5-[[(2,5-二羟基苯基)甲基]氨基]-2-羟基-苯甲酸 | 125697-93-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-[[(2,5-二羟基苯基)甲基]氨基]-2-羟基-苯甲酸
• 中文别名: 5-(2,5-二羟基苄基氨基)水杨酸；5-(2,5-二羟基苄基氨基)-2-羟基苯甲酸；N-(2,5-二羟基苄基)-5-氨基水杨酸
• 英文名称: lavendustin C
• 英文别名: 2-hydroxy-5-(2,5-dihydroxybenzylamino)benzoic acid；HDBA；5-[(2,5-dihydroxyphenyl)methylamino]-2-hydroxybenzoic acid
• CAS: 125697-93-0
• 化学式: C₁₄H₁₃NO₅
• 分子量: 275.261
• InChiKey: LULATDWLDJOKCX-UHFFFAOYSA-N

物化性质

• 熔点：
  193-195°C dec.
• 沸点：
  597.5±50.0 °C(Predicted)
• 密度：
  1.551±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2922509090
• 储存条件：
  -20℃

制备方法与用途

生物活性

Lavendustin C 是一种有效的钙调蛋白依赖性激酶 II (CaMK II) 抑制剂，IC50 为 0.2 µM。它还抑制 EGFR 相关酪氨酸激酶 (IC50=0.012 µM) 和 pp60c-src 激酶 (IC50=0.5 µM)。

靶点

靶点	IC50 (µM)
CaMK II	0.2
EGFR	0.012

体外研究

Lavendustin C（化合物 5）表现出强大的抑制活性，可能是其抑制酪氨酸激酶的关键结构。Lavendustin C 在 10-150 µM 浓度下能够抑制酪氨酸激酶相关的中性粒细胞脱颗粒和超氧物生成。

反应信息

• 作为反应物：
  描述：

  5-[[(2,5-二羟基苯基)甲基]氨基]-2-羟基-苯甲酸 在 吡啶 、 potassium carbonate 、 三乙胺 、 焦碳酸二乙酯 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 5-(2,5-Dihydroxy-benzylamino)-2-hydroxy-N-methyl-benzamide
  参考文献：
  名称：

  Synthesis and biological activity of 5-[(2,5-dihydroxybenzyl)amino]salicylic acid analogs as inhibitors of EGF receptor-associated protein tyrosine kinase

  摘要：

  The synthesis and biological activity of a series of 5-[(2,5-dihydroxybenzyl)amino]salicylic acid derivatives (3-6) as analogs of the active partial structure (2) of the potent EGF-R tyrosine kinase inhibitor lavendustin A (1) are described. Analogs with an electron-withdrawing group in place of the carboxyl group of 2 showed activity. The N-hexylsalicylamide analog 6b (IC50 = 0.9 mu M) was about four times more potent than 2. (C) 1997, Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00014-0
• 作为产物：
  描述：

  5-氨基水杨酸 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 5-[[(2,5-二羟基苯基)甲基]氨基]-2-羟基-苯甲酸
  参考文献：
  名称：

  Synthesis and structure-activity studies of a series of [(hydroxybenzyl)amino]salicylates as inhibitors of EGF receptor-associated tyrosine kinase activity

  摘要：

  The synthesis and structure-activity relationships of a series of [(hydroxybenzylidene)amino] salicylates and a series of [(hydroxybenzyl)amino] salicylates as inhibitors of EGF receptor-associated tyrosine kinase activity are described. Their inhibitory potency was evaluated in vitro using ER 22 cell membranes (CCL 39 cells transfected with EGF receptor) as an enzyme source and the tridecapeptide RRSrc (RRLIEDAEYAARG) as substrate. Their cellular activity was measured by inhibition of the EGF-stimulated DNA synthesis of ER 22 cells. Chemical modifications were made to analyze the role of the different substituents. The amino series was found to be more active than the imino series. The hydroquinone moiety appears to be essential for tyrosine kinase inhibitory activity in the series of 5-[(2,5-dihydroxybenzyl)amino]salicylates. Comparison of the imino and amino series by molecular modeling techniques provides further evidence in support of the hypothesis that the important reduced linking chain, CH2NH, allows the correct positioning of the 2,5-dihydroxybenzyl ring, possibly in a cis-like conformational arrangement.

  DOI：

  10.1021/jm00077a014

文献信息

• Synergistic and residual pesticidal compositions containing plant essentials oils
  申请人：Ecosmart Technologies Inc.

  公开号：EP1634500A2

  公开（公告）日：2006-03-15

  Synergistic and residual pesticidal compositions containing synergistic and residual mixtures of a plant essential oil and pyrethrum. In addition, the present invention is directed to a method for controlling pests by applying a pesticidally effective amount of the above synergistic and residual pesticidal compositions to a locus where pest control is desired.

  含有植物精油和除虫菊酯的增效和残留混合物的增效和残留杀虫组合物。此外，本发明还涉及一种控制害虫的方法，即在需要控制害虫的地方施用杀虫有效量的上述增效和残留杀虫组合物。
• Synergistic and residual pesticidal compositions containing plant essential oils
  申请人：Ecosmart Technologies Inc.

  公开号：EP1779729A2

  公开（公告）日：2007-05-02

  Synergistic and residual pesticidal compositions containing synergistic and residual mixtures of plant essential oils and/or their constituents, plant essential oils and/or their constituents in admixture with known active pesticidal compounds or plant essential oils and/or their constituents in admixture with other compounds not previously used as active ingredients in pesticidal formulations, such as, for example, so called signal transduction modulators. In addition, the present invention is directed to a method for controlling pests by applying a pesticidally effective amount of the above synergistic and residual pesticidal compositions to a locus where pest control is desired.

  增效和残留杀虫组合物，含有植物精油和/或其成分的增效和残留混合物，植物精油和/或其成分与已知活性杀虫化合物的混合物，或植物精油和/或其成分与以前未用作杀虫制剂活性成分的其他化合物的混合物，例如，所谓的信号转导调节剂。此外，本发明还涉及一种控制害虫的方法，即在需要控制害虫的地方施用杀虫有效量的上述增效和残留杀虫组合物。
• MODULATORS OF MYC, METHODS OF USING THE SAME AND METHODS OF IDENTIFYING AGENTS THAT MODULATE MYC
  申请人：Taiga Biotechnologies, Inc.

  公开号：EP2966084A1

  公开（公告）日：2016-01-13

  Disclosed herein are methods of modulation of the viability of a cell. Further disclosed herein are methods of modulating an immune response. Further disclosed herein are methods of identifying agents capable of modulation of the viability of a cell or an immune response. Further disclosed herein are agents and compositions capable of modulation of the viability of a cell or an immune response.

  本文公开了调节细胞活力的方法。本文还公开了调节免疫反应的方法。本文还公开了鉴定能够调节细胞活力或免疫反应的制剂的方法。本文进一步公开了能够调节细胞活力或免疫反应的制剂和组合物。
• MK2/3 INHIBITORS TO TREAT METABOLIC DISTURBANCES OF OBESITY
  申请人：The Trustees of Columbia University in the City of New York

  公开号：EP3072555A1

  公开（公告）日：2016-09-28

  The present invention relates to methods of treating or preventing a metabolic disorder in a subject, methods of treating or preventing coronorary artery disease in a subject with a metabolic disorder, as well as methods of reducing hepatic glucose production in a subject. Such methods include, but are not limited to, the administration to the subject of inhibitors of CaMKII, IP3Rs, calcineurin, p38, MK2/3, or any combination thereof. The invention also provides methods of identifying a compound that inhibits the activity of CaMKII, IP3Rs, calcineurin, p38, or MK2/3, or reduces the activity and/or activation of CaMKII, IP3Rs, calcineurin, p38, or MK2/3.

  本发明涉及治疗或预防受试者代谢紊乱的方法，治疗或预防代谢紊乱受试者冠状动脉疾病的方法，以及减少受试者肝糖生成的方法。这些方法包括但不限于向受试者施用 CaMKII、IP3Rs、钙神经蛋白、p38、MK2/3 或其任意组合的抑制剂。本发明还提供了鉴定抑制 CaMKII、IP3Rs、钙调磷酸酶、p38 或 MK2/3 活性，或降低 CaMKII、IP3Rs、钙调磷酸酶、p38 或 MK2/3 活性和/或活化的化合物的方法。
• Methods for making pancreatic endocrine cells
  申请人：Janssen Biotech, Inc.

  公开号：US10421948B2

  公开（公告）日：2019-09-24

  The present invention provides a method for increasing the expression of MAFA in cells expressing markers characteristic of the pancreatic endocrine lineage comprising the steps of culturing the cells expressing markers characteristic of the pancreatic endocrine lineage in medium comprising a sufficient amount of a cyclin-dependent kinase inhibitor to cause an increase in expression of MAFA.

  本发明提供了一种提高表达胰腺内分泌系特征标记的细胞中 MAFA 表达量的方法，该方法包括以下步骤：在含有足量细胞周期蛋白依赖性激酶抑制剂的培养基中培养表达胰腺内分泌系特征标记的细胞，以引起 MAFA 表达量的增加。