Design of New Benzo[h]chromene Derivatives: Antitumor Activities and Structure-Activity Relationships of the 2,3-Positions and Fused Rings at the 2,3-Positions

• Published in: Molecules (Basel, Switzerland) Vol. 22; no. 3; p. 479
• Main Authors: Okasha, Rawda M, Alblewi, Fawzia F, Afifi, Tarek H, Naqvi, Arshi, Fouda, Ahmed M, Al-Dies, Al-Anood M, El-Agrody, Ahmed M
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 18-03-2017; MDPI
• Subjects: Analgesics; Anticoagulants; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Antitumor activity; Apoptosis; benzochromene; benzochromenopyrimidine; benzochromenotriazolopyrimidine antitumor activities; Benzopyrans - chemical synthesis; Benzopyrans - chemistry; Benzopyrans - pharmacology; Blood platelets; Breast cancer; Breast carcinoma; Cancer; Cell Proliferation - drug effects; Cell Survival; Clinical trials; Colchicine; Colon; Cytotoxicity; Doxorubicin; Drug Screening Assays, Antitumor; Drugs; Ethanol; HCT116 Cells; Hep G2 Cells; Hepatocellular carcinoma; Heterocyclic Compounds, Fused-Ring - chemical synthesis; Heterocyclic Compounds, Fused-Ring - chemistry; Heterocyclic Compounds, Fused-Ring - pharmacology; Humans; MCF-7 Cells; Molecular Structure; Proteins; Pyrimidines; SAR study; Solvents; Structure-Activity Relationship; Structure-activity relationships; Tumor cell lines; Tumors; Ultrasonic imaging; Vinblastine; benzochromenotriazolopyrimidine antitumor activities; benzochromene; benzochromenopyrimidine; SAR study
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules22030479

A series of novel 4
-benzo[
]chromenes
,
-
,
,
; 7
-benzo[
]chromeno[2,3-
]pyrimidines
-
,
, and 14
-benzo[
]chromeno[3,2-
][1,2,4]triazolo[1,5-
]pyrimidine derivatives
-
,
was prepared. The structures of the synthesized compounds were characterized on the basis of their spectral data. Some of the target compounds were examined for their antiproliferative activity against three cell lines; breast carcinoma (MCF-7), human colon carcinoma (HCT-116) and hepatocellular carcinoma (HepG-2). The cytotoxic behavior has been tested using MTT assay and the inhibitory activity was referenced to three standard anticancer drugs: vinblastine, colchicine and doxorubicin. The bioassays demonstrated that some of the new compounds exerted remarkable inhibitory effects as compared to the standard drugs on the growth of the three tested human tumor cell lines. The structure-activity relationships (SAR) study highlights that the antitumor activity of the target compounds was significantly affected by the lipophilicity of the substituent at 2- or 3- and fused rings at the 2,3-positions.