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Chemical Compound Review

CHEMBL341103     2-[4-[(2S)-2-acetamido-2-[4- (3-hydroxy-2...

Synonyms: CHEBI:311515, KB-75314, AC1L9LQ8, 1qxk, 918657-87-1
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Disease relevance of Compound 20

  • Compound 20 showed potent anti-HIV activity with EC50 values of 0.0085 microM against NL4-3, 0.021 microM against PI-R (a multiple protease inhibitor resistant strain), and 0.13 microM against FHR-2 (an HIV strain resistant to 8) [1].

High impact information on Compound 20


Biological context of Compound 20


Anatomical context of Compound 20

  • Diphenolic hydrazone (compound 6) showed maximum uterotrophic inhibition of 70%, whereas compound 20 exhibited cytotoxicity in the range of 50-70% against MCF-7 and ZR-75-1 human malignant breast cell lines [12].

Associations of Compound 20 with other chemical compounds

  • A (2-hydroxy-phenoxy) acetic acid-based phosphotyrosyl mimetic has been linked with an optimized second arylphosphate binding site ligand to produce compound 20 with low micromolar potency against PTP1B, good selectivity over TCPTP (20-fold) and high cell permeability in the Caco-2 system [13].
  • Oximes 15, 16 and compound 20 with a higher degree of oxidation in ring A have been found active in a 60 cell line antitumor prescreen by virtue of their cytotoxic effect against one or more tumor cell line and were further referred for in vivo hollow fiber bioassay [14].

Gene context of Compound 20

  • Among the standard compounds tested, L 652,243 was the most active compound in this test with an ED50 value of 0.01 mg/ear and 1 mg/kg po, but unlike this compound, 20 is a selective inhibitor of 5-LO (IC50 = 2 microM) without any significant activity against CO (IC50 greater than 50 microM) [15].
  • Optimization of this compound class led to compound 20, which inhibits p38alpha in vitro with IC(50)=14 nM and is active in the mouse TNFalpha-release model [16].
  • Compound 20 did not show any agonist activity but was able to inhibit gastrin-induced acid secretion, with lower potency (ED50 = 15 mg/kg) [17].
  • DFT calculations [B3LYP/6-31G(d)] on compound 20 gave important parameters of this pyramidalized alkene, such as the pyramidalization angle (61.7 degrees), the strain energy (72.9 kcal/mol), and the HOMO/LUMO gap (3.79 eV) [18].
  • Furthermore, TZS-8478 (10 mg/kg per day, p.o., for 5 days) had no stimulative effect on uterine growth in ovariectomized rats, and its desulfamoylated compound (20) was little bound to the human estrogen receptor alpha [19].

Analytical, diagnostic and therapeutic context of Compound 20

  • Compound 20 was also studied with microdialysis (to determine effects on DA turnover in striatum) and in unilaterally 6-OH-DA lesioned rats (to determine their potential as DA agonists) [20].


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