Recyclable CuO nanoparticles-catalyzed synthesis of novel-2,5-disubstituted 1,3,4-oxadiazoles as antiproliferative, antibacterial, and antifungal agents

被引：13

作者：

Murty, M. S. R. ^{[1
]}

Penthala, Raju ^{[1
]}

Buddana, Sudheer Kumar ^{[2
]}

Prakasham, R. S. ^{[2
]}

Das, Pompi ^{[3
]}

Polepalli, Sowjanya ^{[3
]}

Jain, N. ^{[3
]}

Bojja, Sreedhar ^{[4
]}

机构：

[1] Indian Inst Chem Technol, Med Chem & Pharmacol Div, Discovery Lab, Hyderabad 500007, Andhra Pradesh, India

[2] Indian Inst Chem Technol, Bioengn & Environm Ctr, Hyderabad 500007, Andhra Pradesh, India

[3] Indian Inst Chem Technol, Ctr Chem Biol, Hyderabad 500007, Andhra Pradesh, India

[4] Indian Inst Chem Technol, Inorgan & Phys Chem Div, Hyderabad 500007, Andhra Pradesh, India

来源：

MEDICINAL CHEMISTRY RESEARCH | 2014年 / 23卷 / 10期

关键词：

1,3,4-Oxadiazoles; CuO nanoparticles; Antiproliferative; Antibacterial; Antifungal activity; BIOLOGICAL EVALUATION; DERIVATIVES; ANTICONVULSANT; FORMAMIDES; ARYLATION; OXIDATION; ANALOGS; DESIGN; POTENT; ACIDS;

D O I：

10.1007/s00044-014-1025-x

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of new 2,5-disubstituted 1,3,4-oxadiazoles have been conveniently synthesized through an oxidative C-O coupling by direct C-H bond activation of N-aroyl-N-arylidinehydrazines using a catalytic quantity of CuO nanoparticles. Twenty compounds have been synthesized in good to excellent yields (75-90 %). All the synthesized compounds were evaluated for their in vitro antiproliferative, antibacterial, and antifungal activity. Compounds 8d and 10d are more promising antiproliferative agents with IC50 value of 3.66 and 3.89 A mu M in MCF-7 cell line, and compounds 8a and 10a were showed more potent antifungal activity than standard drug.

引用

页码：4579 / 4594

页数：16

共 39 条

[21] Hypervalent iodine(III) mediated synthesis of novel unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles as antibacterial and antifungal agents [J].

Prakash, Om ;

Kumar, Manoj ;

Kumar, Rajesh ;

Sharma, Chetan ;

Aneja, K. R. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (09) :4252-4257

[22] Design, synthesis and biological evaluation of a novel series of 1,3,4-oxadiazole bearing N-methyl-4-(trifluoromethyl)phenyl pyrazole moiety as cytotoxic agents [J].

Puthiyapurayil, Pushpan ;

Poojary, Boja ;

Chikkanna, Chandrashekhar ;

Buridipad, Sunil Kumar .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 53 :203-210

[23] Design and Synthesis of Resveratrol-Based Nitrovinylstilbenes as Antimitotic Agents [J].

Reddy, M. Amarnath ;

Jain, Nishant ;

Yada, Deepthi ;

Kishore, Chandan ;

Reddy, Vangala Janakiram ;

Reddy, P. Surendra ;

Addlagatta, Anthony ;

Kalivendi, Shasi V. ;

Sreedhar, Bojja .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (19) :6751-6760

[24] Microwave assisted syntheses of 2,5-disubstituted 1,3,4-oxadiazoles [J].

Rostamizadeh, S ;

Housaini, SAG .

TETRAHEDRON LETTERS, 2004, 45 (47) :8753-8756

[25] An "on-water" exploration of CuO nanoparticle catalysed synthesis of 2-aminobenzothiazoles [J].

Rout, Saroj Kumar ;

Guin, Srimanta ;

Nath, Jayashree ;

Patel, Bhisma K. .

GREEN CHEMISTRY, 2012, 14 (09) :2491-2498

[26] CuO nanoparticles supported on α-Fe2O3-modified CNTs: a magnetically separable catalyst for oxidative C-O coupling of formamides with 1,3-dicarbonyl compounds [J].

Saberi, Dariush ;

Heydari, Akbar .

TETRAHEDRON LETTERS, 2013, 54 (32) :4178-4180

[27] Synthesis and quantitative structure-activity relationships of new 2,5-disubstituted-1,3,4-oxadiazoles [J].

Shi, W ;

Qian, XH ;

Zhang, R ;

Song, GH .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2001, 49 (01) :124-130

[28] SYNTHESIS OF 5-ARYL-2-OXAZOLEPROPIONIC ACIDS AND ANALOGS . ANTIINFLAMMATORY AGENTS [J].

SHORT, FW ;

LONG, LM .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1969, 6 (05) :707-&

[29] Electrosynthesis and screening of novel 1,3,4-oxadiazoles as potent and selective antifungal agents [J].

Singh, Sushma ;

Sharma, Laxmi Kant ;

Saraswat, Apoorv ;

Siddiqui, Ibadur R. ;

Kehri, Harbans K. ;

Singh, Rana K. Pal .

RSC ADVANCES, 2013, 3 (13) :4237-4245

[30] Transition Metal-Catalyzed Formation of N-Heterocycles via Aryl- or Vinyl C-H Bond Amination [J].

Stokes, Benjamin J. ;

Driver, Tom G. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (22) :4071-4088

← 1 2 3 4 →