2,5-二氟-4-羟基苯基硼酸 | 1229584-22-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2,5-二氟-4-羟基苯基硼酸
• 英文名称: 2,5-difluoro-4-hydroxyphenylboronic acid
• 英文别名: (2,5-difluoro-4-hydroxyphenyl)boronic acid
• CAS: 1229584-22-8
• 化学式: C₆H₅BF₂O₃
• 分子量: 173.912
• InChiKey: BKSUWYUPEDFFDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.65
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-hydroxy-2-naphthyl trifluoromethanesulfonate 、 2,5-二氟-4-羟基苯基硼酸 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 150.0 ℃ 、1.5 MPa 条件下， 反应 0.42h， 以47%的产率得到6-(2,6-difluoro-4-hydroxyphenyl)-1-naphthol
  参考文献：
  名称：

  Introduction of an Electron Withdrawing Group on the Hydroxyphenylnaphthol Scaffold Improves the Potency of 17β-Hydroxysteroid Dehydrogenase Type 2 (17β-HSD2) Inhibitors

  摘要：

  Estrogen deficiency in postmenopausal women or elderly men is often associated with the skeletal disease osteoporosis. The supplementation of estradiol (E2) in osteoporotic patients is known to prevent bone fracture but cannot be administered because of adverse effect. As 17 beta-hydroxysteroid dehydrogenase type 2 (17 beta-HSD2) oxidizes E2 to its inactive form estrone (E1) and has been found in osteoblastic cells, it is an attractive target for the treatment of osteoporosis. Twenty-one novel, naphthalene-derived compounds have been synthesized and evaluated for their 17 beta-HSD2 inhibition and their selectivity toward 17 beta-HSD1 and the estrogen receptors (ERs) alpha and beta. Compound 19 turned out to be the most potent and selective inhibitor of 17 beta-HSD2 in cell-free assays and had a very good cellular activity in MDA-MB-231 cells, expressing naturally 17 beta-HSD2. It also showed marked inhibition of the E1-formation by the rat and mouse orthologous enzymes and strong inhibition of monkey 17 beta-HSD2. It is thus an appropriate candidate to be further evaluated in a disease-oriented model.

  DOI：

  10.1021/jm2008453

文献信息

• Discovery of 3-Phenyl Indazole-Based Novel Chemokine-like Receptor 1 Antagonists for the Treatment of Psoriasis
  作者：Bongki Ko、Yongsoo Jang、Seung-hwa Kwak、Hyun You、Jeong-hyun Kim、Jung-Eun Lee、Hee Dong Park、Soo-Kyung Kim、William A. Goddard、Jung Hyun Han、Yong-Chul Kim

  DOI：10.1021/acs.jmedchem.3c01011

  日期：2023.11.9

  Chemokine-like receptor 1 (CMKLR1)─a G protein-coupled receptor─has functional roles in the immune system and related diseases, including psoriasis and metabolic diseases. Psoriasis is a chronic inflammatory disease characterized by skin redness, scaliness, and itching. In this study, we sought to develop novel CMKLR1 antagonists by screening our in-house GPCR-targeting compound library. Moreover,

  趋化因子样受体 1 (CMKLR1)（一种 G 蛋白偶联受体）在免疫系统和相关疾病（包括牛皮癣和代谢性疾病）中发挥功能作用。牛皮癣是一种慢性炎症性疾病，其特征是皮肤发红、鳞屑和瘙痒。在这项研究中，我们试图通过筛选我们内部的 GPCR 靶向化合物库来开发新型 CMKLR1 拮抗剂。此外，我们优化了一种具有拮抗活性的基于苯基吲唑的命中化合物，并在小鼠模型中评估了其口服药代动力学特性。基于人 CMKLR1 同源性模型的结构设计将S - 26d确定为一种优化化合物，可作为有效的口服拮抗剂，在h CMKLR1 转染的 CHO 细胞中 pIC 50值为 7.44 。此外，在咪喹莫特诱导的银屑病样小鼠模型中，与对照组相比，口服S - 26d 1周显着减轻了改良银屑病面积和严重程度指数评分（红斑严重程度、鳞屑、皮肤厚度）。
• Introduction of an Electron Withdrawing Group on the Hydroxyphenylnaphthol Scaffold Improves the Potency of 17β-Hydroxysteroid Dehydrogenase Type 2 (17β-HSD2) Inhibitors
  作者：Marie Wetzel、Sandrine Marchais-Oberwinkler、Enrico Perspicace、Gabriele Möller、Jerzy Adamski、Rolf W. Hartmann

  DOI：10.1021/jm2008453

  日期：2011.11.10

  Estrogen deficiency in postmenopausal women or elderly men is often associated with the skeletal disease osteoporosis. The supplementation of estradiol (E2) in osteoporotic patients is known to prevent bone fracture but cannot be administered because of adverse effect. As 17 beta-hydroxysteroid dehydrogenase type 2 (17 beta-HSD2) oxidizes E2 to its inactive form estrone (E1) and has been found in osteoblastic cells, it is an attractive target for the treatment of osteoporosis. Twenty-one novel, naphthalene-derived compounds have been synthesized and evaluated for their 17 beta-HSD2 inhibition and their selectivity toward 17 beta-HSD1 and the estrogen receptors (ERs) alpha and beta. Compound 19 turned out to be the most potent and selective inhibitor of 17 beta-HSD2 in cell-free assays and had a very good cellular activity in MDA-MB-231 cells, expressing naturally 17 beta-HSD2. It also showed marked inhibition of the E1-formation by the rat and mouse orthologous enzymes and strong inhibition of monkey 17 beta-HSD2. It is thus an appropriate candidate to be further evaluated in a disease-oriented model.