64049-49-6

Usage

InChI:InChI=1/C10H12O4/c11-5-8-1-3-9(4-2-8)14-10(6-12)7-13/h1-5,10,12-13H,6-7H2

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 96-24-2 3-monochloro-1,2-propanediol 
• 40663-68-1 4-(2-propenyloxy)benzaldehyde 
• 14697-49-5 4-(2,3-epoxy)propyloxybenzaldehyde 

Downstream Products

• 854111-05-0 (Z,Z)-5-[4-(2,3-dihydroxypropoxy)benzylidene]-2-isopropylimino-3-phenyl-thiazolidin-4-one 
• 1194522-76-3 C₃₀H₂₄O₄ 

Relevant academic research and scientific papers

Synthesis and biological evaluation of novel 4-hydroxybenzaldehyde derivatives as tyrosinase inhibitors

A series of novel 4-hydroxybenzaldehyde derivatives were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were investigated. Most of target compounds had more potent inhibitory activities than the parent compound 4-hydroxybenzaldehyde (IC50 = 1.22 mM). Interestingly, compound 3c bearing a dimethoxyl phosphate was found to be the most potent inhibitor with IC50 value of 0.059 mM. The inhibition kinetics analyzed by Lineweaver-Burk plots revealed that compound 3c was a non-competitive inhibitor (KI = 0.0368 mM). In particular, compound 3c showed no side effects at dose of 1600 mg/kg in mice. These results suggested that such compounds might be served as lead compounds for further designing new potential tyrosinase inhibitors.

2-Imino-thiazolidin-4-one derivatives as potent, orally active S1P 1 receptor agonists

Sphingosine-1-phosphate (S1P) is a widespread lysophospholipid which displays a wealth of biological effects. Extracellular S1P conveys its activity through five specific G-protein coupled receptors numbered S1P1 through S1P5. Agonists of the S1P1 receptor block the egress of T-lymphocytes from thymus and lymphoid organs and hold promise for the oral treatment of autoimmune disorders. Here, we report on the discovery and detailed structure-activity relationships of a novel class of S1P1 receptor agonists based on the 2-imino-thiazolidin-4-one scaffold. Compound 8bo (ACT-128800) emerged from this series and is a potent, selective, and orally active S1P1 receptor agonist selected for clinical development. In the rat, maximal reduction of circulating lymphocytes was reached at a dose of 3 mg/kg. The duration of lymphocyte sequestration was dose dependent. At a dose of 100 mg/kg, the effect on lymphocyte counts was fully reversible within less than 36 h. Pharmacokinetic investigation of 8bo in beagle dogs suggests that the compound is suitable for once daily dosing in humans.

5-(BENZ- (Z) -YLIDENE) -THIAZOLIDIN-4-ONE DERIVATIVES AS IMMUNOSUPPRESSANT AGENTS

The invention relates to pharmaceutical compositions containing at least one 5- (benz- (Z) -ylidene-thiazolidin-4-one derivative (I), to prevent or treat disorders associated with an activated immune system. Furthermore, the invention relates to novel thi