2,5-二羟基苯甲酰胺 | 52405-73-9

• 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: 2,5-二羟基苯甲酰胺
• 英文名称: gentisamide
• 英文别名: 2,5-dihydroxybenzamide
• CAS: 52405-73-9
• 化学式: C₇H₇NO₃
• 分子量: 153.137
• InChiKey: FRXZIFVYTNMCHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2,5-二羟基苯甲酰胺 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 水 、 异丙醇 为溶剂， 反应 20.0h， 生成 1-[2-(3-carbamoyl-4-hydroxyphenoxy)ethylamino]-3-(2-methoxyphenoxy)propan-2-ol
  参考文献：
  名称：

  .beta.-Adrenergic blocking agents: substituted phenylalkanolamines. Effect of side-chain length on .beta.-blocking potency in vitro

  摘要：

  The synthesis of a group of potential beta-blockers bearing a new 5-ethoxysalicylamide substituent on nitrogen is described. These compounds were tested for beta-adrenergic blocking potency in vitro and compared with analogous compounds bearing a tert-butyl group on nitrogen. The new N-substituent increased the beta-blocking potency substantially. In a series of five homologous compounds of the type Ar(CH2)nCHOHCH2NHR (R = 5-ethoxysalicylamide; n = 0-4), two maxima of beta-blocking potency were found for n = 0 and 2. Moreover, the carbon isostere of the corresponding (aryloxy)propanolamine still proved to be a very potent beta-blocker. The ether oxygen in the side chain is therefore not an absolute requirement for activity. Structure-activity relationships are discussed.

  DOI：

  10.1021/jm00373a003
• 作为产物：
  描述：

  2,5-二羟基苯甲酸 在 ammonium hydroxide 作用下， 反应 6.0h， 以75%的产率得到2,5-二羟基苯甲酰胺
  参考文献：
  名称：

  真菌漆酶催化的核胺化：对羟基苯醌与伯芳香胺的反应产物

  摘要：

  Trametes spec。的真菌漆酶（EC 1.10.3.2）催化了对羟基苯醌与伯芳族胺的核胺化反应。和嗜热毁丝霉菌。这是漆酶催化合成氨基醌的首次报道。在氧气存在下将两种化合物与漆酶一起孵育会导致形成相应的单胺化或二价苯醌。没有形成氢醌类化合物。讨论了在不同的对氢醌和芳香胺与不同的漆酶反应过程中观察到的差异。

  DOI：

  10.1021/jo048454s

文献信息

• Derivatives of 3-aminopropane-1,2-diol
  申请人：Ciba-Geigy Corporation

  公开号：US04497813A1

  公开（公告）日：1985-02-05

  Derivatives of 3-aminopropane-1,2-diol of the formula ##STR1## in which Ar represents optionally substituted aryl, n represents the number 0 or 1, and alk represents alkylene having 2 to 5 carbon atoms, the nitrogen atom and the oxygen atom, or, if n is zero, the phenyl radical, being separated from one another by at least two carbon atoms, and R.sub.1 and R.sub.2, independently of one another, each represents hydrogen or lower alkyl, or together they represent lower alkylene, oxa-lower alkylene, thia-lower alkylene, aza-lower alkylene or N-lower alkyl-aza-lower alkylene, and salts of such compounds, processes for their manufacture, medicaments containing the new compounds and their use for the treatment of Angina pectoris and cardiac arrhythmia, and as blood pressure-reducing agents, as well as for the treatment of reactive or endogenic states of depression.

  3-氨基丙烷-1,2-二醇的衍生物的化学式为##STR1##其中Ar代表可选择取代的芳基，n代表数字0或1，alk代表具有2至5个碳原子的烷基，氮原子和氧原子，或者如果n为零，则苯基与彼此至少相隔两个碳原子，而R.sub.1和R.sub.2，彼此独立地，每个代表氢或较低的烷基，或者它们一起代表较低的烷基，氧杂环较低的烷基，硫杂环较低的烷基，氮杂环较低的烷基或N-较低烷基-氮杂环较低的烷基，以及这类化合物的盐，其制备方法，含有新化合物的药物以及它们用于治疗心绞痛和心律失常，以及作为降血压剂，以及用于治疗反应性或内源性抑郁状态。
• Second Generation Protocol for Multicomponent Coupling Reactions of Aldehydes, Amides and Dienophiles
  作者：Stefan Klaus、Sandra Hübner、Helfried Neumann、Dirk Strübing、Axel Jacobi von Wangelin、Dirk Gördes、Matthias Beller

  DOI：10.1002/adsc.200404056

  日期：2004.7

  three-component coupling reaction of aldehydes, amides and dienophiles (AAD reaction) has been developed. Compared to known protocols for this type of reaction, the use of aromatic solvents in the presence of dehydrating reagents allows an efficient synthesis of previously not accessible products. Condensation of ubiquitous available aldehydes and amides and subsequent Diels–Alder reactions with dienophiles

  已开发出一种改进的一锅法，用于醛，酰胺和亲二烯体的三组分偶联反应（AAD反应）。与用于这种类型反应的已知方案相比，在脱水试剂存在下使用芳族溶剂可以有效合成以前无法获得的产物。普遍存在的醛和酰胺的缩合反应以及随后的Diels-Alder与亲二烯体的反应，可提供产率高的内选择性氨基官能化六氢异吲哚-1,3-二酮和四氢邻苯二甲酸衍生物。
• N-Alkylated aminoalcohols and their pharmaceutical compositions useful
  申请人：Ciba-Geigy Corporation

  公开号：US04460580A1

  公开（公告）日：1984-07-17

  The invention relates to novel N-alkylated aminoalcohols of the formula ##STR1## in which Ar is a radical of aromatic character which is unsubstituted or substituted by hydroxyl, n has the values nought or 1 and Alk is an alkylene radical having 2 to 5 carbon atoms and the nitrogen atom and the oxygen atom or, if n is nought, the salicylamide radical are separated from one another by at least two carbon atoms in the straight-chain, and their salts. The main action of the novel compounds consists in a stimulation of cardiac .beta.-receptors; the compounds also effect a blockage of adrenergic .alpha.-receptors and a lowering in the blood pressure. They can therefore be used as .beta.-stimulators, especially as agents having a positively inotropic action for the treatment of cardiac insufficiency. Compounds of the formula I in which Ar is phenyl, unsubstituted or substituted by 1 or 2 hydroxyl groups, Alk is an alkylene radical having 2 to 4 carbon atoms, n has the value 1, and the nitrogen atom and the oxygen atom are separated from one another by at least 2 carbon atoms in the straight-chain, or salts thereof, exhibit effects on the central nervous system, which are reflected for example in the suppression of the symptoms of impaired sympathetic functions and in the suppression of lack of initiative. Such compounds of the formula I therefore can be used for the treatment of reactive or endogenic states of depression of varying degrees of severity, and also for the treatment of neurotic or other psychic disturbances involving loss of initiative and depressive disorders. Such compounds can also be used for the short-term treatment of post-partum or postoperative depression, or of depression of different origin. Such compounds of the formula I can be used on their own or in combination with other antidepressants.

  该发明涉及具有以下结构的新型N-烷基化氨基醇：##STR1##其中Ar是具有芳香性质的基团，未取代或被羟基取代，n的值为零或1，Alk是具有2至5个碳原子的烷基基团，氮原子和氧原子或者，如果n为零，则是水杨酰胺基团，在直链中至少被至少两个碳原子分开，以及它们的盐。这些新型化合物的主要作用在于刺激心脏β-受体；这些化合物还会阻断肾上腺素α-受体并降低血压。因此，它们可以用作β-激动剂，特别是作为具有正性肌力作用的药物，用于治疗心脏功能不全。其中Ar为苯基，未取代或被1或2个羟基取代，Alk是具有2至4个碳原子的烷基基团，n的值为1，氮原子和氧原子在直链中至少被至少2个碳原子分开，或其盐的化合物，对中枢神经系统产生影响，例如抑制受损交感神经功能的症状和抑制缺乏主动性。因此，这些具有结构I的化合物可用于治疗不同程度的反应性或内源性抑郁状态，以及用于治疗神经症或其他涉及缺乏主动性和抑郁障碍的精神紊乱。这些化合物还可用于短期治疗产后抑郁症或术后抑郁症，或不同起源的抑郁症。这些具有结构I的化合物可以单独使用或与其他抗抑郁药物联合使用。
• COMPOSITIONS AND METHODS FOR TREATMENT OF VIRAL DISEASES
  申请人：Johansen Lisa M.

  公开号：US20100009970A1

  公开（公告）日：2010-01-14

  The present invention features compositions, methods, and kits useful in the treatment of viral diseases. In certain embodiments, the viral disease is caused by a single stranded RNA virus, a flaviviridae virus, or a hepatic virus. In particular embodiments, the viral disease is viral hepatitis (e.g., hepatitis A, hepatitis B, hepatitis C, hepatitis D, hepatitis E) and the agent or combination of agents includes sertraline, a sertraline analog, UK-416244, or a UK-416244 analog. Also featured are screening methods for identification of novel compounds that may be used to treat a viral disease.

  本发明涉及用于治疗病毒性疾病的组合物、方法和试剂盒。在某些实施方式中，病毒性疾病是由单链RNA病毒、黄病毒科病毒或肝病毒引起的。在特定实施方式中，病毒性疾病是病毒性肝炎（例如甲型肝炎、乙型肝炎、丙型肝炎、丁型肝炎、戊型肝炎），药剂或药剂组合包括舍曲林、舍曲林类似物、UK-416244或UK-416244类似物。还包括用于鉴定可用于治疗病毒性疾病的新化合物的筛选方法。
• Structure-activity relationships of natural quinone vegfrecine analogs with potent activity against VEGFR-1 and -2 tyrosine kinases
  作者：Hayamitsu Adachi、Chisato Nosaka、Sonoko Atsumi、Koichi Nakae、Yoji Umezawa、Ryuichi Sawa、Yumiko Kubota、Chie Nakane、Masabumi Shibuya、Yoshio Nishimura

  DOI：10.1038/s41429-021-00445-y

  日期：2021.10

  A series of analogs of vegfrecine, a natural quinone vascular endothelial growth factor receptor (VEGFR) tyrosine kinase inhibitor, was synthesized via oxidative amination of 2,5-dihydroxybenzamide with functionalized arylamine followed by ammonolysis and substitution of the quinone ring. The inhibitory activities of the analogs against the VEGFR-1 and -2 tyrosine kinases were assayed in vitro with

  一系列 vEGfrecine 类似物是一种天然醌血管内皮生长因子受体 (VEGFR) 酪氨酸激酶抑制剂，通过 2,5-二羟基苯甲酰胺与官能化芳胺的氧化胺化，然后氨解和取代醌环合成。体外分析了类似物对 VEGFR-1 和 -2 酪氨酸激酶的抑制活性，目的是确定一种适合治疗癌症和炎症疾病的化合物。检查了苯基官能团的改变、醌环的取代和 1-甲酰胺-2-氨基醌部分的氧化环化以形成异恶唑醌环。在苯环的 5'-位引入卤素和烷基取代基导致对 VEGFR-1 和 -2 酪氨酸激酶的有效抑制。特别是，苯环上 C-5' 处的结构修饰显示出显着影响 VEGFR-1 和 -2 酪氨酸激酶之间抑制的选择性。化合物如图 8 所示，5'-甲基-vEGfrecine 对 VEGFR-2 酪氨酸激酶显示出优于 VEGFR-1 酪氨酸激酶的选择性。

表征谱图