Solid–liquid phase equilibrium of 9-fluorenone and several polynuclear aromatic hydrocarbons

Yin, Wei; Dang, Leping; Zhang, Xiangyang; Cui, Weimin; Wei, Hongyuan

doi:10.1016/j.fluid.2012.01.017

Cited by 9 publications

(12 citation statements)

References 31 publications

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“…1 H NMR and 13 C NMR spectra were recorded on a Bruker-FT-NMR-400 MHz spectrophotometer using CDCl 3 as solvent and TMS as an internal standard. LC-Mass spectra were recorded on a Varian Atlas CH-7 mass spectrometer.…”

Section: Methodsmentioning

confidence: 99%

“…The yield of the product obtained was 95% after column chromatography (silica gel; solvent system -hexane and ethyl acetate 70:30). 1 …”

Section: Synthesis Of N-(2-phenyl Ethyl)-benzamide (3)mentioning

confidence: 99%

“…The resultant compound was purified by recrystallization in ethanol. 1 General procedure for synthesis of 1,3,4-oxadiazoles 2-(1-Phenyl-3,4-dihydroisoquinoline-2(1H)-yl)acetohydrazide (1 m.mol) was dissolved in POCl 3 /SOCl 2 (3 mL). The reaction was stirred on magnetic stirrer under reflux for 3 h and the mixture was cooled to R.T and poured into crushed ice.…”

Section: Synthesis Of 2-(1-phenyl-34-dihydroisoquinoline-2(1h)-yl)acmentioning

confidence: 99%

“…This compound derived from furan by substitution of two methylene groups (-CH-) with two pyridine type nitrogen (-N=) [1][2] . Among three isomers of oxadiazoles such as 1,2,4-oxadiazole, 1,2,3-oxadiazole and 1,3,4-oxadiazole, the most important compound is 1,3,4-oxadiazole.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Characterization of 1,3,4-Oxadiazoles Derivatives from 1,2,3,4-Tetrahydroisoquinoline and their Bioevalution (Antibacterial & Antifungal)

2017

Chem Sci Trans

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New derivatives of 1,3,4-oxadiazole, synthesized by the condensation of different substituted benzoic acids with 2-(1-phenyl-3,4-dihydroisoquinoline-2(1H)-yl) acetohydrazide using SOCl 2 as well as POCl 3 as cyclization reagents. Ethyl-2-(1-phenyl-1,2,3,4-tetrahydroisoquinoline)-ethaonate was synthesized from 1,2,3,4-Tetrahydroisoquinoline and it was converted to the 2-(1-phenyl-3,4-dihydroisoquinoline-2(1H)-yl)acetohydrazide. This compound is the key intermediate for the 1,3,4-oxadiazole compounds. All the synthesized molecules were characterized by advanced spectral data and also studied their biological activity.

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Section: Methodsmentioning

confidence: 99%

“…The yield of the product obtained was 95% after column chromatography (silica gel; solvent system -hexane and ethyl acetate 70:30). 1 …”

Section: Synthesis Of N-(2-phenyl Ethyl)-benzamide (3)mentioning

confidence: 99%

Section: Synthesis Of 2-(1-phenyl-34-dihydroisoquinoline-2(1h)-yl)acmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Characterization of 1,3,4-Oxadiazoles Derivatives from 1,2,3,4-Tetrahydroisoquinoline and their Bioevalution (Antibacterial & Antifungal)

2017

Chem Sci Trans

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“…Introduction:9-fluorenone (IUPAC name 9H-fluoren-9-one) is member of polycyclic aromatic hydrocarbon (PAH), which was widely used in the applications of thermo and light sensitizer, liquid crystal chemistry, luminescence chemistry, spectrophotoetric analysis, molecular chemistry and biochemorphology industry [1,2]. Heterocyclic compounds containing the fivemembered nucleus possess a diversity of useful biological effects.…”

mentioning

confidence: 99%

Synthesis and Characterization of 1,3,4-Oxadiazoles Derived From 9-Fluorenone

Dawood¹

2013

Baghdad Sci.J

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In the present work, 9-fluorenone-2-carboxylic acid methyl ester (1) was prepared from 9-fluorenone-2-carboxylic acid and then converted into the acid hydrazide (2). Compound (2), is the key intermediate for the synthesis of several series of new compounds such as substituted 1,3,4-oxadiazole derivatives (3-6) were synthesized from the condensation of different substituted benzoic acids with compound (2) using POCl3 as condensing agent. Treatment of compound (2) with formic acid gave the N-formyl hydrazide (7), which upon refluxing with phosphorous pentoxide in benzene yielded the corresponding 5-(9-fluorenone-2-yl)-1,3,4-oxadiazole (8). Reaction of hydrazide (2) with phenyl isocyanate to give N-phenyl semicarbazide derivative (9), then this compound (9) convert to 5-(9-fluorenone-2-yl)-N-phenyl-1,3,4-oxadiazole-2-amine (10) via intramolecular cyclization by syrup H3PO4. Also the hydrazide (2) was treated with CS2/KOH afforded 5-(9-fluorenone-2-yl)-1,3,4-oxadiazole-2-thiol (11). Compound (11) was used to react with various alkyl halides and secondary amines to give 5-(9-fluorenone-2-yl)-1,3,4-oxadiazole-2-alkyl thiol (12-15) and 5-(9-fluorenone-2-yl)-1,3,4-oxadiazole-2-N-alkyl (16-19) derivatives respectively.

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Design, synthesis, structure elucidation, antimicrobial, molecular docking, and SAR studies of novel urea derivatives bearing tricyclic aromatic hydrocarbon rings

Sroor,

El‐Sayed,

Abdelraof

2024

Archiv der Pharmazie

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The targeted compounds were prepared using both (9H‐fluoren‐9‐ylidene)hydrazine (1) and 10H‐phenothiazine (2) as starting materials. The treatment of 1 or 2 with different isocyanates afforded the title compounds 7a–d, 8a, and 8b in excellent yield. All compounds were characterized and ascertained by infrared, nuclear magnetic resonance, and elemental analyses as well as single‐crystal X‐ray diffraction. The antimicrobial efficiency of all was tested in vitro, and a noticeable inhibition activity against Bacillus subtilis, Staphylococcus aureus, Pseudomonas aeruginosa, Klebsiella pneumoniae, and Candida albicans was obtained by compounds 7a, 7b, 8a, and 8b. Moreover, the biofilm mechanism activity was strongly inhibited by compounds 7b and 8b for all bacterial pathogens, with a percentage ratio of more than 55%. The findings from the molecular docking simulation revealed that compounds 7a, 7b, 8a, and 8b exhibited favorable binding energies and interacted effectively with the active sites of sterol 14‐demethylase, dihydropteroate synthase, gyrase B, LasR (major transcriptional activator of P. aeruginosa), and carbapenemase for C. albicans, S. aureus, B. subtills, K. pneumoniae, and P. aeruginosa, respectively. These results suggest that the compounds have the potential to inhibit the activity of these enzymes and demonstrate promising antimicrobial properties. Moreover, the in silico evaluation of drug likeness and absorption, distribution, metabolism, excretion, and toxicity (ADMET) profiles for compounds 7a, 7b, 8a, and 8b demonstrated their compatibility with Lipinski's, Ghose's, Veber's, Muegge's, and Egan's rules. These findings suggest that these compounds possess favorable physicochemical properties, making them promising candidates for continued drug development efforts.

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Solid–liquid phase equilibrium of 9-fluorenone and several polynuclear aromatic hydrocarbons

Cited by 9 publications

References 31 publications

Synthesis and Characterization of 1,3,4-Oxadiazoles Derivatives from 1,2,3,4-Tetrahydroisoquinoline and their Bioevalution (Antibacterial & Antifungal)

Synthesis and Characterization of 1,3,4-Oxadiazoles Derivatives from 1,2,3,4-Tetrahydroisoquinoline and their Bioevalution (Antibacterial & Antifungal)

Synthesis and Characterization of 1,3,4-Oxadiazoles Derived From 9-Fluorenone

Design, synthesis, structure elucidation, antimicrobial, molecular docking, and SAR studies of novel urea derivatives bearing tricyclic aromatic hydrocarbon rings

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