Ultrasound assisted synthesis of 4-(1H-indol-3-yl)thieno[2,3-d]pyrimidine derivatives via AcOH mediated C-C bond forming reaction

被引：4

作者：

Adapa, Sowmy ^{[1
]}

Kodali, Unati Sai ^{[2
]}

Taneja, Amit Kumar ^{[3
]}

Bandaru, Vinu ^{[4
]}

Mandava, Bhuvan Tej ^{[5
]}

Balakrishna, Bhagavatula ^{[6
]}

Mandava, Bhagya Tej ^{[7
]}

Panigrahi, Naresh ^{[1
]}

Rao, Mandava Venkata Basaveswara ^{[8
]}

Pal, Manojit ^{[9
]}

机构：

[1] GITAM, GITAM Sch Pharm, Visakhapatnam 530045, Andhra Pradesh, India

[2] NTR Univ Hlth Sci, Dr Pinnamaneni Siddhartha Inst Med Sci & Res Fdn, Dept Internal Med, Vijayawada, Andhra Pradesh, India

[3] Chaudhary Charan Singh Univ, Dept Chem, Meerut, India

[4] Dr BR Ambedkar Univ, Dept Organ Chem, Srikakulam 532410, Andhra Pradesh, India

[5] Sacred Heart Univ, Dept Healthcare Informat, 5151 Pk Ave, Fair Fields, CT 06825 USA

[6] TCG Life Sci Pvt Ltd, Kolkata 700091, India

[7] NRI Acad Med Sci, Dept MBBS, Guntur 522503, Andhra Pradesh, India

[8] Krishna Univ, Dept Chem, Machilipatnam, Andhra Pradesh, India

[9] Univ Hyderabad Campus, Dr Reddys Inst Life Sci, Hyderabad 500 046, India

来源：

TETRAHEDRON LETTERS | 2023年 / 131卷

关键词：

Thieno[23-d]pyrimidine; Ultrasound; AcOH; TNF-alpha; NECROSIS-FACTOR-ALPHA; TNF-ALPHA;

D O I：

10.1016/j.tetlet.2023.154784

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A sonochemical approach for the synthesis of 4-(1H-indol-3-yl)thieno[2,3-d]pyrimidine derivatives has been accomplished via the heteroarylation of 4-chloro thieno[2,3-d]pyrimidines with a range of indoles. The reaction was performed using AcOH as a promoter as well as solvent to give the corresponding products in good to acceptable yields. This metal free method proceeded via the C-C bond forming reaction and offers advantages such as simple conditions, shorter duration and the use of eco-friendly energy. In addition to its drawbacks, the usefulness of the methodology is presented and exemplified by the medicinal value of the compounds synthesized. The compound 3i and 3j showed good inhibition of TNF-alpha in vitro and were identified as the initial hit molecules.

引用

页数：5

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