2-{[乙氧基(氧代)乙酰基]氨基}苯甲酸 | 51679-85-7

• 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-{[乙氧基(氧代)乙酰基]氨基}苯甲酸
• 中文别名: 苯甲酸,2-[(乙氧基氧代乙酰基)氨基]-；2-[(2-乙氧基-2-氧代-乙酰)氨基]苯甲酸；2-[(2-乙氧基-1,2-二氧代乙基)氨基]苯甲酸；2-[(2-乙氧基-2-氧代乙酰基)氨基]苯甲酸
• 英文名称: 2-carboxyoxanilic acid ethyl ester
• 英文别名: 2-(ethoxyoxalylamino)benzoic acid；2-ethoxyoxalylamino-benzoic acid；(2-carboxy-phenyl)-oxalamic acid ethyl ester；N-ethoxyoxalyl-anthranilic acid；N-Aethoxyoxalyl-anthranilsaeure；(2-Carboxy-phenyl)-oxamidsaeureaethylester；2-{[Ethoxy(oxo)acetyl]amino}benzoic acid；2-[(2-ethoxy-2-oxoacetyl)amino]benzoic acid
• CAS: 51679-85-7
• 化学式: C₁₁H₁₁NO₅
• mdl: MFCD00966381
• 分子量: 237.212
• InChiKey: MYXIPVXKCGHPIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2-{[乙氧基(氧代)乙酰基]氨基}苯甲酸 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 60.0h， 以81%的产率得到2-(oxalamino)benzoic acid
  参考文献：
  名称：

  Discovery and SAR of a Novel Selective and Orally Bioavailable Nonpeptide Classical Competitive Inhibitor Class of Protein-Tyrosine Phosphatase 1B

  摘要：

  Reversible phosphorylation and dephosphorylation of key proteins on tyrosine residues are important parts of intracellular signaling triggered by hormones and other agents. Recent knock-out studies in mice have identified PTP1B as a potential target for the treatment of diabetes and obesity. As a consequence, a number of academic and industrial groups are aggressively pursuing the development of selective PTP1B inhibitors. In addition, other protein-tyrosine phosphatases (PTPs) appear to be critically involved in major diseases such as cancer and autoimmunity. Given the diversity of PTPs and their potential as drug targets in different diseases, we have taken a broad approach to develop active site-directed selective inhibitors of specific members of this family of enzymes. Using a high throughput screening, we have previously identified 2-(oxalylamino)benzoic acid 3a as a relatively weak but classical competitive inhibitor of several PTPs.(4) On the basis of our early studies, indicating that 3a might be used as a starting point for the synthesis of selective PTP inhibitors, we now present our efforts in expansion of this concept and provide here a number of new chemical scaffolds for the development of inhibitors of different members of the PTP family. Although the core structure of these inhibitors is charged, good oral bioavailability has been observed in rat for some compounds. Furthermore, we have observed enhancement of 2-deoxy-glucose accumulation in C2C12 cells with prodrug analogues.

  DOI：

  10.1021/jm0209026
• 作为产物：
  描述：

  ethyl indoxylcarboxylate 在 potassium dichromate 、 硫酸 作用下， 生成 2-{[乙氧基(氧代)乙酰基]氨基}苯甲酸
  参考文献：
  名称：

  Bayer, Chemische Berichte, 1882, vol. 15, p. 778

  摘要：

  DOI：

文献信息

• Oxanilic acids, a new series of orally active antiallergic agents
  作者：John H. Sellstedt、Charles J. Guinosso、Albert J. Begany、Stanley C. Bell、Marvin Rosenthale

  DOI：10.1021/jm00243a014

  日期：1975.9

  antiallergic activity using the rat passive cutaneous anaphylaxis (PCA) test. Many of the oxanilic acid esters are active orally, with the most active species having an aryl 2'-carbamoyl group and a 3'-methoxy group. Hydrolysis of the ester from the oxanilic ester moiety causes a loss of oral activity.

  制备了大量的草酸苯甲酸酯和N-杂芳基草酰胺酸酯，并通过大鼠被动皮肤过敏反应（PCA）测试发现具有抗过敏活性。许多草酰苯甲酸酯具有口服活性，最活泼的物种具有芳基2'-氨基甲酰基和3'-甲氧基。酯从草酰胺酯部分水解会导致口服活性下降。
• Guanidinum Chloride as Dehydrocyclization Agent in the Synthesis of 2-Fuctionalized (4<i>H</i>)-3,1-Benzoxazine-4-ones
  作者：Farzad Nikpour、Asrin Bahmani、Forugh Havasi、Mahnaz Sharafi-Kolkeshvandi

  DOI：10.1002/jhet.1649

  日期：2014.1

  A facile and expedient route for the synthesis of 2‐ethoxy‐ and 2‐(ethylcarboxylate)‐(4H)‐3,1‐benzoxazine‐4‐ones is described using guanidinium chloride as a safe and convenient dehydrocyclization agent. High yields of the products obtain under mild reaction conditions without need to use of any catalyst and with easy work‐up of the reaction mixture.

  描述了一种使用氯化胍作为安全，方便的脱氢环化剂合成2-乙氧基和2-（乙基羧酸酯）-（4 H）-3,1-苯并恶嗪-4-酮的简便方法。在温和的反应条件下，无需使用任何催化剂即可轻松获得高收率的产品，而且反应混合物的后处理也很容易。
• Amides and hydrazides of oxalic acid XXXVII. Synthesis and biological activity of substituted carbamidohydroxamic acids
  作者：G. P. Petyunin、R. Erling、Kh. Naumann、D. A. Kulikova、N. V. Ostapchuk

  DOI：10.1007/bf00779057

  日期：1978.6

  L. A. Piruzyan, V. V. Avidon, A. B. Rozenblit, et al., Khim. F a r m . Zh., 5 , 35-40 (1977). V. V. Avidon, V. S. Arolovich, S. P. Kozlova, et al., Khim. F a r m . Zh., 5 , 88 (1978). R. D. Cramer , III, G. Redl, and Ch .E .Be rko f f , J . Med. Chem., 17, 533-535 (1974). V .N.Vapnik and A. Ya. Chervonenkis, T h e o r y of Recognit ion of Samples. Statist ical P rob lems of Ins t ruct ion [in Russian]

  LA Piruzyan、VV Avidon、AB Rozenblit 等人，Khim。农场 。Zh., 5, 35-40 (1977)。VV Avidon、VS Arolovich、SP Kozlova 等人，Khim。农场 。Zh., 5, 88 (1978)。RD Cramer, III, G. Redl, 和 Ch .E.Be rko ff, J. 医学。Chem., 17, 533-535 (1974)。V.N.Vapnik 和 A. Ya。Chervonenkis，样本识别理论。Ins t ruct ion [in Russian] 的统计问题，莫斯科 (1974)，p。63. KE Shennon, in: Resea r ch on the Theory of Information and Cyber​​net ics [in Russian], Moscow (1963)
• Modulators of protein tyrosine phosphatases (PTPases)
  申请人：Novo Nordisk A/S

  公开号：US06225329B1

  公开（公告）日：2001-05-01

  The present invention provides novel compounds of Formula 1, compositions containing these compounds, methods of their use, and methods of their manufacture, where such compounds are pharmacologically useful inhibitors of Protein Tyrosine Phosphatases (PTPase's) such as PTP1B, CD45, SHP-1, SHP-2, PTP&agr;, LAR and HePTP or the like, wherein A, R1, R2, R3, R4, R16 and R17 are as defined in the specification. The compounds are useful in the treatment of type I diabetes, type II diabetes, impaired glucose tolerance, insulin resistance, obesity, immune dysfunctions including autoimmunity diseases with dysfunctions of the coagulation system, allergic diseases including asthma, osteoporosis, proliferative disorders including cancer and psoriasis, diseases with decreased or increased synthesis or effects of growth hormone, diseases with decreased or increased synthesis of hormones or cytokines that regulate the release of/or response to growth hormone, diseases of the brain including Alzheimer's disease and schizophrenia, and infectious diseases.

  本发明提供了一种新颖的化合物Formula 1，包含这些化合物的组合物，它们的使用方法和制备方法，其中这些化合物是药理学上有用的蛋白酪氨酸磷酸酶（PTPase's）抑制剂，如PTP1B、CD45、SHP-1、SHP-2、PTP&agr;、LAR和HePTP等，其中A、R1、R2、R3、R4、R16和R17如规范中所定义。这些化合物在治疗I型糖尿病、II型糖尿病、糖耐量受损、胰岛素抵抗、肥胖、免疫功能障碍包括自身免疫疾病与凝血系统功能障碍、过敏性疾病包括哮喘、骨质疏松症、增生性疾病包括癌症和牛皮癣、合成减少或增加或生长激素作用减少或增加的疾病、合成减少或增加调节生长激素释放或对其反应的激素或细胞因子的疾病、包括阿尔茨海默病和精神分裂症在内的大脑疾病，以及传染病方面具有用处。
• A Homometallic Ferrimagnet Based on Mixed Antiferromagnetic and Ferromagnetic Interactions through Oxamato and Carboxylato Bridges
  作者：Ko Yoneda、Yukari Hori、Masaaki Ohba、Susumu Kitagawa

  DOI：10.1246/cl.2008.64

  日期：2008.1.5

  Two novel coordination polymers (CPs), Cu[Cu(L)(H2O)-(py)]2}n (1) and Cu[Cu(L)(MeOH)]2·2H2O}n (2), were synthesized using 2-(oxaloamino)benzoic acid (H3L) providing oxamate and carboxylate groups, and magnetically characterized. Different 2-D layer structures were formed based on oxamato-bridged tricopper units bridging via the carboxylate group. In compound 1, a simple antiferromagnetic interaction operates through the oxamato bridge in the tricopper core, whereas, 2 showed a tendency for ferrimagnetic ordering at 2 K, resulting from mixed antiferromagnetic and ferromagnetic interactions through oxamato and syn–anti-type carboxylato bridges.

  两种新型配位聚合物（CP），Cu[Cu(L)(H2O)-(py)]2}n (1) 和 Cu[Cu(L)(MeOH)]2·2H2O}n (2)，使用提供草酸酯和羧酸酯基团的 2-(草酰氨基)苯甲酸 (H3L) 合成，并进行磁性表征。基于通过羧酸盐基团桥接的草酸桥联三铜单元形成了不同的二维层结构。在化合物 1 中，简单的反铁磁相互作用通过三铜核中的 oxamato 桥起作用，而 2 在 2 K 时表现出亚铁磁性有序的趋势，这是通过 oxamato 和顺反型羧基桥的混合反铁磁和铁磁相互作用产生的。