131565-87-2

Usage

Uses

Used in Pharmaceutical Industry:
Cis-3,4-Dihydroxypyrrolidine is used as a chiral building block for the synthesis of bioactive compounds, contributing to the development of new drugs and pharmaceutical intermediates. Its unique structure allows for the creation of enantiomerically pure compounds, which is crucial for ensuring the desired biological activity and minimizing potential side effects.
Used in Agrochemical Industry:
In the agrochemical industry, cis-3,4-Dihydroxypyrrolidine serves as a chiral building block for the synthesis of bioactive compounds with potential applications in crop protection and pest control. Its ability to create enantiomerically pure compounds can lead to the development of more effective and environmentally friendly agrochemicals.
Used in Asymmetric Catalysis:
Cis-3,4-Dihydroxypyrrolidine is used as a ligand in asymmetric catalysis, a technique that allows for the selective synthesis of enantiomerically pure compounds. Its chiral properties make it a valuable component in catalytic systems, enabling the production of specific enantiomers with high selectivity and yield.
Used in Materials Science:
Cis-3,4-Dihydroxypyrrolidine has potential applications in the development of new materials due to its unique structural and chemical properties. It can be used as a chiral auxiliary in the synthesis of novel materials with specific properties, such as chiral polymers or chiral catalysts.
Used in Organic Synthesis:
As a chiral auxiliary, cis-3,4-Dihydroxypyrrolidine is used in organic synthesis to facilitate the formation of enantiomerically pure compounds. Its presence can help control the stereochemistry of reactions, leading to the production of desired enantiomers with improved yields and selectivity.

InChI:InChI=1/C4H9NO2/c6-3-1-5-2-4(3)7/h3-7H,1-2H2/t3-,4+

Upstream product

• 131541-27-0 Benzyl t-6-<<(tert-Butyl)dimethylsilyl>oxy>-r-4,c-5-dihydroxy-1,2-oxazinane-2-carboxylate 
• 31970-04-4 1-carboxybenzyl-3-pyrrolidine 
• 76784-33-3 (meso)-N-benzyl-3,4-dihydroxypyrrolidine 
• 109-96-6 3-Pyrroline 
• 122225-42-7 3,4-cis-dihydroxy-pyrrolidine-1-carboxylic acid benzyl ester 

Downstream Products

• 1255304-77-8 {4-[2-((3S,4R)-3,4-dihydroxypyrrolidin-1-yl)ethoxy]pyridin-2-yl}-{3-[4-(4-ethylbenzyloxy)-3-methoxyphenyl]azetidin-1-yl}methanone 

Relevant academic research and scientific papers

Synthesis and α-glucosidase inhibition activity of dihydroxy pyrrolidines

A new series of Deacetylsarmentamide A and B derivatives, amides and sulfonamides of 3,4-dihydroxypyrrolidines as α-glucosidase inhibitors were designed and synthesized. The biological screening test against α-glucosidase showed that some of these compounds have the positive inhibitory activity against α-glucosidase. Saturated aliphatic amides were more potent than the olefinic amides. Among all the compounds, 5o/6o having polar –NH2 group, 10f/11f having polar –OH group on phenyl ring displayed 3–4-fold more potent than the standard drugs. Acarbose, Voglibose and Miglitol were used as standard references. The promising compounds 6i, 5o, 6o, 10a, 11a, 10f and 11f have been identified. Molecular docking simulations were done for compounds to identify important binding modes responsible for inhibition activity of α-glucosidase.

BENZAMIDE DERIVATIVES FOR INHIBITING THE ACTIVITY OF ABL1, ABL2 AND BCR-ABL1

The present invention relates to compounds of formula (I): in which Y, Y, R, R 2, R 3 and R 4 are defined in the Summary of the Invention; capable of inhibiting the activity of BCR-ABL1 and mutants thereof. The invention further provides a process for the preparation of compounds of the invention, pharmaceutical preparations comprising such compounds and methods of using such compounds in the treatment of cancers.

Exocyclic deoxyadenosine adducts of 1,2,3,4-diepoxybutane: Synthesis, structural elucidation, and mechanistic studies

1,2,3,4-Diepoxybutane (DEB) is considered the ultimate carcinogenic metabolite of 1,3-butadiene, an important industrial chemical and environmental pollutant present in urban air. Although it preferentially modifies guanine within DNA, DEB induces a large number of A → T transversions, suggesting that it forms strongly mispairing lesions at adenine nucleobases. We now report the discovery of three potentially mispairing exocyclic adenine lesions of DEB: N6,N6-(2,3-dihydroxybutan-1,4-diyl)-2′- deoxyadenosine (compound 2), 1,N6-(2-hydroxy-3-hydroxymethylpropan-1, 3-diyl) -2′-deoxyadenosine (compound 3), and 1,N6-(1- hydroxymethyl-2-hydroxypropan-1,3-diyl)-2′-deoxyadenosine (compound 4). The structures and stereochemistry of the novel DEB-dA adducts were determined by a combination of UV and NMR spectroscopy, tandem mass spectrometry, and independent synthesis. We found that synthetic N6-(2-hydroxy-3,4- epoxybut-1-yl)-2′-deoxyadenosine (compound 1) representing the product of N6-adenine alkylation by DEB spontaneously cyclizes to form 3 under aqueous conditions or 2 under anhydrous conditions in the presence of an organic base. Compound 3 can be interconverted with 4 by a reversible unimolecular pericyclic reaction favoring 4 as a more thermodynamically stable product. Both 3 and 4 are present in double stranded DNA treated with DEB in vitro and in liver DNA of laboratory mice exposed to 1,3-butadiene by inhalation. We propose that in DNA under physiological conditions, DEB alkylates the N-1 position of adenine in DNA to form N1-(2-hydroxy-3,4-epoxybut-1-yl)-adenine adducts, which undergo an SN2-type intramolecular nucleophilic substitution and rearrangement to give 3 (minor) and 4 (major). Formation of exocyclic DEB-adenine lesions following exposure to 1,3-butadiene provides a possible mechanism of mutagenesis at the A:T base pairs.

Sequential reactions with Grubbs catalyst and ad-mix-α//βusing pdms thimbles

Incompatible Grubbs catalyst and an osmium dihydroxylation catalyst were site-isolated from each other using polydimethylsiloxane thimbles. The Grubbs catalyst was added to the interior of the thimbles, and AD-mix-α//β was added to the exterior. Organic substrates readily fluxed through the walls of the thimbles and reacted with each catalyst. A series of cascade reactions were developed including those with intermediates possessing low boiling points or that were foul smelling.

Alkyne compounds with MCH antagonistic activity and medicaments comprising these compounds

The present invention relates to alkyne compounds of general formula I wherein the groups and radicals A, B, W, X, Y, Z, R1 and R2 have the meanings given in claim 1. Moreover the invention relates to pharmaceutical compositions containing at least one alkyne according to the invention. By virtue of their MCH-receptor antagonistic activity the pharmaceutical compositions according to the invention are suitable for the treatment of metabolic disorders and/or eating disorders, particularly obesity and diabetes.

Alkyne compounds with MCH antagonistic activity and medicaments comprising these compounds

Alkyne compounds of formula I wherein A, B, W, X, Y, Z, R1, and R2 have the meanings given herein, which have MCH-receptor antagonistic activity and are useful for preparing pharmaceutical compositions for the treatment of metabolic disorders and/or eating disorders, particularly obesity and diabetes.

QUINOLONE ANTIBACTERIAL AGENTS

Compounds of formula I and methods for their preparation are disclosed. Further disclosed are methods of making biologically active compounds of formula I as well as pharmaceutically acceptable compositions comprising compounds of formula I. Compounds of formula I as disclosed herein can be used in a variety of applications including use as antibacterial agents.

MODULATORS OF CELLULAR ADHESION

The present invention provides compounds having formula (I): and pharmaceutically acceptable derivatives thereof, wherein R1-R4, n, p, A, B, D, E, L and AR1 are as described generally and in classes and subclasses herein, and additionally provides pharmaceutical compositions thereof, and methods for the use thereof for the treatment of disorders mediated by the CD11/CD18 family of cellular adhesion molecules (e.g., LFA-1).

PYRROLOPYRIDINE-2-CARBOXYLIC ACID AMIDE INHIBITORS OF GLYCOGEN PHOSHORYLASE

Compounds represented by Formula (I): or pharmaceutically acceptable salts thereof, are inhibitors of glycogen phosphorylase and are useful in the prophylactic or therapeutic treatment of diabetes, hyperglycemia, hypercholesterolemia, hyperinsulinemia, hyperlipidemia, hypertension, atherosclerosis or tissue ischemia e.g. myocardial ischemia, and as cardioprotectants.

Processes and intermediates for preparing glycogen phosphorylase inhibitors

The instant invention provides novel processes and intermediates useful in the preparation of certain N-(indole-2-carbonyl)-β-alaninamide compounds, which compounds are glycogen phosphorylase inhibitors useful in the treatment of diseases such as hypercholesterolemia, hyperglycemia, hyperinsulinemia, hyperlipidemia, hypertension, atherosclerosis, diabetes, diabetic cardiomyopathy, infection, tissue ischemia, myocardial ischemia, and in inhibiting tumor growth.