Studies on the reaction of N‐(3‐carbethoxy‐4,5,6,7‐tetrahydrobenzo[b]thien‐2‐yl)‐N′‐phenylthiourea with hydrazine hydrate (Part 1)

El‐Sherief, H. A. H.; El-Naggar, G. M.; Hozien, Zeinab A.; El‐Sawaisi, Suliman M.

doi:10.1002/jhet.5570450226

Cited by 7 publications

(4 citation statements)

References 25 publications

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“…In support of this hypothesis, the possibility of formation of the triazinone 6 was ruled out chemically on the basis of the successful deamination of isolated product, where its treatment with sodium nitrite and acetic acid led to the respective 1-protodeamino analogue 8a. This observation is in complete agreement with previous literature reports on the well established nitrous acid deamination of the exocyclic amino group in related cyclic Naminoamides [36][37][38][39]. Compound 8a displayed a molecular ion peak, which confirmed its molecular formula.…”

Section: Chemistrysupporting

confidence: 93%

Regioselective synthesis and antimicrobial studies of novel bridgehead nitrogen heterocycles containing the thienopyrimidinone skeleton

Gaber

Moussa

2011

Eur. J. Chem.

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KEYWORDSVersatile 2-(alkylthio)pyrimidine-type and 2-(phenacylamino)thiophene building blocks (4ad) and 16 were obtained based on an ortho functionalized thiophene derivative 1. A novel series of thieno[2,3-d]pyrimidin-4-one derivatives with annelated bridgehead nitrogen heterocycles was synthesized starting from precursors 4 and 16 through convenient methods. Cyclocondensation of 2-(phenacylthio)pyrimidinone derivative (4b) with sulfuric acid led to the tricyclic thiazole derivative 5. Initial hydrazinolysis of 3-(carbethoxymethyl)pyrimidinone derivative (4d) followed by nitrous acid deamination of the formed N-aminolactam (7) to obtain a N-protodeamino analogue 8a, which on further treatment with formaldehyde and piperidine yielded the respective Mannich-type base 8b. On the other hand, initial hydrazinolysis of 3-unsubstituted pyrimidinone derivative 4a and subsequent acetylation gave the condensed 3-methyltriazole derivative 12, whereas the condensed pyrrole derivative 19 was obtained by heterocyclization of 2-phenacylamine derivative 16 with malononitrile. All newly-obtained thienopyrimidinones with annelated bridgehead nitrogen were screened for their antimicrobial activity against strains of a representative panel of Gram-positive and Gram-negative bacteria as well as fungi together with reference drugs. The compounds under investigation displayed generally good in vitro antibacterial and antifungal activities, with compound 8b that has a N-piperidinylmethyl moiety showing essentially the highest inhibition in both assays. Despite promising antimicrobial activity of N-1-substituted imidazole derivative 8b, the corresponding N-1-unsubstituted analogue 8a displayed poor activity. The heteroannelation of a N-(piperidinylmethyl)imidazole or 3-methyltriazole moiety to the thienopyrimidinone scaffold could be considered as a potential strategy for the development of new therapeutic antimicrobial agents.Thienopyrimidinone Alkylation Cyclodehydration Hydrazinolysis Acetylation Antimicrobial activity

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Section: Chemistrysupporting

confidence: 93%

Regioselective synthesis and antimicrobial studies of novel bridgehead nitrogen heterocycles containing the thienopyrimidinone skeleton

Gaber

Moussa

2011

Eur. J. Chem.

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“…Pyridine compounds proved to be highly efficient to the C. pipiens (43 and 44). LC 50 values due to effect pyridine derivatives on C. pipienswere 60 and 43% (47). Our results were comparable with findingsfrom other researchers as the Pyridine solution (5 ) with sculpture, was highest their toxic compound to Culexlarvae in comparison with other compounds of pyridine base at the same concentrations.…”

Section: Bioassay Of the Novel Pyridopyrrolopyrimidine On The 4 Th Lasupporting

confidence: 90%

New Condensed Bioactive Pyrimidines. Synthetic Strategies, Structural Characterization and Biorational Studies.

El-Torgoman¹,

Zaki²,

Sherif³

et al. 2016

IJAR

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importance [1-4]. Many studies have been evaluated about the mode of action of different chemicals against pests as well as bacteria and other microorganisms. Mosquitoes are generally controlled by conventional chemical insecticides, but insect growth inhibitors and insect growth regulators, in general, have been employed in the laboratory against different species of mosquitoes. It has been reported [5] that the three chitin synthesis inhibitors (diflubenzuron, nikkomycin Z and polyoxin D) produced toxicities against Anopheles quadrimaculatus. It is well documented[6] that increased resistance of malaria parasites to drug treatment against mosquito vectors to insecticides requires the development of novel chemotherapeutic agents. In recent studies [7, 8], it has been described that benzoylphenyl urea derivatives such as Alsystin (Triflumuron) and Andalin (Flucycloxuron) were found to disturb the growth and development in Culexpipiens. On the other hand, Cassera et al. [6] mentioned that Plasmodium purine and pyrimidine metabolic pathways are distinct from those of their hosts. Thus, targeting purine and pyrimidine metabolic pathways provides a promising route for novel drug development [9]. Furthermore, the pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidine structure was characterized as a new class of potent and selective human A 3 adenosine receptor antagonists [9]. High-affinity radioligand antagonist for this receptor subtype, designated as [ 3 H]MRE2008F20 [10]. Accordingly, an aquatic insect, the larva of the mosquito (CulexpipiensL.) was chosen for the purpose and proved to be an excellent for test. Based on these observations and as part of our ongoing studies in the development of new chemotherapeutic agents [11, 12,13], we embarked upon the synthesis of a series of novel condensed tricyclic derivatives containing a pyrido[3',2':4,5]pyrrolo[3,2-d]pyrimidine core with the objective to assess new biorational agents on mosquitoes Culexpipiensand to improve their efficacy. Materials and methods:-Chemistrymaterials:-Melting points are uncorrected. IR analyses were performed (KBr) with a PyeUnicam SP-1000 spectrophotometer. IR spectra of compounds are expressed by wavenumber (cm-1). NMR spectra were obtained on a Varian Gemini 300 MHz spectrometer in DMSO-d 6 as solvent. Chemical shifts of the 1 H NMR spectra are reported in δ (ppm) from tetramethylsilane with the solvent as the), anhydrous potassium carbonate (0.01 mol) and ethyl glycinate (0.0075 mol) were added. The reaction mixture was heated at reflux for 2.5 h and then allowed to stand at room temperature overnight under stirring. The reaction mixture was then diluted with cold water, whereby the resulting precipitate was collected by filtration, repeatedly washed with cold water and dried. Recrystallization from DMF-H 2 O gave pale yellow crystals of the title compound 2 (0

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“…1 H NMR (400 MHz, DMSO-d 6 ) δ 9.12 (s, 1H, NH), 7.21-7.49 (m, 8H, ArH), 6.82 (s, 1H, =CH), 5.15 (t, 1H, CH), 3.68 (t, 4H, CH 2 ), 3.12-3.22 (m, 4H, CH 2 ), 2.87-2.62 (m, 4H, CH 2 ), 2.35 (m, 4H, CH 2 ); 13 C NMR (100 MHz, DMSO-d 6 ) δ 172. 9,153.3,146.5,144.1,137.2,130.2,129.3,128.6,126.3,125.2,122.3,67.1,56.2,47.3,43.2,40.1,38.2. LCMS 418.63 C,71.92;H,6.52;N,10.06.…”

Section: -(2-(1h-inden-2-yl)phenyl)-3-(2-morpholinoethyl)dihydropyrimentioning

confidence: 99%

A novel synthesis and preliminary in vitro cytotoxic evaluation of dihydropyrimidine-2,4(1H, 3 H)-dione derivatives

2017

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We report the synthesis and characterization of four new compounds: 6-(2-(1H-inden-2-yl) phenyl)-3-(2-morpholinoethyl)dihydropyrimidine-2,4(1H,3H)-dione (13a), 6-(2-(1H-inden-2-yl)phenyl)-3-(2-(pyrrolidin-1-yl)ethyl)dihydropyrimidine-2,4(1H,3H)-dione (13b), 6-(2-(1H-inden-2-yl)phenyl)-3-phenethyldihydropyrimidine-2,4(1H,3H)-dione (13c) and 3-(3-(1H-imidazol-1-yl)propyl)-6-(2-(1H-inden-2-yl)phenyl) dihydropyrimidine-2,4(1H,3H)-dione (13d). A series of dihydropyrimidine-2,4(1H, 3H)-dione moieties was derived from methyl 3-amino-3-(2-chlorophenyl)propanoate precursor in a multi-step synthesis. Acid-amine coupling of 3-(2-(1H-inden-2-yl)phenyl)-3-((tert-butoxycarbonyl)amino)propanoic acid with a series of amine derivatives under mild reaction conditions led to form the corresponding dihydropyrimidine-2,4(1H, 3H)dione derivatives via de-Boc and cyclization reaction in modest yield. Spectroscopic (1 H, 13 C NMR, and Mass) and analytical techniques have been used to identify and confirm the structure of the products.

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Studies on the reaction of N‐(3‐carbethoxy‐4,5,6,7‐tetrahydrobenzo[b]thien‐2‐yl)‐N′‐phenylthiourea with hydrazine hydrate (Part 1)

Cited by 7 publications

References 25 publications

Regioselective synthesis and antimicrobial studies of novel bridgehead nitrogen heterocycles containing the thienopyrimidinone skeleton

Regioselective synthesis and antimicrobial studies of novel bridgehead nitrogen heterocycles containing the thienopyrimidinone skeleton

New Condensed Bioactive Pyrimidines. Synthetic Strategies, Structural Characterization and Biorational Studies.

A novel synthesis and preliminary in vitro cytotoxic evaluation of dihydropyrimidine-2,4(1H, 3 H)-dione derivatives

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