methyl 4-butoxy-3-nitrobenzoate | 4906-26-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-butoxy-3-nitrobenzoate
• 英文别名: methyl 3-nitro-4-butoxybenzoate
• CAS: 4906-26-7
• 化学式: C₁₂H₁₅NO₅
• mdl: MFCD12558967
• 分子量: 253.255
• InChiKey: FDKWUYUKUDJVML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-butoxy-3-nitrobenzoate 在 氯化亚砜 、 sodium hydroxide 作用下， 以 甲醇 、 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：

  Discovery of 4‐(isopentyloxy)‐3‐nitrobenzamide derivatives as xanthine oxidase inhibitors through a non‐anthraquinone exploration

  摘要：

  In 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：

  3-硝基-4-羟基苯甲酸甲酯 、 正溴丁烷 以to afford methyl 4-butoxy-3-nitrobenzoate 68 (260 mg, 1.027 mmol, 67.5% yield) as a white solid的产率得到methyl 4-butoxy-3-nitrobenzoate
  参考文献：
  名称：

  3-AMIDOBENZAMIDES AND USES THEREOF FOR INCREASING CELLULAR LEVELS OF A3G AND OTHER A3 FAMILY MEMBERS

  摘要：

  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。

  公开号：

  US20160052870A1

文献信息

• US9688637B2
  申请人：——

  公开号：US9688637B2

  公开（公告）日：2017-06-27
• [EN] 3-AMIDOBENZAMIDES AND USES THEREOF FOR INCREASING CELLULAR LEVELS OF A3G<br/>[FR] 3-AMIDOBENZAMIDES ET LEURS UTILISATIONS POUR AUGMENTER LES TAUX CELLULAIRES D'A3G
  申请人：UNIV NORTHWESTERN

  公开号：WO2016029136A1

  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.