2-butoxy-5-nitro-benzoic acid methyl ester | 911282-06-9

• 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: 2-butoxy-5-nitro-benzoic acid methyl ester
• 英文别名: Methyl 2-butoxy-5-nitrobenzoate
• CAS: 911282-06-9
• 化学式: C₁₂H₁₅NO₅
• 分子量: 253.255
• InChiKey: ZHZHADPZDHJENH-UHFFFAOYSA-N

物化性质

• 沸点：
  385.5±22.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  2-butoxy-5-nitro-benzoic acid methyl ester 在 palladium on activated charcoal 哌啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 29.0h， 生成 5-Acetylamino-N-(5-amino-2,4-diethoxy-phenyl)-2-butoxy-benzamide
  参考文献：
  名称：

  Hydrogen-Bonding-Mediated Anthranilamide Homoduplexes. Increasing Stability through Preorganization and Iterative Arrangement of a Simple Amide Binding Site

  摘要：

  This paper describes the assembly of two new series of self-complementary duplexes by making use of amide units, the simplest assembling units of hydrogen bonding, as binding sites. All the new monomers possess a rigidified anthranilamide skeleton, which is stabilized by intramolecular hydrogen bonding. Amide units are iteratively introduced to one side of the preorganized skeletons to facilitate the formation of intermolecular hydrogen bonding. Compounds 2 and 3 bear two and three CONH2 units, respectively, while 4, 6, and 7 are incorporated with two, three, and four AcNH units, respectively. For comparison, compound 5, which is similar to 4 but contains one AcNH and one CF3CONH unit, is also prepared. X-ray diffraction analysis of 2, 4, and 5 revealed homodimeric motifs in the solid state which are stabilized by two or more intermolecular hydrogen bonds. H-1 NMR investigations in CDCl3 indicated that all the compounds form hydrogen-bonded homoduplexes. Duplexes 3(.)3, 6(.)6, and 7(.)7 are highly stable in CDCl3, with a lower K-assoc limit of 2.3 x 10(5) M-1. The K-assoc values of the three duplexes in more polar CDCl3/CD3CN (9:1, v/v) were determined with the H-1 NMR dilution method. The result opens the way for the development of new polymeric duplexes of well-ordered structures.

  DOI：

  10.1021/ja064218i
• 作为产物：
  描述：

  2-丁氧基苯甲酸甲酯 在 硫酸 、 硝酸 作用下， 反应 1.0h， 以70%的产率得到2-butoxy-5-nitro-benzoic acid methyl ester
  参考文献：
  名称：

  Hydrogen-Bonding-Mediated Anthranilamide Homoduplexes. Increasing Stability through Preorganization and Iterative Arrangement of a Simple Amide Binding Site

  摘要：

  This paper describes the assembly of two new series of self-complementary duplexes by making use of amide units, the simplest assembling units of hydrogen bonding, as binding sites. All the new monomers possess a rigidified anthranilamide skeleton, which is stabilized by intramolecular hydrogen bonding. Amide units are iteratively introduced to one side of the preorganized skeletons to facilitate the formation of intermolecular hydrogen bonding. Compounds 2 and 3 bear two and three CONH2 units, respectively, while 4, 6, and 7 are incorporated with two, three, and four AcNH units, respectively. For comparison, compound 5, which is similar to 4 but contains one AcNH and one CF3CONH unit, is also prepared. X-ray diffraction analysis of 2, 4, and 5 revealed homodimeric motifs in the solid state which are stabilized by two or more intermolecular hydrogen bonds. H-1 NMR investigations in CDCl3 indicated that all the compounds form hydrogen-bonded homoduplexes. Duplexes 3(.)3, 6(.)6, and 7(.)7 are highly stable in CDCl3, with a lower K-assoc limit of 2.3 x 10(5) M-1. The K-assoc values of the three duplexes in more polar CDCl3/CD3CN (9:1, v/v) were determined with the H-1 NMR dilution method. The result opens the way for the development of new polymeric duplexes of well-ordered structures.

  DOI：

  10.1021/ja064218i

文献信息

• 一种2-丁氧基-5-[3-（2,5-二乙氧基-4-甲磺酰基-苄基）-脲基]-苯甲酸甲酯新化合物、制备方法及用途
  申请人：齐鲁工业大学

  公开号：CN105820077A

  公开（公告）日：2016-08-03

  本发明提供了一种新化合物，该化合物的名称为2-丁氧基-5-[3-（2,5-二乙氧基-4-甲磺酰基-苄基）-脲基]-苯甲酸甲酯，该化合物的分子量为537.6，该化合物的结构见结构式（化合物1）；同时本发明提供了该化合物1的制备方法；本发明提供的化合物有很好的类药性，可用于新药研究领域尤其是II型糖尿病创新药物研究领域。
• Discovery of novel high potent and cellular active ADC type PTP1B inhibitors with selectivity over TC-PTP via modification interacting with C site
  作者：Yongli Du、Yanhui Zhang、Hao Ling、Qunyi Li、Jingkang Shen

  DOI：10.1016/j.ejmech.2017.12.064

  日期：2018.1

  PTP1B serving as a key negative regulator of insulin signaling is a novel target for type 2 diabetes and obesity. Modification at ring B of N-4-[(3-Phenyl-ureido)-methyl]-phenyl}-methane-sulfonamide template to interact with residues Arg47 and Lys41 in the C site of PTP1B by molecular docking aided design resulted in the discovery of a series of novel high potent and selective inhibitors of PTP1B

  PTP1B作为胰岛素信号的关键负调节剂，是2型糖尿病和肥胖症的新靶标。通过分子对接辅助设计修饰N- 4-[（3-苯基-脲基）-甲基]-苯基}-甲烷磺酰胺模板的B环，使其与PTP1B C位的残基Arg47和Lys41相互作用。发现一系列新型的PTP1B高效抑制剂。与PTP1B的C位点相互作用的结构活性关系已得到很好的说明。化合物8和18被证明是高效，最有前途的PTP1B抑制剂，与高度同源的TCPTP和其他PTP相比，具有细胞活性和极大的选择性。
• The discovery of novel, potent ERR-alpha inverse agonists for the treatment of triple negative breast cancer
  作者：Yongli Du、Lianhua Song、Liudi Zhang、Hao Ling、Yanhui Zhang、Haifei Chen、Huijie Qi、Xiaojin Shi、Qunyi Li

  DOI：10.1016/j.ejmech.2017.04.050

  日期：2017.8

  The estrogen-related receptor alpha (ERR alpha) is an orphan receptor and a novel target for solid tumor therapy, conceivably through effects on the regulation of tumor cell energy metabolism associated with energy stress within solid tumor micro environments. Here we describe the discovery of novel potent inverse agonists of ERR alpha. In vitro, compound 11 potently inhibits ERR alpha's transcriptional activity by preventing endogenous PGC-1 alpha and ERR alpha binding and suppresses the proliferation of different human cancer cell lines and the migration of breast cancer cells (MDA-MB-231). In vivo, compound 11 demonstrates a strong inhibitory effect on the growth of human breast cancer xenografts (MDA-MB-231) and the tumor growth is inhibited by 40.9% after treating with compound 11 (30 mg/kg). The binding mode shows that compound 11 interacts with the binding pocket of ERR alpha through hydrogen interactions with the residue Gly397 and hydrophobic interactions with the hydrophobic residues. All these results suggest that compound 11 represents a novel potent ERR alpha inverse agonist and is promising in the discovery of antitumor compounds for the treatment of triple negative breast cancer. (C) 2017 Published by Elsevier Masson SAS.