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Upstream product

• 621-59-0 isovanillin 
• 141-97-9 ethyl acetoacetate 
• 626-34-6 ethyl aminocrotonate 

Downstream Products

• 10354-32-2 diethyl 4-(3,4-dimethoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine 3,5-dicarboxylate 

Relevant academic research and scientific papers

Synthesis and antimicrobial evaluation of 2-aminobenzophenone linked 1,4-dihydropyridine derivatives

A series of novel aminobenzophenone linked 1,4-dihydropyridines (1,4-DHPs) hybrids were synthesized by incorporating aminobenzophenone moiety on 1,4-dihydropyridines scaffold (5a-f) and characterized by IR, 1H NMR and CHN elemental analysis. The synthesized compounds were tested for their in vitro antibacterial activity against the Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria. Among all the synthesized compounds, compounds 5b, 5c and 5e have shown the maximum activity in their group whereas compounds 5a, 5d, 5f have shown the minimum activity.

One-pot synthesis of 1,4-dihydropyridine derivatives using the Fe2ZnAl2O7 catalyzed Hantzsch three-component reaction

A facile, low-cost, and effective one-pot method was developed for the synthesis of 1,4-dihydropyridine derivatives with high yields through the three-component reaction of ammonium acetate, ethyl acetoacetate, and aromatic aldehydes using Fe2ZnAl2O7 as catalyst. The reaction was conducted at 70–80°C temperature under solvent free conditions. The developed method had some great advantages, including safe and clean reaction conditions, high to excellent product yields, short reaction time, and a novel and powerful heterogeneous catalyst. The developed heterogeneous solid catalyst had high efficiency and reusability in one-pot multi-component syntheses such that it was easily reused four to five times without significant loss in efficiency and product yield. The catalyst was characterized by scanning Electron Microscopy (SEM)/energy-dispersive X-ray spectroscopy (EDS) and X-ray diffraction techniques. N2 sorption isotherms of the prepared nanocomposite exhibited surface area 2.1313E+01 m2/g and total pore volume of 3.0957E-02 cm3/g. Substituted dihydropyridine derivatives were characterized and confirmed using 1H NMR and 13C NMR, and elemental spectral data.

Anchored sulfonic acid on silica-layered NiFe2O4: A magnetically reusable nanocatalyst for Hantzsch synthesis of 1,4-dihydropyridines

In this study, the immobilization of sulfonic acid on silica-layered nickel ferrite, NiFe2O4@SiO2@SO3H, was investigated. The sulfonated Ni-nanocatalyst was then characterized using FT-IR, SEM, EDX, XRD and VSM analyses. Catalytic activity of the Ni-nanocomposite was also studied towards Hantzsch synthesis of 1,4-dihydropyridines via one-pot condensation reaction of 1,3-diketones (ethyl acetoacetate or 4-hydroxycoumarin), aromatic aldehydes and aqueous ammonia in H2O (70 °C)as a green solvent. All reactions were carried out within 10–100 min to afford the products in high to excellent yields. The green aspect of this synthetic protocol was more studied by examining the reusability of NiFe2O4@SiO2@SO3H MNPs for seven consecutive cycles without the significant loss of catalytic activity. The current method represents remarkable advantages in terms of mild reaction conditions, using H2O as an environmental-friendly solvent, stability and easy separation of the magnetic nanocatalyst, high yield of products, wide tolerance of starting materials and the perfect reusability of the applied Ni-nanocatalyst.

Hybrid pharmacophore-based drug design, synthesis, and antiproliferative activity of 1,4-dihydropyridines-linked alkylating anticancer agents

Two series of novel substituted 1,4-dihydropyridine derivatives incorporating nitrogen mustard pharmacophore hybrids without spacer DHP-M (4a-4d) and with ethyl spacer DHP-L-M (8a-8g) were designed and synthesized. They were subjected to in silico ADME prediction study to check their drug-like properties and evaluated for their cytotoxicity against: A 549 (lung), COLO 205 (colon), U 87 (glioblastoma), and IMR-32 (neuroblastoma) human cancer cell lines in vitro using 3-(4,5-dimethylthiazole-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay against chlorambucil and docetaxel. Majority of the test compounds exhibited moderate to significant cytotoxic activity. The highest activity in all the investigated cancer cells was displayed by DHP-M (4a). This may be due to the less steric hindrance offered by 4a.

Comparative study of catalytic potential of TBAB, BTEAC, and CTAB in one-pot synthesis of 1,4-dihydropyridines under aqueous medium

Convenient and straightforward tetrabutylammonium bromide (TBAB), benzyltrienthylammonium chloride (BTEAC), and cetyltrimethylammonium bromide (CTAB) catalyzed synthesis of 1,4-dihydropyridines (1,4-DHPs) in water was established for the first time. The catalytic potential of phase-transfer catalysts (PTCs) in three different concentrations was envisioned. Aryl aldehydes and hetero aryl aldehydes afforded good yields of 1,4-DHPs in TBAB and BTEAC reactions. In particular, furfuraldehyde and thienyl-2-carbaldehyde produced excellent yields. Isolation of the products through nonchromatographic methods, good to excellent yields, and benign reaction conditions are the major advantages of this protocol.

Synthesis of some C-3,4,5-substituted 2,6-dimethyl-1,4-dihydropyridines (4-DHPs)

A series of C-3,4,5-substituted 2,6-dimethyl-1,4-dihydropyridines (1,4-DHPs) with pharmacological properties were prepared by a variation from the classical Hantzsch synthesis. The procedure involves treatment of the respective aldehyde with either ethyl-3-aminocrotonate or 3-aminocrotonitrile in anhydrous acetic acid at temperatures not exceeding 60°C, thus minimizing by-product formation. The structures of title compounds were elucidated by 1H NMR, 13C NMR, FTIR, and elemental analysis. Copyright Taylor & Francis Group, LLC.

Microwave-assisted synthesis of antimicrobial dihydropyridines and tetrahydropyrimidin-2-ones: Novel compounds against aspergillosis

Ten 4-aryl-1,4-dihydropyridine and three 4-aryl-1,2,3,4- tetrahydropyrimidin-2-one derivatives have been synthesized and examined for their activity against pathogenic strains of Aspergillus fumigatus and Candida albicans. Although none of the three compo

PROCESS FOR THE PREPARATION OF 1,4-DIHYDROPYRIDINES AND NOVEL 1,4-DIHYDROPYRIDINES USEFUL AS THERAPEUTIC AGENTS

The present invention provides a process for the preparation of 1,4-dihydropyridines of the formula (1), wherein R1 is H, NO2, Cl, OAc, OH, R2 is H, NO2, Cl, -O-CH2-O-, OMe, OAc, OEt, OH, R3 is H, NO2, Cl, N(Me)2, -O- CH2 -O-, OMe, OAc, OH, R4 is H, OMe, OAc, OH, R5 is H, Cl, I, and R6 and R7 are either methyl, ethyl or both by preparing a mixture of an aromatic aldehyde, alkyl acetoacetate and a source of ammonia, adsorbing the prepared mixture and adsorbent till adsorbent becomes free flowing, heating the material so obtained under microwave irradiation, cooling the reaction mixture and recovering the compound of formula (1). The present invention also relates to novel 1,4-dihydropyridines with cardiovascular activity.