4593-27-5

Basic information

• Product Name: o-Myosmine
• Synonyms: 2-(3,4-Dihydro-2H-pyrrol-5-yl)pyridine;Apoferrorosamine;NSC 210764;Ortho-MyosMine
• CAS NO: 4593-27-5
• Molecular Formula: C9H10N2
• Molecular Weight: 146.19
• Product Categories: Nicotine Derivatives;Aromatics;Heterocycles
• Mol File: 4593-27-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 45-46°C
• Boiling Point: 244.7°Cat760mmHg
• Flash Point: 101.8°C
• Appearance: /
• Density: 1.12g/cm³
• Vapor Pressure: 2.06E-05mmHg at 25°C
• Refractive Index: 1.578
• Storage Temp.: -20°C Freezer
• CAS DataBase Reference: o-Myosmine(CAS DataBase Reference)
• NIST Chemistry Reference: o-Myosmine(4593-27-5)
• EPA Substance Registry System: o-Myosmine(4593-27-5)

Safety Data

• Hazardous Substances Data: 4593-27-5(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Cyrstalline Solid

Uses

o-Myosmine is a nicotine derivative.

InChI:InChI=1/C17H22ClNO/c1-16(2)13-7-8-17(16,3)15(10-13)19-20-11-12-5-4-6-14(18)9-12/h4-6,9,13H,7-8,10-11H2,1-3H3/b19-15-

Upstream product

• 614-18-6 3-pyridinecarboxylic acid ethyl ester 
• 2399-66-8 1-benzoylpyrrolidin-2-one 
• 141-52-6 sodium ethanolate 
• 71-43-2 benzene 
• 88-12-0 1-ethenyl-2-pyrrolidinone 
• 2524-52-9 ethyl-2-picolinate 
• 109-04-6 2-bromo-pyridine 
• 161564-41-6 2-oxopyrrolidine-1-carbaldehyde diethyl acetal 
• 2459-07-6 methyl pyridine-2-carboxylate 

Relevant articles and documents

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Design, synthesis, and evaluation of pyrrolidine based CXCR4 antagonists with in vivo anti-tumor metastatic activity

The chemokine receptor CXCR4 has been proposed as a drug target based on its important functions in HIV infection, inflammation/autoimmune diseases and cancer metastasis. Herein we report the design, synthesis and evaluation of novel CXCR4 antagonists based on a pyrrolidine scaffold. The structural exploration/optimization identified numerous potent CXCR4 antagonists, represented by compound 46, which displayed potent binding affinity to CXCR4 receptor (IC50 = 79 nM competitively displacing fluorescent 12G5 antibody) and inhibited CXCL12 induced cytosolic calcium flux (IC50 = 0.25 nM). Moreover, in a transwell invasion assay, compound 46 significantly mitigated CXCL12/CXCR4 mediated cell migration. Compound 46 exhibited good physicochemical properties (MW 367, logD7.4 1.12, pKa 8.2) and excellent in vitro safety profiles (e.g., hERG patch clamp IC50 > 30 μM and minimal CYP isozyme inhibition). Importantly, 46 displayed much improved metabolic stability in human and rat liver microsomes. Lastly, 46 demonstrated marked efficacy in a cancer metastasis model in mice. These results strongly support 46 as a prototypical lead for the development of promising CXCR4 antagonists as clinical candidates.

Pyrrolidine amides of pyrazolodihydropyrimidines as potent and selective KV1.5 blockers

Design and synthesis of pyrazolodihydropyrimidines as KV1.5 blockers led to the discovery of 7d as a potent and selective antagonist. This compound showed atrial selective prolongation of effective refractory period in rabbits and was selected for clinical development.

Aqueous aldol catalysis by a nicotine metabolite

Nornicotine, an endogenous tobacco alkaloid and minor nicotine metabolite, can catalyze aldol reactions at physiological pH. Catalysis appears to be due to a covalent enamine mechanism, an unprecedented reaction with small organic molecule catalysts in aqueous buffer. Kinetic parameters for nornicotine as well as other related alkaloids were measured and demonstrate that both the pyrrolidine and pyridine rings are critical for optimal catalysis. Substrate compatibility of this catalyst and its implications in vivo are discussed. Copyright