi Asano、Shinji Tanaka、Satoshi Yuki、Narihiko Yoshii、Masatake Fujimura、Takashi Horikawa

  DOI：10.1016/j.bmcl.2017.06.078

  日期：2017.8

  We herein describe the results of further evolution of glycogen synthase kinase (GSK)-3β inhibitors from our promising compounds containing a 2-phenylmorpholine moiety. Transformation of the morpholine moiety into a piperazine moiety resulted in potent GSK-3β inhibitors. SAR studies focused on the phenyl moiety revealed that a 4-fluoro-2-methoxy group afforded potent inhibitory activity toward GSK-3β

  我们在本文中描述了糖原合酶激酶（GSK）-3β抑制剂从含有2-苯基吗啉部分的有希望的化合物中进一步进化的结果。吗啉部分转化为哌嗪部分会产生有效的GSK-3β抑制剂。专注于苯基部分的SAR研究表明，4-氟-2-甲氧基对GSK-3β具有有效的抑制活性。基于对接研究，已表明哌嗪部分的氮原子与Gln185主链的氧原子之间存在新的氢键，与相应的苯吗啉类似物相比，这可能有助于增加活性。还讨论了苯基哌嗪部分的立体化学作用。
• Synthesis and biological evaluation of novel flavonols as potential anti-prostate cancer agents
  作者：Robert G. Britton、Emma Horner-Glister、Odette A. Pomenya、Ewan E. Smith、Roanne Denton、Paul R. Jenkins、William P. Steward、Karen Brown、Andreas Gescher、Stewart Sale

  DOI：10.1016/j.ejmech.2012.06.031

  日期：2012.8

  A library of flavonol analogues was synthesised and evaluated as potential anticancer agents against a human prostate cancer cell line, 22rv1. Compounds 3, 8 and 11 (IC50 2.6, 3.3 and 4.0 mu M respectively) showed potent cancer cell growth inhibition, comparable to the lead compound 3',4',5'-trimethoxyflavonol (1) (IC50 3.1 mu M) and superior to the naturally occurring flavonols quercetin (16) and fisetin (22) (both >15 mu M). Results indicate that the 3',4',5'- arrangement of either hydroxy (OH) or methoxy (OMe) residues is important for growth arrest of these cells and that the OMe analogues may be superior to their OH counterparts. Compounds 1, 3, 8 and 11 warrant further investigation as potential agents for the management of prostate cancer. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis and biological evaluation of novel 2′,4′,5′-trimethoxyflavonol derivatives as anti-inflammatory and antimicrobial agents
  作者：Girish D. Hatnapure、Ashish P. Keche、Atish H. Rodge、Rajesh H. Tale、Satish S. Birajdar、Mahendra J. Pawar、Vandana M. Kamble

  DOI：10.1007/s00044-013-0651-z

  日期：2014.1

  A series of novel 3-hydroxy-2-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one (flavonol) derivatives (2a-u) of biological interest have been prepared via CLAISEN-SCHMIDT condensation followed by ALGAR-FLYNN-OYAMADA reaction and to search for the potent nonsteroidal anti-inflammatory agents from this novel series. All the synthesized compounds have been screened for their in vitro proinflammatory cytokines tumor necrosis factor (TNF-alpha) and interleukin-6 (IL-6) inhibitory activity along with antimicrobial activity. As many as three compounds viz. 2h, 2l, and 2q from this novel series were found to be potent TNF-alpha and IL-6 inhibitor (up to 72-81 % TNF-alpha and 86-92 % IL-6 inhibitory activity) but at 10 mu M concentration as compared with the standard dexamethasone (71 % TNF-alpha and 84 % IL-6 inhibitory activities at 1 mu M concentration). While the compounds 2d, 2m, 2n, and 2s were found to be potent antimicrobial agent showing even 2-2.5-fold more potency than that of standard ciprofloxacin and miconazole at the same MIC value of 10 mu g/mL.