Crystal structure of 2-(9H-fluoren-9-ylidene)hydrazine-1-carbothioamide, C14H11N3S

Hijazi, Ahmed K.; Abu‐Salem, Qutaiba; Ajlouni, Abdulaziz M.; Taha, Ziyad A.

doi:10.1515/ncrs-2015-0058

Cited by 3 publications

(4 citation statements)

References 11 publications

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“…The bond lengths of C1–N1 and O1–C14 are 1.287(3) Å and 1.213(3) Å, respectively, which are close to those reported for C═N and C═O bond (1.284(3) Å) and (1.227(3) Å), respectively. [ 27,63 ] Likewise, the bond distances of S1–O2 and S1–O3 are 1.429(2) Å and 1.422(2) Å, respectively, which are similar to those observed in the reported sulfonylurea derivatives. [ 63 ] The bond angles of C1−N1−N2, C14−N2−N1, N2−C14−N3, and C14−N3−S1 are 121.6(2)°, 118.2(2)°, 113.1(2)°, and 127.08(18)°, respectively.…”

Section: Resultssupporting

confidence: 78%

“…Compound 7a was formed as needle crystals in the monoclinic space group C 2/c with eight molecules in the unit cell as depicted in Table 1. The details of crystallographic data were summarized in Table 1 (for more details, see Supporting [27,63] Likewise, the bond distances of S1-O2 and S1-O3 are 1.429(2) Å and 1.422(2) Å, respectively, which are similar to those observed in the reported sulfonylurea derivatives. [63] The bond angles of C1−N1−N2, In addition, the inability of compounds 7c and 7d to cause an inhibitory effect was observed in the case of gram-negative bacteria.…”

Section: Introductionsupporting

confidence: 62%

“…[18][19][20][21][22][23] Moreover, these compounds have attracted great interest due to their unique applications in blue fluorescent organic light-emitting materials, liquid crystal chemistry, medicinal chemistry, luminescence chemistry, molecular chemistry, synthetic chemistry, and biochemorphology industry. [24][25][26][27][28][29][30][31][32][33] Consequently, the development of new organic compounds bearing 9-fluorene scaffold has been the main focus of synthetic and medicinal chemistry in recent years. [24] Fluorene scaffold has been found as the main building core in different approved drugs, such as pavatrin (antispasmodic), cicloprofen (analgesic, anti-inflammatory agent), Lumefantrine (antimalarial), imirestat (aldozreductase inhibitor), and indecainide (antiarrhythmic) (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Resultssupporting

confidence: 78%

Section: Introductionsupporting

confidence: 62%

Section: Introductionmentioning

confidence: 99%

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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 crude solid was recrystallized from ethanol. [15,16]. IR spectrum of compound 2 showed absorption bands at 1618 and 1221 cm -1 associated with C=N and C=S functionalities, respectively.…”

Section: Introductionmentioning

confidence: 98%

Ultrasound Aided Expedient Synthesis, Characterization and Antimicrobial Studies of Fluorenyl-Hydrazono-Thiazole Derivatives

Kaur¹,

Gautam²

2019

Asian J. Chem.

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Ultrasound assisted facile synthesis of fluorenyl-hydrazonothiazoles (4a-d) in quantitative yields by the condensation of 2-(9H-fluoren-9-ylidene)hydrazinecarbothioamide (2) with substituted phenacyl bromides in presence of dimethyl formamide has been reported. The reaction of carbothioamide 2 with α-haloacids resulted in to fluorenyl-hydrazonothiazolidin-4-ones (3). The structural characterization of the cyclized products have been established by elemental analysis and spectral data (IR, NMR and mass). The antimicrobial studies of the synthesized compounds are also reported.

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Synthesis, density functional theory calculations and luminescence of lanthanide complexes with 2,6‐bis[(3‐methoxybenzylidene)hydrazinocarbonyl] pyridine Schiff base ligand

et al. 2017

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A pyridine-diacylhydrazone Schiff base ligand, L = 2,6-bis [(3-methoxy benzylidene) hydrazinocarbonyl]pyridine was prepared and characterized by single crystal X-ray diffraction. homogeneous and heterogeneous catalysis. [16][17][18] Following our recently published work towards the complexation of lanthanide(III) nitrate salts with dimethyl pyridine-2,6-dicarboxylate, we were interested in the synthesis of a 2,6-bis [(3-methoxybenzylidene)hydrazine carbonyl]pyridine L ligand derived from dimethyl pyridine-2,6-dicarboxylate ligand. [19] In comparison with dimethyl pyridine-2,6-dicarboxylate ligand, the L ligand possesses more coordination sites that can bind and stabilize different lanthanide metal ions with high coordination numbers. Moreover it has flexible groups that can accommodate and protect lanthanide metal atoms from solvent molecules, which avoid non-radiative deactivation processes. [20] Moreover, L is efficient in the displacement of water molecules present in the coordination sphere of lanthanide ions that quenches the luminescence by absorption of the emitted radiation in the vibrational excitation processes via the vibrational levels of the O-H of water molecules. [21] This work reports the synthesis of the L ligand by a condensation reaction between 2-methoxybenzaldehyde and 2,6-bis(hydrazinocarbonyl)pyridine in ethanol and describes its crystal structure. Additionally the coordinating behavior of L with lanthanide metals (Ln = La, Pr, Nd, Sm, Eu, Gd, Tb, Dy and Er) has been investigated by elemental analysis, conductivity measurements, spectral analysis (IR, NMR, UV-Vis and mass) and thermal studies.The antioxidant activity and photoluminescence properties of L and Ln-L have been investigated.

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Crystal structure of 2-(9H-fluoren-9-ylidene)hydrazine-1-carbothioamide, C₁₄H₁₁N₃S

Cited by 3 publications

References 11 publications

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

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

Ultrasound Aided Expedient Synthesis, Characterization and Antimicrobial Studies of Fluorenyl-Hydrazono-Thiazole Derivatives

Synthesis, density functional theory calculations and luminescence of lanthanide complexes with 2,6‐bis[(3‐methoxybenzylidene)hydrazinocarbonyl] pyridine Schiff base ligand

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