81226-96-2Relevant academic research and scientific papers
Electronic effect control of regioselectivity in the Michael-Addition inspired cascade reaction of 1,3-dimethyl-6-amino-uracil and 2-hydroxychalcones
Cui, Xin,Huang, Chao,Li, Jing-Peng,Lin, Jun-Jie,Wang, Shuang,Xia, Xian-Song
supporting information, (2022/01/15)
An unexpected Brosnted acid-catalyzed cascade reaction of 1,3-dimethyl-6-aminouracil with 2-hydroxychalcone has been developed to afford pyrido[2,3–d]pyrimidine-2,4-diones derivatives and 2,8-dioxabicyclo[3.3.1]nonane derivatives in moderate to good yield
Novel isoniazid-spirooxindole derivatives: design, synthesis, biological evaluation, in silico ADMET prediction and computational studies
Bhoi, Manoj N.,Borad, Mayuri A.,Jethava, Divya J.,Pandya, Himanshu A.,Patel, Chirag N.,Patel, Hitesh D.
, (2020/07/21)
In the present scenario, the Synthesis of new and desired antimycobacterial agent has an eternal demand to resist Mycobacterium tuberculosis (MTB). The design and identification of new molecules for the treatment of tuberculosis is an important task in organic as well as medicinal chemistry research. In the present study, we have reported the combination of the desired compound using two versatile and significant moieties, isoniazid and spirooxindole derivatives. A series of novel isoniazid-spirooxindole hybrid molecules (6a-6ao) were designed, synthesized, and well-characterized by various spectroscopic methods. We have evaluated for their in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB) strain and MDR-TB. Among them, Compound 6ab was found to be the most effective compare to other compounds. ADMET-related descriptors were to be calculated of all the compounds to predict the pharmacokinetic properties for the selection of the effective and bioavailable compounds. In addition, molecular docking and molecular dynamics studies reveal that the binding modes of all the compounds in the active site of isoniazid-resistant enoyl-ACP(COA) reductase, which helped to establish a structural basis of inhibition of Mycobacterium tuberculosis.
Palladium-Catalyzed Cascade Reactions of 2-(Cyanomethoxy)chalcones with Arylboronic Acids: Selective Synthesis of Emissive Benzofuro[2,3- c]pyridines
Xiong, Wenzhang,Hu, Kun,Lei, Yunxiang,Zhen, Qianqian,Zhao, Zhiwei,Shao, Yinlin,Li, Renhao,Zhang, Yetong,Chen, Jiuxi
supporting information, p. 1239 - 1243 (2020/01/11)
The Pd(II)-catalyzed cascade reactions of 2-(cyanomethoxy)chalcones with arylboronic acids were demonstrated, allowing the rapid construction of benzofuro[2,3-c]pyridine skeletons with excellent selectivity. These transformations involve the domino-style formation of C-C/C-C/C-N bonds through nitrile carbopalladation, intramolecular Michael addition, cyclization, and aromatization. This chemistry allows for the reactions of 2-(cyanomethoxy)chalcones with thiophen-3-ylboronic acid, providing 3-aryl-1-(thiophen-3-yl)benzofuro[2,3-c]pyridines in moderate to good yields. In addition, the resulting products represent a new class of emissive fluorophores.
Highly enantioselective addition of aliphatic aldehydes to 2-hydroxychalcone enabled by cooperative organocatalysts
Chen, Le,Chen, Lu,Gao, Yu-Qi,Hou, Yi,Hu, Jiadong,Wen, Wen,Xie, Weiqing,Xu, Dongyang
supporting information, p. 10018 - 10021 (2020/09/15)
Herein, we developed an enantioselective addition of aliphatic aldehydes to 2-hydroxychalcone promoted by cooperative organocatalysts, giving access to hybrid flavonoids in excellent enantioselectivities. This reaction took advantage of cycloisomerization of 2-hydroxychalcone to form a transient flavylium under the irradiation of 24 W CFL, which was trapped by the in situ generated chiral enamine intermediate. The synergistic action of chiral phosphoric acid secured the excellent outcome of this reaction by ion-pairing with the transient flavylium.
Synthesis, in vitro antigiardial activity, SAR analysis and docking study of substituted chalcones
Cáceres-Castillo, David,Carballo, Rubén M.,Graniel-Sabido, Manlio,Mena-Rejón, Gonzalo J.,Mirón-López, Gumersindo,Moo-Puc, Rosa E.,Quijano-Qui?ones, Ramiro
, (2020/01/08)
A series of 15 chalcones-bearing substituents at positions 2, 4, and 5 of rings A and B were synthesized using microwave-assisted Claissen–Smichdt condensation and evaluated for their activity against Giardia lamblia and Green monkey kidney cells. Five co
Design, synthesis and biological evaluation of tricyclic pyrazolo[1,5-c][1,3]benzoxazin-5(5H)-one scaffolds as selective BuChE inhibitors
Qiu, Guo-Liang,He, Shao-Sheng,Chen, Shi-Chao,Li, Bo,Wu, Hui-Hui,Zhang, Jing,Tang, Wen-Jian
, p. 1506 - 1515 (2018/10/15)
Based on the structural analysis of tricyclic scaffolds as butyrylcholinesterase (BuChE) inhibitors, a series of pyrazolo[1,5-c][1,3]benzoxazin-5(5H)-one derivatives were designed, synthesized and evaluated for their acetylcholinesterase (AChE) and BuChE inhibitory activity. Compounds with 5-carbonyl and 7- or/and 9-halogen substitutions showed potential BuChE inhibitory activity, among which compounds 6a, 6c and 6g showed the best BuChE inhibition (IC50 = 1.06, 1.63 and 1.63 μM, respectively). The structure–activity relationship showed that the 5-carbonyl and halogen substituents significantly influenced BuChE activity. Compounds 6a and 6g were found nontoxic, lipophilic and exhibited remarkable neuroprotective activity and mixed-type inhibition against BuChE (Ki = 7.46 and 3.09 μM, respectively). Docking studies revealed that compound 6a can be accommodated into BuChE via five hydrogen bonds, one Pi–Sigma interaction and three Pi–Alkyl interactions.
Synthesis of Functionalized Chromene and Chroman Derivatives via Cesium Carbonate Promoted Formal [4 + 2] Annulation of 2′-Hydroxychalcones with Allenoates
Rouh, Hossein,Liu, Yangxue,Katakam, Nandakumar,Pham, Lilian,Zhu, Yi-Long,Li, Guigen
, p. 15372 - 15379 (2019/01/04)
A new strategy has been established for the synthesis of functionalized chromene and chroman derivatives via a Cs2CO3-catalyzed domino addition of 2′-hydroxychalcone derivatives with allenoates, which can serve as a general avenue for the construction of multireplaced chromene derivatives. Chemoselectivity of this synthesis was found to depend on substituents on substrates. Good to excellent yields were achieved under simple and mild conditions at room temperature.
Formal cycloaddition of ethyl 2-aroyl-1-chlorocyclopropanecarboxylates:facile synthesis of diversified tetrahydrocyclopropa[b]chromenes
Xiong, Guoxi,Liao, Yong,Liu, Xue-Hui,Tang, Xiangying,Gong, Yuefa
supporting information, p. 1486 - 1491 (2018/02/23)
Tandem reaction of ortho-hydroxy chalcone with ethyl 2-aroyl-1-chlorocyclopropanecarboxylates has been disclosed, affording facile synthesis of diversified tetrahydrocyclopropa[b]chromenes via electron-deficient cyclopropene intermediate.
Synthesis and antimicrobial activity of some 5-chloro-3-phenyl-1H-indole-2-carbonyl azide derivatives
Basavarajaiah,Mramyunjayaswamy
, p. 390 - 399 (2019/05/21)
In the present investigations, a series of new 6-substituted-3-(5-chloro-3-phenyl-lJ?-indole-2yl)-3,4-dihydro-4-substituted-4-substituted-phenacyl-2H-l,3-benzoxazin-2-one 7a-f have been synthesized by two methods making use of 5-chloro-3-phenyl-l/H-ndole-2-carbonyl azide 2 and chalcones 5a-f. In one method, compound 2 on reaction with chalcones 5a-f in presence of triethylamine in dry benzene yields respective open chain carbamates 6a-f, followed by reaction with catalytic amount of potassium hydroxide in dry benzene under reflux condition to afford compounds 7a-f. In another method, compound 5a-f on reaction with compound 2 using dry benzene in presence of catalytic amount of potassium hydroxide under reflux conditions afford cyclized products 7a-f in good yield. Structures of the all the newly synthesized compounds have been confirmed by spectral data. All these compounds have been screened for their antibacterial activity against Staphylococcus aureus, Escherichia coli, Bacillus subtilis, antifungal activity against Aspergillus Niger and Candida albicans and antituberculosis activity against Mycobacterium tuberculosis (H37RV).
Novel hybrids derived from aspirin and chalcones potently suppress colorectal cancer in vitro and in vivo
Lu, Shan,Obianom, Obinna N.,Ai, Yong
, p. 1722 - 1732 (2018/10/26)
Colorectal cancer (CRC) remains the fourth leading cause of cancer deaths around the world despite the availability of many approved small molecules for treatment. The issues lie in the potency, selectivity and targeting of these compounds. Therefore, new
