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Article

Mechanochemical Studies on Coupling of Hydrazines and Hydrazine Amides with Phenolic and Furanyl Aldehydes—Hydrazones with Antileishmanial and Antibacterial Activities

by
Anna Kapusterynska
1,
Christian Bijani
1,
Damian Paliwoda
1,
Laure Vendier
1,
Valérie Bourdon
2,
Nicolas Imbert
3,
Sandrine Cojean
3,
Philippe Marie Loiseau
3,
Deborah Recchia
4,
Viola Camilla Scoffone
4,
Giulia Degiacomi
4,
Abdul Akhir
5,
Deepanshi Saxena
5,
Sidharth Chopra
5,
Vira Lubenets
6 and
Michel Baltas
1,*
1
CNRS, LCC (Laboratoire de Chimie de Coordination), Université de Toulouse, UPS, INPT, Inserm ERL 1289, 205 Route de Narbonne, BP 44099, CEDEX 4, 31077 Toulouse, France
2
Technological and Expert Platform, Chemistry Institute of Toulouse ICT-UAR2599, University of Toulouse, CNRS, 118 Route de Narbonne, CEDEX 9, 31062 Toulouse, France
3
Antiparasite Chemotherapy, UMR 8076 CNRS BioCIS, Faculty of Pharmacy, University Paris-Saclay, 91400 Orsay, France
4
Department of Biology and Biotechnology “Lazzaro Spallanzani”, University of Pavia, 27100 Pavia, Italy
5
Division of Microbiology, CSIR—Central Drug Research Institute, Sector 10, Janakipuram Extension, Sitapur Road, Lucknow 226031, Uttar Pradesh, India
6
Department of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University, S. Bandery, 12, 79013 Lviv, Ukraine
*
Author to whom correspondence should be addressed.
Molecules 2023, 28(13), 5284; https://doi.org/10.3390/molecules28135284
Submission received: 7 June 2023 / Revised: 22 June 2023 / Accepted: 26 June 2023 / Published: 7 July 2023
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Abstract

Hydrazone compounds represent an important area of research that includes, among others, synthetic approaches and biological studies. A series of 17 hydrazones have been synthesized by mechanochemical means. The fragments chosen were phenolic and furanyl aldehydes coupled with 12 heterocyclic hydrazines or hydrazinamides. All compounds can be obtained quantitatively when operating on a planetary ball mill and a maximum reaction time of 180 min (6 cycles of 30 min each). Complete spectroscopic analyses of hydrazones revealed eight compounds (3–5, 8–11, 16) present in one geometric form, six compounds (1, 2, 13–15) present in two isomeric forms, and three compounds (6, 7, 12) where one rotation is restricted giving rise to two different forms. The single crystal X-ray structure of one of the hydrazones bearing the isoniazid fragment (8) indicates a crystal lattice consisting of two symmetry-independent molecules with different geometries. All compounds obtained were tested for anti-infectious and antibacterial activities. Four compounds (1, 3, 5 and 8) showed good activity against Mycobacterium tuberculosis, and one (7) was very potent against Staphylococcus aureus. Most interesting, this series of compounds displayed very promising antileishmanial activity. Among all, compound 9 exhibited an IC50 value of 0.3 µM on the Leishmania donovani intramacrophage amastigote in vitro model and a good selectivity index, better than miltefosine, making it worth evaluating in vivo.
Keywords: mechanochemistry; sustainable synthesis; hydrazones; furanyls; phenolics; anti-infectious; antileishmanial; antibacterial mechanochemistry; sustainable synthesis; hydrazones; furanyls; phenolics; anti-infectious; antileishmanial; antibacterial
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MDPI and ACS Style

Kapusterynska, A.; Bijani, C.; Paliwoda, D.; Vendier, L.; Bourdon, V.; Imbert, N.; Cojean, S.; Loiseau, P.M.; Recchia, D.; Scoffone, V.C.; et al. Mechanochemical Studies on Coupling of Hydrazines and Hydrazine Amides with Phenolic and Furanyl Aldehydes—Hydrazones with Antileishmanial and Antibacterial Activities. Molecules 2023, 28, 5284. https://doi.org/10.3390/molecules28135284

AMA Style

Kapusterynska A, Bijani C, Paliwoda D, Vendier L, Bourdon V, Imbert N, Cojean S, Loiseau PM, Recchia D, Scoffone VC, et al. Mechanochemical Studies on Coupling of Hydrazines and Hydrazine Amides with Phenolic and Furanyl Aldehydes—Hydrazones with Antileishmanial and Antibacterial Activities. Molecules. 2023; 28(13):5284. https://doi.org/10.3390/molecules28135284

Chicago/Turabian Style

Kapusterynska, Anna, Christian Bijani, Damian Paliwoda, Laure Vendier, Valérie Bourdon, Nicolas Imbert, Sandrine Cojean, Philippe Marie Loiseau, Deborah Recchia, Viola Camilla Scoffone, and et al. 2023. "Mechanochemical Studies on Coupling of Hydrazines and Hydrazine Amides with Phenolic and Furanyl Aldehydes—Hydrazones with Antileishmanial and Antibacterial Activities" Molecules 28, no. 13: 5284. https://doi.org/10.3390/molecules28135284

APA Style

Kapusterynska, A., Bijani, C., Paliwoda, D., Vendier, L., Bourdon, V., Imbert, N., Cojean, S., Loiseau, P. M., Recchia, D., Scoffone, V. C., Degiacomi, G., Akhir, A., Saxena, D., Chopra, S., Lubenets, V., & Baltas, M. (2023). Mechanochemical Studies on Coupling of Hydrazines and Hydrazine Amides with Phenolic and Furanyl Aldehydes—Hydrazones with Antileishmanial and Antibacterial Activities. Molecules, 28(13), 5284. https://doi.org/10.3390/molecules28135284

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