Stereochemical design and conformation determinations of new benzimidazole-N-acylhydrazone derivatives

Achi, Patrick‐Armand; Coulibali, Siomenan; Molou, Kouassi Yves Guillaume; Coulibaly, Souleymane; Signo, Kouassi; Sissouma, Drissa; Ouattara, L; Adjou, Ané

doi:10.1080/00397911.2022.2084417

Cited by 7 publications

(3 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Similarly, compound 13 also showed as being a mixture of four isomers. According to the literature [ 45 ] and our previous research results [ 12 , 13 ], we believe that the four configurations were mainly induced by the chirality of C-14 and synperiplanar E/antiperiplanar E configuration of amide. Because the four isomers were similar in polarity, they could not be separated from each other by column chromatography.…”

Section: Resultsmentioning

confidence: 75%

“…In the class of alkyl aldehyde hydrazone derivatives, the activities of the hydrazone derived from straight chain alkyl aldehyde was better than those derived from branched aldehydes. As indicated in Table 1, n-octylaldehyde hydrazone (43) had better activities than cyclohexyl formaldehyde hydrazone (45) and trimethylacetaldehyde hydrazone (44).…”

Section: The Anti-tmv Activity Of 11-butanehydrazone Derivatives Of M...mentioning

confidence: 92%

See 1 more Smart Citation

Design, Synthesis and Various Bioactivity of Acylhydrazone-Containing Matrine Analogues

Song

Wang

et al. 2023

Molecules

View full text Add to dashboard Cite

Compounds with acylhydrazone fragments contain amide and imine groups that can act as electron donors and acceptors, so they are easier to bind to biological targets and thus generally exhibit significant biological activity. In this work, acylhydrazone fragments were introduced to the C-14 or C-11 position of matrine, a natural alkaloid, aiming to enhance their biological activities. The result of this bioassay showed that many synthesized compounds exhibited excellent anti-virus activity against the tobacco mosaic virus (TMV). Seventeen out of 25 14-acylhydrazone matrine derivatives and 17 out of 20 11-butanehydrazone matrine derivatives had a higher inhibitory activity against TMV than the commercial antiviral agent Ribavirin (the in vitro activity, in vivo inactivation, curative and protection activities at 500 µg/mL were 40.9, 36.5 ± 0.9, 38.0 ± 1.6 and 35.1 ± 2.2%, respectively), and four 11-butanehydrazone matrine derivatives even had similar to or higher activity than the most efficient antiviral agent Ningnanmycin (55.4, 57.8 ± 1.4, 55.3 ± 0.5 and 60.3 ± 1.2% at 500 µg/mL for the above four test modes). Among them, the N-benzyl-11-butanehydrazone of matrine formed with 4-bromoindole-3-carboxaldehyde exhibited the best anti-TMV activity (65.8, 71.8 ± 2.8, 66.8 ± 1.3 and 69.5 ± 3.1% at 500 µg/mL; 29, 33.5 ± 0.7, 24.1 ± 0.2 and 30.3 ± 0.6% at 100 µg/mL for the above four test modes), deserving further investigation as an antiviral agent. Other than these, the two series of acylhydrazone-containing matrine derivatives were evaluated for their insecticidal and fungicidal activities. Several compounds were found to have good insecticidal activities against diamondback moth (Plutella xylostella) and mosquito larvae (Culex pipiens pallens), showing broad biological activities.

show abstract

Section: Resultsmentioning

confidence: 75%

Section: The Anti-tmv Activity Of 11-butanehydrazone Derivatives Of M...mentioning

confidence: 92%

Design, Synthesis and Various Bioactivity of Acylhydrazone-Containing Matrine Analogues

Song

Wang

et al. 2023

Molecules

View full text Add to dashboard Cite

show abstract

“…Furthermore, research has shown that the prevalence of nitrogen heterocycles can be attributed to their stability and their tendency to readily bind to deoxyribonucleic acid (DNA) through hydrogen bonding [17]. Therefore, it appeared crucial for us to investigate the stability of the conformers of two benzimidazoles-hydrazides-hydrazones among those which were synthesized by ACHI and collaborators [18]. This will enable the establishment of a reactivity hierarchy among these conformers.…”

Section: Introductionmentioning

confidence: 99%

Stability and Reactivity of Two Benzimidazole Hydrazide-Hydrazone Compounds: A Theoretical Study by DFT Method

Assoma,

Bede,

Achi

et al. 2024

IJCTC

Self Cite

View full text Add to dashboard Cite

This work contributes to theoretical chemistry’s knowledge of benzimidazole-hydrazide-hydrazone. Indeed, hydrazides-hydrazones-benzimidazoles have shown anticancer, antibacterial, antiparasitic activities, and many other activities. A benzimidazole-hydrazide-hydrazone compound can exhibit four conformers: E/Z synperiplanar (Esp, Zsp) and E/Z antiperiplanar (Eap, Zap). Studies have indicated that the prevalence of these compounds is attributed to their stability and their tendency to readily bind to DNA. A theoretical study with advanced methods would make it possible to evaluate the stability of benzimidazole-hydrazide-hydrazone conformers. Therefore, we carried out this theoretical study on the conformers of two benzimidazoles-hydrazides-hydrazones denoted C1 and C2 wich differ by the presence of fluorine atom in the structure of C2. Specifically, we analyze the stability and the reactivity of the compounds based on the dipole moment, Gibbs free energy, HOMO and LUMO energies and UV-visible. For this purpose, calculations were performed in gas phase and DMSO using DFT and TD-DFT methods at the B3LYP/6-311+G(d, p) level theory. The dipole moment values show that Zap conformer is the most polar for both compounds. The Gibbs free energy indicate that Esp conformer emerges as the most stable for both compounds in both phases. The energy gap (ELUMO-EHOMO) and TD-DFT results suggest that Esp conformer is the most reactive conformer for the two compounds.

show abstract

Quinoxaline-linked N-acyl hydrazine: A “turn-off” fluorescent probe for the selective recognition of Fe3+ in real water samples

Narayan,

Kumar,

Sindhu

et al. 2024

Journal of Photochemistry and Photobiology A: Chemistry

View full text Add to dashboard Cite

Stereochemical design and conformation determinations of new benzimidazole-N-acylhydrazone derivatives

Cited by 7 publications

References 35 publications

Design, Synthesis and Various Bioactivity of Acylhydrazone-Containing Matrine Analogues

Design, Synthesis and Various Bioactivity of Acylhydrazone-Containing Matrine Analogues

Stability and Reactivity of Two Benzimidazole Hydrazide-Hydrazone Compounds: A Theoretical Study by DFT Method

Quinoxaline-linked N-acyl hydrazine: A “turn-off” fluorescent probe for the selective recognition of Fe3+ in real water samples

Contact Info

Product

Resources

About