Fmoc-3,4-difluoro-D-phenylalanine
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Fmoc-3,4-difluoro-D-phenylalanine

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Category
Fluorinated amino acids
Catalog number
BAT-007334
CAS number
198545-59-4
Molecular Formula
C24H19F2NO4
Molecular Weight
423.41
Fmoc-3,4-difluoro-D-phenylalanine
IUPAC Name
(2R)-3-(3,4-difluorophenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
Fmoc-D-Phe(3,4-DiF)-OH; Fmoc-3,4-difluoro-D-Phe-OH; (R)-Fmoc-2-amino-3-(3,4-difluorophenyl)propionic acid
Related CAS
198560-43-9 (L-isomer)
Appearance
White crystalline powder
Purity
≥ 98% (HPLC)
Density
1.357 g/cm3
Melting Point
154-161 °C
Boiling Point
622.7°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C24H19F2NO4/c25-20-10-9-14(11-21(20)26)12-22(23(28)29)27-24(30)31-13-19-17-7-3-1-5-15(17)16-6-2-4-8-18(16)19/h1-11,19,22H,12-13H2,(H,27,30)(H,28,29)/t22-/m1/s1
InChI Key
IHSYIDJNVXPQRM-JOCHJYFZSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC(=C(C=C4)F)F)C(=O)O
1.TMP-153, a novel ACAT inhibitor, inhibits cholesterol absorption and lowers plasma cholesterol in rats and hamsters.
Sugiyama Y1, Ishikawa E, Odaka H, Miki N, Tawada H, Ikeda H. Atherosclerosis. 1995 Feb;113(1):71-8.
Effects of TMP-153, N-[4-(2-chlorophenyl)-6,7-dimethyl-3-quinolyl]-N'-(2,4-difluorophe nyl)urea, on intestinal and hepatic acyl-CoA:cholesterol acyltransferase (ACAT) activities, cholesterol absorption and plasma cholesterol level in rats and hamsters were studied. TMP-153 has IC50 values of around 5-10 nM for the hepatic and intestinal ACAT from various animals. The most potent inhibition was observed in the intestinal ACAT from Golden hamsters (IC50 = 2.3 nM). The inhibition mode of TMP-153 was non-competitive for rat intestinal ACAT. TMP-153 inhibited cholesterol esterification both in human colonic adenocarcinoma cells, LS180, and in human hepatoma cells, HepG2 (IC50 = 150 nM and 330 nM, respectively). [14C]cholesterol and cold cholesterol absorption from the small intestine was markedly inhibited by oral administration of TMP-153 (1 mg/kg) without affecting lymph flow and triglyceride absorption. When the compound was given as a dietary admixture, plasma cholesterol was reduced in rats fed a cholesterol diet (ED50 = 0.
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