5-乙酰氨基-2-乙酰氧基苯甲酸 | 6376-29-0

• 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-乙酰氨基-2-乙酰氧基苯甲酸
• 英文名称: 5-acetamido-2-acetoxybenzoic acid
• 英文别名: 5-Acetylamino-aspirin；2-Acetoxy-5-acetamidobenzoic acid；2-acetoxy-5-acetylamino-benzoic acid；O.N-Diacetyl-5-amino-salicylsaeure；2-Acetoxy-5-acetylamino-benzoesaeure；5-Acetamino-2-acetoxy-benzoesaeure；5-acetamido-2-acetyloxybenzoic acid
• CAS: 6376-29-0
• 化学式: C₁₁H₁₁NO₅
• 分子量: 237.212
• InChiKey: LPEQUXVADBGZCC-UHFFFAOYSA-N

物化性质

• 熔点：
  176-177 °C
• 沸点：
  482.1±40.0 °C(Predicted)
• 密度：
  1.373±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  4
• 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

反应信息

• 作为反应物：
  描述：

  5-乙酰氨基-2-乙酰氧基苯甲酸 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 生成 5-乙酰氨基水杨酸
  参考文献：
  名称：

  A polymeric drug for treatment of inflammatory bowel disease

  摘要：

  Sulfasalazine (SASP) consists of salicylic acid azo linked at the 5-position to a pyridine-containing sulfonamide. This drug, currently used in inflammatory bowel disease treatment, is reductively cleaved by anaerobic bacteria in the lower bowel to 5-aminosalicylic acid (5-ASA) and sulfapyridine (SP). Recent reports indicate that 5-ASA is the active therapeutic moiety and that SP is responsible for a variety of adverse clinical side effects. Water-soluble polymer 7, which contains salicylate residues azo linked at the 5-position to an inert polymer backbone, has been synthesized for the site-specific reductive release of 5-ASA in the lower bowel. Preparations of 7 deliver (chemical reduction) greater than 1.96 mmol of 5-ASA/g of polymer. In vitro studies with the polymer in anaerobic rat cecal bacteria demonstrated a reduction rate of approximately 1 mu equiv of azo bond h-1 (mL of cecal content)-1. A pharmacokinetic comparison of polymer and SASP showed similar deliveries of 5-ASA and metabolites to the lower bowel, blood, and urine of orally dosed rats. Polymer 7 proved more active than SASP or 5-ASA in the guinea pig ulcerative colitis model. Potential therapeutic advantages of 7 include nonabsorption/nonmetabolism in the small intestine, direct 5-ASA release at the disease site, and nonabsorption/nonmetabolism of the reduction-released carrier polymer.

  DOI：

  10.1021/jm00363a015
• 作为产物：
  描述：

  5-氨基水杨酸 以 苯 为溶剂， 以42%的产率得到5-乙酰氨基-2-乙酰氧基苯甲酸
  参考文献：
  名称：

  Benzoic acid derivatives and use thereof

  摘要：

  一种用于治疗牛皮癣的药物组合物包括4-氨基水杨酸（4-ASA）或5-氨基水杨酸（5-ASA）或其功能衍生物，所述药物组合物以适合局部给药的形式存在。此外，4-或5-ASA或其功能衍生物被用于制造治疗牛皮癣、特应性皮炎、过敏性皮炎、接触性皮炎、脂溢性皮炎或痤疮疾病的药物组合物。这些衍生物的化学式为：其中W为COOX，其中X为H、Li、Na、K、Mg0.5、Ca0.5、Zn0.5、Al0.33、Fe(II)0.5、Fe(III)0.33、NH4、NH3R1、NH2R12、NHR13、NR14或R1，其中R1为取代或未取代的C1-6-烷基、芳基-C1-4-烷基或杂环芳基-C1-4-烷基；或COX，其中X为NR1R1'，其中R1'具有与上述定义的R1相同的含义，R1和R1'可以相同也可以不同；Y为H或R1CO，其中R1如上定义；Z1和Z2，可能相同也可能不同，为H、R1或R1CO，其中R1如上定义，或Z1和Z2代表R2，其中R2为取代或未取代的C1-6-烷基亚甲基或芳基-C1-6-烷基亚甲基，或杂环芳基-C1-6-烷基亚甲基，或Z1、Z2与它们连接的氮原子一起可能代表3至7成员的饱和或不饱和杂环环，或可能代表具有化学式--N.dbd.N--R3的基团，其中R3为取代或未取代的芳基或取代或未取代的杂环芳基。

  公开号：

  US04933330A1

文献信息

• Aspirin Derivative 5-(Bis(3-methylbut-2-enyl)amino)-2-hydroxybenzoic Acid Improves Thermotolerance via Stress Response Proteins in Caenorhabditis elegans
  作者：Xiao-Bing Huang、Gui-Sheng Wu、Lei-Yu Ke、Xiao-Gang Zhou、Yue-Hu Wang、Huai-Rong Luo

  DOI：10.3390/molecules23061359

  日期：——

  Aging is a major risk factor for many prevalent diseases. Pharmacological intervention to improve the health span and extend the lifespan could be a preventive elixir for aging and age-related diseases. The non-steroid anti-inflammation medicine aspirin was reported to delay aging in Caenorhabditis elegans (C. elegans) and mice. We are wondering if the analogues of aspirin could also present antiaging activity. Here, we synthesized several aspirin derivatives and investigated their thermotolerance and antiaging effect in C. elegans. One of the compounds, 5-(bis(3-methylbut-2-en-1-yl)amino)-2-hydroxybenzoic acid, moderately increased the survival of C. elegans under heat stress, but could not extend the lifespan under optimum conditions. This compound could increase the mRNA level of stress response gene gst-4, and the mRNA and protein expression level of heat shock protein hsp-16.2 under heat stress. The failure of activating the transcription factor DAF-16 might explain why this compound could not act as aspirin to extend the lifespan of C. elegans. Our results would help further the investigation of the pharmacological activity of aspirin analogues and the relationship between structures and activity.

  衰老是许多常见疾病的主要危险因素。通过药物干预提高健康寿命和延长生命可能是延缓衰老和对抗年龄相关疾病的预防良药。非甾体抗炎药阿司匹林已被报道能延缓秀丽隐杆线虫(Caenorhabditis elegans, C. elegans)和小鼠的衰老。我们想知道阿司匹林的类似物是否也能表现出抗衰老活性。本研究中，我们合成了几种阿司匹林衍生物，并检测了它们在C. elegans中的耐热性和抗衰老作用。其中一种化合物，5-(双(3-甲基丁-2-烯-1-基)氨基)-2-羟基苯甲酸，在热胁迫下适度提高C. elegans的存活率，但不能在最佳条件下延长其寿命。该化合物能在热胁迫下增加应激反应基因gst-4的mRNA水平，以及热休克蛋白hsp-16.2的mRNA和蛋白表达水平。未能激活转录因子DAF-16可能是该化合物不能像阿司匹林那样延长C. elegans寿命的原因。我们的结果将进一步推动对阿司匹林类似物药理活性的研究，以及它们结构与活性之间的关系。
• 3,7-Disubstituted-3-cephem-4-carboxylic acids
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04350692A1

  公开（公告）日：1982-09-21

  Preparation of pharmaceutical composition comprising, treatment of human and animal diseases with, and compounds of, 3,7-disubstituted-3-cephem-4-carboxylic acid.

  含有3,7-二取代-3-头孢基-4-羧酸化合物的制药组合物的制备，以及用于治疗人类和动物疾病的方法。
• Aminosalicylic-acid derivatives for the treatment of psoriasis
  申请人：DAK-LABORATORIET A/S

  公开号：EP0291159A2

  公开（公告）日：1988-11-17

  A pharmaceutical composition for use in the treatment of psoriasis comprises 4-aminosalicylic acid (4-ASA) or 5-aminosalicylic acid (5-ASA) or a functional derivative thereof, said pharmaceutical composition being in a form suitable for topical administration. Furthermore, 4-or 5-ASA or a functional derivative thereof are used for the manufacture of pharmaceutical compositions for treating psoriasis, atopic dermatitis, allergic dermatitis, contact dermatitis, seborrhoic dermatitis, or acne diseases. The derivatives have the formulae: where W is COOX, wherein X is H, Li, Na, K, Mg0.5, Ca0.5, Zn0.5, Al0.33, Fe(II)0.5, Fe(III)0.33, NH₄, NH₃R¹, NH₂R¹₂, NHR¹₃, NR¹₄, or R¹, where R¹ is substituted or unsubstituted C1-6-alkyl, aryl-C1-4-alkyl, or heteroaryl-C1-4-alkyl; or COX, where X is NR¹R1ʹ, where R1ʹ has the same meaning as R¹ defined above and R¹ and R¹ʹ may be identical or different; Y is H or R¹CO, where R¹ is defined as above; Z¹ and Z², which may be identical or non-identical are H, R¹ or R¹CO, where R¹ is defined as above, or Z¹ and Z² represent R², where R² is substituted or unsubstituted C1-6-alkylidene or aryl-C1-6-alkylidene, or heteroaryl-C1-6-alkylidene, or Z¹, Z² together with the nitrogen atom to which they are attached may represent a 3 to 7 membered saturated or unsaturated heterocyclic ring, or may represent a group of the formula - N=N-R³ where R³ is substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl.

  一种用于治疗牛皮癣的药物组合物包含 4-氨基水杨酸（4-ASA）或 5-氨基水杨酸（5-ASA）或其功能衍生物，所述药物组合物为适合局部用药的形式。此外，4-ASA 或 5-ASA 或其功能衍生物可用于制造治疗牛皮癣、特应性皮炎、过敏性皮炎、接触性皮炎、脂溢性皮炎或痤疮的药物组合物。这些衍生物的化学式如下 其中 W 是 COOX，其中 X 是 H、Li、Na、K、Mg0.5、Ca0.5、Zn0.5、Al0.33、Fe(II)0.5、Fe(III)0.33、NH₄、NH₃R¹、NH₂R¹₂、NHR¹₃、NR¹₄或 R¹，其中 R¹ 是取代或未取代的 C1-6-烷基、芳基-C1-4-烷基或杂芳基-C1-4-烷基；或 COX，其中 X 是 NR¹R1ʹ，其中 R1ʹ与上文定义的 R¹ 意义相同，且 R¹ 和 R¹ʹ 可以相同或不同；Y 是 H 或 R¹CO，其中 R¹ 定义如上；Z¹和Z²可以是相同或不相同的H、R¹或R¹CO，其中R¹定义如上，或者Z¹和Z²代表R²，其中R²是取代或未取代的C1-6-亚烷基或芳基-C1-6-亚烷基，或杂芳基-C1-6-亚烷基，或Z¹、Z²与所连接的氮原子一起可代表 3 至 7 个成员的饱和或不饱和杂环，或代表式 - N=N-R³ 的基团，其中 R³ 是取代或未取代的芳基或取代或未取代的杂芳基。
• Puxeddu, Gazzetta Chimica Italiana, 1929, vol. 59, p. 14
  作者：Puxeddu

  DOI：——

  日期：——
• US4350692A
  申请人：——

  公开号：US4350692A

  公开（公告）日：1982-09-21