19748-66-4

Usage

Uses

Used in Organic Synthesis:
1-(3-Hydroxypropyl)-pyrrolidine is used as a key intermediate in the synthesis of various organic compounds for [reasons such as its unique structure and reactivity].
Used in Medicinal Chemistry:
1-(3-Hydroxypropyl)-pyrrolidine is used as a building block for the development of pharmaceuticals and biologically active molecules for [reasons such as its potential to enhance the properties of the final compounds].
Used as a Chiral Auxiliary in Asymmetric Synthesis:
1-(3-Hydroxypropyl)-pyrrolidine is used as a chiral auxiliary to induce enantioselectivity in asymmetric synthesis for [reasons such as its ability to control the stereochemistry of the reaction].
Used in Antitumor and Anticancer Research:
1-(3-Hydroxypropyl)-pyrrolidine is used as a potential antitumor and anticancer agent for [reasons such as its demonstrated biological activity in some studies].
Used in Drug Development:
1-(3-Hydroxypropyl)-pyrrolidine is used in the development of novel drugs and medical treatments for [reasons such as its potential to contribute to the discovery of new therapeutic agents].

InChI:InChI=1/C7H15NO/c9-7-3-6-8-4-1-2-5-8/h9H,1-7H2

Upstream product

• 123-75-1 pyrrolidine 
• 627-30-5 1-chloro-3-hydroxypropane 
• 504-63-2 trimethyleneglycol 
• 24299-77-2 methyl 3-(2'-oxo-1'-pyrrolidinyl)propanoate 
• 84032-39-3 5-aza-1-boraspiro<4,4>nonane 
• 22041-21-0 methyl 3-(pyrrolidin-1-yl)propanoate 
• 77357-63-2 4-((3,3-dimethoxypropyl)amino)-1,1-dimethoxybutane 
• 627-32-7 1-iodopropan-3-ol 
• 107-18-6 allyl alcohol 
• 7335-07-1 N-propylpyrrolidine 
• 77357-65-4 4-(N-(3,3-dimethoxypropyl)trifluoroacetamido)-1,1-dimethoxybutane 
• 44768-46-9 3-(prop-2-enylamino)propan-1-ol 
• 627-18-9 1-bromo-3-propanol 
• 5860-49-1 hexahydro-2H-pyrido-<2,1-b><1,3>oxazine 

Downstream Products

• 57616-69-0 1-(3-chloropropyl)pyrrolidine hydrochloride 
• 112972-12-0 2,2-diphenyl-5-pyrrolidino-valeronitrile; hydrochloride 
• 869640-42-6 7-benzyl-2-(3-pyrrolidin-1-ylpropoxy)-5,6,7,8-tetrahydro-1,7-naphthyridine 
• 398127-69-0 4-chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)cinnoline 
• 398487-42-8 4-chloro-6-cyano-7-(3-(pyrrolidin-1-yl)propoxy)quinoline 
• 193964-20-4 methyl 4-[3-(1-pyrrolidinyl)propoxy]benzoate 
• 951774-83-7 C₂₃H₃₅ClN₂O₃ 
• 1014977-95-7 N-(4-chlorobenzyl)-N'-(3-phenylpropionyl)-S-(3-pyrrolidinopropyl)isothiourea 
• 92033-81-3 1-{3-[(4-nitrophenyl)oxy]propyl}pyrrolidine 
• 935279-81-5 4-[6-(3-pyrrolidin-1-ylpropoxy)pyridin-3-yl]tetrahydro-2H-pyran-4-carbonitrile 
• 1259031-99-6 3-(pyrrolidin-1-yl)propanal oxime 
• 1259031-90-7 N-[3-(pyrrolidin-1-yl)propyl]-N-(tert-butyldimethylsilyloxy)-4-methylbenzensulfonamide 

Relevant academic research and scientific papers

Synthesis and Biological Evaluation of the First Triple Inhibitors of Human Topoisomerase 1, Tyrosyl-DNA Phosphodiesterase 1 (Tdp1), and Tyrosyl-DNA Phosphodiesterase 2 (Tdp2)

Tdp1 and Tdp2 are two tyrosyl-DNA phosphodiesterases that can repair damaged DNA resulting from topoisomerase inhibitors and a variety of other DNA-damaging agents. Both Tdp1 and Tdp2 inhibition could hypothetically potentiate the cytotoxicities of topoisomerase inhibitors. This study reports the successful structure-based design and synthesis of new 7-azaindenoisoquinolines that act as triple inhibitors of Top1, Tdp1, and Tdp2. Enzyme inhibitory data and cytotoxicity data from human cancer cell cultures establish that modification of the lactam side chain of the 7-azaindenoisoquinolines can modulate their inhibitory potencies and selectivities vs Top1, Tdp1, and Tdp2. Molecular modeling of selected target compounds bound to Top1, Tdp1, and Tdp2 was used to design the inhibitors and facilitate the structure-activity relationship analysis. The monitoring of DNA damage by γ-H2AX foci formation in human PBMCs (lymphocytes) and acute lymphoblastic leukemia CCRF-CEM cells documented significantly more DNA damage in the cancer cells vs normal cells.

Manganese-Catalyzed Anti-Markovnikov Hydroamination of Allyl Alcohols via Hydrogen-Borrowing Catalysis

Controlling the selectivity in a hydroamination reaction is an extremely challenging yet highly desirable task for the diversification of amines. In this article, a selective formal anti-Markovnikov hydroamination of allyl alcohols is presented. It enables the versatile synthesis of valuable γ-amino alcohol building blocks. A phosphine-free Earth's abundant manganese(I) complex catalyzed the reaction under hydrogen-borrowing conditions. A vast range of aliphatic, aromatic amines, drug molecules, and natural product derivatives underwent successful hydroamination with primary and secondary allylic alcohols with excellent functional group tolerance (57 examples). The catalysis could be performed on a gram scale and has been applied for the synthesis of drug molecules. The mechanistic studies revealed the metal-ligand bifunctionality as well as hemilability of the ligand backbone as the key design principle for the success of this catalysis.

Iron-Catalyzed Anti-Markovnikov Hydroamination and Hydroamidation of Allylic Alcohols

Hydroamination allows for the direct access to synthetically important amines. Controlling the selectivity of the reaction with efficient, widely applicable, and economic catalysts remains challenging, however. This paper reports an iron-catalyzed formal anti-Markovnikov hydroamination and hydroamidation of allylic alcohols, which yields γ-amino and γ-amido alcohols, respectively. Homoallylic alcohol is also feasible. The catalytic system, consisting of a pincer Fe-PNP complex (1-4 mol %), a weak base, and a nonpolar solvent, features exclusive anti-Markovnikov selectivity, broad substrate scope (>70 examples), and good functional group tolerance. The reaction could be performed at gram scale and applied to the synthesis of drug molecules and heterocyclic compounds. When chiral substrates are used, the stereochemistry and enantiomeric excess are retained. Further application of the chemistry is seen in the functionalization of amino acids, natural products, and existing drugs. Mechanistic studies suggest that the reaction proceeds via two cooperating catalytic cycles, with the iron complex catalyzing a dehydrogenation/hydrogenation process while the amine substrate acts as an organocatalyst for the Michael addition step.

AZAINDENOISOQUINOLINE COMPOUNDS AND USES THEREOF

Tyrosyl-DNA Phosphodiesterases 1 and 2 (Tdp1 and Tdp2) can repair damaged DNA resulting from topoisomerase inhibitors and a variety of other DNA-damaging agents. Both Tdp1 and Tdp2 inhibition could hypothetically potentiate the cytotoxicities of topoisomerase inhibitors. Series of 7-azaindenoisoquinolines that act as triple inhibitors of Top1, Tdp1 and Tdp2 are disclosed. Also described are methods for treating patients of a cancer using the disclosed azaindenoisoquinoline compounds or a pharmaceutical formulation thereof.

NAPHTHYLUREA DERIVATIVES AND MEDICAL APPLICATIONS THEREOF

The present invention relates to naphthylurea derivatives. Such substances can significantly inhibit VEGFR2 and PDGFR-β receptor tyrosine kinase phosphorylation at nanomolar concentration levels. It is a novel type of tyrosine kinase inhibitors which can be used in the treatment of tyrosine kinase-mediated diseases or symptoms such as malignancies and ocular diseases accompanied with pathologic neovascularization

FUSED 1,4-DIHYDRODIOXIN DERIVATIVES AS INHIBITORS OF HEAT SHOCK TRANSCRIPTION FACTOR 1

The present invention relates to compounds of formula I wherein A1, A2 R4 and Q are as defined herein. The compounds of the present invention are inhibitors of heat shock factor 1 (HSF1). In particular, the present invention relates to the use of these compounds as therapeutic agents for the treatment and/or prevention of proliferative diseases, such as cancer. The present invention also relates to processes for the preparation of these compounds, and to pharmaceutical compositions comprising them.

Platinum-Catalyzed, Terminal-Selective C(sp3)-H Oxidation of Aliphatic Amines

This Communication describes the terminal-selective, Pt-catalyzed C(sp3)-H oxidation of aliphatic amines without the requirement for directing groups. CuCl2 is employed as a stoichiometric oxidant, and the reactions proceed in high yield at Pt loadings as low as 1 mol%. These transformations are conducted in the presence of sulfuric acid, which reacts with the amine substrates in situ to form ammonium salts. We propose that protonation of the amine serves at least three important roles: (i) it renders the substrates soluble in the aqueous reaction medium; (ii) it limits binding of the amine nitrogen to Pt or Cu; and (iii) it electronically deactivates the C-H bonds proximal to the nitrogen center. We demonstrate that this strategy is effective for the terminal-selective C(sp3)-H oxidation of a variety of primary, secondary, and tertiary amines.

Visible light photooxidative cyclization of amino alcohols to 1,3-oxazines

1,3-Amino alcohols were prepared to examine how structure affects the oxidation of tertiary amines in visible light photocatalysis. These substrates were cyclized to produce oxazines following the photooxidative formation of iminium ions using catalytic Ru(bpy)3Cl2. Amino alcohol derivatives of tetrahydroisoquinoline, tetrahydroquinoline, pyrrolidine, and Δ3-piperidine all were found to be viable substrates. In the case of the unsaturated piperidines, cyclization is accompanied by addition of methanol across the alkene; most likely occurring via a conjugate addition to an intermediate α,β-unsaturated iminium ion prior to oxazine formation.

Catalytic hydrogenation of amides to amines under mild conditions

Under (not so much) pressure: A general method for the hydrogenation of tertiary and secondary amides to amines with excellent selectivity using a bimetallic Pd-Re catalyst has been developed. The reaction proceeds under low pressure and comparatively low temperature. This method provides organic chemists with a simple and reliable tool for the synthesis of amines. Copyright

Novel antagonists of serotonin-4 receptors: Synthesis and biological evaluation of pyrrolothienopyrazines

Based on the definition of a 5-HT4 receptor antagonist pharmacophore, a series of pyrrolo[1,2-a]thieno[3,2-e] and pyrrolo[1,2-a]thieno[2,3-e] pyrazine derivatives were designed, prepared, and evaluated to determine the properties necessary for high-affinity binding to 5-HT4 receptors. The compounds were synthesized by substituting the chlorine atom of the pyrazine ring with various N-alkyl-4-piperidinylmethanolates. They were evaluated in binding assays with [3H]GR113808 (1) as the 5-HT4 receptor radioligand. The affinity values (Ki or inhibition percentages) were affected by both the substituent on the aromatic ring and the substituent on the lateral piperidine chain. A methyl group on the tricyclic ring produced a marked increase in affinity while an N-propyl or N-butyl group gave compounds with nanomolar affinities. Among the most potent ligands, 34d was selected for further pharmacological studies and evaluated in vivo. This compound acts as an antagonist/weak partial agonist in COS-7 cells stably expressing the 5-HT4(a) receptor and is of great interest as a peripheral antinociceptive agent.