| Identification | Back Directory | [Name]
ITD-1 | [CAS]
1099644-42-4 | [Synonyms]
ITD-1
AOB6123
CS-1731
SCHEMBL3239096
ITD1;ITD-1;ITD 1
ETHYL 4-{[1,1'-BIPHENYL]-4-YL}-2,7,7-TRIMETHYL-5-OXO-1,4,6,8-TETRAHYDROQUINOLINE-3-CARBOXYLATE
4-[1,1'-Biphenyl]-4-yl-1,4,5,6,7,8-hexahydro-2,7,7-trimethyl-5-oxo-3-quinolinecarboxylic acid ethyl ester
3-Quinolinecarboxylic acid, 4-[1,1'-biphenyl]-4-yl-1,4,5,6,7,8-hexahydro-2,7,7-trimethyl-5-oxo-, ethyl ester | [Molecular Formula]
C27H29NO3 | [MDL Number]
MFCD28133391 | [MOL File]
1099644-42-4.mol | [Molecular Weight]
415.52 |
| Chemical Properties | Back Directory | [Boiling point ]
569.9±50.0 °C(Predicted) | [density ]
1.18±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
≥28.05 mg/mL in DMSO; insoluble in H2O; insoluble in EtOH | [form ]
solid | [pka]
1.33±0.70(Predicted) | [color ]
Light yellow to yellow | [InChI]
1S/C27H29NO3/c1-5-31-26(30)23-17(2)28-21-15-27(3,4)16-22(29)25(21)24(23)20-13-11-19(12-14-20)18-9-7-6-8-10-18/h6-14,24,28H,5,15-16H2,1-4H3 | [InChIKey]
ULFUJLFTRWWLPO-UHFFFAOYSA-N | [SMILES]
O=C(CC(C)(C)C1)C2=C1NC(C)=C(C(OCC)=O)C2C(C=C3)=CC=C3C4=CC=CC=C4 |
| Hazard Information | Back Directory | [Uses]
ITD-1 is a selective inhibitor of TGF-β signaling and induces cardiomyocyte differentiation in embryonic stem cells (ESCs). | [Biological Activity]
tgfβ signalling has been shown to be important at an early stage in cardiac development, with most previous investigations focussing on the role during formation of the cardiac cushions. these cushions, which develop between embryonic day e9.5 and e11.5 in the mouse, are essential precursors of the mature valves, and intimately involved in septation. it is well known that tgfβ signalling promotes endothelial to mesenchymal transition, and subsequent migration of mesenchymal cells to the cardiac jelly. itd-1 is the first selective tgfβ inhibitor. | [Synthesis]
P-phenylbenzaldehyde (1 mmol), 5,5-dimethyl-1,3-cyclohexanedione (0.14 g, 1 mmol), ethyl acetoacetate (0.13 g, 1 mmol), ammonium acetate (0.115 g, 1.5 mmol), and Fe2O3 (catalytic amount) loaded on hydroxyapatite (HAP, catalytic amount) were used as raw materials and melamine (0.15 g) was added as an additive, and the reaction was heated at 80 °C. The reaction process was monitored by thin layer chromatography (TLC, unfolding agent was hexane/ethyl acetate, 10:3, v/v). Upon completion of the reaction, the reaction mixture was cooled to room temperature, washed with hot ethyl acetate and the catalyst was removed by magnetic separation. The solid residue was separated and purified by recrystallization in hot ethanol to afford the target product ethyl 4-([1,1'-biphenyl]-4-yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate. | [in vitro]
itd-1 has been used to evaluate tgfβ involvement in mesoderm formation and cardiopoietic differentiation, which occur sequentially during early development, indicating an essential role in both processes in esc cultures. itd-1 selectively enhanced the uncommitted mesoderm differentiation to cardiomyocytes, but not to vascular smooth muscle and endothelial cells. in summary, itd-1 is the first selective tgfβ inhibitor and reveals an unexpected role for tgfβ signaling in controlling the differentiation of cardiomyocyte from multipotent cardiovascular precursors [1]. | [storage]
+4°C | [References]
[1] willems e, cabral-teixeira j, schade d, cai w, reeves p, bushway pj, lanier m, walsh c, kirchhausen t, izpisua belmonte jc, cashman j, mercola m. small molecule-mediated tgf-β type ii receptor degradation promotes cardiomyogenesis in embryonic stem cells. cell stem cell. 2012 aug 3;11(2):242-52. |
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