cas 21829-25-4, Nifedipine | Articles data

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Protective role of the novel hybrid 3,5-dipalmitoyl-nifedipine in a cardiomyoblast culture subjected to simulated ischemia/reperfusion
This work investigated the acute effects of the calcium channel blocker nifedipine and its new fatty hybrid derived from palmitic acid, 3,5-dipalmitoyl-nifedipine, compared to endocannabinoid anandamide during the process of inducing ischemia and reperfusion in cardiomyoblast H9c2 heart cells. The cardiomyoblasts were treated in 24 or 96-well plates (according to the test being performed) and maintaining the treatment until the end of hypoxia induction. The molecules were tested at concentrations of 10 and 100?μM, cells were treated 24?h after assembling the experimental plates and immediately before the I/R. Cell viability, apoptosis and necrosis, and generation of reactive oxygen species were evaluated. Nifedipine and 3,5-dipalmitoyl-nifedipine were used to assess radical scavenging potential and metal chelation. All tested molecules managed to reduce the levels of reactive oxygen species compared to the starvation?+?vehicle group. In in vitro assays, 3,5-dipalmitoyl-nifedipine showed more antioxidant activity than nifedipine. These results indicate the ability of this molecule to act as a powerful ROS scavenger. Cell viability was highest when cells were induced to I/R by both concentrations of anandamide and the higher concentration of DPN. These treatments also reduced cell death. Therefore, it was demonstrated that the process of hybridization of nifedipine with two palmitic acid chains assigns a greater cardioprotective effect to this molecule, thereby reducing the damage caused by hypoxia and reoxygenation in cardiomyoblast cultures.
Santa-Helena, Eduarda,Teixeira, Stefanie,Castro, Micheli Rosa de,Cabrera, Diego da Costa,D'Oca, Caroline Da Ros Montes,D'Oca, Marcelo G. Montes,Votto, Ana Paula S.,Nery, Luiz Eduardo Maia,Gon?alves, Carla Amorim Neves
p. 356 - 364
(2017)
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Catalytic effect of nanosized metal oxides on the Hantzsch reaction
The effect of nanosized copper and aluminum oxides, which have a higher sorption capacity than that of bulk samples, on the Hantzsch reaction was studied. The adsorption of starting benzaldehydes and ethyl acetoacetate on the surface of copper and aluminum nanooxides resulted in the activation of these molecules and accelerated the Hantzsch reaction. In addition, considerable activation of ammonia and intermediates (chalcone and enamine) on the surface of aluminum nanooxide facilitated an increase in the rate and selectivity of the process. The experimental results were used to develop a one-pot method for the preparation of nifedipine and nitrendipine.
Fedorova,Koryakova,Valova,Ovchinnikova,Titova,Rusinov,Charushin
p. 566 - 572
(2010)
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Approaches to combinatorial synthesis of heterocycles: A solid-phase synthesis of 1,4-dihydropyridines
N-Immobilized enamino esters 2 derived from amine-functionalized PAL or Rink polystyrene resins react with preformed 2-arylidene β-keto esters or directly with β-keto esters and aldehydes to afford, upon trifluoroacetic acid cleavage, 1,4-dihydropyridine (DHP) derivatives in good yields. The mechanism of this transformation on solid support has been studied using 13C NMR and IR spectroscopies. This new solid-phase synthesis has been applied to the preparation of several bioactive DHPs and is designed to be amenable to the 'split and pool' protocol for combinatorial library synthesis.
Gordeev, Mikhail F.,Patel, Dinesh V.,Gordon, Eric M.
p. 924 - 928
(1996)
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Conformational preferences and dynamics of 4-isoxazolyl-1,4-dihydropyridine calcium channel antagonists as determined by variable-temperature NMR and NOE experiments
A series of 14 4-(3′,5′-disubstituted isoxazolyl)-1,4-dihydropyridine calcium channel antagonists were examined using variable-temperature proton nuclear magnetic resonance spectroscopy and nuclear Overhauser effect (NOE) experiments. Two of these compounds, the 1,4-dihydro-2,6-dimethyl-4-[5′-methyl-3′-(4″-fluorophenyl) isoxazol-4′-yl]-3,5-pyridinedicarboxylic acid dimethyl ester (3a) and 1,4-dihydro-2,6-dimethyl-4-[5′-methyl-3′-(4″-bromophenyl) isoxazol-4′-yl]-3,5-pyridinedicarboxylic acid dimethyl ester (5a), were synthesized to assist in the clarification of ambiguities discovered in the low-temperature spectra of 1,4-dihydro-2,6-dimethyl-4-(5′-methyl-3′-phenylisoxazol-4′yl)- 3,5-pyridinedicarboxylic acid diethyl ester (2b). The solid-state structure of 3a is also reported. The solution-state rotameric preferences of the 14 compounds are reported and compared with those calculated at the AM1 level. C-4 - C-4′ bond rotation barriers were also calculated at the AM1 level for nine of the systems examined. Several species failed to display temperature-dependent signals associated with hindered rotation owing to highly biased rotameric equilibria at the temperatures required to freeze out the rotation. The seven experimental rotation barriers (ΔG≠ from ≤26 to 40.4 kJ mol-1) reported are 1-6.8 kJ mol-1 higher than ΔH≠ calculated at the AM1 level).
Palmer, Robert B.,Andro, Tina M.,Natale, Nicholas R.,Andersen, Niels H.
p. 495 - 504
(1996)
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METHODS FOR TREATING CHRONIC FATIGUE SYNDROME AND MYALGIC ENCEPHALOMYELITIS
In one aspect the invention relates to a method of treatment selected from the group consisting of: (a) treating a symptom such as pain in a subject identified or diagnosed as having Myalgic Encephalomyelitis/Chronic Fatigue Syndrome (ME/CFS); (b) treating a symptom such as pain in a subject having dysfunctional TRPM3 ion channel activity; (c) restoring NK cell function in a subject having dysfunctional TRPM3 ion channel activity; and (d) restoring calcium homeostasis in a subject having dysfunctional TRPM3 ion channel activity. The method comprises the step of administering to the subject a therapeutically effective amount of at least one therapeutic compound selected from the group consisting of: (i) an opioid receptor antagonist; (ii) an opioid antagonist; and (iii) a therapeutic compound that restores TRPM3 ion channel activity. In some embodiments the therapeutic compound is naltrexone hydrochloride.
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(2021/03/13)

Aqueous CO2fixation: construction of pyridine skeletons in cooperation with ammonium cations
A simple and green method is explored for the synthesis of fused pyridines by [2 + 2 + 1 + 1] the cycloaddition of ketones with an ammonium cation under a CO2atmosphere. The reactions employed ammonium cation as a nitrogen source and CO2gas as a carbon source in an aqueous solution. Monoethanolamine (MEA) was used as an additive to increase the solubility of CO2in an aqueous solution. The scope and versatility of the method are demonstrated with 38 examples. Products are found to be photosensitive and show potential applications as organic optoelectronic materials. A selectfluor-promoted reaction mechanism is proposed based on the experimental studies. Our work is superior as it is a metal-free system, uses CO2as a carbon source and MEA as an additive in aqueous synthesis.
Fan, Weibin,Guo, Shiwei,Huang, Deguang,Li, Yinghua,Xiang, Shiqun,Zhang, Wei
supporting information
p. 7950 - 7955
(2021/10/29)

Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer
A photoinduced iron-catalyzed ipso-nitration of aryl halides with KNO2 has been developed, in which aryl iodides, bromides, and some of aryl chlorides are feasible. The mechanism investigations show that the in situ formed iron complex by FeSO4, KNO2, and 1,10-phenanthroline acts as the light-harvesting photocatalyst with a longer lifetime of the excited state, and the reaction undergoes a photoinduced single-electron transfer (SET) process. This work represents an example for the photoinduced iron-catalyzed Ullmann-type couplings.
Wu, Cunluo,Bian, Qilong,Ding, Tao,Tang, Mingming,Zhang, Wenkai,Xu, Yuanqing,Liu, Baoying,Xu, Hao,Li, Hai-Bei,Fu, Hua
p. 9561 - 9568
(2021/08/06)

Preparation method of nifedipine
The invention provides a preparation method of nifedipine, belonging to the technical field of organic drug synthesis. According to the preparation method of nifedipine, under the action of a nitrogen-containing heterocyclic carboxylic acid catalyst, an intermediate methyl (o-nitrobenzylidene)acetoacetate and 3-aminocrotonic acid methyl ester are subjected to an addition reaction in a C1-C4 loweraliphatic alcohol solvent so as to prepare nifedipine. The time of the addition reaction is obviously shortened, and particularly, the content of special impurities in a crude nifedipine product is obviously reduced, so a subsequent refining process is greatly simplified, and an efficient, simple, convenient and novel method is provided for the batch production of the nifedipine in the future.
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Paragraph 0051-0061

(2020/07/02)

Preparation method and application of novel ionic beta-naphthol aldehyde Schiff base zirconium complex
The invention belongs to the technical field of catalytic organic synthesis, and particularly relates to a preparation method and application of a novel ionic beta-naphthol aldehyde Schiff base zirconium complex. Zirconium atoms are coordinated with a beta-naphthol aldehyde Schiff base ligand and water molecules, and two perfluoroalkyl (aryl) sulfonic acid groups are combined with central atom zirconium through covalent bonds and ionic bonds respectively. The preparation method comprises the following steps: dissolving beta-naphthol aldehyde Schiff base zirconium dichloride in a solvent, adding a silver salt under the protection of N2, reacting the mixture for 1-4 hours in a dark place at room temperature, performing filtration, adding n-hexane into filtrate until layering, putting the solution into a refrigerator, and freezing the solution for 24 hours to separate out the beta-naphthol aldehyde Schiff base zirconium complex. The beta-naphthol aldehyde Schiff base zirconium complex hashigh air stability and strong Lewis acidity, and can efficiently catalyze the Hantzsch reaction of aldehyde, beta-ketoester and ammonium acetate to synthesize 1,4-dihydropyridine derivatives.
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Paragraph 0041; 0070-0071

(2019/12/02)

Method for synthesizing 1,4-dihydropyridines derivatives
The invention relates to a method for synthesizing 1,4-dihydropyridines derivatives. According to the method, a fluorescence-marked nonmetal organic boron-nitrogen lewis acid-alkali dual-functional complex is used as a catalyst, so that the pollution of heavy metals is effectively avoided; the catalyst can be recycled, and a residual amount of the catalyst in a product can be rapidly detected; and the source of raw materials is wide, the target yield is close to 100 percent, the reaction process is a homogenous reaction, and a product is obtained by virtue of chromatographic separation. The whole reaction system can be directly amplified, and the industrialization prospect is significant.
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Paragraph 0138; 0139

(2017/10/27)

Sulfated polyborate: An efficient and reusable catalyst for one pot synthesis of Hantzsch 1,4-dihydropyridines derivatives using ammonium carbonate under solvent free conditions
A simple and efficient method for the synthesis of four-component 1,4-dihydropyridines of various aldehydes, β-ketoesters and ammonium carbonate catalyzed by sulfated polyborate with high yields under a solvent free condition at 90?°C is described. The key advantages of the present method are high yields, short reaction time, solvent free condition, easy workup, recyclability of catalyst and ability to tolerate a variety of functional groups which gives economical as well as ecological rewards.
Rekunge, Deelip S.,Khatri, Chetan K.,Chaturbhuj, Ganesh U.
supporting information
p. 1240 - 1244
(2017/03/02)

An efficient and recyclable 3D printed α-Al2O3 catalyst for the multicomponent assembly of bioactive heterocycles
A catalytic methodology is reported that enables the efficient, operationally simple and environmentally friendly synthesis of diverse 1,4-dihydropyridines and 3,4-dihydropyrimidin-2(1H)-ones, including some relevant drugs and pharmacologically active derivatives. This strategy is based on the use of a 3D printed Al2O3 woodpile material that was sintered to generate a rigid structure with controlled porosity and noteworthy catalytic performance. The 3D printed Al2O3 catalyst exhibits remarkable efficacy as a Lewis acid in Biginelli and Hantzsch reactions and it can be recovered and reused ten times without any decrease in the activity. Remarkable E factors, excellent recyclability and scalability, broad substrate scope, short reaction times, excellent yields, solvent-free conditions and easy isolation procedures are key features of this methodology.
Azuaje, Jhonny,Tubío, Carmen R.,Escalante, Luz,Gómez, Mónica,Guitián, Francisco,Coelho, Alberto,Caama?o, Olga,Gil, Alvaro,Sotelo, Eddy
p. 203 - 210
(2016/12/09)

Synthesis, docking simulation, biological evaluations and 3D-QSAR study of 1,4-dihydropyridines as calcium channel blockers
Resurgence to target L-type voltage-dependent calcium channels has been applied by the synthesis of two series of nifedipine analogues where the ortho- or a meta-nitrophenyl ring is retained. A pre-synthetic molecular docking study with a receptor model followed by molecular alignment has been performed on 47 compounds to predict the most active member. The IC50 values revealed that some of the compounds are similar to or more active than nifedipine. Substitution of groups at the 3- and 5-positions of the dihydropyridine (DHP) ring gave 3k, which is more active than nifedipine. Our valid three-dimensional quantitative structure–activity relationship (3D-QSAR) model prefigures the influence of lipophilicity, bulkiness and chelating effects of the C3 and C5 substituents. Bulky groups interfere with ring-to-ring hydrophobic interaction with tyrosine (Tyr)4311 and limit the efficiency of increasing the length of the hydrocarbon chain of esters at the 3- and 5-positions of the DHP ring as an approach to increasing the activity. The presence of a chelating substituent on the phenyl ring at the 4-position of the DHP ring ensures strong binding to the receptor and hence stabilization of the closed-channel conformation. The validation of 3D-QSAR model indicated its proficiency in predicting activity of newly compounds belonging to the same chemical class.
El-Moselhy, Tarek Fathy,Sidhom, Peter Ayoub,Esmat, Eman Ahmed,El-Mahdy, Nageh Ahmed
p. 893 - 903
(2018/10/31)

Method for synthesis of nifedipine in continuous flow micro-reactor
The invention discloses a method for synthesis of nifedipine in a continuous flow micro-reactor. The method comprises the following steps: 1) injecting an ethanol solution containing 1-2 M of 2-nitrobenzaldehyde and 1-2 M of methyl acetoacetate in a micro mixer at a flow speed of 5-50 [mu]l/min through a connecting pipe, at the same time, injecting an ammonium acetate aqueous solution (20-30 wt%) in the micro mixer at the same flow speed through a connecting pipe with the same diameter as the connecting pipe, mixing, then allowing to enter a micro-tube reactor, and carrying out a reaction, wherein the oil bath temperature of the micro-tube reactor is 100 DEG C-120 DEG C, the micro-tube diameter of the micro-tube reactor is 0.5 mm, and the tube length is 1-3 m; and collecting a solution of a nifedipine crude product at an outlet of the reactor with a cooled container, and precipitating to obtain nifedipine; and 2) carrying out recrystallization of the nifedipine crude product with 95% ethanol, filtering, washing, and drying to obtain the nifedipine. The nifedipine is synthesized in the continuous flow micro-reactor; by strengthening raw material mixing and condensation reaction conditions, the reaction speed is accelerated, the incidence of adverse reactions is reduced, the purification operation is simplified, and the yield of the nifedipine is improved.
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Paragraph 0031

(2016/10/09)

Benzyltrimethylammoniumfluoride Hydrate: An Efficient Catalyst for One-Pot Synthesis of Hantzsch 1,4-Dihydropyridines and Their Aromatization
An efficient, cost-effective and simple protocol has been developed for the synthesis of Hantzsch 1,4-dihydropyridines and their oxidation into pyridines using benzyltrimethylammonium fluoride hydrate as an excellent catalyst under solvent-free condition. All of the products synthesized by this method are characterized by various spectroscopic methods (IR, 1H NMR, 13C NMR, and DEPT).
Khaskel, Anamika,Barman, Pranjit
p. 114 - 120
(2016/04/01)

A Simple and Efficient One-pot Synthesis of 1,4-dihydropyridines Using Nano-WO3-supported Sulfonic Acid as an Heterogeneous Catalyst under Solvent-free Conditions
Nano-tungsten trioxide-supported sulfonic acid (n-WSA) was found to be an effective heterogeneous catalyst for the one-pot reaction of aromatic aldehydes, β-dicarbonyl compounds and ammonium acetate to afford 1,4-dihydropyridine derivatives in good to excellent yields. The other main advantages of the present method are short reaction times, simple workup, ease in purification and environmentally benign methodology. The reaction conditions were optimized employing Response Surface Method technique (Central Composite Design (CCD)) which is economically considerable because of the minimum number of experiments required to evaluate the effects of multiple parameters on the response.
Bitaraf, Mehrnoosh,Amoozadeh, Ali,Otokesh, Somayeh
p. 336 - 344
(2016/05/09)

Synthesis of hantzsch 1,4-dihydropyridines in a continuous flow microreactor
A simple and efficient synthesis of Hantzsch 1,4-dihydropyridines from the condensation of benzaldehydes with alkyl acetoacetates/benzoylacetate and aqueous ammonia in the absence of catalyst has been developed by using a continuous flow microreactor. Under optimized condition, various 1,4-dihydropyridines were obtained in 80-93% yield with high atom efficiency. Compared with using batch system, the present smooth procedure greatly accelerated the reaction due to the excellent mixing and mass transfer of reactant in micro flow system.
Gao, Peiyuan,Sun, Xuan,Lei, Ming,Zhang, Hong
p. 755 - 761
(2017/04/10)

First Report About the Use of Micellar Keggin Heteropolyacids as Catalysts in the Green Multicomponent Synthesis of Nifedipine Derivatives
Abstract: Micellar Keggin heteropolyacid catalysts were prepared using hexadecyltrimethylammonium bromide (cetyltrimethylammonium bromide—CTAB), 1-hexadecyl-pyridinium chloride, and Keggin heteropolyacids H3PMo12O40 and H4PMo11VO40 as precursors. Four catalysts were prepared (PMo12C16, PMo11VC16, PMo12C16Py, and PMo11VC16Py) and characterized by 31P NMR, FT-IR, XRD, SEM analysis and textural properties (SBET). The acidic characteristics of the catalysts were determined by potentiometric titration with n-butylamine. A series of bioactive 1,4-dihydropyridine derivatives such as nifedipine and nemadipine B were synthesized using these new materials, in a one-pot procedure in ethanol. This methodology requires a reaction time of 8?h, and a temperature of 78?°C to obtain good to excellent yields of 1,4-dihydropyridine derivatives. The micellar Keggin catalysts are insoluble in polar media, which allows easy removal of the reaction products without affecting their catalytic activity. The leaching test showed that they have an excellent stability and can be used five times as heterogeneous catalysts without appreciable loss of the catalytic activity. Using the same material, unsymmetrical 1,4-dihydropyridines such as nitrendipine can be obtained through a sequence of steps in very good yield (78?%). Graphical Abstract: [Figure not available: see fulltext.]
Palermo, Valeria,Sathicq, ángel G.,Constantieux, Thierry,Rodríguez, Jean,Vázquez, Patricia G.,Romanelli, Gustavo P.
p. 1634 - 1647
(2016/08/30)

Study of temperature dependent three component dynamic covalent assembly VIa Hantzsch reaction catalyzed by dioxido- and oxidoperoxidomolybdenum(VI) complexes under solvent free conditions
Tridentate ONO donor ligands derived from heterocyclic compound 4-acetyl-3-methyl-1-phenyl-2-pyrazoline-5-one (Hap) and aromatic hydrazides {benzoyl hydrazide (Hbhz), isonicotinoyl hydrazide (Hinh), nicotinoyl hydrazide (Hnah) and furoyl hydrazide (Hfah)} react with [MoVIO2(acac)2] (Hacac = acetylacetone) in equimolar ratio in methanol to give dioxidomolybdenum(vi) complexes, [MoO2(ap-bhz)(MeOH)] 1, [MoO2(ap-inh)(MeOH)] 2, [MoO2(ap-nah)(MeOH)] 3 and [MoO2(ap-fah)(MeOH)] 4. Reaction of these ligands with in situ generated oxidoperoxidomolybdenum(vi) precursor results in the formation of oxidoperoxidomolybdenum(vi) complexes, [MoO(O2)(ap-bhz)(MeOH)] 5, MoO(O2)(ap-inh)(MeOH)] 6, MoO(O2)(ap-nah)(MeOH)] 7 and MoO(O2)(ap-fah)(MeOH)] 8. These complexes have been characterized by elemental analysis, spectroscopic techniques (infrared, UV-vis, 1H and 13C NMR) and thermogravemetric analysis. The structures of complexes [MoVIO2(ap-bhz)(H2O)] 1a (water coordinated), [MoVIO2(ap-bhz)(DMSO)] 1b (DMSO coordinated), [MoVIO2(ap-nah)(DMF)] 3a (DMF coordinated), [MoVIO(O2)(ap-bhz)(MeOH)] 5 (methanol coordinated) and [MoVIO(O2)(Hap-nah)(OMe)]·MeOH 7a (methoxy coordinated) have been confirmed by single crystal X-ray studies. X-ray diffraction study also reveals that tridentate ligands bind to the metal center through enolic oxygen (of pyrazolol), azomethine nitrogen and enolic oxygen (of hydrazide) atoms. In complex 7a, pyridinic nitrogen is protonated. These complexes [dioxidomolybdenum(vi) as well as oxidoperoxidomolybdenum(vi)] have been tested as catalysts for temperature dependent one pot three component (methylacetoacetate, benzaldehyde and ammonium acetate) dynamic covalent assembly, via Hantzsch reaction, using 30% H2O2 as a green oxidant under solvent free conditions. Various parameters such as the amount of catalyst, oxidant and temperature of the reaction mixture have been taken into consideration to optimize the reaction conditions. In the Hantzsch reaction, the temperature and oxidant control the conversion and selectivity of the desired product.
Maurya, Mannar R.,Saini, Neeraj,Avecilla, Fernando
p. 12993 - 13009
(2016/02/12)

METHOD FOR PRODUCING PULVERIZED ORGANIC COMPOUND PARTICLE
Disclosed is a method for producing pulverized particles of a crystalline organic compound which is poorly water-soluble. Also disclosed is a pulverized organic compound particle produced by such a method. Specifically disclosed is a method for producing a poorly water-soluble organic compound particle for medical use, which is characterized in that a poorly water-soluble organic compound for medical use is mixed with a physiologically acceptable salt and a physiologically acceptable polyol, and subjected to wet milling. Also specifically disclosed is a poorly water-soluble organic compound particle for medical use, which is produced by such a production method.
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(2015/12/19)

L-Tyrosine loaded nanoparticles: An efficient catalyst for the synthesis of dicoumarols and Hantzsch 1,4-dihydropyridines
Environmentally benign l-tyrosine loaded nanoparticles are fabricated and characterized by PCS, TEM, FT-IR and AFM studies. A novel straightforward green approach was applied for the synthesis of dicoumarols and Hantzsch 1,4-dihydropyridines using this catalyst. The structures and purity of these compounds were confirmed by FT-IR and NMR (1H, 13C and DEPT). The flexible and swelling properties of the polymer coating increase l-tyrosine dispersion and its high catalytic activity in organic reactions. This journal is
Khaskel, Anamika,Barman, Pranjit,Jana, Utpal
p. 13366 - 13373
(2015/02/19)

Air-stable zirconocene bis(perfluorobutanesulfonate) as a highly efficient catalyst for synthesis of N-heterocyclic compounds
Zirconocene bis(perfluorobutanesulfonate) is air- and water-stable and proved to be ionic on basis of conductivity measurements. It exhibits high catalytic efficiency for the synthesis of N-heterocyclic compounds under solvent-free condition, such as benzimidazoles, benzodiazepines, dihydropyrimidinones and dihydropyridines under mild condition. Furthermore, it can be reused without loss of activity in a test of five cycles. This catalytic system affords a simple and efficient approach for the synthesis of N-heterocyclic compounds.
Wang, Jinying,Li, Ningbo,Qiu, Renhua,Zhang, Xiaohong,Xu, Xinhua,Yin, Shuang-Feng
p. 61 - 67
(2015/03/30)

Synthesis, anticonvulsant activity and molecular properties prediction of dialkyl 1-(di(ethoxycarbonyl)methyl)-2,6-dimethyl-4-substituted-1,4- dihydropyridine-3,5-dicarboxylates
The synthesis and anticonvulsant properties of new N-diethylmalonyl derivatives of nifedipine and other isosteric analogues (7a-7n) were described. Anticonvulsant screening was performed by subcutaneous pentylenetetrazole (scPTZ) and maximal electroshock (MES) induced seizures tests. Majority of the compounds were effective in scPTZ and MES screens. Compound 7k showed good activity displaying maximum protection, which may be due to the presence of styryl moiety at position 4 of 1,4-dihydropyridine nucleus and the methyl groups of diester functionality. Compounds 7a-7d, 7g, 7i and 7k obeyed the Lipinski's "rule of five" and have drug-likeness. Based on computational prediction of molecular and pharmacokinetic properties, it was found that the compounds have good oral absorption.
Prasanthi,Prasad,Bharathi
p. 97 - 104
(2014/01/17)

Metal-free-mediated oxidation aromatization of 1,4-dihydropyridines to pyridines using visible light and air
A metal-free and environmentally friendly aerobic aromatization photosensitized by organic dye eosin Y bis(tetrabutyl ammonium salt) (TBA-eosinY) has been developed. With the aid of K2CO3, the aerobic catalytic system converts 1,4-dihydropyridines to their corresponding pyridine derivatives efficiently under visible light irradiation (λ=450 nm) at room temperature.
Wei, Xiaojing,Wang, Lin,Jia, Wenliang,Du, Shaofu,Wu, Lizhu,Liu, Qiang
supporting information
p. 1245 - 1250
(2015/02/05)

Bio-inspired catalytic imine reduction by rhodium complexes with tethered hantzsch pyridinium groups: Evidence for direct hydride transfer from dihydropyridine to metal-activated substrate
Inspired by Nature: A conceptually new design for a catalyst, combining a metal center abutted to an organic hydride donor, is demonstrated for the formate-driven transfer hydrogenation of imines under ambient conditions. A key step, transfer of hydride from the organohydride donor to the metal-polarized substrate, mirrors that in metallo-(de)hydrogenase enzymes.
McSkimming, Alex,Bhadbhade, Mohan M.,Colbran, Stephen B.
supporting information
p. 3411 - 3416
(2013/05/08)

PEG-mediated catalyst-free synthesis of Hantzsch 1,4-dihydropyridines and polyhydroquinoline derivatives
Hantzsch 1,4-dihydropyridines and polyhydroquinoline derivatives were synthesized in good yields by PEG-mediated, catalyst-free synthesis under solvent-free conditions. The products were directly recrystallized from hot methanol. The reaction gave excellent yields with low- as well as high-molecular-weight polyethylene glycols. Taylor & Francis Group, LLC.
Siddaiah,Basha, G. Mahaboob,Rao, G. Padma,Prasad, U. Viplava,Rao, R. Suryachendra
experimental part
p. 627 - 634
(2011/12/22)

Facile and green synthesis of 1,4-dihydropyridine derivatives in n-butyl pyridinium tetrafluoroborate
l,4-Dihydropyridine derivatives were synthesized from the one-pot condensation of aldehydes, acetoacetates, and ammonium acetate in room-temperature ionic liquid n-butyl pyridinium tetrafluoroborate ([BPy][BF4]). Compared with classical Hantzsch reaction conditions, this new method has the advantage of excellent yields, short reaction time, and easy workup. The recovered ionic liquid could be recycled for at least five runs without losing its activity. Taylor & Francis Group, LLC.
Wu, Xiao Yun
experimental part
p. 454 - 459
(2011/12/02)

A new In-SiO2 composite catalyst in the solvent-free multicomponent synthesis of Ca2+ channel blockers nifedipine and nemadipine B
An In-SiO2 composite was prepared by the sol-gel method and was applied as a heterogeneous Lewis acid catalyst in the multicomponent Hantzsch synthesis of symmetrical and non-symmetrical 1,4-DHPs. The Ca2+ channel blockers nifedipine and nemadipine B were synthesized in a single step through a solvent-free protocol. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2012.
Affeldt, Ricardo F.,Benvenutti, Edilson V.,Russowsky, Dennis
experimental part
p. 1502 - 1511
(2012/07/30)

Synthesis and evaluation of antioxidant, anti-inflammatory and antiulcer activity of conjugates of amino acids with nifedipine
A new series of novel (2S)-2-({2-[1,4-dihydro-3,5-bis(methoxycarbonyl)-2,6- dimethyl-4-(2-nitrophenyl)pyridin-1-yl]-2-oxoethyl}amino)-3-(4-hydroxyphenyl) propanoic acid (3a) and its analogues 3b-j has been synthesized. These compounds were evaluated for their in vitro antioxidant activity, anti-inflammatory activity and antiulcer activity. Compounds 3b and f exhibited significant antioxidant action comparable with that of standard. Efficacy against inflammation and ulceration was also found to be significant. The chemical structures of these compounds were confirmed on the basis of spectral data.
Subudhi, Bharat Bhusan,Sahoo, Shakti Prasanna
experimental part
p. 1153 - 1156
(2011/10/18)

Floating pharmaceutical composition comprising an active phase and a non-active phase
The invention concerns a floating pharmaceutical composition consisting of at least a first phase comprising at least a high dose active principle combined with one or several carriers and at least a second phase comprising at least a gas-generating system. The invention also concerns tablets comprising such a pharmaceutical composition and a method for preparing such tablets.
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(2010/04/23)

Sulfonic acid-functionalized silica: A remarkably efficient heterogeneous reusable catalyst for the one-pot synthesis of 1, 4-dihydropyridines
An efficient one-pot method for the synthesis of 1, 4-dihydropyridines from β-dicarbonyl compounds, aldehyde, and ammonium acetate is reported using sulfonic acid-functionalized silica at 90 ° C under solvent-free conditions with good to excellent yields. The catalyst is easily prepared, stable (up to 300 ° C), reusable, and efficiently used under reaction conditions. tuebitak.
Mohammadi, Behzad,Hosseini Jamkarani, Sayyed Mohammad,Kamali, Taghi A.,Nasrollahzadeh, Mahmoud,Mohajeri, Ali
experimental part
p. 613 - 619
(2010/11/05)

THERAPY FOR COMPLICATIONS OF DIABETES
A method for enhancing glycemic control and/or insulin sensitivity in a human subject having diabetic nephropathy and/or metabolic syndrome comprises administering to the subject a selective endothelin A (ETA) receptor antagonist in a glycemic control and/or insulin sensitivity enhancing effective amount. A method for treating a complex of comorbidities in an elderly diabetic human subject comprises administering to the subject a selective ETA receptor antagonist in combination or as adjunctive therapy with at least one additional agent that is (i) other than a selective ETA receptor antagonist and (ii) effective in treatment of diabetes and/or at least one of said comorbidities other than hypertension. A therapeutic combination useful in such a method comprises a selective ETA receptor antagonist and at least one antidiabetic, anti-obesity or antidyslipidemic agent other than a selective ETA receptor antagonist.
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(2009/07/02)

ANTIHYPERTENSIVE THERAPY
A new use of darusentan is provided in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy with one or more drugs. The composition comprises darusentan in an amount providing a therapeutically effective daily dose; wherein (a) the composition is orally deliverable and/or (b) the daily dose of darusentan is effective to provide a reduction of at least about 3 mmHg in one or more blood pressure parameters selected from trough sitting systolic, trough sitting diastolic, 24-hour ambulatory systolic, 24-hour ambulatory diastolic, maximum diurnal systolic and maximum diurnal diastolic blood pressures. Further provided is a new use of darusentan in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy, wherein the composition is administered adjunctively with at least one diuretic and at least one antihypertensive drug selected from ACE inhibitors, angiotensin II receptor blockers, beta-adrenergic receptor blockers and calcium channel blockers.
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(2009/09/08)

Synthesis, characterization and anticonvulsant activity evaluation of some 1,4-dihydropyridines and 3,5-(substituted)oxycarbonyl-1,4-dihydro-2,6-dimethyl- n- [2-(4-sulfamoylphenylamino)-acetyl]-4-(substituted)pyridines
A series of 3,5-(substituted)oxycarbonyl-1,4-dihydro-2,6-dimethyl-4- (substituted)pyridines (1a-j) were synthesized by Hantzsch method for pyridine synthesis. Treatment with chloroacetyl chloride produced N-(2-chloroacetyl)-3,5- (substituted)oxycarbonyl-1,4-dihydro-2,6-dimethyl-4-(substituted)pyridines (2a-e), which on further treatment with sulfanilamide resulted in 3,5-(substituted)oxycarbonyl-1,4-dihydro-2,6- dimethyl-N-[2-(4- sulfamoylphenylamino)-acetyl]-4-(substituted)pyridines (3a-e). The structures has been established on the basis of spectral (IR, 1H-NMR, mass) and elemental analysis. Compounds 1a-j and 3a-e (5 mg/kg and 10 mg/kg) were evaluated for their anticonvulsant effect against pentylenetetrazole-induced convulsions with diazepam (4 mg/kg) as the reference. Compounds 3a-e exhibited significant (p 0.01) anticonvulsant activity compared to the control.
Subudhi, Bharat Bhusan,Panda, Prasanna K.,Swain, Sarada P.,Sarangi, Priyambada
experimental part
p. 147 - 153
(2009/06/28)

Efficient synthesis of Hantzsch esters and polyhydroquinoline derivatives in aqueous micelles
Hantzsch 1,4-dihydropyridine and polyhydroquinoline derivatives were synthesized in excellent yields in aqueous micelles. The reaction is catalyzed by PTSA and strongly accelerated by ultrasonic irradiation. Georg Thieme Verlag Stuttgart.
Kumar, Atul,Maurya, Ram Awatar
p. 883 - 885
(2008/12/22)

Hantzsch synthesis of polyhydroquinolines - A simple, efficient and neat protocol
A variety of polyhydroquinolines have been synthesized under eco-benign conditions. The reaction proceeds smoothly without any catalyst at room temperature in short reaction time. The yields and purity are excellent.
Arumugam, Pandurangan,Perumal, Paramasivan T.
p. 1084 - 1090
(2008/12/23)

Magnesium nitride as a convenient source of ammonia: preparation of dihydropyridines
(Chemical Equation Presented) Magnesium nitride (Mg3N 2) has been investigated for the preparation of dihydropyridines. This is a commercially available, bench-stable solid that generates ammonia upon treatment with protic solvents. The main features of the process are the facile reaction setup and good yields obtained in the majority of cases.
Bridgwood, Katy L.,Veitch, Gemma E.,Ley, Steven V.
scheme or table
p. 3627 - 3629
(2009/05/07)

Covalently anchored sulfonic acid on silica gel as an efficient and reusable heterogeneous catalyst for the one-pot synthesis of Hantzsch 1,4-dihydropyridines under solvent-free conditions
A highly efficient one-pot synthesis of Hantzsch 1,4-dihydropyridines under solvent-free conditions catalyzed by sulfonic acid covalently anchored onto the surface of silica gel is reported here. All types of aldehydes, including aromatic, unsaturated, and heterocyclic aldehydes, gave excellent yields. The silica gel/sulfonic acid catalyst (SiO2-SO3H) is completely heterogeneous and can be recycled for eight consecutive runs without significant loss of activity. Georg Thieme Verlag Stuttgart.
Gupta, Raman,Gupta, Rajive,Paul, Satya,Loupy, Andre
p. 2835 - 2838
(2008/03/13)

Cu(OTf)2 Catalyzed high yield synthesis of Hantzsch 1,4-dihydropyridines
Copper(II) triflate catalyzes efficiently the three-component condensation of aldehydes, β-ketoesters and ammonium acetate in acetonitrile at 25°C to afford the corresponding Hantzsch 1,4-dihydropyridines in high yields.
Paraskar, Abhimanyu S.,Sudalai, Arumugam
p. 331 - 335
(2008/02/09)

Synthesis of Hantzsch 1,4-dihydropyridines under solvent-free condition using Zn[(L)proline]2 as Lewis acid catalyst
The present short communication describes a Lewis acid (Zn[(L)proline] 2) catalysed one pot synthesis of Hantzsch 1,4-dihydropyridine (DHP) derivatives under solvent-free condition by conventional heating and microwave irradiation. The Lewis acid catalyst Zn[(L)proline]2 used in this reaction afford moderate to good yield. The catalyst is reusable upto five cycles without appreciable loss of its catalytic activity.
Sivamurugan,Kumar, R. Suresh,Palanichamy,Murugesan
p. 969 - 974
(2007/10/03)

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.
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Page 17

(2008/06/13)

Iron and transition metal transport into erythrocytes mediated by nifedipine degradation products and related compounds
The aim of this investigation was to determine the mechanism of action of the nitrosophenylpyridine derivative of nifedipine ("nitrosonifedipine", NN) on Fe(II) transport into erythrocytes. Nifedipine is rapidly degraded to NN by daylight. We used rabbit erythrocytes, NN, and several chemically related substances, and examined their effects on the transfer of iron and other transition metals (cadmium, cobalt, manganese, nickel, zinc) into and out of the cells. NN mediated the transfer of iron and zinc but not the other metals into the cell cytosol. The transfer of Fe(II) was not affected by changes in cell membrane potential and could not be ascribed to free radical production. Two hydroxamic acid compounds chemically related to NN also stimulated iron and zinc uptake, but no evidence was obtained for cell-induced transformation of NN to them. In vivo, NN is probably converted to a lactam derivative. This compound was found to have no effect on iron uptake by the cells. It is concluded that NN has a relatively high specificity for the transport of iron compared with other transition metals, and small changes in its structure markedly affect this action. Also, because the lactam to which NN is converted in vivo is inactive, it is unlikely that nifedipine will affect iron metabolism after therapeutic administration.
Savigni, Donna L.,Wege, Dieter,Cliff, Garth S.,Meesters, Mark L.H.,Morgan, Evan H.
p. 1215 - 1226
(2007/10/03)

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 on adsorbent till adsorbent becomes free flowing, heating the material so obtained under microwave irradiation, cooling the reaction mixture and recovering the compound of formula I. The present invention also relates to novel 1,4-dihydropyridines.
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(2008/06/13)

1,4-dihydropyridine derivative with a guaiacoxypropanolamine and/or phenoxypropanolamine moiety
The invention disclosed some 1,4-dihydropiridine derivative chemically with guaiacoxypropanolamine based phenoxypropanolamine moiety and pharmacologically with β-adrenoceptor blocking and partial β2-agonist activities, is now emerging. The compound of 1,4-dihydropiridine derivative wherein has the formula I, wherein R selected from four group as follow R1 selected from X, H, NO2 saturated C1-C6 alkyl chain, unsaturated C6-C6 alkyl chain, R2 selected from H, CH3 R3 and R4 are individually selected from saturated C1-C6 alkyl chain, unsaturated C1-C6 alkyl chain; R5 selected from OH, saturated C1-C6 alkyl chain, unsaturated C1-C6 alkyl chain.
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(2008/06/13)

Chemical compounds having ion channel blocking activity for the treatment of immune dysfunction
The present invention relates to chemical compounds having inhibitory activity on an intermediate conductance Ca 2+ activated potassium channel (IK Ca), and the use of such compounds for the treatment or alleviation of diseases or conditions relating to immune dysfunction. Moreover, the invention relates to a method of screening a chemical compound for inhibitory activity on an intermediate conductance Ca 2+ activated potassium channel (IK Ca).
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(2008/06/13)

Synthesis of hantzsch 1,4-dihydropyridines under microwave irradiation
Biologically active substituted 1,4-dihydropyridines have been synthesized in excellent yields by the reaction of aldehydes, ethyl or methyl acetoacetic ester and ammonium acetate under microwave irradiation (MWI) within 0.75-3 min.
Anniyappan, Marimuthu,Muralidharan,Perumal, Paramasivan T.
p. 659 - 663
(2007/10/03)

Rapidly disintegrating solid oral dosage form
Disclosed is a rapidly disintegrating solid oral dosage form of a poorly soluble active ingredient and at least one pharmaceutically acceptable water-soluble or water-dispersible excipient, wherein the poorly soluble active ingredient particles have an average diameter, prior to inclusion in the dosage form, of less than about 2000 nm. The dosage form of the invention has the advantage of combining rapid presentation and rapid dissolution of the active ingredient in the oral cavity.
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(2008/06/13)

Scaling up of dihydropyridine ester synthesis by using aqueous hydrotrope solutions in a continuous microwave reactor
We report here the scaling up of clinically important dihydropyridine by using a continuous microwave reactor (CMR). We also report the use of aqueous hydrotrope solution as a cheap, safe and "green" alternative to organic solvent to carry out homogeneous reactions under microwave heating. We have studied different aqueous hydrotrope solutions for the reaction in batch as well as continuous-flow process.
Khadilkar, Bhushan M.,Madyar, Virendra R.
p. 452 - 455
(2013/09/07)

Method of producing multi-layer medicaments in solid form for oral or rectal administration
PCT No. PCT/EP96/04601 Sec. 371 Date Apr. 15, 1998 Sec. 102(e) Date Apr. 15, 1998 PCT Filed Oct. 23, 1996 PCT Pub. No. WO97/15293 PCT Pub. Date May 1, 1997The present invention relates to a process for producing multilayer, solid drug forms for oral or rectal administration, which comprises coextrusion of at least two compositions which in each case comprise a thermoplastic, pharmacologically acceptable polymeric binder which is soluble or swellable in a physiological environment, and at least one of which contains a pharmaceutical active ingredient, and shaping the coextruded multilayer material to the required drug form.
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(2008/06/13)

Molecular and crystalline structure of dimethyl 4,6-dimethyl-2-(2-nitrophenyl)-,2-dihydropyridine-3,5-dicarboxylate, by-product in the synthesis of nifedipine
Dimethyl 4,6-dimethyl-2-(2-nitrophenyl)-1,2-dihydropyridine-3,5-dicarboxylate was isolated and identified among by-products formed in the synthesis of Nifedipine. According to the X-ray diffraction data, the heteroring occurs in the distorted (unsymmetrical) boat conformation, the nitrophenyl group occupies the axial position and is almost orthogonal to the dihydropyridine fragment. The geometric parameters of the heteroring suggest that its conjugation system does not include the sp3 -hybridized carbon atom. The experimental geometric parameters of the title compound were compared with those for other substituted 1,2-dihydropyridines and with those obtained by quantum-chemical calculations.
Bredikhin,Bredikhina,Gubaidullin,Litvinov
p. 1372 - 1376
(2007/10/03)

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.
Palacios, Francisco,Herran, Esther,Rubiales, Gloria
p. 6239 - 6246
(2007/10/03)

Process for the preparation of 1,4-dihydropyridinedicarboxylic esters
Benzylidene intermediates, useful in the preparation of dihydropyridines such as nifedipine and amlodipine, are formed by reaction of a ketocarboxylic adid ester with an aldehyde in the presence of a catalytic amount of dimethylamine acetate.
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(2008/06/13)