139933-35-0

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide 
• 70223-97-1 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl bromide 
• 5160-10-1 2,3,6-tetra-O-acetyl-4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-D-glucopyranosylbromide 
• 623-27-8 terephthalaldehyde, 
• 34213-32-6 lactose octaacetate 

Downstream Products

• 1219692-63-3 C₃₄H₄₃NO₁₉ 
• 1219692-52-0 C₃₃H₄₁NO₁₉ 
• 1243251-89-9 N-phenyl-C-4-(2,3,4,6,2',3',6'-hepta-O-acetyl-β-D-lactosyloxy)phenyl nitrone 

Relevant academic research and scientific papers

Colorimetric calcium-response of β-lactosylated μ-oxo-bis-[5,15- meso-diphenylporphyrinatoiron(III)]

β-Lactosylated 5,15-meso-diphenylporphyrinatoiron(III) chloride was prepared by ironization of the corresponding free base porphyrin having acetylated lactoside-units followed by deacetylation with ammonia in a water-methanol mixture. The resultant 5,15-m

Synthesis of glycosylated cationic porphyrins as potential agents in photodynamic therapy

Trisalkylpyridinium porphyrins substituted by one glycosyl (glucosyl, maltosyl, and lactosyl) moiety have been prepared in acceptable yields. These glycosylated cationic porphyrins have been synthesized from pyrrole condensed with 4-pyridinecarboxaldehyde, and suitable ortho- or para peracetylglycosyloxybenzaldehyde derivatives in refluxing propionic acid - Ac2O followed by action of alkyliodide in DMF. Deprotection of the glycosylated moieties led to a new class of representative glycosylated porphyrins. Trisalkylpyridinium porphyrins substituted by one glycosyl (glucosyl, maltosyl, and lactosyl) moiety have been prepared in acceptable yields. These glycosylated cationic porphyrins have been synthesized from pyrrole condensed with 4-pyridinecarboxaldehyde, and suitable ortho- or para peracetylglycosyloxybenzaldehyde derivatives in refluxing propionic acid - Ac2O followed by action of alkyliodide in DMF. Deprotection of the glycosylated moieties led to a new class of representative glycosylated porphyrins.

Comparative study of surface-active and biological properties of lactose-derived acylhydrazones

In this study, we report the first preparation of a series of lactose-derived acylhydrazone compounds with alkyl side chains ranging from 5 to 10 carbons in length through condensation reactions as a new type of nonionic surfactants. The surface-active, foaming properties, emulsifying properties, thermal stability as well as cytotoxicity were studied to establish the structure-property profile, which revealed that the acylhydrazone derivatives bearing medium-length side chains had better overall performance than their analogs and other selected commercial references. The results could serve as basis for the further development of lactose-derived acylhydrazones as emulsifiers in, for example, food and pharmaceutical industries.

Functionalised bicyclic tetramates derived from cysteine as antibacterial agents

Routes to bicyclic tetramates derived from cysteine permitting ready incorporation of functionality at two different points around the periphery of a heterocyclic skeleton are reported. This has enabled the identification of systems active against Gram-positive bacteria, some of which show gyrase and RNA polymerase inhibitory activity. In particular, tetramates substituted with glycosyl side chains, chosen to impart polarity and aqueous solubility, show high antibacterial activity coupled with modest gyrase/polymerase activity in two cases. An analysis of physicochemical properties indicates that the antibacterially active tetramates generally occupy physicochemical space with MW of 300-600, clog D7.4 of -2.5 to 4 and rel. PSA of 11-22%. This work demonstrates that biologically active 3D libraries are readily available by manipulation of a tetramate skeleton.

Discovery of 4-functionalized phenyl-O-β-d-glycosides as a new class of mushroom tyrosinase inhibitors

A series of 4-functionalized phenyl-O-β-d-glycosides were designed, synthesized and evaluated as a new class of mushroom tyrosinase inhibitors. The results demonstrated that compounds 6a-13a bearing a thiosemicarbazide moiety exhibited potent activities with IC50 values range from 0.31 to 52.8 μM. Particularly, compound 9a containing acetylated glucose moiety was found to be the most active molecule with an IC50 value of 0.31 μM. SARs analysis suggested that (1) the thiosemicarbazide moiety remarkably contributed to the increase of inhibitory effects on tyrosinase; (2) the configuration and bond type of sugar moiety also played a very important role in determining their inhibitory activities. The inhibition kinetics and inhibition mechanism study revealed that compound 9a was reversible and competitive type inhibitor, whereas compound 13a was reversible and competitive-uncompetitive mixed-II type inhibitor.

Synthesis and biological evaluation of helicid analogues as novel acetylcholinesterase inhibitors

A series of helicid analogues were prepared and evaluated in vitro for the cholinesterase (AChE and BuChE) inhibitory activities via UV spectroscopy. The results indicated that compounds 5, 6d and 8 exhibited potent AChE inhibitory activities with IC50 values of 0.45 ± 0.02 μM, 0.49 ± 0.02 μM, and 0.20 ± 0.01 μM, respectively. High selectivity for AChE over BuChE was also observed. Kinetic study showed that the mechanism of AChE inhibition of compounds 5, 6d and 8 was all mixed-type.

Study on glycosylated prodrugs of toxoflavins for antibody-directed enzyme tumor therapy

Eight novel toxoflavin glycosides, which are potential prodrugs in antibody directed enzyme prodrug therapy (ADEPT), were synthesized. The structures of all toxoflavin glycosides were characterized by 13C NMR spectroscopy, elemental analysis, and MS. Their enzymatic hydrolysis activities were tested against β-glucosidase (EC.3.2.1.21).