Design, Synthesis, and Biological Evaluation of Novel 1,3,4‐Thiadiazolylpyrazolines Compounds Containing Ferrocene

Abstract

The synthesis of 1,3,4‐thiadiazole skeleton compounds exhibiting high fungicidal activities has been demonstrated. Thirteen novel 1,3,4‐thiadiazolyl‐pyrazolines compounds containing ferrocene were designed and synthesized from the ferrocenylchalcones intermediates 3a–3m and the 2‐hydrazino‐5‐phenyl‐1,3,4‐thiadiazole intermediate 8. All compounds were characterized by 1H NMR, 13C NMR, FT‐IR spectra, and HR‐MS, and the structure of one of the new compounds N‐(4‐phenyl‐1,3,4‐thiadiazol‐2‐yl)‐3‐ferrocenyl‐5‐phenyl‐pyrazoline 9a was further determined by X‐ray diffraction analysis. The preliminary results of a biological activity assay indicated that all the title compounds exhibited significant fungicidal activities against Pythium solani, Gibberella saubinetii, and Gibberella nicotiancola. Furthermore, compounds 9e and 9h displayed even higher fungicidal activities against the three fungal species compared with the control drug pyraclostrobin.

Acetylcholinesterase inhibitory potencies of new pyrazoline derivatives

“…According to Ki values, compound 1 has been found as the most effective compound of series. This study reported synthesis and AChE inhitory potency of the new pyrazoline derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9). The results indicated that compound 1 had the greatest inhibitory potency with both IC50 (1.30 μM) and Ki (0.13±0.004 μM) values.…”

“…2-Pyrazolines are most popular heterocyclic structure in drug design. They have various important biological activities such as as antimicrobial [6], antifungal [7], antimalarial [8], antiinflammatory [9][10], analgesic [10], anti-Alzheimer's disease [11], anti-Parkinson's disease [12], antidepressant [13][14], anticancer [15][16] and monoamine oxidase (MAO) inhibitory activities [17][18]. In recent years, pyrazoline derivatives are shown to have inhibiting or activating effects on several enzymes such as cholinesterases [19], MAOs, and carbonic anhydrases [20][21].…”

“…It was aimed to synthesize new 2-(3-(4-methoxyphenyl)-5-aryl-4,5-dihydro-1H-pyrazol-1yl)benzo [d]thiazoles (1)(2)(3)(4)(5)(6)(7)(8)(9) to investigate their AChE inhibitory effects to ascertain possible lead compounds in this study. When the 1 H NMR spectra were examined, the proton of the C-5 carbon of the pyrazoline ring resonated as a doublet of doublet between the range of 6.40-5.61 ppm.…”

POCl3 mediated one-pot deoxygenative aromatization and electrophilic chlorination of dihydroxy-2-methyl-4-oxo-indeno[1,2-b]pyrroles

“…N -oxide and S -oxide derivatives of nitrogen or sulfur-bearing heterocycles are typical examples of materials used in these reactions. 2 Furthermore, the great attention paid to POCl 3 stems from its diverse applications in chlorination, 3 dehydration, 4 Bischler–Napieralski cyclization, 5 and Vilsmeier–Haack formylation. 6 Dihydroxy-4-oxo-indeno[1,2- b ]pyrroles possessing two vicinal hydroxyl groups have been deoxygenated by reagents such as triphenylphosphine (route A in Scheme 1 ), 7 thionyl chloride, 8 and tetraalkylthionylamides ((NR 2 ) 2 SO) (route B in Scheme 1 ).…”