4-amino-2-benzyloxybenzoic acid | 193803-83-7

• 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: 4-amino-2-benzyloxybenzoic acid
• 英文别名: 4-Amino-2-phenylmethoxybenzoic acid
• CAS: 193803-83-7
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: XVCMYXIQBHPGHZ-UHFFFAOYSA-N

物化性质

• 熔点：
  160 °C
• 沸点：
  465.5±35.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-2-benzyloxybenzoic acid 、 苯甲醛 在 sodium cyanoborohydride 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以34%的产率得到4-benzylamino-2-benzyloxybenzoic acid
  参考文献：
  名称：

  Selective endothelin A receptor ligands. 1. Discovery and structure-activity of 2,4-disubstituted benzoic acid derivatives

  摘要：

  This paper describes the discovery of a new non-peptide endothelin A (ETA) selective ligand, 2,4-dibenzyloxybenzoic acid 3, which inhibits the binding of [I-125]ET-1 to ETA receptors with an IC50 of 9 mu M (ET-1 = endothelin-1). Optimisation of 3 resulted in compound 52 which had an IC50 of 1 mu M. One of the analogues of 3, compound 15, was examined in a functional assay and shown to antagonise ET-1-induced contraction of rat aorta. The identification of 3 was made through the application of ChemDBS-3D searching of our corporate database. The 3D query, using an aromatic ring to a carboxylic acid group separated by 10.2 +/- 1.1 Angstrom, was derived from an examination of common pharmacophoric distances found in the low energy conformations of two known ETA antagonists, the cyclic pentapeptide BQ 123 1 and myriceron caffeoyl ester 2.

  DOI：

  10.1016/s0223-5234(97)81678-9
• 作为产物：
  描述：

  4-硝基水杨酸 在 sodium hydroxide 、 乙醇 、 铂 作用下， 生成 4-amino-2-benzyloxybenzoic acid
  参考文献：
  名称：

  Jensen; Ingvorsen, Acta Chemica Scandinavica (1947), 1952, vol. 6, p. 161,164

  摘要：

  DOI：

文献信息

• Design, synthesis, and <i>in vitro</i> evaluation of BP-1-102 analogs with modified hydrophobic fragments for STAT3 inhibition
  作者：Patrik Oleksak、Miroslav Psotka、Marketa Vancurova、Olena Sapega、Jana Bieblova、Milan Reinis、David Rysanek、Romana Mikyskova、Katarina Chalupova、David Malinak、Jana Svobodova、Rudolf Andrys、Helena Rehulkova、Vojtech Skopek、Pham Ngoc Lam、Jiri Bartek、Zdenek Hodny、Kamil Musilek

  DOI：10.1080/14756366.2020.1871336

  日期：2021.1.1

  Twelve novel analogs of STAT3 inhibitor BP-1-102 were designed and synthesised with the aim to modify hydrophobic fragments of the molecules that are important for interaction with the STAT3 SH2 domain. The cytotoxic activity of the reference and novel compounds was evaluated using several human and two mouse cancer cell lines. BP-1-102 and its two analogs emerged as effective cytotoxic agents and were further tested in additional six human and two murine cancer cell lines, in all of which they manifested the cytotoxic effect in a micromolar range. Reference compound S3I-201.1066 was found ineffective in all tested cell lines, in contrast to formerly published data. The ability of selected BP-1-102 analogs to induce apoptosis and inhibition of STAT3 receptor-mediated phosphorylation was confirmed. The structure-activity relationship confirmed a demand for two hydrophobic substituents, i.e. the pentafluorophenyl moiety and another spatially bulky moiety, for effective cytotoxic activity and STAT3 inhibition.
• Foye; Feldmann, Journal of the American Pharmaceutical Association (1912), 1956, vol. 45, p. 30,33
  作者：Foye、Feldmann

  DOI：——

  日期：——
• Selective endothelin A receptor ligands. 1. Discovery and structure-activity of 2,4-disubstituted benzoic acid derivatives
  作者：PC Astles、TJ Brown、CM Handscombe、MF Harper、NV Harris、RA Lewis、PM Lockey、C McCarthy、IM McLay、B Porter、AG Roach、C Smith、RJA Walsh

  DOI：10.1016/s0223-5234(97)81678-9

  日期：1997.5

  This paper describes the discovery of a new non-peptide endothelin A (ETA) selective ligand, 2,4-dibenzyloxybenzoic acid 3, which inhibits the binding of [I-125]ET-1 to ETA receptors with an IC50 of 9 mu M (ET-1 = endothelin-1). Optimisation of 3 resulted in compound 52 which had an IC50 of 1 mu M. One of the analogues of 3, compound 15, was examined in a functional assay and shown to antagonise ET-1-induced contraction of rat aorta. The identification of 3 was made through the application of ChemDBS-3D searching of our corporate database. The 3D query, using an aromatic ring to a carboxylic acid group separated by 10.2 +/- 1.1 Angstrom, was derived from an examination of common pharmacophoric distances found in the low energy conformations of two known ETA antagonists, the cyclic pentapeptide BQ 123 1 and myriceron caffeoyl ester 2.
• Jensen; Ingvorsen, Acta Chemica Scandinavica (1947), 1952, vol. 6, p. 161,164
  作者：Jensen、Ingvorsen

  DOI：——

  日期：——