83301-14-8

Upstream product

• 631-61-8 ammonium acetate 
• 123-11-5 4-methoxy-benzaldehyde 
• 623-47-2 propynoic acid ethyl ester 
• 10601-80-6 ethyl 3,3-diethoxypropanoate 
• 17061-61-9 4-methoxybenzylamine hydrochloride 
• 173065-27-5 (E)-3-<(triphenylphosphoranylidene)amino>propenoic acid ethyl ester 

Downstream Products

• 83301-08-0 1-Acetyl-4-(4-methoxy-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester 
• 83301-06-8 1-Methyl-4-(4-methoxyphenyl)-3,5-diethoxycarbonyl-1,4-dihydropyridine 
• 120533-68-8 4-(4-Methoxy-phenyl)-1,4-dihydro-pyridine-3,5-dicarbothioic acid di-O-ethyl ester 
• 83301-07-9 4-(4-Methoxy-phenyl)-4H-pyridine-1,3,5-tricarboxylic acid triethyl ester 

Relevant academic research and scientific papers

Hetero-intermolecular [2+2] photocycloaddition of 1,4-dihydropyridines: A combined experimental and DFT study

In this article, the hetero-intermolecular [2+2] photocycloaddition of 1,4-dihydropyridines (1,4-DHPs) in solution was reported, wherein head-to-tail (HT) dimeric products (syn-dimers and cage dimers) were formed exclusively through successive inter- and intra-molecular [2+2] cycloaddition. The effects of irradiation wavelength, solvents and substituents on the efficiency of these transformations were investigated. To shed light on the intrinsic characteristics and stereoselectivity of the photocycloaddition, DFT and TDDFT theoretical calculations were carried out to reveal detailed reaction processes.

Highly regioselective photodimerization of 1,4-dihydropyridines: An efficient synthesis of novel 3,6-diazatetraasteranes

Conventional photocycloaddition of 1,4-dihydropyridines does not afford novel head-to-head 3,6-diazatetraasteranes. Herein, we describe a highly regioselective method to synthesize 3,6-diazatetraasteranes via an intramolecular photodimerization of 1,4-dih

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

Multicomponent reactions for diverse synthesis of N-substituted and NH 1,4-dihydropyridines

The multicomponent reactions of aldehydes, electron deficient alkynes and amines have been successfully performed to yield a number of symmetrical 2,6-unsubstituted 1,4-dihydropyridines (1,4-DHPs). This method has been found generally applicable for the s

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.

Reaction of N-vinylic phosphazenes derived from β-amino acids with aldehydes. Azadiene-mediated synthesis of dihydropyridines, pyridines, and polycyclic nitrogen derivatives

Enamino phosphonium salts 2 are obtained by 1,2-addition of hydrogen chloride to N-vinylic phosphazenes 1 derived from triphenylphosphine. Aza- Wittig reaction of phosphazenes 1 derived from triphenylphosphine and 6 derived from diphenylmethylphosphine with aldehydes 3 leads to the formation of 2-azadienes 7. Reaction of azadienes 7 with enamines affords dihydropyridines 9 and 11, pyridines 12, and bicyclic nitrogen heterocycles 15-18 in a regioselective fashion, while heterodiene 20 reacts in the same way with pyrrolidinocyclohexanone giving 1-azaphenanthrene compound 21. Reaction of enamino phosphonium salts 2 with aldehydes 3 gives symmetrical dihydropyridines 5.

Unusual reactivity of (vinylimino)phosphoranes and their utility in the preparation of pyridine and dihydropyridine derivatives

New reactions of (vinylimino)phosphoranes with aldehydes involving an initial nucleophilic attack of the β-carbon atom of the vinyl side chain on the carbonyl carbon atom are reported. Iminophosphorane 4 derived from ethyl β-azidoacrylate reacts with substituted cinnamyl aldehydes to give a mixture of 2-arylpyridine and 4-styryldihydropyridine derivatives, whereas the reaction with substituted benzaldehydes provides 4-aryldihydropyridine derivatives. However, the iminophosphorane 16 derived from the diethyl azidofumarate reacts with cinnamyl aldehydes through the expected aza-Wittig fashion to give 4-arylpyridine derivatives after dehydrogenation of the resulting dihydropyridine.

Synthetic Application of Vinyliminophosphoranes Based on the Reactivity of the Vinyl Side Chain. Preparation of Dihydropyridines

New reactions of vinyliminophosphoranes with aldehydes involving an initial nucleophilic attack of the β-carbon atom of the vinyl side chain on the carbonylic carbon atom is reported.The resulting betaines undergo either intra- or intermolecular cyclization to give pyridines or dihydropyridines.

SYNTHESIS AND PROPERTIES OF 1-SUBSTITUTED DERIVATIVES OF DIETHYL 4-ARYL-1,4-DIHYDROPYRIDINE-3,5-DICARBOXYLIC ACID ESTERS

1-Unsubstituted 4-aryl-3,5-diethoxycarbonyl-1,4-dihydropyridines in the presence of NaH form anions that react with alkyl halides, acid chlorides, and halo acid esters to form the corresponding 1-substituted derivatives of 1,4-dihydropyridine.Hydrolysis o