41255-30-5Relevant articles and documents
Flavone-based hydrazones as new tyrosinase inhibitors: Synthetic imines with emerging biological potential, SAR, molecular docking and drug-likeness studies
Alsantali, Reem?I.,Mughal, Ehsan?Ullah,Naeem, Nafeesa,Alsharif, Meshari?A.,Sadiq, Amina,Ali, Anser,Jassas, Rabab.?S.,Javed, Qamar,Javid, Asif,Sumrra, Sajjad Hussain,Alsimaree, Abdulrahman?A.,Zafar, Muhammad?Naveed,Asghar, Basim?H.,Altass, Hatem?M.,Moussa, Ziad,Ahmed, Saleh?A.
, (2021/11/30)
Targeting tyrosinase (TYR), a key enzyme responsible for melanogenesis disorders, is a well-known approach utilized for the development of melanogenesis inhibitor. A variety of dermatological disorders and microbial skin infections can cause hyperpigmentation. Hence, exploring new scaffolds for the treatment of melanogenesis disease is an inspiring goal. In this context, a series of varyingly substituted flavone-based hydrazones have been designed, synthesized and characterized successfully. The present study describes the discovery of novel mushroom tyrosinase inhibitors (TIs) for treating hyperpigmentation. In due course, flavone scaffold has been incorporated into the novel chemotypes that exhibit in vitro inhibitory effects against mushroom tyrosinase for the purpose of discovering anti‐melanogenic agents. Biological investigations of prepared analogs herein demonstrated moderate to excellent activity against most of the fungal-bacterial strains and their activity is comparable to those of commercially available antibiotics i.e., Ciprofloxacin and Ketoconazole. Based on in vitro tyrosinase inhibitory assay, some compounds exhibited potent inhibition particularly, 3g (IC50 = 1.40 ± 0.16 μM), 3j (IC50 = 0.95 ± 0.07 μM), 3o (IC50 = 1.13 ± 0.11 μM), and 3q (IC50 = 1.01 ± 0.1 μM) showed best inhibition i.e., 0.7, 0.5, 0.6 and 0.5 folds, respectively, than kojic acid (IC50 = 1.79 ± 0.6 μM). Lineweaver-Burk plots demonstrated that the most potential derivative 3j tyrosinase inhibition proceeds via non-competitive pathway and the Michaelis-Menton constant (Km) value is 0.0265. Molecular modeling was performed for all tested analogs (3a–3q) using a model of mushroom tyrosinase to find crucial binding modes liable for inhibitory activity. The SARs were preliminarily examined, and the docking study revealed that analogs 3j, 3o and 3p had a strong binding association to tyrosinase (2Y9X). Furthermore, a drug-likeness study was employed and confirmed the favorable activity of the new analogs as a new anti-tyrosinase agent.
CF3SOCl-promoted intramolecular cyclization of β-diketones: An efficient synthesis of flavones
Sun, Dong-Wei,Zhou, Yong-Yan,Jiang, Min,Nian, Tang,Liu, Jin-Tao
, (2021/05/31)
An efficient intramolecular cyclization reaction of β-diketones containing a phenyl group with an ortho-hydroxyl substituent was achieved. Using CF3SOCl as an additive, the reaction took place under transition-metal-free and mild conditions. A series of flavones were synthesized in moderate to excellent yields.
Thermally regulated molybdate-based ionic liquids toward molecular oxygen activation for one-pot oxidative cascade catalysis
Song, Zhibin,Huang, Wei,Zhou, Yan,Tian, Zi-Qi,Li, Zhang-Min,Tao, Duan-Jian
, p. 103 - 109 (2020/01/21)
One-pot oxidative cascade catalysis plays a central role in the synthesis of key pharmaceutical and industrial molecules. Although ionic liquids are one of the most promising solvents and reaction media, the breakthrough of their catalysis in aerobic oxidation is very challenging due to the difficulty in the direct activation of molecular oxygen. Herein, a family of novel thermally regulated molybdate-based ionic liquids (Mo-ILs) has been designed and developed for the first time toward molecular oxygen activation for highly efficient tandem oxidative catalysis. Three diverse one-pot oxidative cascade processes for the syntheses of various flavones, imines, and benzyl benzoates were achieved with good to excellent yields using the Mo-IL [Bmim]2[MoO4] as a catalyst under air conditions. The results of spectroscopic investigations and quantum-chemical calculations further demonstrated that a thermally regulated proton migration between the cation [Bmim] and anion [MoO4] was the key to forming N-heterocyclic carbene and thereby to effortlessly promoting the generation of O2- active species from molecular oxygen, which results in excellent catalytic performance in these three aerobic tandem oxidations. Our work extends the application area of ILs as the sole catalyst to one-pot aerobic oxidative cascade catalysis, which could have pronounced implications in future work.
