Ultrasound Assisted Synthesis of 2-alkynyl Pyrazolo[1,5-a] pyrimidines as Potential Anti-cancer Agents

被引：4

作者：

Bharath, Yarlagadda ^{[1
]}

Rao, Mandava V. Basaveswara ^{[2
]}

Pal, Manojit ^{[3
]}

机构：

[1] Univ VFSTR Univ, Vignans Fdn Sci Technol & Res, Chem Div, Dept Sci & Humanities, Guntur 522213, Andhra Prades, India

[2] Krishna Univ, Dept Chem, Machilipatnam, Andhra Prades, India

[3] Dr Reddys Inst Life Sci, Univ Hyderabad Campus, Hyderabad 500046, Andhra Prades, India

来源：

LETTERS IN DRUG DESIGN & DISCOVERY | 2017年 / 14卷 / 10期

关键词：

Pyrazolo[1,5-a] pyrimidine; Pd/C; coupling; ultrasound; cancer; anticancer agents; ACETYLENES; ANALOGS;

D O I：

10.2174/1570180814666170125125654

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Background: The 2-alkynyl pyrazolo[1,5-a] pyrimidine derivatives have been explored as new and potential anti-proliferative agents. Methods: Ultrasound assisted synthesis of these compounds was carried out by using a multi-step method involving the H3PO3 mediated construction of pyrazolo[1,5-a] pyrimidine ring possessing a bromo group at C-2 position followed by Pd/C-Cu catalyzed alkynylation methodology as the key steps. Results and Conclusion: All these compounds showed selective growth inhibition of cancer cell lines when tested against MDA-MB 231 and K562 cell lines along with non-cancerous HEK293 cells.

引用

页码：1206 / 1214

页数：9

共 23 条

[1]

[Anonymous], 2018, ANTI-CANCER DRUG, DOI [DOI 10.3322/caac.20115, DOI 10.1097/CAD.0000000000000617]

[2]

Beslija S, 2003, BREAST CANCER RES TR, V81, pS25

[3] Resourceful synthesis of pyrazolo[1,5-a]pyrimidines under ultrasound irradiation [J].

Buriol, Lilian ;

Muenchen, Taiana S. ;

Frizzo, Clarissa P. ;

Marzari, Mara R. B. ;

Zanatta, Nib O. ;

Bonacorso, Helio G. ;

Martins, Marcos A. P. .

ULTRASONICS SONOCHEMISTRY, 2013, 20 (05) :1139-1143

[4] Recent advances in Sonogashira reactions [J].

Chinchilla, Rafael ;

Najera, Carmen .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5084-5121

[5] Novel Pyrazolo[1,5-a]pyrimidines as Translocator Protein 18 kDa (TSPO) Ligands: Synthesis, in Vitro Biological Evaluation, [18F]-Labeling, and in Vivo Neuroinflammation PET Images [J].

Damont, Annelaure ;

Medran-Navarrete, Vincent ;

Cacheux, Fanny ;

Kuhnast, Bertrand ;

Pottier, Geraldine ;

Bemards, Nicholas ;

Marguet, Frank ;

Puech, Frederic ;

Boisgard, Raphael ;

Dolle, Frederic .

JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (18) :7449-7464

[6] 2-Pyrones possessing antimicrobial and cytotoxic activities [J].

Fairlamb, IJS ;

Marrison, LR ;

Dickinson, JM ;

Lu, FJ ;

Schmidt, JP .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (15) :4285-4299

[7] Covalent analogues of DNA base-pairs and triplets. Part 2. Synthesis and cytostatic activity of bis(purin-6-yl) acetylenes, -diacetylenes and related compounds [J].

Hocek, M ;

Votruba, I .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (07) :1055-1058

[8] A facile, regioselective synthesis of pyrazolo[1, 5-a]pyrimidine analogs in the presence of KHSO4 in aqueous media assisted by ultrasound and their anti-inflammatory and anti-cancer activities [J].

Kaping, Shunan ;

Kalita, Utpalparna ;

Sunn, Melboureen ;

Singha, Laishram Indira ;

Vishwakarma, Jai Narain .

MONATSHEFTE FUR CHEMIE, 2016, 147 (07) :1257-1276

[9] Synthesis and biological evaluations of pyrazolo[3,4-d] pyrimidines as cyclin-dependent kinase 2 inhibitors [J].

Kim, DC ;

Lee, YR ;

Yang, BS ;

Shin, KJ ;

Kim, DJ ;

Chung, BY ;

Yoo, KH .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2003, 38 (05) :525-532

[10] Synthesis and biological activity of 8-azapurine and pyrazolo[4,3-d]pyrimidine analogues of myoseverin [J].

Krystof, Vladimir ;

Moravcova, Daniela ;

Paprskarova, Martina ;

Barbier, Pascale ;

Peyrot, Vincent ;

Hlobilkova, Alice ;

Havlicek, Libor ;

Strnad, Miroslav .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2006, 41 (12) :1405-1411

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