Conformational analysis of 4-aryl-dihydropyrimidine calcium channel modulators. A comparison of ab initio, semiempirical and X-ray crystallographic studies

Kappe, C. Oliver; Fabian, Walter M. F.; Semones, Marcus A.

doi:10.1016/s0040-4020(97)00022-7

Cited by 377 publications

(18 citation statements)

References 25 publications

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“…In the following decades the original cyclocondensation reaction has been extended widely to include variations in all three components, allowing access to a large number of multifunctionalized dihydropyrimidine derivatives [3]. Largely ignored for many years, the Biginelli reaction has recently attracted a great deal of renewed attention, and several improved procedures for the preparation of dihydropyrimidines of type 8 – 12 have been reported within the past few years [4,5]. Various solid phase modifications of the Biginelli reaction suitable for combinatorial chemistry have also been described [6,7,8,9].…”

Section: Introductionmentioning

confidence: 99%

An Efficient One-Pot Protocol for the Synthesis of Substituted 3,4-Dihydropyrimidin-2(1H)-ones Using Metallophthalocyanines (MPcs) as Potent Heterogeneous Catalysts: Synthesis, Characterization, Aggregation and Antimicrobial Activity

et al. 2017

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In this study, novel phthalonitrile 3 and their corresponding metal-free 4 and metallophthalocyanine derivatives 5–7 bearing 2-isopropenyl-4-methoxy-1-methylbenzene groups were synthesized and characterized. 3,4-Dihydropyrimidinones have been synthesized by a modified Biginelli-type reaction with various metallophthalocyanines 5–7 as catalysts. Compared to the classical Biginielli reaction, the new method has the advantages of good yield and short reaction time. Among the various metallophthalocyanines studied, cobalt (II)-phthalocyanine was found to be most active for this transformation. The newly prepared compounds were characterized using elemental analyses, MS, IR, 1H/13C-NMR and UV-Vis spectroscopy. In addition; the 3,4-dihydropyrimidinones (DHPMs) 8–12 were investigated for antimicrobial activities and revealed good activity. The minimum inhibitory concentration (MIC) was determined by the microdilution technique in Mueller-Hinton broth. The MICs were recorded after 24 hours of incubation at 37 °C. These results are promising, showing these compounds are biologically active.

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Section: Introductionmentioning

confidence: 99%

An Efficient One-Pot Protocol for the Synthesis of Substituted 3,4-Dihydropyrimidin-2(1H)-ones Using Metallophthalocyanines (MPcs) as Potent Heterogeneous Catalysts: Synthesis, Characterization, Aggregation and Antimicrobial Activity

et al. 2017

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“…Dihydropyrimidinones (DHPMs) and their derivatives are well known heterocyclic units in the realm of natural and synthetic organic chemistry due to their wide spectrum of biological and therapeutic properties such as antibacterial, antiviral, antitumor and anti-inflammatory activities [1,2,3]. Recently, appropriately functionalized DHPM analogs have emerged as integral backbones of several calcium channel blockers, antihypertensive agents and α-la-adrenergic receptor antagonists [4,5].…”

Section: Introductionmentioning

confidence: 99%

Copper(II) Sulfamate: An Efficient Catalyst for the One-Pot Synthesis of 3,4-Dihydropyrimidine-2(1H)-ones and thiones

Liu

Wang

2009

Molecules

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“…There has been considerable interest in the development of preparative methods for the production of pyrimidines. This seems that pyrimidines represent one of the most active classes of compounds, possessing a wide spectrum of biological activities, namely, diuretic [1], antitumor [2], anti-HIV [3], cardiovascular [4], analgesic [5], calcium antagonist [6], anti-inflammatory [7], CNS depressant activity [8], and antimalarialactivity [9].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Some New Pyrimidine-Azitidinone Analogues and Their Antioxidant,In VitroAntimicrobial, and Antitubercular Activities

Chandrashekaraiah

Lingappa²,

Gowda

et al. 2014

Journal of Chemistry

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A series of 1-(3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)-4-methylphenyl)-3-chloro-4-(2-mercaptoquinolin-3-yl)azetidin-2-one (7a-j) have been synthesized from the condensation of aromatic amines withN-phenylacetamide. The thione nucleus formed from 2-chloroquionoline-3-carbadehyde using sodium sulphide in dimethyl formamide (DMF) was followed by the reaction with pyrimidine amine to form the Schiff base intermediates. Attempt has been made to derive final azetidinone analogues from Schiff bases by using chloroacetyl chloride. The newly synthesized analogues were examined for the antimicrobial activity against some bacterial and fungal strains andin vitroantituberculosis activity against mycobacterium tuberculosis. These observations provide some predictions to design further antibacterial and antituberculosis active compounds prior to their synthesis according to molecular studies.

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Conformational analysis of 4-aryl-dihydropyrimidine calcium channel modulators. A comparison of ab initio, semiempirical and X-ray crystallographic studies

Cited by 377 publications

References 25 publications

An Efficient One-Pot Protocol for the Synthesis of Substituted 3,4-Dihydropyrimidin-2(1H)-ones Using Metallophthalocyanines (MPcs) as Potent Heterogeneous Catalysts: Synthesis, Characterization, Aggregation and Antimicrobial Activity

An Efficient One-Pot Protocol for the Synthesis of Substituted 3,4-Dihydropyrimidin-2(1H)-ones Using Metallophthalocyanines (MPcs) as Potent Heterogeneous Catalysts: Synthesis, Characterization, Aggregation and Antimicrobial Activity

Copper(II) Sulfamate: An Efficient Catalyst for the One-Pot Synthesis of 3,4-Dihydropyrimidine-2(1H)-ones and thiones

Synthesis of Some New Pyrimidine-Azitidinone Analogues and Their Antioxidant,In VitroAntimicrobial, and Antitubercular Activities

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