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TD 139

Product Name: TD 139
CAS No.: 1450824-22-2
Chemical Name: TD 139
Synonyms: 33DFTG;TD 139;CS-2525;TD-139; TD 139;Olitigaltin (TD-139);3,3'-dideoxy-3,3'-di-[4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl]-1,1'-surfanediyl-di-D-galactopyranoside;(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);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-
CBNumber: CB73167095
Molecular Formula: C28H30F2N6O8S
Formula Weight: 648.64
MOL File: 1450824-22-2.mol

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TD 139 Property

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

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 28400
Product name: TD139
Packaging: 1mg
Price: $80
Updated: 2021/12/16

Cayman Chemical

Product number: 28400
Product name: TD139
Packaging: 10mg
Price: $640
Updated: 2021/12/16

Cayman Chemical

Product number: 28400
Product name: TD139
Packaging: 5mg
Price: $360
Updated: 2021/12/16

AK Scientific

Product number: 7602DW
Product name: (2S,3R,4S,5R,6R)-4-[4-(3-Fluorophenyl)triazol-1-yl]-2-[(2S,3R,4S,5R,6R)-4-[4-(3-fluorophenyl)triazol-1-yl]-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl-6-(hydroxymethyl)oxane-3,5-diol
Packaging: 25mg
Price: $387
Updated: 2021/12/16

Biosynth Carbosynth

Product number: BT173009
Product name: TD 139
Packaging: 100mg
Price: $500
Updated: 2021/12/16

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TD 139 Chemical Properties,Usage,Production

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

TD 139 Preparation Products And Raw materials

Raw materials

Preparation Products

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1450824-22-2, TD 139Related Search:

4-BENZYL-2-METHYL-1,2,4-THIADIAZOLIDINE-3,5-DIONE

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)

1450824-22-2

C28H30F2N6O8S