5-methoxysalicylamine | 109972-88-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-methoxysalicylamine
• 英文别名: 2-(Aminomethyl)-4-methoxyphenol
• CAS: 109972-88-5
• 化学式: C₈H₁₁NO₂
• mdl: MFCD00870502
• 分子量: 153.181
• InChiKey: HURFIFVKMMRHHO-UHFFFAOYSA-N

物化性质

• 沸点：
  305.7±27.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxysalicylamine 在 盐酸 作用下， 以 水 为溶剂， 生成 2-(Aminomethyl)-4-methoxyphenol hydrochloride
  参考文献：
  名称：

  Characterization of Scavengers of γ-Ketoaldehydes That Do Not Inhibit Prostaglandin Biosynthesis

  摘要：

  Expression Of cyclooxygenase-2 (COX-2) is associated with the development of many pathologic conditions. The product of COX-2, prostaglandin H(2) (PGH(2)), can spontaneously rearrange to form reactive gamma-ketoaldehydes called levuglandins (LGs). This gamma-keloaldehyde structure confers a high degree of reactivity on the LGs, which rapidly form covalent adducts with primary amines of protein residues. Formation of LG adducts of proteins has been demonstrated in pathologic conditions (e.g., increased levels in the hippocampus in Alzheimer's disease) and during physiologic function (platelet activation). On the basis of knowledge that lipid modification of proteins is known to cause their translocation and to alter their function. we hypothesize that modification of proteins by LG could have functional consequences. Testing this hypothesis requires an experimental approach that discriminates between the effects of protein modification by LG and the, effects of cyclooxygenase-derived prostanoids acting through their G-protein Coupled receptors. TO achieve this goal, we have synthesized and evaluated it series of scavengers that react with LG with a potency More than 2 orders of magnitude greater than that with the epsilon-amine of lysine. A Subset of these scavengers are shown to block the formation of LG adducts of proteins in cells without inhibiting the catalytic activity of the cyclooxygenases. Ten of these selective scavengers did not produce cytotoxicity. These results demonstrate that small molecules can scavenge LGs in cells without interfering with the formation of prostaglandins. They also provide a working hypothesis for the development of pharmacologic agents that could be used in experimental animals in vivo to assess the pathophysiological contribution of levuglandins in diseases associated with cyclooxygenase up-regulation.

  DOI：

  10.1021/tx900407a
• 作为产物：
  描述：

  2-羟基-5-甲氧基苯甲醛 在 盐酸羟胺 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 5-methoxysalicylamine
  参考文献：
  名称：

  靶向14-3-3η蛋白的新型1H-吲哚-2-羧酸衍生物的设计、合成和抗肿瘤评价

  摘要：

  在这项工作中，设计并合成了一系列针对14-3-3η蛋白的新型1H-吲哚-2-羧酸衍生物，用于治疗肝癌。经过多轮结构优化，C11与14-3-3η的亲和力相对较好，对Bel-7402、SMMC-7721、SNU-387、Hep等几种典型人肝癌细胞系的抑制活性最好G2 和 Hep 3B 细胞。化合物C11对化疗耐药的 Bel-7402/5-Fu 细胞也表现出最好的抑制活性。此外，C11对 hERG 相当安全，在肝微粒体中具有中等的 T 1/2和 CL 值。在抗增殖、反式孔和细胞凋亡测定中，C11也显示出其作为强效抗肿瘤剂的巨大潜力。然后，进行蛋白质印迹分析，通过分子对接分析，揭示了这种小分子抑制剂的抗增殖机制。此外，C11被证明在肝癌细胞中诱导 G 1 -S 期细胞周期停滞。

  DOI：

  10.1016/j.ejmech.2022.114402

文献信息

• Substituted 6-(Benzylamino) Purine Riboside Derivatives, Use Thereof and Compositions Containing These Derivatives
  申请人：Szucova Lucie

  公开号：US20120071433A1

  公开（公告）日：2012-03-22

  The invention relates to 2-substituted-6-(substituted benzylamino)purine riboside derivatives of the general formula I. These compounds possess antiapoptotic, anti-inflammatory and differentiating activities. The invention relates also to the compositions, which contain these derivatives as active ingredients.

  该发明涉及一般式I的2-取代-6-(取代苯基氨基)嘌呤核苷衍生物。这些化合物具有抗凋亡、抗炎和分化活性。该发明还涉及包含这些衍生物作为活性成分的组合物。
• SUBSTITUTION DERIVATIVES OF N6-BENZYLADENOSINE-5' -MONOPHOSPHATE, METHODS OF PREPARATION THEREOF, USE THEREOF AS MEDICAMENTS, AND THERAPEUTIC PREPARATIONS CONTAINING THESE COMPOUNDS
  申请人：Zatloukal Marek

  公开号：US20130040908A1

  公开（公告）日：2013-02-14

  Substitution derivatives of N 6 -benzyladenosine-5′-monophosphate of the general formula I, wherein (R) n represents 1 to 4 substituents (n is in the range 1-4), which can be the same or different, and R is selected from the group comprising C 1 to C 8 alkyl, C 1 to C 8 alkoxy, amino, halogen, hydroxy, mercapto and nitro groups, and the pharmaceutically acceptable salts thereof. A Method for their preparation, their use as medicaments and in other applications, and a therapeutic composition containing these derivatives is also disclosed.

  通式I的N6-苄基腺苷-5'-磷酸的取代衍生物，其中（R）n表示1至4个取代基（n在1-4范围内），可以相同也可以不同，R选自包括C1到C8烷基，C1到C8烷氧基，氨基，卤素，羟基，巯基和硝基基团的群体，并且其药用盐。还公开了它们的制备方法，作为药物和其他应用中的使用，以及含有这些衍生物的治疗组合物。
• Selective A3 adenosine receptor antagonists derived from nucleosides containing a bicyclo[3.1.0]hexane ring system
  作者：Artem Melman、Ben Wang、Bhalchandra V. Joshi、Zhan-Guo Gao、Sonia de Castro、Cara L. Heller、Soo-Kyung Kim、Lak Shin Jeong、Kenneth A. Jacobson

  DOI：10.1016/j.bmc.2008.08.007

  日期：2008.9

  We have prepared 50-modified derivatives of adenosine and a corresponding (N)-methanocarba nucleoside series containing a bicyclo[3.1.0]hexane ring system in place of the ribose moiety. The compounds were examined in binding assays at three subtypes of adenosine receptors (ARs) and in functional assays at the A3 AR. The H-bonding ability of a group of 9-riboside derivatives containing a 50-uronamide

  我们已经制备了 50 种修饰的腺苷衍生物和相应的 (N)-methanocarba 核苷系列，其中含有双环 [3.1.0] 己烷环系统代替核糖部分。在三种亚型腺苷受体 (AR) 的结合试验和 A3 AR 的功能试验中检查了这些化合物。NH 的修饰降低了一组含有 50-尿醛酰胺部分的 9-核苷衍生物的 H 键合能力；然而，这些衍生物没有显示出作为选择性 A3 AR 拮抗剂所需的活性，如 50-N,N-二甲基脲酰胺所发生的那样。然而，缺乏 40-羟甲基的截短的 (N)-methanocarba 类似物是人类 A3 AR 的高效选择性拮抗剂。这些化合物是使用 50-羧基中间体的还原性自由基脱羧从 D-核糖合成的。一种效率较低的合成方法始于 L-核糖，它类似于 (N)-methanocarba A3AR 激动剂的已发表合成。化合物 33b-39b（N6-3-卤代苄基和相关的芳烷基衍生物）是有效的 A3AR
• Discussion of the proton potential with proton-transfer equilibria: thermodynamic data and infrared continua as a function of temperature
  作者：Rainer Krämer、Georg Zundel、Bogumił Brzezinski、Jerzy Olejnik

  DOI：10.1039/ft9928801659

  日期：——

  The infrared continua caused with intramolecular hydrogen bonds of the type AH⋯B ⇌ A–⋯H+B have been studied as a function of the ΔpKa of the hydrogen-bond donor and acceptor as well as a function of the temperature. From the behaviour of these continua it is shown that the shape of the proton potential may change with decreasing temperature from a double minimum with the deeper well at the donor to proton potential with the deeper well at the acceptor. The In (KPT) over 1/T plots result, however, always in negative apparent ‘ΔH° values’. Hence with all such proton-transfer hydrogen bonds the deeper well of the double-minimum proton potentials should always be at the acceptor group.Using the reaction-field theory, it is shown that for proton-transfer equilibria the slope of these In KPT vs. 1/T plots remains linear since ∂P/∂T, i.e. the derivative of the Onsager parameter P against the temperature T is constant if it is considered with not too large a temperature range, and since ΔH° changes with temperature by a term which is linear in T. Therefore, from the In (KPT)vs. 1/T plots apparent ‘ΔH° values’ are obtained from which the true values can be calculated if ∂P/∂T is known.

  我们研究了分子内氢键 AH⋯B ⇌ A-⋯H+B 类型引起的红外连续波，它是氢键供体和受体的 ΔpKa 的函数，也是温度的函数。这些连续曲线的行为表明，质子势的形状可能会随着温度的降低而改变，从供体处较深井的双最小值变为受体处较深井的质子势。然而，In (KPT) over 1/T 图的结果总是负的表观 "ΔH° 值"。因此，在所有这类质子转移氢键中，双最小质子势的深井应始终位于受体基团。利用反应场理论可以证明，对于质子转移平衡，由于 ∂P/∂T，即 Onsager 参数的导数，In KPT vs. 1/T 图的斜率保持线性。因此，从 In (KPT)vs. 1/T 图中可以得到明显的 "ΔH° 值"，如果知道 ∂P/∂T，就可以从中计算出真实值。
• Substituted 6-(2-hydroxybenzylamino)purine Derivatives, Their Use as Medicaments and Compositions Containing These Derivatives
  申请人：Zatloukal Marek

  公开号：US20120070512A1

  公开（公告）日：2012-03-22

  The invention relates to substituted 6-(2-hydroxybenzylamino)purines of general formula I, to their activity as cyclin-dependent kinases 2, 5, 7 and 9 inhibitors and to their use as medicaments, particularly in the treatment of disorders involving cell proliferation or inflammation. The invention further includes pharmaceutical compositions containing the substituted 6-(2-hydroxybenzylamino)purines.

  本发明涉及一般式I的取代6-(2-羟基苯基氨基)嘌呤，其作为周期素依赖性激酶2、5、7和9的抑制剂的活性以及它们在药物治疗中的使用，特别是在涉及细胞增殖或炎症的疾病治疗中。本发明还包括含有取代6-(2-羟基苯基氨基)嘌呤的药物组合物。