(2E)-2-[1-(1,3-Benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propylidene]-N-(2-chlorophenyl)hydrazine carboxamide: Synthesis, X-ray Structure, Hirshfeld Surface Analysis, DFT Calculations, Molecular Docking and Antifungal Profile

Abstract

Life-threatening fungal infections accounts for a major global health burden especially for individuals suffering from cancer, acquired immune deficiency syndrome (AIDS), or autoimmune diseases. (2E)-2-[1-(1,3-Benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propylidene]-N-(2-chlorophenyl)hydrazinecarboxamide has been synthesized and characterized using various spectroscopic tools to be evaluated as a new antifungal agent. The (E)-configuration of the imine moiety of the title molecule has been unequivocally identified with the aid of single crystal X-ray analysis. The molecular structure of compound 4 was crystallized in the monoclinic, P21/c, a = 8.7780 (6) Å, b = 20.5417 (15) Å, c = 11.0793 (9) Å, β = 100.774 (2)°, V = 1962.5 (3) Å3, and Z = 4. Density functional theory computations have thoroughly explored the electronic characteristics of the title molecule. Moreover, molecular docking studies and Hirshfeld surface analysis were also executed on the title compound 4. The in vitro antifungal potential of the target compound was examined against four different fungal strains.

Design, Synthesis, Crystal Structure, and Fungicidal Activity of L-Carvone Derivatives Containing an Oxime Ester Moiety

“…The crystal packing diagrams and crystal structure of compound 4r are 8) nm) are also analogous to the aromatic C-C bonds of phenyl ring (0.1370～0.1467 nm). [34][35] The bromo-substituted benzene ring is linked together with the cyclohexene ring via an oxygen atom with C(12)-C(11)-O(1) and O(1)-N(1)-C(2) bond angles of 108.4(5)° and 108.9(4)°, respectively. The dihedral angle between benzene ring and cyclohexene is 10.7°.…”

Preface of the Special Issue “Pharmaceutical Crystals”

“…This substance has in vitro nanomolar inhibitory activity against the hepatitis B virus (HBV). Another docking study was reported by Al-Wabli et al [10], where a newly synthesized compound was crystallographically characterized. Furthermore, the structure was analyzed using molecular docking studies and Hirshfeld surface analysis.…”

Potansiyel Antikolinesteraz Ajanlar Olarak Yeni İmidazol Türevlerinin Sentezi ve Karakterizasyonu

“…İmidazol ve türevlerinin yapılan çalışmalar sonucu canlı metabolizmasındaki farklı görevleri ortaya konulmuştur. İmidazol türevlerinin literatür kayıtları arasında antikanser [9,10], antifungal [11] etkileri yanında antikolinesteraz etkileri ilgili çalışmaların varlığı [12,13] ve günümüzde kullanılan birçok ilaç molekülünün yapısına girmiş olması bizi bu tür çalışmaya yönlendirmiştir. [8,14].…”