5-苄基-2-羟基苯甲酸 | 4386-41-8

• 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-苄基-2-羟基苯甲酸
• 英文名称: 5-benzyl-2-hydroxybenzoic acid
• 英文别名: 5-Benzyl-2-hydroxy-benzoesaeure；4-Oxy-diphenylmethan-carbonsaeure-(3)；5-Benzyl-salicylsaeure
• CAS: 4386-41-8
• 化学式: C₁₄H₁₂O₃
• mdl: MFCD08059184
• 分子量: 228.247
• InChiKey: AFIMKCDXMUVHON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2918290000

反应信息

• 作为反应物：
  描述：

  5-苄基-2-羟基苯甲酸 在 乙醇 、 硝酸 、 镍 、 溶剂黄146 作用下， 生成 3-amino-5-benzyl-2-hydroxy-benzoic acid
  参考文献：
  名称：

  Rubzow et al., Zhurnal Obshchei Khimii, 1953, vol. 23, p. 1209,1213; engl. Ausg. S. 1271, 1274

  摘要：

  DOI：
• 作为产物：
  描述：

  5-溴水杨酸 在 palladium on activated charcoal 氢气 、 叔丁基锂 作用下， 反应 1.0h， 生成 5-苄基-2-羟基苯甲酸
  参考文献：
  名称：

  Lithiation of polyhydric compounds. Salicylic acids

  摘要：

  Polylithiated derivatives of salicylic and oligosalicylic acids can be generated by means of the halogen-to-metal exchange reaction. Dehydrobromination and other byproducts can be kept to a minimum by working with the preformed lithium salts which are soluble in THF. Even base sensitive salicylic acids such as 6-bromolasalocid acid can be functionalized under these conditions.

  DOI：

  10.1021/jo00067a048

文献信息

• Convulsive Status Epilepticus in Children with Intractable Epilepsy is Frequently Focal in Origin
  作者：Mohammed M.S. Jan、Brian G.R. Neville、Timothy C. Cox、Rod C. Scott

  DOI：10.1017/s0317167100001748

  日期：2002.2

  Convulsive status epilepticus (CSE) is a common neurological emergency. Our objectives were to study children with recurrent nonfebrile CSE to assess the evidence for focal origin.

  Series of 18 children with recurrent CSE and intractable epilepsy were identified by chart review. Clinical, radiological, and EEG data were reviewed. Focal structural abnormalities were identified on MRI and CT images by one neuroradiologist who was unaware of the clinical details.

  The patient's ages ranged between 6-22 years (mean 15.3, SD 4), and 67% were males. Most children (89%) had a severe cognitive and / or behavioural disorder. Most patients (89%) had multiple seizure types and 95% of these were partial seizures. Twelve (67%) children had at least one episode of CSE with focal features identified clinically. Focal brain abnormalities were detected on 18% and 55% of CTand MRI films respectively. Overall, 53% had a focal abnormality on structural neuroimaging. Interictal EEG revealed focal or multifocal abnormalities on at least one occasion in 94% and 22% of patients respectively. Overall, 17 patients had focal features on at least one EEG. Thirteen ictal EEGs were recorded on 11 (61%) patients. Ten (91%) of these recordings revealed a focal onset.

  Many handicapped children with recurrent CSE have focal clinical, radiological, or electrographic features. This supports a focal origin for CSE in most children with intractable epilepsy.

  背景：惊厥性癫痫状态（CSE）是一种常见的神经系统急症。我们的目的是研究反复发作的非发热性CSE患儿，以评估病灶起源的证据。方法：通过病历审查确定了18名反复发作的CSE和难治性癫痫患儿。回顾了临床、放射学和脑电图数据。结果：患者年龄在6-22岁之间（平均15.3岁，SD为4），67%为男性。大多数儿童（89%）患有严重的认知和/或行为障碍。大多数患者（89%）有多种癫痫发作类型，其中 95% 为部分性癫痫发作。12名患儿（67%）至少有一次CSE发作，临床上发现其具有局灶性特征。分别有 18% 和 55% 的 CT 和核磁共振成像片检测到局灶性脑部异常。总体而言，53%的患儿在神经结构影像学检查中发现局灶性异常。分别有 94% 和 22% 的患者在发作间期脑电图上发现至少一次局灶性或多灶性异常。总体而言，17 名患者至少有一次脑电图出现局灶性特征。11 名患者（61%）记录了 13 次发作期脑电图。结论：许多复发性 CSE 的残障儿童具有局灶性临床、放射学或电图特征。这支持了大多数难治性癫痫患儿的CSE起源于病灶。
• Mono- and disalicylic acid derivatives: PTP1B inhibitors as potential anti-obesity drugs
  作者：Suja Shrestha、Bharat Raj Bhattarai、Keun-Hyeung Lee、Hyeongjin Cho

  DOI：10.1016/j.bmc.2007.07.010

  日期：2007.10

  A series of compounds containing one or two salicylic acid moieties were synthesized, and their efficacy to inhibit the phosphohydrolase activity of PTP1B examined. Some of the methylenedisalicylic acid derivatives were potent inhibitors of PTP1B. Of those derivatives, 3c exhibited about a 14-fold selectivity against TC-PTP, and this compound was tested in a mouse model for its efficacy to prevent

  合成了一系列包含一个或两个水杨酸部分的化合物，并研究了其抑制PTP1B磷酸水解酶活性的功效。一些亚甲基二水杨酸衍生物是PTP1B的有效抑制剂。在这些衍生物中，3c对TC-PTP表现出约14倍的选择性，并在小鼠模型中测试了该化合物预防饮食引起的肥胖的功效。它有效地抑制了体重和脂肪的增加，而没有任何明显的毒性作用。该化合物还可以防止血浆甘油三酸酯，胆固醇和非酯化脂肪酸浓度的增加。因此，将其治疗潜力扩展到其他相关的代谢性疾病，例如高脂血症和高胆固醇血症。
• Color developer for pressure-sensitive recording paper
  申请人：Sumitomo Durez Company, Ltd.

  公开号：US05034370A1

  公开（公告）日：1991-07-23

  A color developer for pressure-sensitive recording paper is produced by admising components comprising: (A) 100 parts by weight of a polyvalent metal salt of a co-condensation product of a substituted salicylic acid, an aromatic hydrocarbon and an aldehyde. Such a co-condensation product is obtained by reacting: (a) a substituted salicylic acid, (b) one or more aromatic hydrocarbons having 4 to 9 carbon atoms, and (c) an aldehyde of 1 to 8 carbon atoms, in the presence of an acidic catalyst; and (B) 5 to 200 parts by weight of one or more members selected from the group consisting of petroleum resins, terpene resins, modified terpene resins, coumaarone resins and modified coumarone resins. The color developer is excellent in color density, resistance to yellow staining, fastness to light of color images and resistance to fading in water of color images, and in addition is capable of forming color images at a markedly increased speed.

  一种用于压敏记录纸的色素显影剂，由以下组分制备而成：（A）100份重量的多价金属盐，其为取代水杨酸、芳香族碳氢化合物和醛的共缩聚产物。这样的共缩聚产物是通过在酸性催化剂存在下反应以下物质得到的：（a）取代水杨酸，（b）一个或多个具有4至9个碳原子的芳香族碳氢化合物，和（c）1至8个碳原子的醛；以及（B）5至200份重量的石油树脂、萜烯树脂、改性萜烯树脂、香豆素树脂和改性香豆素树脂中的一种或多种。该色素显影剂具有优异的色密度、抗黄染性、彩色图像的耐光性和彩色图像在水中的耐褪色性，并且能够以明显增加的速度形成彩色图像。
• Process for preparing zinc salt of salicyclic acid compound
  申请人：Fuji Photo Film Co., Ltd.

  公开号：EP0322091A2

  公开（公告）日：1989-06-28

  For preparing a zinc salt of a salicyclic acid compound, a salicyclic acid compound preferably of the general formula (I) and/or an alkali metal salt thereof is reacted with a zinc compound, in a mixture of water and an organic solvent which has a water solubility of not more than 0.1 g/100 g water at 25°C and in which the zinc salt has a solubility of not less than 10 g/100 g organic solvent at 25°C, e.g. an aromatic compound substituted with an alkyl or alkoxy group or halogen atom. The organic solvent is preferably in an amount of 0.05 to 15 wt. parts per part of the zinc salt product. After reaction the water-soluble by products are removed by liquid-liquid separation. The organic solvent is then removed, e.g. by distillation at reduced pressure. The salt crystals can be ground to a powder which is useful as an electron-acceptor in recording materials.

  为了制备水杨酸化合物的锌盐，最好将通式(I)的水杨酸化合物和/或其碱金属盐与锌化合物在水和有机溶剂的混合物中反应，有机溶剂在25℃时的水溶性不大于0.1克/100克水，锌盐在25℃时的溶解度不小于10克/100克有机溶剂，例如用烷基或烷氧基或卤原子取代的芳香族化合物。有机溶剂的用量最好为每份锌盐产品 0.05 至 15 重量份。 反应后，通过液-液分离除去水溶性副产物。然后通过减压蒸馏等方法除去有机溶剂。盐晶体可以研磨成粉末，在记录材料中用作电子受体。
• SAR optimization studies on modified salicylamides as a potential treatment for acute myeloid leukemia through inhibition of the CREB pathway
  作者：Hee-Don Chae、Nick Cox、Samanta Capolicchio、Jae Wook Lee、Naoki Horikoshi、Sharon Kam、Andrew A. Ng、Jeffrey Edwards、Tae-León Butler、Justin Chan、Yvonne Lee、Garrett Potter、Mark C. Capece、Corey W. Liu、Soichi Wakatsuki、Mark Smith、Kathleen M. Sakamoto

  DOI：10.1016/j.bmcl.2019.06.023

  日期：2019.8

  Disruption of cyclic adenosine monophosphate response element binding protein (CREB) provides a potential new strategy to address acute leukemia, a disease associated with poor prognosis, and for which conventional treatment options often carry a significant risk of morbidity and mortality. We describe the structure-activity relationships (SAR) for a series of XX-650-23 derived from naphthol AS-E phosphate that disrupts binding and activation of CREB by the CREB-binding protein (CBP). Through the development of this series, we identified several salicylamides that are potent inhibitors of acute leukemia cell viability through inhibition of CREB-CBP interaction. Among them, a biphenyl salicylamide, compound 71, was identified as a potent inhibitor of CREB-CBP interaction with improved physicochemical properties relative to previously described derivatives of naphthol AS-E phosphate.