2-hydroxy-5-methylbenzylamine | 65456-39-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-hydroxy-5-methylbenzylamine
• 英文别名: 2-aminomethyl-4-methylphenol；5-methylsalicylamine；methylsalicylamine；2-Aminomethyl-4-methyl-phenol；2-(aminomethyl)-4-methylphenol；2-hydroxy-5-methyl-benzylamine
• CAS: 65456-39-5
• 化学式: C₈H₁₁NO
• 分子量: 137.181
• InChiKey: WIHBICITCXSMDU-UHFFFAOYSA-N

物化性质

• 熔点：
  75 °C
• 沸点：
  259.5±25.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hydroxy-5-methylbenzylamine 在 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 生成 1-(2-(2-chloropyrimidin-4-yloxy)-5-methylbenzyl)-3-(3-t-butyl-1-p-tolyl-1H-pyrazol-5-yl)urea
  参考文献：
  名称：

  Design and synthesis of novel p38α MAP kinase inhibitors: Discovery of pyrazole-benzyl ureas bearing 2-molpholinopyrimidine moiety

  摘要：

  The discovery that pyrazole-benzyl urea derivatives bearing a 2-molpholinopyrimidine moiety are novel p38 alpha inhibitors is described. A comparative view of the binding modes of SB-203580 and BIRB-796 by structural alignment of two X-ray co-crystal structures was utilized to identify this novel series. Modification of the benzyl group led to compound 2b, a highly potent p38 alpha inhibitor. In in vivo studies, 2b inhibited the production of tumor necrosis factor-alpha in lipopolysaccharide-treated mouse in a dose-dependent manner. Furthermore, the results of a 5-day repeated oral dose toxicity study suggest that 2b has low hepatotoxicity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.095
• 作为产物：
  描述：

  2-hydroxy-5-methylbenzaldehyde oxime 在 sodium amalgam 、 水 作用下， 生成 2-hydroxy-5-methylbenzylamine
  参考文献：
  名称：

  来自 6-苄氨基嘌呤的细胞分裂素受体拮抗剂

  摘要：

  最近我们报道了 6-(2-hydroxy-3-methylbenzylamino)purine (PI-55) 作为第一个在受体水平拮抗细胞分裂素活性的分子。在这里，我们报告了在苄基环和嘌呤部分的 C2、N7 和 N9 位置取代的 11 种 BAP 衍生物的合成和体外生物测试。这些化合物与拟南芥细胞分裂素受体 AHK3 和 CRE1/AHK4 相互作用的能力在细菌受体和活细胞结合试验中以及在拟南芥 ARR5:GUS（拟南芥反应调节剂 5）报告基因试验中进行了测试。在经典的细胞分裂素生物测试（烟草愈伤组织、小麦叶衰老和苋属植物生物测定）中测定了化合物的细胞分裂素活性。6-(2,5-Dihydroxybenzylamino)purine (LGR-991) 被鉴定为细胞分裂素受体拮抗剂。在分子水平上，LGR-991 以与 PI-55 相同的效力阻断细胞分裂素受体 CRE1/AHK4。此外，LGR-991

  DOI：

  10.1016/j.phytochem.2010.01.018

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。
• N6-Benzyladenosine Derivatives as Novel N-Donor Ligands of Platinum(II) Dichlorido Complexes
  作者：Pavel Štarha、Igor Popa、Zdeněk Trávníček、Ján Vančo

  DOI：10.3390/molecules18066990

  日期：——

  The platinum(II) complexes trans-[PtCl2(Ln)2]∙xSolv 1–13 (Solv = H2O or CH3OH), involving N6-benzyladenosine-based N-donor ligands, were synthesized; Ln stands for N6-(2-methoxybenzyl)adenosine (L1, involved in complex 1), N6-(4-methoxy-benzyl)adenosine (L2, 2), N6-(2-chlorobenzyl)adenosine (L3, 3), N6-(4-chlorobenzyl)-adenosine (L4, 4), N6-(2-hydroxybenzyl)adenosine (L5, 5), N6-(3-hydroxybenzyl)-adenosine (L6, 6), N6-(2-hydroxy-3-methoxybenzyl)adenosine (L7, 7), N6-(4-fluoro-benzyl)adenosine (L8, 8), N6-(4-methylbenzyl)adenosine (L9, 9), 2-chloro-N6-(3-hydroxy-benzyl)adenosine (L10, 10), 2-chloro-N6-(4-hydroxybenzyl)adenosine (L11, 11), 2-chloro-N6-(2-hydroxy-3-methoxybenzyl)adenosine (L12, 12) and 2-chloro-N6-(2-hydroxy-5-methylbenzyl)adenosine (L13, 13). The compounds were characterized by elemental analysis, mass spectrometry, IR and multinuclear (1H-, 13C-, 195Pt- and 15N-) and two-dimensional NMR spectroscopy, which proved the N7-coordination mode of the appropriate N6-benzyladenosine derivative and trans-geometry of the title complexes. The complexes 1–13 were found to be non-toxic in vitro against two selected human cancer cell lines (HOS and MCF7; with IC50 > 50.0 µM). However, they were found (by ESI-MS study) to be able to interact with the physiological levels of the sulfur-containing biogenic biomolecule L-methionine by a relatively simple 1:1 exchange mechanism (one Ln molecule was replaced by one L-methionine molecule), thus forming a mixed-nitrogen/sulfur-ligand dichlorido-platinum(II) coordination species.

  合成了铂(II)复合物trans-[PtCl2(Ln)2]∙xSolv 1–13（Solv = H2O或CH3OH），这些复合物涉及以N6-苄基腺苷为基础的N供体配体；Ln代表N6-(2-甲氧基苄基)腺苷（L1，复合物1中涉及），N6-(4-甲氧基苄基)腺苷（L2，复合物2），N6-(2-氯苄基)腺苷（L3，复合物3），N6-(4-氯苄基)腺苷（L4，复合物4），N6-(2-羟基苄基)腺苷（L5，复合物5），N6-(3-羟基苄基)腺苷（L6，复合物6），N6-(2-羟基-3-甲氧基苄基)腺苷（L7，复合物7），N6-(4-氟苄基)腺苷（L8，复合物8），N6-(4-甲基苄基)腺苷（L9，复合物9），2-氯-N6-(3-羟基苄基)腺苷（L10，复合物10），2-氯-N6-(4-羟基苄基)腺苷（L11，复合物11），2-氯-N6-(2-羟基-3-甲氧基苄基)腺苷（L12，复合物12）和2-氯-N6-(2-羟基-5-甲基苄基)腺苷（L13，复合物13）。通过元素分析、质谱、红外光谱以及多核（1H、13C、195Pt和15N）和二维核磁共振谱对这些化合物进行了表征，证明了适当的N6-苄基腺苷衍生物的N7配位模式和标题复合物的反式几何结构。复合物1–13在体外对选定的人癌细胞系（HOS和MCF7；IC50 > 50.0 µM）被发现无毒。然而，通过ESI-MS研究发现，它们能够通过相对简单的1:1置换机制（一个Ln分子被一个L-甲硫氨酸分子替换）与生理水平的含硫生物源生物分子L-甲硫氨酸相互作用，从而形成混合氮/硫配体的二氯铂(II)配位物。
• 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。
• 6,9-Disubstituted Purine Derivatives and Their Use as Cosmetics and Cosmetic Compositions
  申请人：Szucova Lucie

  公开号：US20090170879A1

  公开（公告）日：2009-07-02

  Certain 6,9-disubstituted purine derivatives and their pharmaceutically acceptable salts are provided. These 6,9-disubstituted purine derivatives and their pharmaceutically acceptable salts are useful in compositions for treating mammalian cells, and especially human skin cells, in order to ameliorate the adverse effects of aging, treat skin disease states, treat immunological responses resulting from or associated with inflammation, and the like.

  提供了某些6,9-二取代嘌呤衍生物及其药学上可接受的盐。这些6,9-二取代嘌呤衍生物及其药学上可接受的盐在组合物中对于治疗哺乳动物细胞，尤其是人类皮肤细胞，以缓解衰老的不良影响，治疗皮肤疾病状态，治疗由炎症引起或与之相关的免疫反应等方面非常有用。
• 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。