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.
A series of novel 4H-benzo[h]chromenes4,6-11,13,14; 7H-benzo[h]chromeno[2,3-d]pyrimidines15-18,20, and 14H-benzo[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives19a-e,24was 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.
Chemistry Department, Faculty of Science, Taibah University, 30002 Al-Madinah Al-Munawarah, Saudi Arabia. rawdao@yahoo.com.
Rawda M
RM
Okasha
Chemistry Department, Faculty of Science, Taibah University, 30002 Al-Madinah Al-Munawarah, Saudi Arabia. rawdao@yahoo.com.
Fawzia F
FF
Alblewi
Chemistry Department, Faculty of Science, Taibah University, 30002 Al-Madinah Al-Munawarah, Saudi Arabia. ffs_chem334@hotmail.com.
Tarek H
TH
Afifi
Chemistry Department, Faculty of Science, Taibah University, 30002 Al-Madinah Al-Munawarah, Saudi Arabia. afifith@yahoo.com.
Arshi
A
Naqvi
Chemistry Department, Faculty of Scinece, King Khalid University, P.O. Box 9004, 61413 Abha, Saudi Arabia. amfouda@hotmail.com.
Ahmed M
AM
Fouda
Chemistry Department, Faculty of Scinece, King Khalid University, P.O. Box 9004, 61413 Abha, Saudi Arabia. nood-mansyaa@hotmail.com.
Al-Anood M
AM
Al-Dies
Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City 11884, Cairo, Egypt. elagrody_am@yahoo.com.
Ahmed M
AM
El-Agrody
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival; D004354:Drug Screening Assays, Antitumor; D045325:HCT116 Cells; D056945:Hep G2 Cells; D000072471:Heterocyclic Compounds, Fused-Ring / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D061986:MCF-7 Cells; D015394:Molecular Structure; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D001578:Benzopyrans; D000072471:Heterocyclic Compounds, Fused-Ring
SAR study; benzochromene; benzochromenopyrimidine; benzochromenotriazolopyrimidine antitumor activities