Design, synthesis and biological evaluation as immunosuppressant of amino alcohol derivatives containing thioether

2021 ◽  
Vol 11 (5) ◽  
pp. 773-780
Author(s):  
Yanjie Li ◽  
Yongqiang Li ◽  
Liu Yang ◽  
Zhi Liu ◽  
Ruimeng Zhang ◽  
...  
Keyword(s):  
Amino Alcohol ◽  
Coupling Reaction ◽  
Biological Evaluation ◽  
Design Synthesis ◽  
Suzuki Coupling Reaction ◽  
Sphingosine 1 Phosphate ◽  
Potential Activity ◽  
Key Steps ◽  
Synthesis And Biological Evaluation

To develop a safer immunosuppressant for organ transplantation and autoimmune disease treatment, in this study, several of novel amino alcohol derivatives containing thioether moiety were synthesized with 7-bromo-tetralin-2-one as starting material, and Suzuki coupling reaction and Bucherer-Bergs reaction as key steps. Their activity as sphingosine 1-phosphate receptor type 1 (S1P1) agonists were evaluated by [γ-35S] GTP binding assay. Among the thioether substituted compounds, compound 10 showed good activity as S1P1 agonist at low micromolar concentration (EC50 = 0.698 μmol/L). The result suggested that it has potential activity against autoimmune diseases and immunosuppressant of organ transplantations.

scholarly journals 2′-Deoxyuridines with a 5-Heteroaromatic Substituent: Synthesis and Biological Evaluation

1995 ◽  
Vol 6 (4) ◽  
pp. 262-270 ◽  
Author(s):  
I. Luyten ◽  
L. Jie ◽  
A. Van Aerschot ◽  
C. Pannecouque ◽  
P. Wigerinck ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Biological Evaluation ◽  
Dipolar Cycloaddition ◽  
Cross Coupling Reaction ◽  
Simplex Virus ◽  
New Compounds ◽  
Synthesis And Biological Evaluation ◽  
Derivatives Of ◽  
Hsv 1

A series of novel 2′-deoxyuridines with a thienyl substituent in the 5-position were synthesized as potential anti-HSV-1 agents. The brominated derivatives (1d, 1e and 3b) were obtained via halogenation reactions of the protected 5-(thien-2-yl)-2′-deoxyuridine and 5-(thien-3-yl)-2′-deoxyuridine, respectively. The palladium-catalysed cross-coupling reaction with stannylated thiophene was used for the synthesis of ( E)-5-(2-thienylvinyl)-2′-deoxyuridine and 5-(5,2′-dithien-2-yl)-2′-deoxyuridine. These compounds show moderate to good activity against herpes simplex virus type 1 (HSV-1) in the order of decreasing activity 1d>4>1e>3b∼5. Finally, two substituted 5-isoxazol derivatives of 2′-deoxyuridine (6a and 6b) were obtained via a 1,3-dipolar cycloaddition of the protected 5-ethynyl-2′-deoxyuridine. These new compounds demonstrated poor affinity for the virus-specific enzyme thymidine kinase.

scholarly journals Design, synthesis and biological evaluation of bifunctional inhibitors of membrane type 1 matrix metalloproteinase (MT1-MMP)

2019 ◽  
Vol 27 (1) ◽  
pp. 196-207 ◽  
Author(s):  
Doretta Cuffaro ◽  
Elisa Nuti ◽  
Valentina Gifford ◽  
Noriko Ito ◽  
Caterina Camodeca ◽  
...  
Keyword(s):  
Matrix Metalloproteinase ◽  
Biological Evaluation ◽  
Design Synthesis ◽  
Membrane Type ◽  
Synthesis And Biological Evaluation
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