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A series of 1H-benzo[f]chromene moieties (4a–z) were synthesised under Ultrasonic irradiation and confirmed with spectral analyses. Derivative 4i solely possessed an X-ray single crystal. The anti-proliferative efficacy of the desired molecules has been explored against three cancer cells: MCF-7, HCT-116, and HepG-2 with the cytotoxically active derivatives screened against MCF-7/ADR and normal cells HFL-1 and WI-38. Furthermore, compounds 4b–d, 4k, 4n, 4q, and 4w, which possessed good potency against MCF-7/ADR, were tested as permeability glycoprotein (P-glycoprotein [P-gp]) expression inhibitors. The attained data confirmed that 4b–d, 4q, and 4w exhibited strong expression inhibition against the P-gp alongside its cytotoxic effect on MCF-7/ADR. The western blot results and Rho123 accumulation assays showed that compounds 4b–d, 4q, and 4w effectively inhibited the P-gp expression and efflux function. Meanwhile, 4b–d, 4q, and 4w induced apoptosis and accumulation of the treated MCF-7/ADR cells in the G1 phase and 4k and 4n in the S phase of the cell cycle. [ABSTRACT FROM AUTHOR]

In the present study, novel derivatives of 4 H -benzo[ h ]chromene and 7 H -benzo[ h ]chromeno[2,3- d ]pyrimidine were prepared and evaluated for their anti-proliferative activity against three human tumor cell lines breast adenocarcinoma (MCF-7), human colon carcinoma (HCT-116) and hepatocellular carcinoma (HepG-2) in comparison with the standard drugs Doxorubicin, Vinblastine and Colchicine using MTT colorimetric assay. The structures of the target compounds were established on the basis of spectral data. We explored the Structure–Activity Relationship (SAR) of 4 H -benzo[ h ]chromenes with modification at the 2- or 3- and 2, 3-positions. It was found that several compounds showed good antitumor activity against the cell lines MCF-7, HCT-116 and HepG-2 as compared to the standard drugs. The SAR study revealed that the antitumor activity of the synthesized compounds was significantly affected by the lipophilicity (hydrophobic or hydrophilic) of the substituent at 2- or 3- and 2, 3-positions. [ABSTRACT FROM AUTHOR]

Three new series of chromene molecules have been synthesized in order to explore their antimicrobial activity. The series encompass 2-substituted 14-(4-halophenyl)-12-methoxy-14H-benzo[h]chromeno[3,2-e][1,2,4]-triazolo[1,5-c]pyrimidines 7a–o, 9-benzylideneamino-7-(4-halo-phenyl)-5-methoxy-8-imino-7H-benzo-[h]chromeno[2,3-d]pyrimidines 8a–b and 3-ethoxycarbonyl-14-(4-halophenyl)-12-methoxy-14H-benzo-[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-2-one derivatives 12a–b. The structure of these novel compounds were confirmed using IR, 1H- and 13C-NMR as well as MS spectroscopy. The new compounds were evaluated in vitro for their antimicrobial activity and it was demonstrated that 7H-benzochromenopyrimidine and derivatives of 14H-benzochromenotriazolopyrimidine exhibited the most promising antibacterial activities compared to the reference antimicrobial agents. The structure activity relationship (SAR) studies of the target compounds agreed with the in vitro essays and confirmed higher potent antimicrobial activity against some of the tested microorganisms. [ABSTRACT FROM AUTHOR]

A series of 2-amino-4 H-benzo[ h]chromene and 2,7-diamino-4 H-benzo[ h]chromene derivatives were prepared as potential cytotoxic agents. The structures of the synthesised compounds were established on the basis of spectral data. The in-vitro cytotoxic activity of the synthesised compounds against the cell lines MCF-7, HCT-116 and HepG-2 was investigated in comparison with vinblastine and colchicine, using an MTT colorimetric assay. The structure-activity relationship of 4 H-benzo[ h]chromenes with modification at the 3-, 4- and 7-positions was explored. The results of the anti-tumour evaluation revealed that compounds VIIIc, VIId, VIIb, VIIe, VIIIg and VIIIc, VIId, VIIb, VIIe, VIIIg, VIIc, VIIIe, Vf, IIIa inhibited the growth of MCF-7 in comparison with vinblastine and colchicine, while VIIb, VIId, VIIe, IIIa, VIIa, VIIIc, VIIc, IIId, IIIg, IIIf, IIIb, IIIh, VIIIb, VIIIa, VIIIe, IIIc, Vg, IIIe, VIIIg, Vf, IIIf inhibited the growth of HCT-116 in comparison with colchicine. In addition, compounds VIIe, IIIg, IIIa, VIIc and VIIe, IIIg, IIIa, VIIc, VIIb, VIIa, VIIIf, VIIIe inhibited the growth of HepG-2 in comparison with vinblastine and colchicine, respectively. [ABSTRACT FROM AUTHOR]

Novel fused chromenes (4,7–11) and pyrimidines (12–16) were designed, synthesized, and evaluated for their mammary gland breast cancer (MCF-7), human colon cancer (HCT-116), and liver cancer (HepG-2) activities. The structural identity of the synthesized compounds was established according to their spectroscopic analysis, such as FT-IR, NMR, and mass spectroscopy. The preliminary results of the bioassay disclosed that some of the target compounds were proven to have a significant antiproliferative effect against the three cell lines, as compared to Doxorubicin, Vinblastine, and Colchicine, used as reference drugs. Particularly, compounds 7 and 14 exerted promising anticancer activity towards all cell lines and were chosen for further studies, such as cell cycle analysis, cell apoptosis, caspase 3/7 activity, DNA fragmentation, cell invasion, and migration. We found that these potent cytotoxic compounds induced cell cycle arrest at the S and G2/M phases, prompting apoptosis. Furthermore, these compounds significantly inhibit the invasion and migration of the different tested cancer cells. The structure-activity relationship (SAR) survey highlights that the antitumor activity of the desired compounds was affected by the hydrophobic or hydrophilic nature of the substituent at different positions. [ABSTRACT FROM AUTHOR]

Abstract This work presents the combined microwave assisted synthesis, spectroscopic analyses, cytotoxic effects, and molecular docking studies of the chromene fused ring systems with various substituents of the terminal halogenated phenyl ring derivatives of 6-methoxy-4 H -benzo [ h ]chromene (4a-m). The structures of the synthesized compounds were established on the basis of their spectral data, IR, 1H NMR, 13C NMR, 13C NMR-DEPT, and MS data. The target compounds were evaluated for their antitumor activities against three cancer cell lines: MCF-7, HCT-116, and HepG-2, in comparison to Vinblastine and Colchicine as reference drugs with the usage of a MTT colorimetric assay. The most active compounds were subjected to further mechanistic analysis through the assay of the c-Src Kinase inhibition activity. The SAR studies reported that the substitution at the 4-position of the 2-amino-4 H -benzo [ h ]chromene nucleus with specific halogen atoms and lipophilic characters increased the ability of the molecule against the different cell lines. The Molecular Operating Environment (MOE) was used to evaluate the interactions between the ligand and the c-Src Kinase enzyme. Compound 4m , having the 3,5-dibromo-2-methoxyphenyl group attached to the 4 H -benzo [ h ]chromene moiety at the 4-postion, exhibited a promising interaction with the c-Src Kinase, which leads to a strong inhibition of this enzyme. Graphical abstract Image 1 Highlights • A novel series of halogenated derivatives of 6-methoxy-4 H -benzo [ h ]chromene. • The assessment of the antitumor activities against three cancer cell lines. • The c-Src Kinase inhibition activity. • The role of halogen atoms at position 4. [ABSTRACT FROM AUTHOR]

• Benzochromene-based analogues linked to pyrimidine and triazolopyrimidine were synthesized. • The target components have been screened for antibacterial and antifungal activity. • Some compounds displayed favorable antimicrobial activities. • Molecular modeling analyses focusing on the docking of active compounds and their ADMET properties were studied. 7 H -Benzo[7,8]chromeno[2,3- d pyrimidin-9(8 H)-amine (6a,b) have been synthesized via hydrazinolysis of the imidates (5a,b). Polysubstituted chromenotriazolopyrimidine (7a-j), (12a,b) and Schiff base (8a,b) derivatives have also been prepared. The new heterocyclic derivatives were affirmed by spectral data. The target compounds have been screened for antibacterial and antifungal activity. Compounds 6a,b and 7a-c, g,h displayed the most favorable antimicrobial activities in resemblance to the reference antimicrobial agents by IZ range over 24 mm. In addition, MIC, MBC and MFC were also tested and screen for most active compound 6a by 6.25 µg/mL showing bactericidal effect. SAR study revealed that the antimicrobial vitality of the target compounds was safely influenced by the lipophilicity substituents and the calculated log P value. The potent compounds were subjected into in vitro enzyme screening (14 α -Demethylase and DNA Gyrase) against both interesting targets and showed good inhibitory profile. Molecular modeling analyses were introduced and discussed focusing on the docking of active compounds into two essential targets, and their ADMET properties were studied. [ABSTRACT FROM AUTHOR]