Design and the synthesis of 1-heteroaryl-1,2,3-triazoles connected to coumarins via ether linker

被引：5

作者：

Nibin Joy, Muthipeedika ^{[1
]}

Beliaev, Nikolai ^{[2
]}

Beryozkina, Tetyana V. ^{[2
]}

Bakulev, Vasiliy A. ^{[2
]}

机构：

[1] Ural Fed Univ, Inst Chem Technol, Innovat Ctr Chem & Pharmaceut Technol, 19 Mira St, Ekaterinburg 620002, Russia

[2] Ural Fed Univ, TOS Dept, 19 Mira St, Ekaterinburg 620002, Russia

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2020年 / 57卷 / 08期

基金：

俄罗斯科学基金会;

关键词：

HOCKEY-STICK-LIKE; IN-VITRO; CLICK CHEMISTRY; BIOLOGICAL EVALUATION; EFFICIENT SYNTHESIS; MOLECULAR DOCKING; TRIAZOLE HYBRIDS; ANTIMYCOBACTERIAL; DERIVATIVES; AZIDES;

D O I：

10.1002/jhet.4025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper, we report an efficient and versatile methodology for the synthesis of a series of novel heteroaryl-1,2,3-triazoles connected to 4-methylcoumarin (4-methyl-2H-chromen-2-one) via oxymethylene linker. The desired molecules were accessed by both two-step synthesis and the one-pot copper catalyzed cycloaddition reaction of heteroaromatic azides with coumarin containing acetylenes. The developed protocol was found to be facile and effective for preparing a series of novel heteroaryl-1,2,3-triazole-coumarin conjugates in excellent yields. Practical utility of one-pot protocol has been confirmed by the successful gram-scale synthesis of 1,3-Dimethyl-6-(4-[([4-methyl-2-oxo-2H-chromen-7-yl]oxy)methyl]-1H-1,2,3-triazol-1-yl)pyrimidine-2,4(1H,3H)-dione.

引用

页码：3173 / 3185

页数：13

共 62 条

[1] Design, Synthesis and Biological Evaluation of Novel 4-Substituted Coumarin Derivatives as Antitumor Agents [J].

An, Ran ;

Hou, Zhuang ;

Li, Jian-Teng ;

Yu, Hao-Nan ;

Mou, Yan-Hua ;

Guo, Chun .

MOLECULES, 2018, 23 (09)

[2] Biscoumarin-1,2,3-triazole hybrids as novel anti-diabetic agents: Design, synthesis, in vitro α-glucosidase inhibition, kinetic, and docking studies [J].

Asgari, Mohammad Sadegh ;

Mohammadi-Khanaposhtani, Maryam ;

Kiani, Mitra ;

Ranjbar, Parviz Rashidi ;

Zabihi, Ebrahim ;

Pourbagher, Roghayeh ;

Rahimi, Rahmatollah ;

Faramarzi, Mohammad Ali ;

Biglar, Mahmood ;

Larijani, Bagher ;

Mahdavi, Mohammad ;

Hamedifar, Haleh ;

Hajimiri, Mir Hamed .

BIOORGANIC CHEMISTRY, 2019, 92

[3] Dimers of coumarin-1,2,3-triazole hybrids bearing alkyl spacer: Design, microwave-assisted synthesis, molecular docking and evaluation as antimycobacterial and antimicrobial agents [J].

Ashok, Dongamanti ;

Gundu, Srinivas ;

Aamate, Vikas Kumar ;

Devulapally, Mohan Gandhi ;

Bathini, Raju ;

Manga, Vijjulatha .

JOURNAL OF MOLECULAR STRUCTURE, 2018, 1157 :312-321

[4] Triazolbenzo[d]thiazoles: Efficient synthesis and biological evaluation as neuroprotective agents [J].

Avila, Belem ;

Roth, Aaron ;

Streets, Heather ;

Dwyer, Donard S. ;

Kurth, Mark J. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (18) :5976-5978

[5]

Bakulev V.A., 2004, CHEM 1 2 3 THIADIAZO, P241

[6]

BAKULEV VA, 1993, B SOC CHIM BELG, V102, P493

[7] NH-1,2,3-triazoles: synthesis and reactions with electrophilic agents [J].

Bakulev, Vasiliy A. ;

Beryozkina, Tetyana V. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (01) :4-6

[8] A novel appiroach to fused 1,2,4-triazines by intramolecular cyclization of 1,2-diaza-1,3-butadienes bearing allyl(propargyl)sulfanyl and cyclic tert-amino groups [J].

Belskaia, Natala P. ;

Deryabina, Tatyana G. ;

Koksharov, Alexandr V. ;

Kodess, Mikhail I. ;

Dehaen, Wim ;

Lebedev, Albert T. ;

Bakulev, Vasiliy A. .

TETRAHEDRON LETTERS, 2007, 48 (52) :9128-9131

[9] In situ click chemistry generation of cyclooxygenase-2 inhibitors [J].

Bhardwaj, Atul ;

Kaur, Jatinder ;

Wuest, Melinda ;

Wuest, Frank .

NATURE COMMUNICATIONS, 2017, 8

[10] Simple coumarins and analogues in medicinal chemistry: Occurrence, synthesis and biological activity [J].

Borges, F ;

Roleira, F ;

Milhazes, N ;

Santana, L ;

Uriarte, E .

CURRENT MEDICINAL CHEMISTRY, 2005, 12 (08) :887-916

← 1 2 3 4 5 6 7 →