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

共 50 条

[1] Synthesis of some new functionalized pyrano[2,3-c]pyrazoles and pyrazolo[4′,3′:5,6] pyrano[2,3-d]pyrimidines bearing a chromone ring as antioxidant agents
Ali, Tarik E.
Bakhotmah, Dina A.
Assiri, Mohammed A.
SYNTHETIC COMMUNICATIONS, 2020, 50 (21) : 3314 - 3325
[2] Synthesis of Some Novel 2-{Pyrano[2,3-c]Pyrazoles-4-Ylidene}Malononitrile Fused with Pyrazole, Pyridine, Pyrimidine, Diazepine, Chromone, Pyrano[2,3-c]Pyrazole and Pyrano[2,3-d]Pyrimidine Systems as Anticancer Agents
Bakhotmah, Dina A.
Ali, Tarik E.
Assiri, Mohammed A.
Yahia, Ibrahim S.
POLYCYCLIC AROMATIC COMPOUNDS, 2022, 42 (05) : 2136 - 2150
[3] Ultrasonic-Promoted One-Pot Synthesis of 4H-chromenes, pyrano[2,3-d]pyrimidines, and 4H-pyrano[2,3-c]pyrazoles
Azarifar, Davood
Nejat-Yami, Razieh
Sameri, Fatemeh
Akrami, Zahra
LETTERS IN ORGANIC CHEMISTRY, 2012, 9 (06) : 435 - 439
[4] Ultrasound Assisted One-Pot Three-Component Reaction for Synthesis of Novel Functionalized 4-Thioxo-Pyrano[2,3-c]Pyrazoles, 5-Thioxo-Pyrano[2,3-d]Pyrimidines and 5-Thioxo-Pyrido[2,3-d]Pyrimidines Catalyzed by Triethylamine
Ali, Tarik E.
Assiri, Mohammed A.
POLYCYCLIC AROMATIC COMPOUNDS, 2023, 43 (07) : 5860 - 5868
[5] Using magnetized water as a solvent for a green, catalyst-free, and efficient protocol for the synthesis of pyrano[2,3-c]pyrazoles and pyrano[4′,3′:5,6]pyrazolo [2,3-d]pyrimidines
Mohammad Bakherad
Ali Keivanloo
Mostafa Gholizadeh
Rahele Doosti
Mohaddese Javanmardi
Research on Chemical Intermediates, 2017, 43 : 1013 - 1029
[6] Using magnetized water as a solvent for a green, catalyst-free, and efficient protocol for the synthesis of pyrano[2,3-c]pyrazoles and pyrano[4′,3′: 5,6]pyrazolo [2,3-d]pyrimidines
Bakherad, Mohammad
Keivanloo, Ali
Gholizadeh, Mostafa
Doosti, Rahele
Javanmardi, Mohaddese
RESEARCH ON CHEMICAL INTERMEDIATES, 2017, 43 (02) : 1013 - 1029
[7] An Efficient and Facile Synthesis of 5-(Thiophene-2-carbonyl)-6-(trifluoromethyl)-tetrahydro-pyrimidin-2(1H)-one and 6-(Thiophen-2-yl)-4,5-dihydropyrimidin-2(1H)-one from Same Substrates Under Different Conditions
Rong Liang-Ce
Zha, Yunyun
Xia, Sheng
Ji, Linlin
Zhang, Jing
Cai, Peijun
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (01) : 56 - 63
[8] One-Pot Three-Component Synthesis of a Series of 2-Amino-4-(4-oxo-4H-chromen-3-yl)-5-(2,2,2-trifluoroacetyl)-6-(trifluoromethyl)-4H-pyrans and 2-Amino-4-(4-oxo-4H-chromen-3-yl)-5-(thiophene-2-carbonyl)-6-(trifluoromethyl)-4H-pyrans as Promising Anticancer Agents
T. E. Ali
M. A. Assiri
A. A. Shati
M. Y. Alfaifi
S. E. I. Elbehairi
Russian Journal of Organic Chemistry, 2022, 58 : 584 - 591
[9] Studies on 6-[(dimethylamino)methylene]aminouracils: A facile one-pot synthesis of novel pyrido[2,3-d]pyrimidines
Saikia, P
Thakur, AJ
Prajapati, D
Sandhu, JS
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2002, 41 (04): : 804 - 807
[10] One-Pot Three-Component Synthesis of a Series of 2-Amino-4-(4-oxo-4H-chromen-3-yl)-5-(2,2,2-trifluoroacetyl)-6-(trifluoromethyl)-4H-pyrans and 2-Amino-4-(4-oxo-4H-chromen-3-yl)-5-(thiophene-2-carbonyl)-6-(trifluoromethyl)-4H-pyrans as Promising Anticancer Agents
Ali, T. E.
Assiri, M. A.
Shati, A. A.
Alfaifi, M. Y.
Elbehairi, S. E., I
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 58 (04) : 584 - 591

← 1 2 3 4 5 →