120533-76-8

Usage

Uses

Used in Pharmaceutical Industry:
Diethyl 1-benzyl-1,4-dihydro-4-phenylpyridine-3,5-dicarboxylate is used as a therapeutic agent for the treatment of various diseases, including cancer, cardiovascular, metabolic, inflammatory, and neurodegenerative diseases. Its ability to activate SIRT modulators makes it a potential candidate for these applications.
Used in Cancer Treatment:
Diethyl 1-benzyl-1,4-dihydro-4-phenylpyridine-3,5-dicarboxylate is used as a cell-permeable and potent SIRT activator for inducing cell cycle arrest in cancer cells. This property makes it a valuable tool in the development of cancer treatments, as it can potentially halt the progression of the disease and provide a therapeutic advantage.
Used in Drug Development:
In the field of drug development, diethyl 1-benzyl-1,4-dihydro-4-phenylpyridine-3,5-dicarboxylate serves as a lead compound for the design and synthesis of new SIRT modulators. Its selectivity and potency make it an attractive starting point for the development of more effective and targeted therapies for a range of diseases.
Used in Research:
Diethyl 1-benzyl-1,4-dihydro-4-phenylpyridine-3,5-dicarboxylate is used as a research tool to study the role of SIRT1 and its potential as a therapeutic target in various diseases. Its cell-permeable nature and ability to induce cell cycle arrest make it a valuable compound for investigating the underlying mechanisms of disease progression and the development of novel treatment strategies.

References

1) Mai et al. (2009), Study of 1,4-dihydropyridine structural scaffold: discovery of novel sirtuin activators and inhibitors; J. Med.Chem.,52 5496

Upstream product

• 100-52-7 benzaldehyde 
• 100-46-9 benzylamine 
• 623-47-2 propynoic acid ethyl ester 
• 10601-80-6 ethyl 3,3-diethoxypropanoate 
• 3287-99-8 benzylamine hydrochloride 
• 27845-50-7 (E)-N-benzylidenebenzylamine 
• 261896-16-6 tetraethyl 1,5-dibenzyl-1,5,8,8bα-tetrahydro-4,8-diphenylcyclobuta[1,2-b:3,4-b']dipyridine-3,4aα,7,8aβ(4H,4bβH)-tetracarboxylate 

Downstream Products

• 120533-81-5 1-Benzyl-4-phenyl-1,4-dihydro-pyridine-3,5-dicarbothioic acid di-O-ethyl ester 
• 261896-16-6 tetraethyl 1,5-dibenzyl-1,5,8,8bα-tetrahydro-4,8-diphenylcyclobuta[1,2-b:3,4-b']dipyridine-3,4aα,7,8aβ(4H,4bβH)-tetracarboxylate 
• 1053417-68-7 tetraethyl 3,9-dibenzyl-6,12-diphenyl-3,9-diazahexacyclo[6.4.0.0(2.7).0(4.11).0(5.10)]dodecane-1,5,7,11-tetracarboxylate 
• 252671-48-0 3,9-dibenzyl-1,5,7,11-tetrahydroxymethyl-6,12-diphenyl-3,9-diazapentacyclo[6.4.0.0^2,7.0^4,11.0^5,10]dodecane-1,5,7,11-tetracarboxylate 
• 875779-49-0 1-benzyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylic acid 

Relevant academic research and scientific papers

Synthesis and biological evaluation of the first N-alkyl cage dimeric 4- aryl-1,4-dihydropyridines as novel nonpeptidic HIV-1 protease inhibitors

A first series of novel NH and N-alkyl-substituted cage dimeric 4-aryl- 1,4-dihydropyridines 3a-f has been synthesized and evaluated as HIV-1 protease inhibitors in in vitro assays. While the NH and N-methyl derivatives 3a,b,e,f were almost inactive with

Biological evaluation of 4-aryl-1,4-dihydropyridines as VEGFR-2 kinase inhibitors

Vascular endothelial growth factor-2 receptor (VEGFR-2) kinase is a promising target for the development of novel anticancer drugs. Molecular docking modeling was performed on a series of 4-aryl-1,4-dihydropyridines derivatives to evaluate the structural basis for VEGFR-2 inhibitory activity. Some 4-aryl-1,4-dihydropyridines were synthesized in the reaction of aromatic aldehydes and ethyl propiolate with anilines in acetic acid. The biological activities were evaluated against the cells A549, A431 and Hep-G2. The results indicated that 4-aryl-1,4-dihydropyridines could be the promising potential VEGFR-2 inhibitors.

Synthesis of 1,4-dihydropyridines and their fluorescence properties

We have successfully synthesized 3,4,5-substituted 1,4-dihydropyridines (1,4-DHPs) from amine hydrochloride salts, aldehydes, and acetals in good yields without the addition of a catalyst. The synthesized 1,4-DHPs exhibit various wavelengths of fluorescen

1,4- DIHYDROPYRIDINE DERIVATIVES WITH HSP MODULATING ACTIVITY

The invention provides 1,4-dihydropyridine derivatives of formula (I) wherein R1 is optionally substituted C6-24aryl group or 5 to 6 membered heteroaryl group comprising 1 to 3 nitrogen atoms or other heteroatoms like oxygen and sulp

Design, synthesis and biological evaluation Of 3,9-Diazatetraasteranes as novel matrilysin inhibitors

Matrilysin is an ideal biological target to develop novel inhibitors because it is overexpressed in malignant tumour cells. A series of 3,9-diazatetraasteranes was designed as inhibitors of matrilysin, which was an ideal biological target because it is responsible for aggressive malignant phenotypes and poor prognoses implicated in many cancers. Docking simulation supported the initial pharmacophore hypothesis and suggested a common interaction mechanism of 3,9-diazatetraasteranes with the catalytic site of matrilysin. The 3,9-diazatetraasteranes were synthesized by the photocyclization of 4-aryl-1,4-dihydropyridines, and their structures were determined using 1H NMR, 13C NMR and MS. The inhibitory activities of these compounds on matrilysin were investigated in vitro using an MTT assay in A549 (small cell lung cancer) cells. The results show that the 3,9-diazatetraasteranes can inhibit the growth of A549 tumour cells. The best IC50 value is approximately 50 μm. This result indicates that 3,9-diazatetraasteranes will be useful pharmacological tools for the investigation of matrilysin inhibitors. A series of 3,9-diazatetraasteranes was designed and synthesized as matrilysin inhibitors. These compounds were evaluated for their inhibitory activity against A549 (small cell lung cancer) cells and displayed potent activities.

1,4- DIHYDROPYRIDINE DERIVATIVES WITH HSP MODULATING ACTIVITY

The invention provides 1,4-dihydropyridine derivatives of formula (I) wherein R1 is optionally substituted C6-24aryl group or 5 to 6 membered heteroaryl group comprising 1 to 3 nitrogen atoms or other heteroatoms like oxygen and sulp

Novel structure-activity relationships and selectivity profiling of cage dimeric 1,4-dihydropyridines as multidrug resistance (MDR) modulators

Synthesized series of cage dimeric 1,4-dihydropyridines have been systematically evaluated as MDR modulators in in vitro assays to investigate structure-dependent selectivity properties of inhibiting most cancer-relevant efflux pump proteins. Structure-ac

Study of 1,4-dihydropyridine structural scaffold: Discovery of novel sirtuin activators and inhibitors

NAD+-dependent sirtuin deacetylases have emerged as potential therapeutic targets for treatment of human illnesses such as cancer, metabolic, cardiovascular, and neurodegenerative diseases. The benefits of sirtuin modulation by small molecules

Catalytic synthesis of 1,4-dihydropyridine derivatives using scandium(III) triflate

Scandium(III) triflate smoothly catalyzed the reaction of imines with ethyl propiolate (2.5 equiv) to produce the corresponding N-substituted 1,4-dihydropyridines in good yields in toluene or BTF under reflux conditions. It also catalyzed the reaction of

Synthesis and biological evaluation of first N-alkyl syn dimeric 4-aryl-1,4-dihydropyridines as competitive HIV-1 protease inhibitors

A first series of novel N-alkyl substituted syn dimeric 4-aryl-1,4-dihydropyridines 12-17 have been synthesised and evaluated as HIV-1 protease inhibitors in in vitro assays. While the N-methyl derivatives 12 and 13 were almost inactive, with IC50-values of about 225 μM, the N-benzyl compounds with varied ester groups all exhibited stronger activities, with IC50-values of 11-12 μM for the presently best compounds 16 and 17 with ethyl ester functions. The type of HIV-1 protease inhibition of the novel inhibitors was characterised as competitive. With the increase of observed activity from N-methyl derivatives to N-benzyl compounds the binding mode may correspond to that of cyclic ureas with hydrophobic interactions of the four aromatic residues to the S1/S1′ and S2/S2′ regions of HIV-1 protease.