Microwave-assisted synthesis of novel 1,2,3-triazole derivatives and their antimicrobial activity

被引：52

作者：

Ashok, D. ^{[1
]}

Gandhi, D. Mohan ^{[1
]}

Srinivas, G. ^{[1
]}

Kumar, A. Vikas ^{[1
]}

机构：

[1] Osmania Univ, Dept Chem, Hyderabad 500007, Andhra Pradesh, India

来源：

MEDICINAL CHEMISTRY RESEARCH | 2014年 / 23卷 / 06期

关键词：

Microwave irradiation; Click chemistry; 1,2,3-Triazoles; Antimicrobial activity; ANTIHYPERTENSIVE ACTIVITY; OXYGENATED CHALCONES;

D O I：

10.1007/s00044-013-0880-1

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

An environmentally benign and economic synthesis of 1-[7-(1-benzyl-1H-[1,2,3]triazol-4-ylmethoxy)-2,2-dimethyl-chroman-6-yl]-3-aryl-2-propen-1-ones and 1-[5-(1-benzyl-1H-[1,2,3]triazol-4-ylmethoxy)-2,2-dimethyl-chroman-6-yl]-3-aryl-propen-1-ones is described. The procedure takes place by the 1,3-dipolar cycloaddition (''click-reaction'') between azides and alkynes catalysed by copper (I) salts. The simplicity of this reaction and the ease of formation and purification of the resulting products have opened new opportunities in generating vast arrays of compounds with biological potential. The structures of the synthesized compounds have been established on the basis of physical and spectral data. All the synthesized compounds were tested in vitro for their antibacterial and antifungal activities. Compounds 8a (R-1=H, R-2=H, R-3=H), 8b (R-1=H, R-2=CH3, R-3=H), 8d (R-1=OCH3, R-2=OCH3, R-3=H), 8e (R-1=OCH3, R-2=OCH3, R-3=OCH3), 13a (R-1=H, R-2=H, R-3=H), 13d (R-1=OCH3, R-2=OCH3, R-3=H) and 13e (R-1=OCH3, R-2=OCH3, R-3=OCH3) showed significant antimicrobial properties.

引用

页码：3005 / 3018

页数：14

共 19 条

[11] Amberlyst 15 catalyzed prenylation of phenols: One-step synthesis of benzopyrans [J].

Kalena, GP ;

Jain, A ;

Banerji, A .

MOLECULES, 1997, 2 (07) :100-105

[12] Synthesis, antioxidant activities and urease inhibition of some new 1,2,4-triazole and 1,3,4-thiadiazole derivatives [J].

Khan, Imtiaz ;

Ali, Sajid ;

Hameed, Shahid ;

Rama, Nasim Hasan ;

Hussain, Muhammad Tahir ;

Wadood, Abdul ;

Uddin, Reaz ;

Ul-Haq, Zaheer ;

Khan, Ajmal ;

Ali, Sajjad ;

Choudhary, M. Iqbal .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (11) :5200-5207

[13] Synthesis and anti-HIV activity of new modified 1,2,3-triazole acyclonucleosides [J].

Lazrek, HB ;

Taourirte, M ;

Oulih, T ;

Barascut, JL ;

Imbach, JL ;

Pannecouque, C ;

Witrouw, M ;

De Clercq, E .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2001, 20 (12) :1949-1960

[14] Synthetic and biological activity evaluation studies on novel 1,3-diarylpropenones [J].

Mukherjee, S ;

Kumar, W ;

Prasad, AK ;

Raj, HG ;

Bracke, ME ;

Olsen, CE ;

Jain, SC ;

Parmar, VS .

BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (02) :337-345

[15] Oxygenated chalcones and bischalcones as potential antimalarial agents [J].

Ram, VJ ;

Saxena, AS ;

Srivastava, S ;

Chandra, S .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (19) :2159-2161

[16]

RAY S, 1976, J MED CHEM, V19, P276, DOI 10.1021/jm00224a014

[17] Leuconostoc mesenteroides subsp mesenteroides FR52 synthesizes two distinct bacteriocins [J].

RevolJunelles, AM ;

Mathis, R ;

Krier, F ;

Fleury, Y ;

Delfour, A ;

Lefebvre, G .

LETTERS IN APPLIED MICROBIOLOGY, 1996, 23 (02) :120-124

[18] Synthesis and antihyperglycemic activity of chalcone based aryloxypropanolamines [J].

Satyanarayana, M ;

Tiwari, P ;

Tripathi, BK ;

Srivastava, AK ;

Pratap, R .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (05) :883-889

[19] The antileishmanial activity of novel oxygenated chalcones and their mechanism of action [J].

Zhai, L ;

Chen, M ;

Blom, J ;

Theander, TG ;

Christensen, SB ;

Kharazmi, A .

JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 1999, 43 (06) :793-803

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