Synthesis, hypotensive and antiarrhythmic activities of 3-alkyl-1-(2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydro-3-naphthalenyl)ureas or thioureas and their guanidine analogues

Chalina, E.; Chakarova, Lidia

doi:10.1016/s0223-5234(99)80022-1

Cited by 40 publications

(15 citation statements)

References 19 publications

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“…Thiourea has received considerable attention because of its applications. The significance of thioureas lies in their pharmaceutically relevant physiological activity encompassing antibacterial, [4] antimalarial, [5] antiviral, [6] antitumor, [7] antitubercular, [8] anticancer, [9] insecticidal, herbicidal, [10] antithyroid, [11] antiarrhythmic, [12] RTinhibitor, [13] and antihypertensive [14] activities and on connection with biomimetic models. [15] Thiourea derivatives are valuable building blocks for the synthesis of amides, guanidines, and a variety of heterocycles.…”

Section: Introductionmentioning

confidence: 99%

Green Process Development for the Synthesis of Aliphatic SymmetricalN,N′-Disubstituted Thiourea Derivatives in Aqueous Medium

Jangale

Kumavat

Wagh

et al. 2014

Synthetic Communications

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A highly efficient green process for the synthesis of N,N 0 -disubstituted aliphatic thiourea derivatives using primary aliphatic amines and carbon disulfide in an aqueous medium at room temperature via a nonisothiocyanate route is described. This protocol illustrates the rapid preparation of N,N 0 -disubstituted aliphatic thiourea derivatives in excellent yields with some advantages such as no catalyst and simple workup without any side product formation. Moreover, the new route is concise, does not require chromatography, and is adaptable to pilot-scale preparation.

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Section: Introductionmentioning

confidence: 99%

Green Process Development for the Synthesis of Aliphatic SymmetricalN,N′-Disubstituted Thiourea Derivatives in Aqueous Medium

Jangale

Kumavat

Wagh

et al. 2014

Synthetic Communications

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“…Literature survey indicated that the hydrazone group plays an important role for the antimicrobial activity. A number of hydrazide-hydrazone derivatives also have been claimed to possess interesting bioactivity such as antibacterialantifungal [20,21], anti-inflammatory [22], antimalarial [23], anticonvulsant [24], antituberculosis [25,26], and anticancer [27] activities. So a few pyrazole carbohydrazide hydrazone derivatives have also been reported, which have been synthesized by many methods [28][29][30].…”

Section: Introductionmentioning

confidence: 99%

Use of transesterified 1,3-diketoesters in the synthesis of trisubstituted pyrazoles and their biological screening

Siddiqui¹,

Idrees²,

Khati³

et al. 2012

Bull. Chem. Soc. Eth.

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ABSTRACT. Starting from 2-acetylbenzofuran derivatives 1a-d, methyl/ethyl 4-substituted/unsubstituted benzofuran-2-yl)-2,4-dioxobutanoate 2a-d and 3a-d have been synthesized by Claisen's condensation reaction with diethyloxalate. The transesterified product, 1,3-diketoester 2a-d on condensation with phenyl hydrazine undergo cyclization to afford the corresponding methyl 5-(substituted/unsubstituted benzofuran-2-yl)-1-phenyl-1H-pyrazole-3-carboxylate 4a-d, which upon further condensation with hydrazine hydrate yielded 5-(substituted/unsubstituted benzofuran-2-yl)-1-phenyl-1H-pyrazole-3-carbohydrazide 5a-d. The structures of the newly synthesized compounds 2a-d, 3a-d, 4a-d and 5a-d were characterized by their elemental analysis and spectral studies such as IR, 1 H NMR, 13 C NMR and MS. All the synthesized compounds were screened for their antimicrobial activity. Most of the synthesized compounds showed high sensitivity against the selected bacteria and fungi at various concentrations.

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“…8 Furthermore, a number of hydrazide-hydrazone derivatives also have been claimed to possess interesting bioactivity such as antibacterial-antifungal, anticonvulsant, antiinfloammatory, antimalarial, analgesic, anticancer acticities. 9 So, a few of pyrazole carbohydrazide hydrazone derivatives have also been reported, which have been synthesized in many methods. 10,11 On the other hand, oxadiazoline are important for both chemical and biological purposes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Bioactivity of Novel Bis‐heterocyclic Compounds Containing Pyrazole and Oxadiazoline

Yang

Cao

Liu

et al. 2011

J Chinese Chemical Soc

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Nucleophilic addition of the starting material 3-aryl-1-phenyl-4-formylpyrazoles (1~3) and 4-substituted aryloxyacetyl hydrazine (4a~4e) afford hydrazone compounds containg pyrazolyl (5a~5e, 6a~6e, 7a~7e) in the ethanol. These adducts were refluxed in Ac 2 O and furnished a series of novel bis-heterocyclic compounds. (8a~8e, 9a~9e, 10a~10e) via cyclic reaction. The structures of all newly synthesized compounds were established by IR, 1 H NMR, MS and elemental analysis. New compounds conducted preliminary tests of antibacterial activities about Fusarium oxyaporium, Verticillium dahliae, Rhizoctonia solani, Pychium aphanidermatum, Alternaria solani, Sclerotinia sclerotiorum. The results showed that the inhibiting rate of the bis-heterocyclic compounds (8a~8e, 9a~9e, 10a~10e) was higher than the pyrazolyl hydrazones (5a~5e, 6a~6e, 7a~7e) obviously.

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Synthesis, hypotensive and antiarrhythmic activities of 3-alkyl-1-(2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydro-3-naphthalenyl)ureas or thioureas and their guanidine analogues

Cited by 40 publications

References 19 publications

Green Process Development for the Synthesis of Aliphatic SymmetricalN,N′-Disubstituted Thiourea Derivatives in Aqueous Medium

Green Process Development for the Synthesis of Aliphatic SymmetricalN,N′-Disubstituted Thiourea Derivatives in Aqueous Medium

Use of transesterified 1,3-diketoesters in the synthesis of trisubstituted pyrazoles and their biological screening

Synthesis and Bioactivity of Novel Bis‐heterocyclic Compounds Containing Pyrazole and Oxadiazoline

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