5-methoxynaphthalen-2-yl trifluoromethanesulfonate | 590369-69-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-methoxynaphthalen-2-yl trifluoromethanesulfonate
• 英文别名: 5-methoxy-2-naphthyl trifluoromethanesulfonate；(5-methoxynaphthalen-2-yl) trifluoromethanesulfonate
• CAS: 590369-69-0
• 化学式: C₁₂H₉F₃O₄S
• 分子量: 306.262
• InChiKey: SCRXRZPKSKZRTK-UHFFFAOYSA-N

物化性质

• 沸点：
  381.5±42.0 °C(Predicted)
• 密度：
  1.465±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-methoxynaphthalen-2-yl trifluoromethanesulfonate 在 1,1'-双(二苯基膦)二茂铁 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 四(三苯基膦)钯 、 potassium acetate 、 三溴化硼 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， -78.0~150.0 ℃ 、1.5 MPa 条件下， 反应 4.42h， 生成 5-(5-hydroxy-2-naphthyl)biphenyl-2-ol
  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
• 作为产物：
  描述：

  5-甲氧基-2-萘满酮 在 palladium 10% on activated carbon 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 53.08h， 生成 5-methoxynaphthalen-2-yl trifluoromethanesulfonate
  参考文献：
  名称：

  WO2023/4400

  摘要：

  公开号：

文献信息

• Azabicyclic compounds for the treatment of disease
  申请人：——

  公开号：US20030236270A1

  公开（公告）日：2003-12-25

  The invention provides compounds of Formula I: 1 wherein Azabicyclo is 2 W is a six-membered heterocyclic ring system having 1-2 nitrogen atoms or a 10-membered bicyclic-six-six-fused-ring system having up to two nitrogen atoms within either or both rings, provided that no nitrogen is at a bridge of the bicyclic-six-six-fused-ring system, and further having 1-2 substitutents independently selected from R 3 . These compounds may be in the form of pharmaceutical salts or compositions, may be in pure enantiomeric form or racemic mixtures, and are useful in pharmaceuticals to treat diseases or conditions in which &agr;7 is known to be involved.

  本发明提供了式I的化合物： 1 其中Azabicyclo是 2 W是一个六元杂环体系，具有1-2个氮原子，或一个10元双环六六并环体系，在任一或两个环中最多有两个氮原子，前提是该双环六六并环体系的桥上没有氮原子，并且还具有1-2个独立选自R 3 的取代基。 这些化合物可以是药物盐或组合物，可以是纯净的对映异构体形式或外消旋混合物，并且在制药中用于治疗那些已知涉及α7的疾病或状况。
• Synthesis of Phenol and Quinone Metabolites of Benzo[<i>a</i>]pyrene, a Carcinogenic Component of Tobacco Smoke Implicated in Lung Cancer
  作者：Daiwang Xu、Trevor M. Penning、Ian A. Blair、Ronald G. Harvey

  DOI：10.1021/jo801864m

  日期：2009.1.16

  12-BP phenols and the BP 1,6-, 3,6-, 6,12-, and 9,10-quinones are now reported. The syntheses of the BP phenols (except 6-HO-BP) involve the key steps of Pd-catalyzed Suzuki−Miyaura cross-coupling of a naphthalene boronate ester with a substituted aryl bromide or triflate ester. The BP quinones were synthesized from the corresponding BP phenols by direct oxidation with the hypervalent iodine reagents

  多环芳烃（PAH）是有机物燃烧时产生的广泛环境污染物。 PAHs存在于汽车尾气和烟草烟雾中，最近被指定为人类致癌物。目前的证据表明，PAH 被酶促激活，产生与 DNA 相互作用的诱变代谢物。有证据表明存在三种激活途径：二醇环氧化物途径、自由基-阳离子途径和醌途径。这些途径对人类肺癌的相对重要性尚未确定。我们现在报道了原型 PAH 致癌物苯并[ a ]芘 (BP) 的主要苯酚和醌异构体的合成，已知或怀疑这些异构体是人支气管肺泡细胞中 BP 的代谢产物。合成方法被设计为适用于BP代谢物的13 C标记类似物的制备。这些化合物需要作为敏感 LC−MS/MS 方法的标准品，用于分析肺细胞中形成的 BP 代谢物。目前已报道了 1-、3-、6-、9- 和 12-BP 苯酚以及 BP 1,6-、3,6-、6,12- 和 9,10-醌的高效新型合成方法。 BP 苯酚（6-HO-BP 除外）的合成涉及萘硼酸酯与取代的芳基溴或三氟甲磺酸酯的
• Identification of the 5,5-dioxo-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidine derivatives as highly selective PDE4B inhibitors
  作者：Taiji Goto、Akiko Shiina、Takeshi Murata、Masato Tomii、Takanori Yamazaki、Ken-ichi Yoshida、Toshiharu Yoshino、Osamu Suzuki、Yoshitaka Sogawa、Kiyoshi Mizukami、Nana Takagi、Tomomi Yoshitomi、Maki Etori、Hiroshi Tsuchida、Tsuyoshi Mikkaichi、Naoki Nakao、Mizuki Takahashi、Hisashi Takahashi、Shigeki Sasaki

  DOI：10.1016/j.bmcl.2013.12.076

  日期：2014.2

  A PDE4B subtype selective inhibitor is expected to have a wider therapeutic window than non-selective PDE4 inhibitors. In this Letter, two series of 7,8-dihydro-6H-thiopyrano[3,2-d] pyrimidine derivatives and 5,5-dioxo-7,8-dihydro-6H-thiopyrano[3,2-d] pyrimidine derivatives were evaluated for their PDE4B subtype selectivity using human PDE4B2 and PDE4D2 full length enzymes. To improve their PDE4B selectivity over PDE4D, we optimized the substituents on the pyrimidine ring and the side chain phenyl ring, resulting in several derivatives with more than 100-fold selectivity for PDE4B. Consequently, we identified 2-( 3-chloro-4-methoxy-phenyl)-5,5-dioxo-7,8-dihydro-6H-thiopyrano[3,2-d] pyrimidine derivative 54 as a highly selective PDE4B inhibitor, which had potent hPDE4B inhibitory activity with an IC50 value of 3.0 nM and 433-fold PDE4B selectivity over PDE4D. (C) 2014 Elsevier Ltd. All rights reserved.
• AZABICYCLIC COMPOUNDS WITH ALFA7 NICOTINIC ACETYLCHOLINE RECEPTOR ACTIVITY
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP1478646A1

  公开（公告）日：2004-11-24
• US7001900B2
  申请人：——

  公开号：US7001900B2

  公开（公告）日：2006-02-21