TD 139
TD 139 Basic information
- Product Name:
- TD 139
- Synonyms:
-
- TD 139
- 3,3'-dideoxy-3,3'-di-[4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl]-1,1'-surfanediyl-di-D-galactopyranoside
- CS-2525
- TD-139; TD 139
- β-D-Galactopyranoside, 3-deoxy-3-[4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl]-β-D-galactopyranosyl 3-deoxy-3-[4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl]-1-thio-
- (2R,2'R,3R,3'R,4S,4'S,5R,5'R,6S,6'S)-6,6'-Thiobis(4-(4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,5-diol)
- 33DFTG
- Olitigaltin (TD-139)
- CAS:
- 1450824-22-2
- MF:
- C28H30F2N6O8S
- MW:
- 648.64
- Mol File:
- 1450824-22-2.mol
TD 139 Chemical Properties
- Boiling point:
- 1017.2±75.0 °C(Predicted)
- Density
- 1.76±0.1 g/cm3(Predicted)
- pka
- 12.33±0.70(Predicted)
- form
- Solid
- color
- White to off-white
- InChIKey
- YGIDGBAHDZEYMT-YNKUJGNYNA-N
TD 139 Usage And Synthesis
Uses
TD 139 is used as a galactoside inhibitors of galectins, suitable for treating pulmonary fibrosis; such as idiopathic pulmonary fibrosis in mammals.
Synthesis
1193784-39-2
2561-17-3
1450824-22-2
Bis-(3-azido-3-deoxy-β-D-galactopyranosyl)-thiane (11) and 3-fluorophenylacetylene (3 eq.) were synthesized by cycloaddition reaction in the presence of a Cu(I) catalyst (0.2 eq.) and triethylamine (2 eq.) in N,N-dimethylformamide (DMF, 100 mL/mmol of thiane) under room temperature conditions TD139.The progress of the reaction was monitored by thin layer chromatography (TLC) until completion. After the reaction mixture was concentrated, it was first initially purified by fast column chromatography (eluent: CH2Cl2:MeOH, 8:1), followed by final purification by preparative high-performance liquid chromatography (HPLC) to afford TD139 in 76% yield as a white amorphous solid.1H-NMR (CD3OD, 400 MHz) δ 8.59 (s, 2H, triazole-H ), 7.63 (br d, 2H, J = 7.6 Hz, Ar-H), 7.57 (br d, 2H, J = 8.4 Hz, Ar-H), 7.41 (dt, 2H, J = 6.0, 8.0 Hz, Ar-H), 7.05 (br dt, 2H, J = 2.4, 6.4 Hz, Ar-H), 4.93 (dd, 2H, J = 2.4 , 10.4 Hz, H3), 4.92 (d, 2H, J = 10.4 Hz, H1), 4.84 (d, 2H, J = 10.4 Hz, H2), 4.18 (d, 2H, J = 2.4 Hz, H4), 3.92 (dd, 2H, J = 4.2, 7.6 Hz, H5), 3.84 (dd, 2H, J = 7.6, 11.4 Hz , H6), 3.73 (dd, 2H, J = 4.2, 11.4 Hz, H6); the FAB-HRMS m/z calculated value of C28H30F2N6NaO8S (M + Na+) was 671.1712 and the measured value was 671.1705.
in vivo
In primary lung AECs TD139 reduces TGF-β1–induced β-catenin translocation to the nucleus, with most of the β-catenin remaining at the cell surface. TD139 blocks TGF-β1–induced β-catenin phosphorylation. A marked reduction in fibrosis and β-catenin activation accompanied by decreased galectin-3 expression is observed in the lungs of WT mice treated with TD139[1]. Pretreatment of WT C57BL/6 mice with TD139 leads to the attenuation of liver injury and milder infiltration of IFNγ- and IL-17- and -4-producing CD4(+) T cells, as well as an increase in the total number of IL-10-producing CD4(+) T cells and F4/80(+) CD206(+) alternatively activates macrophages and preventes the apoptosis of liver-infiltrating MNCs[2].
References
[1] Patent: US2014/121179, 2014, A1. Location in patent: Paragraph 0188; 0200
[2] Patent: WO2014/78655, 2014, A1. Location in patent: Page/Page column 90; 94
[3] ChemBioChem, 2016, vol. 17, # 18, p. 1759 - 1770
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