99494-01-6

Usage

Uses

Used in Pharmaceutical Synthesis:
N-Methyl-D-prolinol is used as a chiral auxiliary for controlling the stereochemistry of reactions in the synthesis of pharmaceuticals. Its ability to improve the selectivity of various transformations is crucial for the production of chiral compounds, which are essential in the development of effective and safe medications.
Used in Organic Chemistry:
In the field of organic chemistry, N-Methyl-D-prolinol is utilized as a catalyst and ligand in asymmetric reactions. Its high efficiency and versatility make it a valuable tool for enhancing the selectivity of complex organic molecule syntheses, thereby facilitating the creation of enantiomerically pure compounds.
Used in Drug Discovery and Development:
N-Methyl-D-prolinol is employed as a potential candidate in drug discovery and development due to its reported biological activities. Its antitumor and antiviral properties make it a promising agent for the treatment of various diseases, contributing to the advancement of novel therapeutics.
Used in Catalyst and Ligand Design:
In the design of catalysts and ligands for asymmetric reactions, N-Methyl-D-prolinol is used to enhance the efficiency and selectivity of these processes. Its unique structural features and chiral nature allow for the fine-tuning of reaction pathways, leading to improved outcomes in the synthesis of complex organic molecules.

Upstream product

• 175725-27-6 (R)-1-ethoxycarbonylprolin 
• 68078-09-1 N-methylproline 
• 68832-13-3 D-prolinol 
• 74-88-4 methyl iodide 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 59378-81-3 1-(tert-butoxycarbonyl)prolin-2R-ol 
• 895160-34-6 (R)-pyrrolidine-1,2-dicarboxylic acid 2-tert-butyl ester 1-ethyl ester 
• 265660-44-4 (2S)-(+)-N-methyl-2-tributylstannylpyrrolidine 
• 344-25-2 D-Prolin 
• 475-11-6 N-methyl-D-proline 

Downstream Products

• 909783-58-0 (R)-2-(2-Methoxy-4-nitro-phenoxymethyl)-1-methyl-pyrrolidine 
• 909783-62-6 3-Methoxy-4-((R)-1-methyl-pyrrolidin-2-ylmethoxy)-phenylamine 
• 1269662-73-8 (E)-N-[4-[[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolinyl]-3-[(2R)-1-methylpyrrolidin-2-yl]propan-2-enoylamine 
• 1269662-76-1 (E)-N-[4-[(3-chloro-4-fluorophenyl)amino]-7-(2-methoxyethoxy)quinazolin-6-yl]-3-[(2R )-1-methylpyrrolidin-2-yl]propan-2-enoylamine 
• 1269662-77-2 (E)-N-[4-[(3-chloro-4-fluorophenyl)amino]-7-ethoxyquinazolin-6-yl]-3-[(2R)-1-methylpyrrolidin-2-yl]propan-2-enoylamine 
• 1428555-25-2 C₁₃H₁₅F₃N₂O₃ 
• 1428555-18-3 C₂₁H₂₄BrF₃N₂O₅S 
• 1397922-61-0 (E)-N-[4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolyl]-3-[(2R)-1-methylpyrrolidin-2-yl]prop-2-enamide maleate 
• 1397922-62-1 (E)-N-[4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolyl]-3-[(2R)-1-methylpyrrolidin-2-yl]prop-2-enamide L-malate 
• 128573-84-2 Acetic acid (3R,4S)-4-(4-methoxy-phenyl)-1-((R)-1-methyl-pyrrolidin-2-ylmethyl)-2-oxo-6-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl ester 

Relevant academic research and scientific papers

FUMAGILLOL COMPOUNDS AND METHODS OF MAKING AND USING SAME

Disclosed herein, in part, are fumagillol compounds and methods of use in treating medical disorders, such as obesity. Pharmaceutical compositions and methods of making fumagillol compounds are provided. The compounds are contemplated to have activity against methionyl aminopeptidase 2.

6-AMINO QUINAZOLINE OR 3-CYANO QUINOLINE DERIVATIVES, PREPARATION PROCESS AND PHARMACEUTICAL USE THEREOF

The present disclosure relates to 6-amino quinazoline or 3-cyano quinoline derivatives, preparation processes and pharmaceutical compositions containing them. Specifically, the present disclosure relates to novel 6-amino quinazoline or 3-cyano quinoline derivatives presented by formula (I), or its tautomer, enantiomer, diastereomer, racemate or pharmaceutically acceptable salts thereof, or metabolite, metabolic precursor or prodrug thereof, and the uses for treatment especially for protein kinase inhibitors, in which each substitute group of general formula (I) is as defined in the specification.

PHARMACEUTICALLY ACCEPTABLE SALT OF (E)-N-[4-[[3-CHLORO-4-(2-PYRIDYLMETHOXY)PHENYL]AMINO]-3-CYANO-7-ETHOXY-6-QUINOLYL]-3-[(2R)-1-METHYLPYRROLIDIN-2-YL]PROP-2-ENAMIDE, PREPARATION METHOD THEREFOR, AND MEDICAL USE THEREOF

Provided as represented by formula (I) is a pharmaceutically acceptable salt of (E)-N-[4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolyl] -3-[(2R)-1-methylpyrrolidin-2-yl]prop-2-enamide, a preparation method therefor, and a use thereof as a therapeutic agent and especially as a protein kinase inhibitor.

PHARMACEUTICALLY ACCEPTABLE SALT OF (E)-N-[4-[[3-CHLORO-4-(2-PYRIDYLMETHOXY)PHENYL]AMINO]-3-CYANO-7-ETHOXY-6-QUINOLYL]-3-[(2R)-1-METHYLPYRROLIDIN-2-YL]PROP-2-ENAMIDE, PREPARATION METHOD THEREOF, AND MEDICAL USE THEREOF

Provided as represented by formula (I) is a pharmaceutically acceptable salt of (E)-N-[4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolyl]-3-[(2R)-1-methylpyrrolidin-2-yl]prop-2-enamide, a preparation method thereof, and a use thereof as a therapeutic agent, and especially as a protein kinase inhibitor.

6-AMINO QUINAZOLINE OR 3-CYANO QUINOLINE DERIVATIVES, PREPARATION METHODS AND PHARMACEUTICAL USES THEREOF

6-amino quinazoline or 3-cyano quinoline derivatives, preparation methods and pharmaceutical uses thereof are disclosed. Specifically, the present disclosure discloses novel 6-amino quinazoline or 3-cyano quinoline derivatives presented by general formula (I), or tautomers, enantiomers, diastereomers, racemates or pharmaceutically acceptable salts thereof, or metabolites, metabolic precursors or prodrugs thereof, and their uses as treatment agents especially as protein kinase inhibitors, in which each substitutent group of general formula (I) is as defined in the specification.

QUATERNARY AMMONIUM SALTS AS M3 ANTAGONISTS

Compounds of formula (I), in salt or zwitterionic form, wherein J, L, M, R1, R2, R3, R4 and R5 have the meanings as indicated in the specification, are useful for treating conditions that are mediated by the muscarinic M3 receptor. Pharmaceutical compositions that contain the compounds and a process for preparing the compounds are also described.

Enantioselective, facially selective carbomagnesation of cyclopropenes

Described is the facially selective and enantioselective addition of carbon nucleophiles to prochiral 3-hydroxymethylcyclopropenes. The process creates up to four stereocenters in a tandem addition/capture sequence that combines three simple materials to give complex and diverse products. The asymmetry is induced by the inexpensive and recoverable ligand (S)-N-methylprolinol. The enantioselectivity (90-98% ee with MeMgCl) is high for a range of cyclopropenes and electrophiles. Importantly, the diastereoselectivity is complementary to that obtained by enantioselective cyclopropanation with aryldiazoacetates. High enantioselectivities are obtained only when methoxide is included in the reaction. Evidence is provided that at least two chiral ligands are involved in the enantioselectivity-determining step. Copyright

Analogues of carbacholine: Synthesis and relationship between structure and affinity for muscarinic and nicotinic acetylcholine receptors

A series of acyclic and heterocyclic analogues of carbacholine (1) was synthesized using N-methylcarbacholine (MCC, 2), N,N-dimethylcarbacholine (DMCC, 3), and the corresponding tertiary amine (4) as leads. Whereas nicotinic acetylcholine receptor affinity was determined using [3H]nicotine as the radioactive ligand, [3H]oxotremorine-M ([3H]Oxo-M) and [3H]quinuclidinyl benzilate ([3H]QNB), in some cases supplemented with [3H]pirenzepine ([3H]PZ), were used as radioligands for muscarinic acetylcholine receptors on rat brain membranes. On the basis of receptor binding data, nicotinic/muscarinic (N/M) selectivity factors were determined, and muscarinic receptor efficacy (M agonist index) and M1 selectivity (M2/M1 index) estimated. In most cases, quaternized analogues showed higher affinity than the corresponding tertiary amines for muscarinic and, in particular, nicotinic receptor sites. Among the new compounds, N,N-diethylcarbacholine (9e) (IC50 = 0.046 μM), (S)-1-methyl-2-(N,N-dimethylaminocarbonyloxymethyl)pyrrolidine (17k) (IC50 = 0.068 μM), and the corresponding quaternized analogue, 18k (IC50 = 0.018 μM) showed the highest nicotinic receptor affinity. The tertiary amine, 17k showed much higher nicotinic receptor affinity than the acyclic analogue, 4 (IC50 = 5.7 μM), and the N/M selectivity factor determined for 17k (150) is an order of magnitude lower than that of nicotine (1400). The N/M selectivity factors for MCC (2) and DMCC (3), previously reported to be highly selective nicotinic receptor ligands, were shown to be 6.5 and 60, respectively, the latter value being comparable with that of 18k (89).

Alkylation of 2-Lithio-N-Methylpiperidines and -pyrrolidines: Scope, Limitations, and Stereochemistry

The scope and limitations of the alkylation of racemic and nonracemic 2-lithipiperidines and -pyrrolidines, obtained by transmetalation of the corresponding stannanes, is reported.These organolithiums react with a variety of electrophiles to afford 2-substituted pyrrolidines and piperidines in excellent yield.With primary alkyl halides the reaction proceeds with net inversion of configuration at the metal-bearing carbon in the piperidines; in the pyrrolidines there is a mixture of inversion and retention, with the former predominating.With most carbonyl electrophiles (carbon dioxide, dimethyl carbonate, methyl chloroformate, pivaloyl chloride, benzaldehyde, and dialkyl ketones), retention is observed in both cases.Electrophiles such as benzophenone, benzyl bromide, and tert-butyl bromoacetate afford racemic coupling products.A mechanistic interpretation is presented.

Search for Configurationally Stable, Aracemic α-Amino Organolithiums

The search for configurationally stable α-amino carbanions has led to an interesting observation of differing reactivity of diastereomeric organolithiums and to the characterization of aracemic 2-lithio-N-methylpiperidine and 2-lithio-N-methylpyrrolidine as configurationally stable α-aminoorganolithiums.Details for the preparation of these and related α-lithioheterocycles, evaluation of their and configurational stability, and a preliminary evaluation of the stereoselevtivity of their reactions with electrophiles is presented. - Keywords: α-Amino organolithiums; α-amino carbaions; 2-lithiopiperidine; 2-lithiopyrrrolidine; configurationally stable carbanions.