350680-25-0Relevant articles and documents
Molecular hybridization based design and synthesis of new benzo[5,6]chromeno[2,3-b]-quinolin-13(14H)-one analogs as cholinesterase inhibitors
Macha, Baswaraju,Kulkarni, Ravindra,Bagul, Chandrakant,Garige, Anil Kumar,Akkinepally, Raghuramrao,Garlapati, Achaiah
, p. 685 - 701 (2021/01/13)
A Series of new tacrine analogs were designed, synthesized, characterized by respective spectral data and evaluated for cholinesterase inhibitory activity to be useful in Alzheimer’s disease. Most of the synthesized compounds showed good in vitro inhibitory activities toward acetyl cholinesterase (AChE) and butyrylcholinesterase (BuChE) enzymes. Among the compounds, 6i, 6o and 6r with increased saturated carboxylic ring size attached to the pyridine moiety and having 3,4-dihydroxy, 3,4,5-trimethoxy substituents on the aromatic ring attached at the stereogenic center have shown equal potency to that of tacrine with IC50values 0.65 ± 0.06, 1.32 ± 0.02 and 0.85 ± 0.05, 1.65 ± 0.12 and 0.92 ± 0.03, 1.91 ± 0.12 μM against AChE and BuChE, respectively. Standard drug tacrine exhibited IC50 values of 0.47 ± 0.02 and 0.65 ± 0.08, while Donepezil showed IC50 0.71 ± 0.06 and 0.31 ± 0.04 μM against AChE and BuChE, respectively. Docking studies of all the molecules disclosed close hydrogen bond interactions with the binding site.
Aqua one-pot, three-component synthesis of dihydropyrano[3,2-c]chromenes and amino-benzochromenes catalyzed by sodium malonate
Kiyani, Hamzeh,Tazari, Mohsen
, p. 6639 - 6650 (2017/10/06)
The widespread biological properties of dihydropyrano[3,2-c]chromenes, 2-amino-4-aryl-4H-benzo[h]chromenes, and 3-amino-1-aryl-1H-benzo[f]chromenes have led to increasing efforts for the development of tremendously effective synthetic protocols aimed at their synthesis. In this contribution, sodium malonate was employed for the first time as an efficient catalyst for the one-pot, three-component tandem Knoevenagel–cyclocondensation reaction of 4-hydroxycoumarin (or naphthols), malononitrile/ethyl cyanoacetate, and various aldehydes. These compounds underwent Knoevenagel–Michael–Thorpe–Ziegler cyclization upon heating at 70?°C in water to give the respective medicinally relevant dihydropyrano[3,2-c]chromenes and amino-benzochromenes. The method is versatile and amenable to many substrates as it requires no specialized devices such as microwave, ultrasound and ball-milling. Also, the salient features of this high-yielding protocol are green reaction conditions, the use of commercially available catalyst, easy purification processes by a simple filtration, and relatively shorter reaction times.
A simple green protocol for the synthesis of ethyl 3-amino-1-aryl-1H-benzo[f] chromene-2-carboxylates in aqueous media
Qian, Siran,Li, Mingjie,Liu, Jiaming,Wang, Cunde
, p. 487 - 490 (2017/08/18)
An eco-friendly and efficient straightforward method has been developed for the synthesis of ethyl 3-amino-1-aryl-1H-benzo[f]chromene-2-carboxylate derivatives via 1,4-diazabicyclo[2.2.2]octane (DABCO)-catalysed cyclisation of β-naphthol and 3-aryl-2-cyanoacrylates using water as a green solvent. All products precipitated from the reaction mixture and were isolated by simple filtration. No further workup nor purification was necessary. The structure of ethyl 3-amino-1-aryl-1H-benzo[f]chromene-2-carboxylate was further confirmed by X-ray single crystal analysis.
Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water
Kiyani, Hamzeh,Ghorbani, Fatemeh
, p. 7847 - 7882 (2015/02/19)
A variety of 4H-chromenes, benzochromenes, 4,5-dihydropyrano[3,2-c]chromenes, 4H-pyran-3-carboxylates, and 3,4-disubstituted isoxazol-5(4H)-ones have been synthesized in high yields by using potassium hydrogen phthalate (KHP) as an inexpensive, commercially available catalyst. It was found that the three-component tandem reaction enabled synthesis of pyran-annulated heterocycles in water at 50 °C. 3,4-Disubstituted isoxazol-5(4H)-ones were synthesized by use of 10 mol% KHP in water at room temperature. Also, treatment of methylene-containing compounds (malononitrile or ethyl cyanoacetate) with aromatic aldehydes in the presence of 5 mol% KHP resulted in α,β-unsaturated nitriles. The procedure is an easily performed, straightforward method for synthesis of a variety of pyran-annulated compounds, isoxazol-5(4H)-one-containing heterocycles, and Knoevenagel adducts. The reaction is safe, uses mild conditions, and is environmentally benign. Other notable advantages are reuse of the catalyst, no use of hazardous organic solvents, and ease of work-up.
Potassium phthalimide-catalysed one-pot multi-component reaction for efficient synthesis of amino-benzochromenes in aqueous media
Kiyani, Hamzeh,Ghorbani, Fatemeh
, p. 1104 - 1112 (2014/05/20)
2-Amino-4-aryl-4H-benzo[h]chromenes and 3-amino-1-aryl-1H-benzo[f]chromenes were prepared by treating cyano-methylene compounds (malononitrile or ethyl cyanoacetate), substituted aromatic aldehydes, and naphtholic compounds in the presence of potassium phthalimide as a green, mild, efficient, and commercially available organocatalyst in aqueous media. The procedure was readily conducted and affords remarkable advantages such as safety, short reaction times, environmentally benign milder reaction conditions, no organic solvent required, and high yields.
