- Synthesis, characterization, DFT, docking studies and molecular dynamics of some 3-phenyl-5-furan isoxazole derivatives as anti-inflammatory and anti-ulcer agents
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A vast number of nitrogen heterocyclic derivatives comprising oxygen atom is considered as a valuable combination of therapeutic agents in curative chemistry. In particular, isoxazole, a five-member heterocyclic ring, is detected along with some of the ma
- M, Pallavi H,Al-Ostoot, Fares Hezam,Vivek, Hamse Kameshwar,Khanum, Shaukath Ara
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- Electronic effect control of regioselectivity in the Michael-Addition inspired cascade reaction of 1,3-dimethyl-6-amino-uracil and 2-hydroxychalcones
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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
- Cui, Xin,Huang, Chao,Li, Jing-Peng,Lin, Jun-Jie,Wang, Shuang,Xia, Xian-Song
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supporting information
(2022/01/15)
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- Palladium-Catalyzed Cascade Reactions of 2-(Cyanomethoxy)chalcones with Arylboronic Acids: Selective Synthesis of Emissive Benzofuro[2,3- c]pyridines
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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.
- Xiong, Wenzhang,Hu, Kun,Lei, Yunxiang,Zhen, Qianqian,Zhao, Zhiwei,Shao, Yinlin,Li, Renhao,Zhang, Yetong,Chen, Jiuxi
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supporting information
p. 1239 - 1243
(2020/01/11)
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- One-Pot Allylation-Intramolecular Vinylogous Michael Addition-Isomerization Cascade of o-Hydroxycinnamates and Congeners: Synthesis of Substituted Benzofuran Derivatives
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A unique intramolecular vinylogous Michael addition leading to the synthesis of heterocycles has been disclosed. Base-promoted one-pot sequential O-allylation of o-hydroxy-cinnamates or -cinnamonitrile or -chalcones with γ-bromocrotonates followed by an intramolecular conjugate addition of vinylogous Michael donors resulted in the formation of highly substituted benzofuran derivatives in good to excellent yields. The intramolecular event followed by two [1,3]-H shifts leading to aromatization appears to be the key to the success of this unprecedented transformation.
- Harish, Battu,Subbireddy, Manyam,Obulesu, Owk,Suresh, Surisetti
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supporting information
(2019/03/19)
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- Enantioselective synthesis of 2-amino-3-nitrile-chromenes catalyzed by cinchona alkaloids: A remarkable additive effect
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2-Amino-3-nitrile-chromenes with potential antitumor activity were constructed by a novel catalytic system. In combination with α-naphthol, quinine could effectively promote the Michael-cyclization process of malononitrile with functionalized chalcones in high yields and moderate to good enantioselectivity (up to 84% ee). It is notable that the enantioselectivity could be greatly improved when α-naphthol was employed as additive.
- Zheng, Yuan-Qin,Luan, Chun-Feng,Wang, Zhi-Jing,Yao, Yong-Qi,Shi, Zhi-Chuan,Li, Xue-Feng,Zhao, Zhi-Gang,Chen, Feng
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supporting information
p. 25 - 30
(2016/01/25)
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- ZrCl4-catalysed synthesis of new 4-(2-hydroxyphenyl)pyrazolo[3,4-b]pyridine derivatives
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In the presence of a catalytic amount of zirconium(IV) chloride, an efficient synthesis of new 4-(2-hydroxyphenyl)pyrazolo[3,4-b]pyridines has been developed by the reaction 2-hydroxychalcones with 3-methyl-1-phenyl-1H-pyrazol-5-amine in refluxing ethanol. All these novel compounds have been characterised by 1H NMR, 13C NMR, HRMS, IR spectra and X-ray crystallographic analysis.
- Liu, Meilin,Yin, Guodong
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p. 236 - 266
(2015/06/02)
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- Enantioselective Synthesis of Highly Substituted Chromans via the Oxa-Michael-Michael Cascade Reaction with a Bifunctional Organocatalyst
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A highly enantioselective synthesis of chiral chroman derivatives via an oxa-Michael-Michael cascade reaction has been developed using a bifunctional thiourea organocatalyst. The products were obtained with excellent enantioselectivities (up to >99%), good yields (up to 95%), and diastereoselectivities (up to 5:1).
- Saha, Prasenjit,Biswas, Arnab,Molleti, Nagaraju,Singh, Vinod K.
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p. 11115 - 11122
(2015/11/18)
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- Thieny/furanyl-hydroxyphenylpropenones as inhibitors of LPS-induced ROS and NO production in RAW 264.7 macrophages, and their structure-activity relationship study
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Twelve thienyl/furanyl-hydroxyphenylpropenones were systematically designed and synthesized, and evaluated for their inhibitory effect on LPS-induced ROS and NO production in RAW 264.7 macrophages. Compound 11 displayed the most significant inhibitory activity of LPS-induced ROS and NO production in RAW 264.7 macrophages. Structure-activity relationship study indicated that para-hydroxyphenyl moiety plays an important role for inhibitory activities on both LPS-induced ROS and NO production as well as 3- thienyl moiety on molecule.
- Kadayat, Tara Man,Kim, Mi Jin,Nam, Tae-Gyu,Park, Pil-Hoon,Lee, Eung-Seok
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p. 2481 - 2486
(2014/09/17)
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- Organocatalyzed michael-michael cascade reaction: Asymmetric synthesis of polysubstituted chromans
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An enantioselective cascade Michael-Michael reaction between chalcones enolates and nitromethane catalyzed by a bifunctional thiourea is developed. This reaction provides a mild but efficient approach to chiral benzopyrans bearing three consecutive stereocenters in high yields with excellent stereoselectivities, and the benzopyrans can be easily transformed to the corresponding tricyclic product.
- Jia, Zhen-Xin,Luo, Yong-Chun,Cheng, Xi-Na,Xu, Peng-Fei,Gu, Yu-Cheng
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p. 6488 - 6494
(2013/07/26)
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- Synthesis and QSAR analysis of chalcone derivatives as nitric oxide inhibitory agent
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In this study, thirty-eight chalcone analogs were synthesized and evaluated for nitric oxide (NO) inhibition activity on RAW 264.7 cells. Among these compounds, chalcones bearing furanyl group showed remarkable anti-inflammatory activity. Both compounds 2d and 2j were identified as the most potent NO inhibitor on IFN-γ/LPS-activated RAW 264.7 cells. In order to examine the structure-activity relationship, a 3D QSAR analysis was carried out by comparative molecular field analysis (CoMFA) method on the selected chalcones. Partial least square analysis produced a statistically coherent model with good predictive value, r2 = 0.989 and a good cross validated value, q 2 = 0.583.
- Lam, Kok Wai,Lajis, Nordin H.,Uddin, Reaz,Ul-Haq, Zaheer,Liew, Choi Yi,Tham, Chau Ling,Israf, Daud A.,Syahida, Ahmad,Rahman, Mohd. Basyaruddin Abdul
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p. 1953 - 1966,14
(2020/07/30)
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- A novel route to synthesis of flavones from salicylaldehyde and acetophenone derivatives
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Convenient, facile, and alternate synthesis of medicinally important flavones is reported. The 2-hydroxychalcones derived from condensation between acetophenones and salicylaldehyde, underwent oxidative cyclization on heating in the presence of catalytic iodine, generating diversified flavones under solvent-free conditions. Eleven compounds have been synthesized in good to excellent yields and their mechanism of formation is described.
- Sashidhara, Koneni V.,Kumar, Manoj,Kumar, Abdhesh
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scheme or table
p. 2355 - 2359
(2012/07/14)
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- Synthesis of functionalized 2-aryl-4-(indol-3-yl)-4H-chromenes via iodine-catalyzed domino Michael addition-intramolecular cyclization reaction
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An efficient synthesis of novel functionalized 2-aryl-4-(indol-3-yl)-4H- chromenes has been developed, in the presence of a catalytic amount of iodine, from easily available starting materials, 2-hydroxychalcone derivatives. Indole, substituted indoles and 7-azaindole are suitable for this transformation. The possible domino Michael addition-intramolecular cyclization reaction mechanism is proposed.
- Yin, Guodong,Fan, Ling,Ren, Tianbing,Zheng, Chunyang,Tao, Qing,Wu, Anxin,She, Nengfang
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p. 8877 - 8883
(2013/01/15)
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- Synthesis and antibacterial activity of some heterocyclic chalcone analogues alone and in combination with antibiotics
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A series of simple heterocyclic chalcone analogues have been synthesized by Claisen Schmidt condensation reactions between substituted benzaldehydes and heteroaryl methyl ketones and evaluated for their antibacterial activity. The structures of the synthe
- Tran, Thanh-Dao,Nguyen, Thi-Thao-Nhu,Do, Tuong-Ha,Huynh, Thi-Ngoc-Phuong,Tran, Cat-Dong,Thai, Khac-Minh
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experimental part
p. 6684 - 6696
(2012/08/28)
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