53104-32-8

Usage

Uses

Used in Pharmaceutical Industry:
(5-AMINO-2,2-DIMETHYL-[1,3]DIOXAN-5-YL)-METHANOL is used as a building block for the synthesis of pharmaceuticals due to its unique functional groups that can be utilized in the development of new drugs with specific biological properties.
Used in Agrochemical Industry:
In the agrochemical industry, (5-AMINO-2,2-DIMETHYL-[1,3]DIOXAN-5-YL)-METHANOL is used as a building block for the synthesis of agrochemicals, leveraging its chemical structure to create compounds with targeted effects on pests or crops.
Used in Organic Synthesis:
(5-AMINO-2,2-DIMETHYL-[1,3]DIOXAN-5-YL)-METHANOL is used as a versatile building block in organic synthesis for creating a wide range of organic compounds, capitalizing on its functional groups to form diverse molecular structures with potential applications in various industries.

InChI:InChI=1/C7H15NO3/c1-6(2)10-4-7(8,3-9)5-11-6/h9H,3-5,8H2,1-2H3

Upstream product

• 4728-14-7 2,2-dimethyl-5-hydroxymethyl-5-nitro-1,3-dioxane 
• 1185-53-1 tris hydrochloride 
• 77-76-9 2,2-dimethoxy-propane 
• 104-15-4 toluene-4-sulfonic acid 
• 77-86-1 2-amino-2-hydroxymethyl-1,3-propanediol 

Downstream Products

• 321948-05-4 3-{2,2-bis-[2-(5-amino-2,2-dimethyl-[1,3]dioxan-5-ylmethoxycarbonyl)-ethoxymethyl]-3-[2-(5-hydroxymethyl-2,2-dimethyl-[1,3]dioxan-5-ylcarbamoyl)-ethoxy]-propoxy}-propionic acid 5-amino-2,2-dimethyl-[1,3]dioxan-5-ylmethyl ester 
• 53104-33-9 2,2-dimethyl-1,3-dioxane-5-spiro-4'-(2'-phenyl-4',5'-dihydrooxazole) 
• 1143451-52-8 acetic acid [3-chlorocarbonyl-5-(5-hydroxymethyl-2,2-dimethyl-[1,3]dioxan-5-ylcarbamoyl)-2,4,6-triiodo-phenylcarbamoyl]-methyl ester 
• 123176-46-5 diphenylmethyl 2-(2,2-dimethyl-1,3-dioxan-5-ylidene)-2-<(N-methylthiomethylene)amino>acetate 
• 123176-46-5 diphenylmethyl 2-(2,2-dimethyl-1,3-dioxan-5-ylidene)-2-<(N-methylthiomethylene)amino>acetate 
• 123176-45-4 benzyl 2-(2,2-dimethyl-1,3-dioxan-5-ylidene)-2-<(N-methylthiomethylene)amino>acetate 
• 90602-92-9 benzyl 2-(2,2-dimethyl-1,3-dioxan-5-ylidene)-2-<(N-methylthiomethylene)amino>acetate 

Relevant academic research and scientific papers

Structural development of p-carborane-based potent non-secosteroidal vitamin D analogs

Non-secosteroidal vitamin D receptor (VDR) ligands are promising candidates for many clinical applications. We recently developed novel non-secosteroidal VDR agonists based on p-carborane (an icosahedral carbon-containing boron cluster) as a hydrophobic c

Enzymatic and organocatalyzed asymmetric aldolization reactions for the synthesis of thiosugar scaffolds

We studied the synthesis of original thiosugar scaffolds by enantioselective aldolization. L-Proline-catalyzed C-C bond formation was the key step in the synthesis of L-erythro-thioketoses (3S,4R), whereas fructose-6-phosphate aldolase-catalyzed reactions yielded the D-threo-thioketose series (3S,4S). By the organocatalytic approach, 5-thio-L-ribulofuranose (1) and 5-deoxy-6-thio-L-psicopyranose (2) were obtained in satisfactory overall yields from 2-haloacetaldehydes, whereas 5-thio-D-xylulofuranose (3) was synthesized in 50 % overall yield by an enzymatic aldolization reaction in only two steps from the same starting material.

Glycodendrimersomes from Sequence-Defined Janus Glycodendrimers Reveal High Activity and Sensor Capacity for the Agglutination by Natural Variants of Human Lectins

A library of eight amphiphilic Janus glycodendrimers (Janus-GDs) presenting d-lactose (Lac) and a combination of Lac with up to eight methoxytriethoxy (3EO) units in a sequence-defined arrangement was synthesized via an iterative modular methodology. The length of the linker between Lac and the hydrophobic part of the Janus-GDs was also varied. Self-assembly by injection from THF solution into phosphate-buffered saline led to unilamellar, monodisperse glycodendrimersomes (GDSs) with dimensions predicted by Janus-GD concentration. These GDSs provided a toolbox to measure bioactivity profiles in agglutination assays with sugar-binding proteins (lectins). Three naturally occurring forms of the human adhesion/growth-regulatory lectin galectin-8, Gal-8S and Gal-8L, which differ by the length of linker connecting their two active domains, and a single amino acid mutant (F19Y), were used as probes to study activity and sensor capacity. Unpredictably, the sequence of Lac on the Janus-GDs was demonstrated to determine bioactivity, with the highest level revealed for a Janus-GD with six 3EO groups and one Lac. A further increase in Lac density was invariably accompanied by a substantial decrease in agglutination, whereas a decrease in Lac density resulted in similar or lower bioactivity and sensor capacity. Both changes in topology of Lac presentation of the GDSs and seemingly subtle alterations in protein structure resulted in different levels of bioactivity, demonstrating the presence of regulation on both GDS surface and lectin. These results illustrate the applicability of Janus-GDs to dissect structure-activity relationships between programmable cell surface models and human lectins in a highly sensitive and physiologically relevant manner.

One-Component Multifunctional Sequence-Defined Ionizable Amphiphilic Janus Dendrimer Delivery Systems for mRNA

Efficient viral or nonviral delivery of nucleic acids is the key step of genetic nanomedicine. Both viral and synthetic vectors have been successfully employed for genetic delivery with recent examples being DNA, adenoviral, and mRNA-based Covid-19 vaccines. Viral vectors can be target specific and very efficient but can also mediate severe immune response, cell toxicity, and mutations. Four-component lipid nanoparticles (LNPs) containing ionizable lipids, phospholipids, cholesterol for mechanical properties, and PEG-conjugated lipid for stability represent the current leading nonviral vectors for mRNA. However, the segregation of the neutral ionizable lipid as droplets in the core of the LNP, the "PEG dilemma", and the stability at only very low temperatures limit their efficiency. Here, we report the development of a one-component multifunctional ionizable amphiphilic Janus dendrimer (IAJD) delivery system for mRNA that exhibits high activity at a low concentration of ionizable amines organized in a sequence-defined arrangement. Six libraries containing 54 sequence-defined IAJDs were synthesized by an accelerated modular-orthogonal methodology and coassembled with mRNA into dendrimersome nanoparticles (DNPs) by a simple injection method rather than by the complex microfluidic technology often used for LNPs. Forty four (81%) showed activity in vitro and 31 (57%) in vivo. Some, exhibiting organ specificity, are stable at 5 °C and demonstrated higher transfection efficiency than positive control experiments in vitro and in vivo. Aside from practical applications, this proof of concept will help elucidate the mechanisms of packaging and release of mRNA from DNPs as a function of ionizable amine concentration, their sequence, and constitutional isomerism of IAJDs.

A Condensed, Scalable Synthesis of Racemic Koningic Acid

The natural product koningic acid (KA) is a selective covalent inhibitor of glyceraldehyde-3-phosphate dehydrogenase (GAPDH), a critical node in the glycolysis pathway. While KA is available commercially, sources are limited and its cost becomes rapidly prohibitive beyond the milligram scale. Additionally, a practical and flexible synthetic route to KA and analogs remains to be developed. Here we detail a new route that is operationally safer, scalable and offers a five-step reduction in the previously reported longest linear sequence.

Oxetanyl Amino Acids for Peptidomimetics

Peptides are important in the drug discovery process. In analogy to nonpeptidic small-molecule counterparts, they can sometimes suffer from disadvantages such as their low bioavailability and poor metabolic stability. Herein, we report the synthesis of new oxetanyl dipeptides and their incorporation into Leu-enkephalin analogues as proof-of-principle studies. The modular approach that is described enables the incorporation of a variety of oxetanyl amino acids into potential peptide therapeutics.

Novel lipid-mimetic prodrugs delivering active compounds to adipose tissue

Obesity and associated pathologies are a dramatically growing problem. New therapies to prevent and/or cure them are strongly needed. Adipose tissue is a logical target for pharmacological intervention, since it is now recognized to exert an important endocrine function, secreting a variety of adipokines affecting, for example, adiposity and insulin resistance. This proof of principle work focuses on the development of novel lipid-mimetic prodrugs reaching fat deposits by the same lymphatic absorption route followed by dietary triglycerides. Pterostilbene, a natural phenolic compound with potential anti-obesity effects, was used as model “cargo”, attached via a carbamate group to an ω-aminodecanoate chain linked to either position 1 or position 2 of the glycerol moiety of synthetic triglycerides. The prodrugs underwent position-selective hydrolysis when challenged with pancreatic lipases in vitro. Pterostilbene-containing triglycerides as well as pterostilbene and its metabolites were present in the adipose tissue of mice fed an obesogenic diet containing one or the other of the derivatives. For the first time this approach is used to deliver an obesity antagonist to the adipose tissue. The results demonstrate the feasibility of delivering active compounds to adipose tissue by reversibly incorporating them into triglyceride-mimetic structures. Upon release in the target site these compounds are expected to exert their pharmacological activity precisely where needed.

Mimicking biological membranes with programmable glycan ligands self-assembled from amphiphilic Janus glycodendrimers

An accelerated modular synthesis produced 18 amphiphilic Janus glycodendrimers with three different topologies formed from either two or one carbohydrate head groups or a mixed constellation with a noncarbohydrate hydrophilic arm. By simple injection of their THF solutions into water or buffer, all of the Janus compounds self-assembled into uniform, stable, and soft unilamellar vesicles, denoted glycodendrimersomes. The mixed constellation topology glycodendrimersomes were demonstrated to be most efficient in binding plant, bacterial, and human lectins. This evidence with biomedically relevant receptors offers a promising perspective for the application of such glycodendrimersomes in targeted drug delivery, vaccines, and other areas of nanomedicine.

CONTRAST AGENTS

Compounds of formula (I) RA—CO—N(R2)—(CR12)n—N(R5)—RB and salts or optical active isomers thereof, wherein each R1 independently are the same or different and denotes

AMINE COMPOUND AND PHARMACEUTICAL USE THEREOF

Provided is a novel amine compound represented by the following formula (I) having a superior peripheral blood lymphocyte decreasing action and superior in the immunosuppressive action, rejection suppressive action and the like, which shows decreased side effects of, for example, bradycardia and the like, or a pharmaceutically acceptable acid addition salt thereof, or a hydrate thereof, or a solvate thereof. wherein each symbol is as defined in the specification.