53219-65-1Relevant academic research and scientific papers
An unexpected Cu(II) complex of oxidized 1,4-dydropyridine derivative: Synthesis, characterization and DFT calculations
Fan, Qiangwen,Wu, Guorong,Chen, Yong,He, Yanling,Zhu, Longwei,Ren, Huijun,Lin, Hailu
, (2021/02/16)
A Cu(II) complex of 4-phenyl-3,5-dicarboxylic-pyridine (HL2), [Cu(HL2)Py], was isolated unexpectedly during studying coordination reaction of 3,5-dicarboxylic-1,4-dihydropyridine-4-phenyl ligand (HL1) with copper(II) nitra
Studies on chemoselective synthesis of 1,4- And 1,2-dihydropyridine derivatives by a Hantzsch-like reaction: A combined experimental and DFT study
Li, Peng,Song, Xiuqing,Tian, Nana,Wang, Juan,Wang, Shijie,Yan, Hong
, p. 3882 - 3892 (2021/05/14)
In the experimental process of preparing diethyl 3,5-dicarboxylate-1,4-dihydropyridine (1,4-DHP) by a Hantzsch-like reaction, it was found that a by-product named diethyl 3,5-dicarboxylate-1,2-dihydropyridine (1,2-DHP) was produced in the reaction. To discuss this phenomenon, the effects of the reaction conditions on the yield ratio of 1,4-DHP and 1,2-DHP were studied by using aromatic amines, aromatic aldehydes and ethyl propiolate as raw materials. The mechanisms for the formation of 1,4-DHP and 1,2-DHP were proposed based on the isolated intermediate named diethyl 4-((phenylamino)methylene)pent-2-enedioate generated by the Michael addition of aniline and ethyl propiolate. The transition state structures were optimized and the reaction energy barriers of intermediates in the speculated mechanisms were calculated by DFT calculations at the M062X/def2TZVP//B3LYP-D3/def-SVP level. It was found that the reaction energy barriers and dominant configurations of intermediates IM2 and IM3′ are the determinants for the chemoselectivity. Together, these results demonstrate a high chemoselectivity in the synthesis of 1,4-DHPs and 1,2-DHPs by a Hantzsch-like reaction and that 1,4-DHPs and 1,2-DHPs can be easily obtained under different conditions. This journal is
Highly regioselective photodimerization of 1,4-dihydropyridines: An efficient synthesis of novel 3,6-diazatetraasteranes
Tan, Hong-Bo,Zhao, Zhi-Chang,Ma, Zong-Shan,Yan, Hong
, p. 529 - 534 (2018/01/01)
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
Hetero-intermolecular [2+2] photocycloaddition of 1,4-dihydropyridines: A combined experimental and DFT study
Fan, Qiangwen,Tan, Hongbo,Li, Peng,Yan, Hong
, p. 16795 - 16805 (2018/10/23)
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.
Intermolecular [2 + 2] Cycloaddition of 1,4-Dihydropyridines with Olefins via Energy Transfer
Wang, Chengfeng,Lu, Zhan
supporting information, p. 5888 - 5891 (2017/11/10)
A highly regio- and diastereoselective visible-light-promoted [2 + 2] cycloaddition between readily available 1,4-dihydropyridines and olefins has been developed. This strategy is operationally simple and atom-economical and enables the construction of strained polysubstituted 2-azabicyclo[4.2.0]octanes with three all-carbon quaternary centers with good functional group tolerance. These products can be easily converted to various structurally unique derivatives. The primary mechanistic studies demonstrated that the reaction proceeds through an energy transfer pathway.
Biological evaluation of 4-aryl-1,4-dihydropyridines as VEGFR-2 kinase inhibitors
Sun,Ma,Yan
, p. 2891 - 2899 (2017/03/22)
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.
Oxidative activation of dihydropyridine amides to reactive acyl donors
Funder, Erik Daa,Trads, Julie B.,Gothelf, Kurt V.
, p. 185 - 198 (2015/01/16)
Amides of 1,4-dihydropyridine (DHP) are activated by oxidation for acyl transfer to amines, alcohols and thiols. In the reduced form the DHP amide is stable towards reaction with amines at room temperature. However, upon oxidation with DDQ the acyl donor is activated via a proposed pyridinium intermediate. The activated intermediate reacts with various nucleophiles to give amides, esters, and thio-esters in moderate to high yields. This journal is
Synthesis of 1,4-dihydropyridines and their fluorescence properties
Sueki, Shunsuke,Takei, Ryo,Zaitsu, Yuto,Abe, Junya,Fukuda, Akane,Seto, Keisuke,Furukawa, Yukio,Shimizu, Isao
, p. 5281 - 5301 (2014/10/15)
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
Design, synthesis and biological evaluation Of 3,9-Diazatetraasteranes as novel matrilysin inhibitors
Liu, Yanlan,Tan, Hongbo,Yan, Hong,Song, Xiuqing
, p. 567 - 578 (2013/11/06)
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.
Enaminones in a multicomponent synthesis of 4-aryldihydropyridines for potential applications in photoinduced intramolecular electron-transfer systems
Al-Awadi, Nouria A.,Ibrahim, Maher R.,Elnagdi, Mohamed H.,John, Elizabeth,Ibrahim, Yehia A.
supporting information; experimental part, p. 441 - 447 (2012/06/29)
An efficient three component reaction with enaminones, primary amines and aldehydes resulted in easy access to 1,4-dihydropyridines with different substituents at the 1-, 3-, 4- and 5-positions. Microwaves improved the reaction yield, reducing also considerably the reaction time and the amount of solvent used. Chiral primary amines gave chiral 1-substituted-1,4-dihydropyridines. The 4-(1-naphthyl) and 4-(phenanthren-9-yl)dihydropyridine derivatives exhibited an interesting photoluminescence behavior, which suggests their potential application as suitable photoinduced intramolecular electron-transfer systems.
