Lipophilic 2-(4-chlorophenyl)-4-thiazolyl-1,4-dihydropyridines: synthesis, calcium channel antagonist activity, and protection against pentylenetetrazole-induced seizure

Samzadeh‐Kermani, Alireza; Shafaroodi, Hamed; Miri, Ramin; Mirkhani, Hossein; Vosooghi, Mohsen; Shafiee, Abbas

doi:10.1007/s00044-008-9112-5

Cited by 14 publications

(6 citation statements)

References 10 publications

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“…In continuation of our research program in discovering new anticonvulsant agents (Samzadeh-Kermani et al, 2009;Emami et al, 2006;Foroumadi et al, 2007;Zarghi et al, 2005;Almasirad et al, 2007) in this paper we report the synthesis and anticonvulsant activity of new derivatives of 4-(2-phenoxyphenyl)semicarbazones 6a-k and 7a-i.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and anticonvulsant activity of 4-(2-phenoxyphenyl)semicarbazones

et al. 2009

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A new series of 4-(2-phenoxyphenyl)semicarbazones were synthesized as potential anticonvulsant agents. Thus, the reaction of 4-(2-phenoxyphenyl)semicarbazide with various benzaldehydes and acetophenones in ethanol yielded the corresponding semicarbazones 6a-k and 7a-i, respectively. Structures of the synthesized compounds were confirmed by spectral data and elemental analysis. All compounds were evaluated for their anticonvulsant activity in pentylenetetrazole (PTZ)-induced kindling model in adult male Wistar rats. The neurotoxicity of active compounds was also assessed using the rotorod method. The results showed that two compounds (6g and 6i) showed greater protection from seizure than sodium valproate at dose of 100 mg/kg. Compounds 6g and 6i showed no neurotoxicity at the maximum dose administered (300 mg/kg).

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Section: Introductionmentioning

confidence: 99%

Synthesis and anticonvulsant activity of 4-(2-phenoxyphenyl)semicarbazones

et al. 2009

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“…Multicomponent reactions represent an attractive synthetic strategy, as they offer the advantages of simplicity, atom-economy, selectivity, and efficient rapid access to complex organic compounds. [1][2][3][4][5] The Hantzsch reaction is one of the most common multicomponent routes for the synthesis of 1,4-dihydropyridines, which have a broad spectrum of biological and pharmacological activities, including anticancer, 6 antiviral, 7 anticonvulsant, 8 antitubercular, 9 antiinflammatory, 10 anticonvulsant, 11 and anti-Alzheimer activities. 12 In addition, pyrazolo [1,5-a]pyrimidine derivatives exhibit a wide range of bioactivities, that include KDR kinase inhibitory activity, 13 CRF-1 receptor antagonistic activity, 14 antiproliferative activity, 15 and antischistosomal activity.…”

Section: -82%mentioning

confidence: 99%

Hantzsch-Like One-Pot Three-Component Synthesis of Heptaazadicyclopenta[a,j]anthracenes: A New Ring System

Abdelhamid

Abdelmoniem

Sroor

et al. 2020

Synlett

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A concise and efficient approach to novel tetrahydroheptaazadicyclopenta[a,j]anthracene-5,7-diones, by the reaction of aldehydes with two moles of 7-amino-2-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-5-one is reported. Also, pyrazolo[1,5-a]pyrido[3,2-e]pyrimidine-7-carbonitrile derivatives were prepared by a three-component reaction of aldehydes, 7-amino-2-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-5-one, and 3-aminocrotononitrile.

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“…The discovery that the 1,4‐dihydropyridine class of calcium channel antagonists inhibits Ca 2+ influx represented a major therapeutic advancement in the treatment of cardiovascular disease including hypertension, angina pectoris, and other spastic smooth muscle disorders (61–63). Moreover, some other biological applications were reported for DHPs making them a reliable class for widespread drug development (63–66).…”

Section: Dihydropyridinesmentioning

confidence: 99%

Dihydropyridines and Multidrug Resistance: Previous Attempts, Present State, and Future Trends

2010

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Multidrug resistance is defined as the resistance of a tumor cell to the cytotoxic action of divergent drugs used in chemotherapy. Dihydropyridines are a class of calcium channel antagonists that were discovered to have a multidrug resistance reversing effect and prompted investigations resulting in the synthesis of hundreds of new derivatives. Most of the investigators tried to achieve two goals: a decrease in Ca 2+ channel-blocking activity and an increase in the multidrug resistance reversing effect. Most of the synthesized compounds failed in the later stages of studies especially in clinical trials because of pharmacokinetic or pharmacodynamic limitations. Therefore, it will be necessary to include new methods, such as combinatorial synthesis, and, more importantly, to apply computational methods based on global structure-activity relationship models that consider all problems. Moreover, some compounds should be synthesized that are effective on several multidrug resistance targets.

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Lipophilic 2-(4-chlorophenyl)-4-thiazolyl-1,4-dihydropyridines: synthesis, calcium channel antagonist activity, and protection against pentylenetetrazole-induced seizure

Cited by 14 publications

References 10 publications

Synthesis and anticonvulsant activity of 4-(2-phenoxyphenyl)semicarbazones

Synthesis and anticonvulsant activity of 4-(2-phenoxyphenyl)semicarbazones

Hantzsch-Like One-Pot Three-Component Synthesis of Heptaazadicyclopenta[a,j]anthracenes: A New Ring System

Dihydropyridines and Multidrug Resistance: Previous Attempts, Present State, and Future Trends

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