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147923-08-8-BOC-L-4,4/'-BIPHENYLALANINE BOC-L-4,4/'-BIPHENYLALANINE

BOC-L-4,4/'-BIPHENYLALANINE

For research use only. Not for therapeutic Use.

  • CAT Number: M093220
  • CAS Number: 147923-08-8
  • Molecular Formula: C20H23NO4
  • Molecular Weight: 341.407
  • Purity: ≥95%
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Related Small Molecules: ALLYL METHACRYLATES CROSSPOLYMER     6-Methoxyisoindole     H-PHG-OME HCL    

Catalog Number M093220
CAS Number 147923-08-8
Synonyms

(S)-3-([1,1′-Biphenyl]-4-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid

Molecular Formula C20H23NO4
Purity ≥95%
Storage -20°C
IUPAC Name (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-phenylphenyl)propanoic acid
InChI InChI=1S/C20H23NO4/c1-20(2,3)25-19(24)21-17(18(22)23)13-14-9-11-16(12-10-14)15-7-5-4-6-8-15/h4-12,17H,13H2,1-3H3,(H,21,24)(H,22,23)/t17-/m0/s1
InChIKey NBVVKAUSAGHTSU-KRWDZBQOSA-N
SMILES CC(C)(C)OC(=O)NC(CC1=CC=C(C=C1)C2=CC=CC=C2)C(=O)O
Reference

[1]. ChemMedChem. 2016 Sep 20;11(18):2063-83. doi: 10.1002/cmdc.201600218. Epub 2016 Aug 9.<br />
4-Biphenylalanine- and 3-Phenyltyrosine-Derived Hydroxamic Acids as Inhibitors of the JumonjiC-Domain-Containing Histone Demethylase KDM4A.<br />
Morera L(1), Roatsch M(1), F&uuml;rst MC(2), Hoffmann I(1), Senger J(1), Hau M(1), Franz H(3)(4), Sch&uuml;le R(3), Heinrich MR(2), Jung M(5).<br />
Author information: (1)Institute of Pharmaceutical Sciences, Albert Ludwigs University Freiburg, Albertstra&szlig;e 25, 79104, Freiburg im Breisgau, Germany. (2)Department of Chemistry and Pharmacy, Friedrich Alexander University ErlangenNuremberg, Schuhstra&szlig;e 19, 91052, Erlangen, Germany. (3)Central Clinical Research, University Medical Center Freiburg, Breisacher Stra&szlig;e 66, 79106, Freiburg im Breisgau, Germany. (4)Institute of Anatomy and Cell Biology, Albert Ludwigs University Freiburg, Albertstra&szlig;e 17, 79104, Freiburg im Breisgau, Germany. (5)Institute of Pharmaceutical Sciences, Albert Ludwigs University Freiburg, Albertstra&szlig;e 25, 79104, Freiburg im Breisgau, Germany. [email protected].<br />
Overexpression of the histone lysine demethylase KDM4A, which regulates H3K9 and H3K36 methylation states, has been related to the pathology of several human cancers. We found that a previously reported hydroxamate-based histone deacetylase (HDAC) inhibitor (SW55) was also able to weakly inhibit this demethylase with an IC50 value of 25.4 &mu;m. Herein we report the synthesis and biochemical evaluations, with two orthogonal in vitro assays, of a series of derivatives of this lead structure. With extensive chemical modifications on the lead structure, also by exploiting the versatility of the radical arylation with aryldiazonium salts, we were able to increase the potency of the derivatives against KDM4A to the low-micromolar range and, more importantly, to obtain demethylase selectivity with respect to HDACs. Cell-permeable derivatives clearly showed a demethylase-inhibition-dependent antiproliferative effect against HL-60 human promyelocytic leukemia cells. &copy; 2016 WILEY-VCH Verlag GmbH &amp; Co. KGaA, Weinheim. DOI: 10.1002/cmdc.201600218 PMID: 27505861 [Indexed for MEDLINE]

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