Azide-alkyne cycloaddition en route to 1H-1,2,3-triazole-tethered 7-chloroquinoline-isatin chimeras: Synthesis and antimalarial evaluation

被引：121

作者：

Raj, Raghu ^{[1
]}

Singh, Pardeep ^{[1
]}

Singh, Parvesh ^{[2
]}

Gut, Jiri ^{[3
]}

Rosenthal, Philip J. ^{[3
]}

Kumar, Vipan ^{[1
]}

机构：

[1] Guru Nanak Dev Univ, Dept Chem, Amritsar 143005, Punjab, India

[2] Durban Univ Technol, Dept Chem, ZA-4000 Durban, South Africa

[3] Univ Calif San Francisco, Dept Med, San Francisco, CA USA

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2013年 / 62卷

关键词：

7-Chloroquinoline-isatin conjugates; 1H-1,2,3-triazole; Antimalarial evaluation; Structure activity relationship; IN-VITRO; ANTI-HIV; HYBRID MOLECULES; ISATIN; DESIGN; ARTEMISININ; DRUG; DERIVATIVES; RESISTANCE; CHEMISTRY;

D O I：

10.1016/j.ejmech.2013.01.032

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

We describe the synthesis and antimalarial activities of 1H-1,2,3-triazole tethered 7-chloroquinoline-isatin hybrids. Activity against cultured parasites was dependent on the C-5 substituent of the isatin ring as well as the alkyl chain length between the isatin and 7-chloroquinoline moieties. Compound 8h, with an optimum alkyl chain length (n = 3) and a chloro substituent at the C-5 position of the isatin ring, displayed the best activity among the test compounds, with IC50 value of 1.21 mu M against cultured W2-strain Plasmodium falciparum. (C) 2013 Elsevier Masson SAS. All rights reserved.

引用

页码：590 / 596

页数：7

共 50 条

[31] Advances in the Synthesis of Fused 1,2,3-Triazoles via a MCR-Intramolecular Azide-Alkyne Cycloaddition Approach
Rahul, P.
Thomas, Joice
Dehaen, Wim
John, Jubi
MOLECULES, 2023, 28 (01):
[32] Copper(II) complexes supported by click generated mixed NN, NO, and NS 1,2,3-triazole based ligands and their catalytic activity in azide-alkyne cycloaddition
Mendoza-Espinosa, Daniel
Enrique Negron-Silva, Guillermo
Angeles-Beltran, Deyanira
Alvarez-Hernandez, Alejandro
Suarez-Castillo, Oscar R.
Santillan, Rosa
DALTON TRANSACTIONS, 2014, 43 (19) : 7069 - 7077
[33] Silica immobilized copper N-heterocyclic carbene: An effective route to 1,2,3-triazoles via azide-alkyne cycloaddition and multicomponent click reaction
Garg, Anirban
Borah, Nobomi
Sultana, Jasmin
Kulshrestha, Akshay
Kumar, Arvind
Sarma, Diganta
APPLIED ORGANOMETALLIC CHEMISTRY, 2021, 35 (09)
[34] Copper(I)-Catalyzed Azide-Alkyne Cycloaddition Microwave-Assisted: Preparation of 7-(4-Substituted-1H-1,2,3-Triazol-1-yl)-Fluoroquinolones
Hernandez-Lopez, Hiram
Leyva-Ramos, Socorro
Delia Moncada-Martinez, Rosa
Adrian Lopez, Jesus
Cardoso-Ortiz, Jaime
CHEMISTRYSELECT, 2019, 4 (40): : 11899 - 11902
[35] Efficient synthesis of novel A-ring-substituted 1,2,3-triazolylcholestane derivatives via catalytic azide-alkyne cycloaddition
Kadar, Zalan
Frank, Eva
Schneider, Gyula
Molnar, Judit
Zupko, Istvan
Koti, Janos
Schoenecker, Bruno
Woelfling, Janos
ARKIVOC, 2012, : 279 - 296
[36] Design, synthesis, anti-proliferative evaluation and docking studies of 1H-1,2,3-triazole tethered ospemifene-isatin conjugates as selective estrogen receptor modulators
Kumar, Sumit
Gu, Liang
Palma, Gabriella
Kaur, Mandeep
Singh-Pillay, Ashona
Singh, Parvesh
Kumar, Vipan
NEW JOURNAL OF CHEMISTRY, 2018, 42 (05) : 3703 - 3713
[37] Synthesis and in vitro evaluation of novel substituted isatin-propylene-1H-1,2,3-triazole-4-methylene-moxifloxacin hybrids for their anti-mycobacterial activities
Yan, Xinjia
Lv, Zaosheng
Wen, Jing
Zhao, Shijia
Xu, Zhi
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 143 : 899 - 904
[38] Efficient click chemistry towards novel 1H-1,2,3-triazole-tethered 4H-chromene-D-glucose conjugates: Design, synthesis and evaluation of in vitro antibacterial, MRSA and antifungal activities
Nguyen Dinh Thanh
Do Son Hai
Vu Thi Ngoc Bich
Pham Thi Thu Hien
Nguyen Thi Ky Duyen
Nguyen Thi Mai
Tran Thi Dung
Vu Ngoc Toan
Hoang Thi Kim Van
Le Hai Dang
Duong Ngoc Toan
Tran Thi Thanh Van
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2019, 167 : 454 - 471
[39] Synthesis and preliminary in vitro activity of mono- and bis-1H-1,2,3-triazole-tethered β-lactam–isatin conjugates against the human protozoal pathogen Trichomonas vaginalis
Raghu Raj
Vaishali Sharma
Melissa J. Hopper
Neal Patel
Dominique Hall
Lisa A. Wrischnik
Kirkwood M. Land
Vipan Kumar
Medicinal Chemistry Research, 2014, 23 : 3671 - 3680
[40] Environmental Friendly Azide-Alkyne Cycloaddition Reaction of Azides, Alkynes, and Organic Halides or Epoxides in Water: Efficient "Click" Synthesis of 1,2,3-Triazole Derivatives by Cu Catalyst
Liu Jianming
Liu Muwen
Yue Yuanyuan
Yao Meihuan
Zhuo Kelei
CHINESE JOURNAL OF CHEMISTRY, 2012, 30 (03) : 644 - 650

← 1 2 3 4 5 →