A Review: Alternative Methods of Preparing 1, 4- Dihydropyridine Derivatives by Hantzsch Reaction (original) (raw)
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Synthesis, Charecterisation and biological Evaluation of Novel Hantzsch 1,4-dihydropyridines
We report a library consisting of some novel Hantzsch dihydropyridines of biological interest as well as their synthesis and analysis. The important steps in the synthetic part were found to be Hantzsch reactions. The synthesized compounds were screened for their in vitro antibacterial activity against two gram-positive bacteria: Staphylococcus aureus and Bacillus subtilis. The title compounds did not exhibit potential antibacterial activity. Furthermore, compounds were subjected to in vitro cytotoxicity against Vero cells. Compounds exhibited weak, moderate, or high cytotoxicity. Compounds 9b, 9c, 9d, 9e, 9f, 9g exhibited potential cytotoxicity.
PREPARATION OF NEW 1,4-DIHYDROPYRIDINES
ln the last two decades considerable attention has been paid to the development of a very heterogeneous group of drugs whose pharmacological activity derives from their capacity to block potential-dependent transmembrane ion channels, that are opened during depolarization and mainly located in cardiac and vascular smooth muscle. These are the so-called calcium antagonists which are mainly used in clinical practice as anti-anginal and antihypertensive agents (1,2). The most important group of these drugs is that of 1,4-dihydropyridines (DHP), whose principal representative, nifedipine, has been subjected to many structural manipulations oriented towards obtaining more potent and selective agents or achieving more prolonged effects. Together with their useful pharmacological activ¡ties, 1 ,4-DH P show a number of other effects, namely, spasmo-lit¡c (3), antihistaminic (4), antiulcer (5), anti-inflammatory (6), PAF antagonistic (7), which could also be therapeutically useful if potentiation of any of these capacities could be attained. Revising the great number of structures reported for the previously prepared 1,4-DHP derivatives and considering the main structure-activity relationships described for Caantagonist and antihypertensive activities, we planned to ascerta¡n the role of the 4-phenyl substituent on those secondary effects and if they were intrinsically dependent on the existence of the 1,4-DHP moiety. ln this work we describe the preparation of three series of 1,4-DHP having methylthioethyl, methylsulfinylethyl and methylsulfonylethyl chains rather than the typical phenyl substituted ring at position 4 of the dihydropyridine.
Chemical and Medicinal Versatility of Substituted 1,4-Dihydropyridines
Current Bioactive Compounds, 2017
Background: Despite considerable evidence showing the importance of the 1,4dihydropyridines, there are very few review articles which provide full access to systematic literature. This review aims to provide synthetic strategy of 1,4-dihydropyridines and medicinal application of different substituted dihydropyridines to develop potent molecules. Methods: A detailed structured search of bibliographic databases was undertaken for peer reviewed research literature using a focused criteria and by different database searches like Pubmed, Scifinder, Elsevier and ACS search. Results: Sixty six papers were included in the review. Molecules containing dihydropyridine scaffold bind to the L-type calcium channel and act as a multifunctional lead molecule for the various cardiovascular activities like antihypertensive, antianginal, vasodilator and cardiac depressants. Apart from the CVS activities, antitubercular, anticonvulsant, antitumor, analgesic, anti-inflammatory, stress protection, antiulcer and antioxidant activities were also observed. The present review highlights the reactivity of DHPs (dihydropyridines) including various synthetic routes as well as specified structural activity features with corresponding pharmacological activities. Conclusion: The findings of this review confirm the significance of a 1,4-dihydropyridines as a privileged scaffold in medicinal chemistry. The major role of this scaffold is in the prevention or treatment of the various diseases. The DHPs are versatile molecules, which exhibit various pharmacological activities such as antimicrobial, antihypertensive, anti-HIV, anticancer, etc.
SYNTHESIS AND SIGNIFICATION OF 1,4-DIHYDROPYRIDINES ANALOGS IN DIFFERENT PHARMACEUTICAL DRUG
World Journal of Pharmaceutical Research, 2015
In the recent past year, The 1,4-dihydropyridines derivatives have been covering a large area of studding because of their synthetic possibility, different chemical behavior, there biological activities and different applications in the pharmaceutical drug. The 1,4-benzothiazine forms an important class of heterocyclic system, it include the N and Smolecules in the ring. The novel 1,4-benzothiazine derivatives occupancy several biological activities such as anti-inflammatory, antirheumatic, antimicrobial, antioxidant, anti-hypertensive, anti-HIV, cardiovascular , ATP-sensitive potassium channel opener, ant malarial, cytotoxic, immunomodulation, neuroprotective and aldose reeducates inhibitor etc.
Royal Society Open Science, 2017
A novel green and efficient one-pot multicomponent reaction of dihydropyridine derivatives was reported as having good to excellent yield. In the presence of the catalyst ceric ammonium nitrate (CAN), different 1,3-diones and same starting materials as 5-bromothiophene-2-carboxaldehyde and ammonium acetate were used at room temperature under solvent-free condition for the Hantzsch pyridine synthesis within a short period of time. All compounds were evaluated for their in vitro antibacterial and antifungal activity and, interestingly, we found that 5(b–f) show excellent activity compared with Ampicillin, whereas only the 5e compound shows excellent antifungal activity against Candida albicans compared with griseofulvin. The cytotoxicity of all compounds has been assessed against breast tumour cell lines (BT-549), but no activity was found. The X-ray structure of one such compound, 5a , viewed as a colourless block crystal, corresponded accurately to a primitive monoclinic cell.
A new synthetic approach to N-substituted 1,4-dihydropyridines
Tetrahedron, 2001
AbstractÐSome novel N-substituted 1,4-dihydropyridines (DHPs) (15a±d) have been synthesized by reaction of 2-amino-5-formyl-4Hpyran (10) with primary amines. Formation of 1,4-DHPs involves ring cleavage of the 4H-pyran ring by nucleophilic attack of the respective amine and subsequent 6-exo-dig cyclization. Treatment of the pyran system 10 with hydrazines under the same reaction conditions leads, however, to the corresponding hydrazone derivatives 12a,b. Two different reaction routes are observed depending whether the amine or hydrazine derivative is used as nucleophilic reagent. A competition between 1,4 versus 1,2 addition reaction pathway is proposed. q
Preparation of four 1,4-dihydropyridine derivatives (DHPs) labeled with carbon-14
Journal of labelled compounds & radiopharmaceuticals, 2018
The importance of DHPs compounds and the need for examining the mechanism of their effect, mandated us to synthesize a number of carbon-14 labeled 1,4-dihydropyridine derivatives for pharmacological studies. Simple preparation and suitable radiochemical yield were advantages of this preparation.
2016
1,4-Dihydropyridines (1,4-DHPs) are recognized as one of the most versatile pharmacophores present as central core in many pharmaceuticals. Low yield and harsh reaction conditions prompted the researchers for the development of new environmental-friendly methods for the synthesis of 1,4-DHPs. This review explored the development of various green chemistry approaches using new catalysts developed for constructing novel 1,4-dihydropyridine and its derivatives. The present review also encompasses the synthesis of some novel 1, 4-DHPs derivatives with novel pharmacological actions. We have restricted our review of synthesis and pharmacological actions of 1,4-DHPs from 2006 onwards.
Synthesis and Evaluation of New Series of 1,4-Dihydropyridine Derivatives as Anticancer Agents
International Journal of Sciences: Basic and Applied Research, 2016
1,4-dihydropyridine derivatives represent one of the important classes of compounds possessing a wide variety of biological activities including anticancer activity. In the present study, (4-Alkyl/Aryl-1-substituted 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxilicacid, 3,5-bis [2(aminothioxomethyl)hydrazides]) (6 a-l) were synthesized by the reaction of 4-alkyl/aryl-3,5-dicarboalkoxy-2,6-dimethyl-1,4-dihydropyridines (4 a-l) with thisemicarbazide and evaluated for their anti-cancer properties. All the synthesized compounds were characterized by IR, NMR and Mass spectra and were screened to evaluating for anticancer activity against three cell lines (MCF-7, HeLa and Hep G 2 ) by using MTT assay method. The results showed that compounds 6j and 6l showed significant cytotoxicity with IC 50 values ranging from 56µM - 74µM.