4-丁氧基-3-硝基苯甲酸 | 4906-28-9

• 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: 4-丁氧基-3-硝基苯甲酸
• 英文名称: 4-butoxy-3-nitro benzoic acid
• 英文别名: 3-nitro-4-butoxybenzoic acid；4-butoxy-3-nitrobenzoic acid；4-butoxy-3-nitro-benzoic acid；4-Butoxy-3-nitro-benzoesaeure；4-n-butoxy-3-nitrobenzoic acid
• CAS: 4906-28-9
• 化学式: C₁₁H₁₃NO₅
• mdl: MFCD09743859
• 分子量: 239.228
• InChiKey: WMMDYUIWNRMKKM-UHFFFAOYSA-N

物化性质

• 熔点：
  166-167 °C
• 沸点：
  397.1±27.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  4-丁氧基-3-硝基苯甲酸 在 氯化亚砜 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.75h， 生成 N-(3-nitro-4-butoxybenzoyl)-L-phenylglycine
  参考文献：
  名称：

  10.1002/ardp.202400137

  摘要：

  AbstractIn our previous study, we reported a series of N‐(9,10‐anthraquinone‐2‐carbonyl) amino acid derivatives as novel inhibitors of xanthine oxidase (XO). Recognizing the suboptimal drug‐like properties associated with the anthraquinone moiety, we embarked on a nonanthraquinone medicinal chemistry exploration in the current investigation. Through systematic structure–activity relationship (SAR) studies, we identified a series of 4‐(isopentyloxy)‐3‐nitrobenzamide derivatives exhibiting excellent in vitro potency against XO. The optimized compound, 4‐isopentyloxy‐N‐(1H‐pyrazol‐3‐yl)‐3‐nitrobenzamide (6k), demonstrated exceptional in vitro potency with an IC50 value of 0.13 μM. Compound 6k showed favorable drug‐like characteristics with ligand efficiency (LE) and lipophilic ligand efficiency (LLE) values of 0.41 and 3.73, respectively. In comparison to the initial compound 1d, 6k exhibited a substantial 24‐fold improvement in IC50, along with a 1.6‐fold enhancement in LE and a 3.7‐fold increase in LLE. Molecular modeling studies provided insights into the strong interactions of 6k with critical amino acid residues within the active site. Furthermore, in vivo hypouricemic investigations convincingly demonstrated that 6k significantly reduced serum uric acid levels in rats. The MTT results revealed that compound 6k is nontoxic to healthy cells. The gastric and intestinal stability assay demonstrated that compound 6k exhibits good stability in the gastric and intestinal environments. In conclusion, compound 6k emerges as a promising lead compound, showcasing both exceptional in vitro potency and favorable drug‐like characteristics, thereby warranting further exploration.

  DOI：

  10.1002/ardp.202400137
• 作为产物：
  描述：

  4-羟基-3-硝基苯甲酸 在 sodium hydroxide 、 硫酸 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-丁氧基-3-硝基苯甲酸
  参考文献：
  名称：

  Prasad, Veena; Rao, D. S. Shankar; Prasad, S. Krishna, Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2003, vol. 397, p. 79 - 88

  摘要：

  DOI：

文献信息

• Substituted N-aryl heterocycles, process for their preparation and their use as medicaments
  申请人：Aventis Pharma Deutschland GmbH

  公开号：US20040220191A1

  公开（公告）日：2004-11-04

  The invention relates to substituted N-aryl heterocycles and to the physiologically tolerated salts and physiologically functional derivatives thereof. Compounds of the formula I 1 in which the radicals have the stated meanings, the N-oxides and the physiologically tolerated salts thereof and process for the preparation thereof are described. The compounds are suitable for example as anorectic agents.

  这项发明涉及取代N-芳基杂环化合物及其生理耐受盐和生理功能衍生物。式I的化合物 1 其中基团具有所述含义，其N-氧化物及其生理耐受盐以及其制备方法被描述。这些化合物例如适用作为厌食剂。
• PROCESS FOR PRODUCING 3-NITRO-4-ALKOXYBENZOIC ACID
  申请人：Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo

  公开号：EP1621528A1

  公开（公告）日：2006-02-01

  The present invention provides a process for preparing 3-nitro-4-alkoxybenzoic acid, which comprises the step of subjecting a mixture comprising 4-alkoxybenzoic acid and 40-80% nitric acid, wherein the amount of the 40-80% nitric acid is equal to or more than 8 times that of 4-alkoxybenzoic acid by weight, to a reaction at a temperature of 30-100°C.

  本发明提供了一种制备3-硝基-4-烷氧基苯甲酸的方法，包括将含有4-烷氧基苯甲酸和40-80%硝酸的混合物置于30-100°C的温度下反应，其中40-80%硝酸的量按重量至少是4-烷氧基苯甲酸的8倍。
• Substituted N-aryl Heterocycles, Process For Their Preparation and Their Use As Medicaments
  申请人：Schwink Lothar

  公开号：US20070207991A1

  公开（公告）日：2007-09-06

  The invention relates to substituted N-aryl heterocycles and to the physiologically tolerated salts and physiologically functional derivatives thereof. Compounds of the formula I in which the radicals have the stated meanings the N-oxides and the physiologically tolerated salts thereof and process for the preparation thereof are described. The compounds are suitable for example as anorectic agents.

  该发明涉及取代的N-芳基杂环化合物及其生理耐受盐和生理功能衍生物。描述了公式I中化合物，其中基团具有所述的含义，以及其N-氧化物和生理耐受盐和其制备方法。这些化合物例如适用于作为抑制食欲的药物。
• 3-AMIDOBENZAMIDES AND USES THEREOF FOR INCREASING CELLULAR LEVELS OF A3G AND OTHER A3 FAMILY MEMBERS
  申请人：Northwestern University

  公开号：US20160052870A1

  公开（公告）日：2016-02-25

  Disclosed are novel benzamide compounds and the uses thereof for treating diseases and disorders in a patient in need thereof by increasing cellular levels of A3G and/or other members of the A3 family of proteins in the patient. The disclosed compounds include 3 -benzamide compounds that may be administered to treat an HIV-1 infection or cancer in a patient.

  本发明涉及一种新型苯甲酰胺化合物及其用途，通过增加患者体内A3G和/或A3家族蛋白的细胞水平来治疗患者需要的疾病和障碍。所披露的化合物包括3-苯甲酰胺化合物，可用于治疗患者的HIV-1感染或癌症。
• Derivatives of 4-Amino-2-hydroxybenzoic Acid. II
  作者：R. O. Clinton、U. J. Salvador、S. C. Laskowski、Mary Wilson

  DOI：10.1021/ja01123a005

  日期：1952.2