An effective green one-pot synthesis of some novel 5-(thiophene-2-carbonyl)-6-(trifluoromethyl)pyrano[2,3-c]pyrazoles and 6-(thiophene-2-carbonyl)-7-(trifluoromethyl)pyrano[2,3-d]pyrimidines bearing chromone ring as anticancer agents

被引：12

作者：

Ali, Tarik E. ^{[1
,2
]}

Assiri, Mohammed A. ^{[1
]}

Alzahrani, Abdullah Y. ^{[3
]}

Salem, Mohamed A. ^{[3
,4
]}

Shati, Ali A. ^{[5
]}

Alfaifi, Mohammad Y. ^{[5
]}

Elbehairi, Serag Eldin, I ^{[5
,6
]}

机构：

[1] King Khalid Univ, Fac Sci, Dept Chem, Abha, Saudi Arabia

[2] Ain Shams Univ, Fac Educ, Dept Chem, Cairo, Egypt

[3] King Khalid Univ, Fac Sci & Arts, Dept Chem, Mohail Assir, Saudi Arabia

[4] Al Azhar Univ, Fac Sci, Dept Chem, Nasr City, Egypt

[5] King Khalid Univ, Fac Sci, Dept Biol, Abha, Saudi Arabia

[6] Egyptian Org Biol Prod & Vaccines, Cell Culture Lab, Agouza, Egypt

来源：

SYNTHETIC COMMUNICATIONS | 2021年 / 51卷 / 21期

关键词：

Chromone; multicomponent reactions; pyranopyrimidines; 2-thenoyltrifluoroacetone; thiophene pyranopyrazole; DESIGN; PYRANOPYRAZOLES; DERIVATIVES; EFFICIENT; REAGENTS;

D O I：

10.1080/00397911.2021.1966804

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An effective green one-pot and catalyst-free synthesis of a series of novel 5-(thiophene-2-carbonyl)-6-(trifluoromethyl)pyrano[2,3-c]pyrazoles and 6-(thiophene-2-carbonyl)-7-(trifluoromethyl)pyrano[2,3-d]pyrimidines bearing chromone ring was achieved. The method depended on a one-pot three-component reaction of readily available starting materials 4-oxo-4H-chromene-3-carboxaldehyde, 2-thenoyltrifluoroacetone, and cyclic active methylene compounds in water as solvent. The targeted compounds were assessed for their in vitro anticancer activity against mammary gland breast cancer cell line (MCF-7), liver cancer (HepG-2), and human colon cancer (HCT-116) by using sulphorhodamine B assay (SRB) method, while doxorubicin, was utilized as standard reference drug. Compounds 4a, 4c, and 6b exhibited excellent anticancer activity versus all cancer cell lines with IC50 values ranging from 1.7 to 9.9 mu g/mL.

引用

页码：3267 / 3276

页数：10

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