Facial synthesis of novel 3-(2-methylbenzofuran-3-yl)-5-((4-(phenoxymethyl)-1H-1,2,3-triazole-1-yl)methyl)-1,2,4-oxadiazole derivatives

被引：3

作者：

Anterbedy, Jagram ^{[1
]}

Mokenapelli, Sudhakar ^{[1
]}

Thalari, Gangadhar ^{[1
]}

机构：

[1] Osmania Univ, Nat Prod Lab, Dept Chem, Univ Coll Sci, Hyderabad 500007, Telangana, India

来源：

SYNTHETIC COMMUNICATIONS | 2021年 / 51卷 / 09期

关键词：

Benzofuran; click reaction; 1; 3-dipolar cycloaddition; 2; 4-oxadiazole; 3-triazole;

D O I：

10.1080/00397911.2021.1884881

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and practical methodology was developed for rapid and green synthesis of novel benzofuran-1,2,4-oxadiazole-1,2,3-triazole hybrids (6a-n) from 5-(chloromethyl)-3-(2-methylbenzofuran-3-yl)-1,2,4-oxadiazoles (4a-b) by in situ generation of 5-(azidomethyl)-3-(2-methylbenzofuran-3-yl)-1,2,4-oxadiazoles followed by 1,3-dipolar cycloaddition with substituted-1-(prop-2-yn-1-yloxy)benzenes (5a-g) through Click reaction under mild reaction conditions with good to excellent yields (70-86%).

引用

页码：1417 / 1424

页数：8

共 50 条

[1] Structure-activity relationship (SAR) study and design strategies of nitrogen-containing heterocyclic moieties for their anticancer activities [J].

Akhtar, Jawaid ;

Khan, Ahsan Ahmed ;

Ali, Zulphikar ;

Haider, Rafi ;

Yar, M. Shahar .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 125 :143-189

[2] Synthesis, antimicrobial activity, pharmacophore analysis of some new 2-(substitutedphenyl/benzyl)-5-[(2-benzofuryl)carboxamido]benzoxazoles [J].

Alper-Hayta, Sabiha ;

Arisoy, Mustafa ;

Temiz-Arpaci, Oezlem ;

Yildiz, Ilkay ;

Aki, Esin ;

Ozkan, Semiha ;

Kaynak, Fatma .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (11) :2568-2578

[3] OXADIAZOLES AS BIOISOSTERIC TRANSFORMATIONS OF CARBOXYLIC FUNCTIONALITIES .1. [J].

ANDERSEN, KE ;

JORGENSEN, AS ;

BRAESTRUP, C .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1994, 29 (05) :393-399

[4] Peptidomimetics via copper-catalyzed azide-alkyne cycloadditions [J].

Angell, Yu L. ;

Burgess, Kevin .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (10) :1674-1689

[5] Synthesis and antiproliferative activity of benzofuran-based analogs of cercosporamide against non-small cell lung cancer cell lines [J].

Bazin, Marc-Antoine ;

Bodero, Lizeth ;

Tomasoni, Christophe ;

Rousseau, Benedicte ;

Roussakis, Christos ;

Marchand, Pascal .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 69 :823-832

[6] The 1,2,3-triazole ring as a bioisostere in medicinal chemistry [J].

Bonandi, Elisa ;

Christodoulou, Michael S. ;

Fumagalli, Gaia ;

Perdicchia, Dario ;

Rastelli, Giulio ;

Passarella, Daniele .

DRUG DISCOVERY TODAY, 2017, 22 (10) :1572-1581

[7] Triazole derivatives and their antiplasmodial and antimalarial activities [J].

Chu, Xue-Mei ;

Wang, Cong ;

Wang, Wen-Ling ;

Liang, Li-Li ;

Liu, Wen ;

Gong, Kai-Kai ;

Sun, Kun-Lai .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2019, 166 :206-223

[8] 1,2,4-OXADIAZOLES [J].

CLAPP, LB .

ADVANCES IN HETEROCYCLIC CHEMISTRY, 1976, 20 :65-116

[9] Synthesis and hypoglycemic evaluation of substituted pyrazole-4-carboxylic acids [J].

Cottineau, B ;

Toto, P ;

Marot, C ;

Pipaud, A ;

Chenault, J .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (16) :2105-2108

[10] From Oxiranes to Oligomers: Architectures of US FDA Approved Pharmaceuticals Containing Oxygen Heterocycles [J].

Delost, Michael D. ;

Smith, David T. ;

Anderson, Benton J. ;

Njardarson, Jon T. .

JOURNAL OF MEDICINAL CHEMISTRY, 2018, 61 (24) :10996-11020

← 1 2 3 4 5 →