Synthesis, &lt;i&gt;in Vitro&lt;/i&gt; and &lt;i&gt;in Silico&lt;/i&gt; Studies of Some Novel 5-Nitrofuran-2-yl Hydrazones as Antimicrobial and Antitubercular Agents

Abdel‐Aziz, Hatem A.; Eldehna, Wagdy M.; Farès, Mohamed; Elsaman, Tilal; Abdel‐Aziz, Marwa M.; Soliman, Dalia H.

doi:10.1248/bpb.b15-00439

Cited by 18 publications

(8 citation statements)

References 51 publications

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“…All new and known hydrazonoyl chlorides were fully characterized by melting point, standard spectroscopic and analytical techniques, as well as 1 H and 13 C NMR spectrometry. It is noted that in all cases the NMR spectral data of the prepared known hydrazonoyl chlorides could not be compared and matched to anything described in the literature because none of the related published works described any NMR data or included spectra in the Supplementary Materials Sections [ 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 ]. In addition, melting point values and IR spectra were only available for three known compounds ( 29f , 29h , 29i ) [ 39 , 41 ].…”

Section: Resultsmentioning

confidence: 99%

First X-ray Crystal Structure Characterization, Computational Studies, and Improved Synthetic Route to the Bioactive 5-Arylimino-1,3,4-thiadiazole Derivatives

Moussa

Paz

Judeh

et al. 2023

IJMS

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N-arylcyanothioformamides are useful coupling components for building key chemical intermediates and biologically active molecules in an expedited and efficient manner. Similarly, substituted (Z)-2-oxo-N-phenylpropanehydrazonoyl chlorides have been utilized in numerous one-step heteroannulation reactions to assemble the structural core of several different types of heterocyclic compounds. Herein, we demonstrate the effectiveness of the reaction of N-arylcyanothioformamides with various substituted (Z)-2-oxo-N-phenylpropanehydrazonoyl chlorides to produce, stereoselectively and regioselectively, a range of 5-arylimino-1,3,4-thiadiazole derivatives decorated with a multitude of functional groups on both aromatic rings. The synthetic methodology features mild room-temperature conditions, large substrate scope, wide array of functional groups on both reactants, and good to high reaction yields. The products were isolated by gravity filtration in all cases and structures were confirmed by multinuclear NMR spectroscopy and high accuracy mass spectral analysis. Proof of molecular structure of the isolated 5-arylimino-1,3,4-thiadiazole regioisomer was obtained for the first time by single-crystal X-ray diffraction analysis. Crystal-structure determination was carried out on (Z)-1-(5-((3-fluorophenyl)imino)-4-(4-iodophenyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl)ethan-1-one and (Z)-1-(4-phenyl-5-(p-tolylimino)-4,5-dihydro-1,3,4-thiadiazol-2-yl)ethan-1-one. Similarly, the tautomeric structures of the N-arylcyanothioformamides and (Z)-geometries of the 2-oxo-N-phenylpropanehydrazonoyl chloride coupling partners were proven by X-ray diffraction studies. As representative examples, crystal-structure determination was carried out on (4-ethoxyphenyl)carbamothioyl cyanide and (Z)-N-(2,3-difluorophenyl)-2-oxopropanehydrazonoyl chloride. Density functional theory calculations at the B3LYP-D4/def2-TZVP level were carried out to rationalize the observed experimental findings.

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Section: Resultsmentioning

confidence: 99%

First X-ray Crystal Structure Characterization, Computational Studies, and Improved Synthetic Route to the Bioactive 5-Arylimino-1,3,4-thiadiazole Derivatives

Moussa

Paz

Judeh

et al. 2023

IJMS

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“…[173] Reaction of thiophene-2-carbohydrazide with several hydrazonoyl chlorides produced hydrazones 195 (Figure 21), which were all devoid of antibacterial and antifungal activity, with the exception of compound 195 (R = Cl), which was moderately potent against A. fumigatus (MIC = 15.6 μg/ml). [174] F I G U R E 21 Various derivatives of thiophene-containing carboxylic acids with antimicrobial activity Thiophene-2-carboxaldehyde 196 (Figure 22) were prepared through the Suzuki-Miyaura cross-coupling between 4bromothiophene-2-carboxaldehyde and variously substituted arylboronic acids or esters and were screened for antibacterial activity at concentrations of 25 and 50 μg/ml using the disc diffusion technique. [175] No conclusion from comparing the activity of the test compounds with the activity of the standard drug streptomycin (used in the form of commercial standard antibiotic discs) can be drawn, as the latter's concentration has not been specified in the article.…”

Section: Two Ethyl Esters Of Cyclohepta[b]thiophene-3-carboxylic Acidsmentioning

confidence: 99%

“…Reaction of thiophene‐2‐carbohydrazide with several hydrazonoyl chlorides produced hydrazones 195 (Figure 21), which were all devoid of antibacterial and antifungal activity, with the exception of compound 195 (R = Cl), which was moderately potent against A. fumigatus (MIC = 15.6 μg/ml). [ 174 ]…”

Section: Antimicrobial Compounds Based On Thiophene Carboxylic Acids ...mentioning

confidence: 99%

Thiophene‐containing compounds with antimicrobial activity

Roman¹

2022

Archiv der Pharmazie

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Thiophene, as a member of the group of five-membered heterocycles containing one heteroatom, is one of the simplest heterocyclic systems. Many synthetic strategies allow the accurate positioning of various functionalities onto the thiophene ring. This review provides a comprehensive, systematic and detailed account of the developments in the field of antimicrobial compounds featuring at least one thiophene ring in their structure, over the last decade.

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“…In light of the aforementioned findings, and following up on our earlier efforts to identify promising anti-tubercular candidates [35][36][37][38][39][40][41], we decided to broaden our investigation by bioisosterically replacing the 3,4,5-trimethoxy benzylidene moiety in lead compound IV with the privileged isatin motif to afford the first series of targeted molecules Q6a-h (Figure 2). Furthermore, the isatin motif in series Q6 was N-substituted with either a methyl or benzyl group to furnish the second series of target molecules Q8a-h (Figure 2).…”

Section: Introductionmentioning

confidence: 99%

Development of Novel Isatin-Tethered Quinolines as Anti-Tubercular Agents against Multi and Extensively Drug-Resistant Mycobacterium tuberculosis

et al. 2022

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We describe the design and synthesis of two isatin-tethered quinolines series (Q6a–h and Q8a–h), in connection with our research interest in developing novel isatin-bearing anti-tubercular candidates. In a previous study, a series of small molecules bearing a quinoline-3-carbohydrazone moiety was developed as anti-tubercular agents, and compound IV disclosed the highest potency with MIC value equal to 6.24 µg/mL. In the current work, we adopted the bioisosteric replacement approach to replace the 3,4,5-trimethoxy-benzylidene moiety in the lead compound IV with the isatin motif, a privileged scaffold in the TB drug discovery, to furnish the first series of target molecules Q6a–h. Thereafter, the isatin motif was N-substituted with either a methyl or benzyl group to furnish the second series Q8a–h. All of the designed quinoilne-isatin conjugates Q6a–h and Q8a–h were synthesized and then biologically assessed for anti-tubercular actions towards drug-susceptible, MDR, and XDR strains. Superiorly, the N-benzyl-bearing compound Q8b possessed the best activities against the examined M. tuberculosis strains with MICs equal 0.06, 0.24, and 1.95 µg/mL, respectively.

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Synthesis, <i>in Vitro</i> and <i>in Silico</i> Studies of Some Novel 5-Nitrofuran-2-yl Hydrazones as Antimicrobial and Antitubercular Agents

Cited by 18 publications

References 51 publications

First X-ray Crystal Structure Characterization, Computational Studies, and Improved Synthetic Route to the Bioactive 5-Arylimino-1,3,4-thiadiazole Derivatives

First X-ray Crystal Structure Characterization, Computational Studies, and Improved Synthetic Route to the Bioactive 5-Arylimino-1,3,4-thiadiazole Derivatives

Thiophene‐containing compounds with antimicrobial activity

Development of Novel Isatin-Tethered Quinolines as Anti-Tubercular Agents against Multi and Extensively Drug-Resistant Mycobacterium tuberculosis

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