2-(5-chloro-2-hydroxylbenzylideneamino)benzoic acid | 74240-56-5

• 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-(5-chloro-2-hydroxylbenzylideneamino)benzoic acid
• 英文别名: (5-chloro-salicylidene)-anthranilic acid；N-(5-chloro-2-hydroxy-benzyliden)-anthranilic acid；N-(5-Chlor-2-hydroxy-benzyliden)-anthranilsaeure；N-<5-Chlor-salicyliden>-anthranilsaeure；N-(2-Carboxyphenyl)-5-chlor-salicylaldimin；2-[(5-Chloro-2-hydroxyphenyl)methylideneamino]benzoic acid
• CAS: 74240-56-5
• 化学式: C₁₄H₁₀ClNO₃
• 分子量: 275.691
• InChiKey: QWFRBJDSYMNYSJ-UHFFFAOYSA-N

物化性质

• 沸点：
  518.1±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(5-chloro-2-hydroxylbenzylideneamino)benzoic acid 在 溶剂黄146 、 铂 作用下， 生成 N-(5-chloro-2-hydroxy-benzyl)-anthranilic acid
  参考文献：
  名称：

  Reisner; Borick, Journal of the American Pharmaceutical Association (1912), 1955, vol. 44, p. 148

  摘要：

  DOI：
• 作为产物：
  描述：

  邻氨基苯甲酸 、 5-氯代水杨醛 以 乙醇 为溶剂， 反应 3.0h， 以80%的产率得到2-(5-chloro-2-hydroxylbenzylideneamino)benzoic acid
  参考文献：
  名称：

  Synthesis and evaluation of copper complexes of Schiff-base condensates from 5-substituted-2-hydroxybenzaldehyde and 2-substituted-benzenamine as selective inhibitors of protein tyrosine phosphatases

  摘要：

  Five copper complexes, [Cu(bhbb,chbb,ohbb)(H2O)(n)] (tridentate-ligands: H(2)bhbb = 2-(5-bromo-2-hydroxylbenzylideneamino)benzoic acid, 1; H(2)chbb = 2-(5-chloro-2-hydroxylbenzylideneamino)benzoic acid, 2; H(2)nhbb = 2-(5-nitro-2-hydroxyl-benzylideneamino)benzoic acid, 3) and [Cu(cpmp,npmp)(2)] (bidentate-ligands: Hcpmp = 4-chloro-2-((phenylimino)methyl)phenol, 4; Hnpmp = 4-bromo-2-((phenyl-imino)methyl)phenol, 5) have been prepared and characterized by EA, IR, EPR UV-Vis, and ESI-MS. Structure-activity relationship of copper complexes in inhibiting protein tyrosine phosphatases (protein tyrosine phosphatase 1B, PTP1B; T-cell protein tyrosine phosphatase, TCPTP; megakaryocyte protein-tyrosine phosphatase, PTP-MEG2; Src homology phosphatase 1, SHP-1 and Src homology phosphatase 2, SHP-2) is investigated. Inhibitory activities of complexes against the five PTPs indicate that they potently inhibit PTP1B, TCPTP, PTP-MEG2 and SHP-1, but do not inhibit SHP-2. In the complexes, 5 exhibits very strong inhibition (IC50, 0.059 mu M) and better selectivity against PTP1B while 1 and 2 show very strong inhibition (IC50 = 0.089 and 0.067 mu M) and a little selectivity against TCPTP. Compared with the oxovanadium(IV) complexes of same ligands, the copper complexes increase the inhibitory ability against TCPTP, PTP-MEG2 and SHP-1 but decrease the inhibition against SHP-2. For complex 5, the inhibition over PTP1B, TCPTP, PTP-MEG2 and SHP-1 are all improved about 5- to 15-fold compared with the oxovanadium(IV) complex. The results demonstrate that both the ligand structures and the center metals influence the inhibition and selectivity against different PTPs. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.05.018

文献信息

• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Cu: MVol.B4, 169, page 1821 - 1824
  作者：

  DOI：——

  日期：——
• Agarwal, A. K.; Kumar, R.; Singh, N., 1980, vol. 27, p. 31 - 35
  作者：Agarwal, A. K.、Kumar, R.、Singh, N.、Kansal, B. D.

  DOI：——

  日期：——
• Muto, Y., Bulletin of the Chemical Society of Japan, 1960, vol. 33, p. 1242 - 1247
  作者：Muto, Y.

  DOI：——

  日期：——
• Muto, Nippon Kagaku Zasshi, 1955, vol. 76, p. 1407,1408
  作者：Muto

  DOI：——

  日期：——
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Th: SVol.E, 1.8.4, page 184 - 198
  作者：

  DOI：——

  日期：——