On the Synthesis and Anticancer Testing of &amp;#945;,&amp;#946;-Unsaturated Ketones as Analogs of Combretastatin-A4

Chavda, Sameer; Davis, Ryan R.; Ferguson, Amanda; Riddering, Camille; Dittenhafer, Kristin; Mackay, Hilary; Babu, Balaji; Lee, Moses; Siegfried, Adam; Pennington, William T.; Shadfan, Miriam; Mooberry, Susan L.; Mishra, Bijay K.; Pati, Hari N.

doi:10.2174/157018009789108277

Cited by 4 publications

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“…Abdel-Aziz et al (2010), Babu et al (2011) and Chavda et al (2009) describe the use of conjugated styryl ketones and related compounds as potential cytotoxic and anticancer agents. Satam et al (2011) gives background to compounds with a thiazolidinone pharmacophore and describe structures related to the title compound.…”

Section: Related Literaturementioning

confidence: 99%

5-Benzylidene-3-phenyl-2-phenylimino-1,3-thiazolidin-4-one

et al. 2011

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The title compound, C22H16N2OS, is a chalcone analog with a thiazolidinone core that was synthesized as a potential cytotoxic and anticancer agent. The structure is commensurately modulated by unit-cell doubling along the direction of the a axis of the cell. The two crystallographically independent molecules are differerentiated by the dihedral angle between the mean planes of the benzylidene phenyl group against the thiazolidin-4-one moiety, which is 5.01 (7)° in one molecule, and 17.41 (6)° in the other. The two molecules are otherwise close to being indistinguishable and are related by crystallographic pseudo-translation. The two molecules are not planar but are slightly bent with the benzylidene and phenylimino substituents being bent upwards with respect to the center planes of the two molecules. The degree of bending of the two halves of the thiazolidin-4-one moieties (defined as the planes that intersect at the S atom) are 11.08 (7) and 15.88 (7)°. Packing of the molecules is facilitated by C—H⋯π interactions and slipped π–π stacking between one of the phenyl rings and a neighboring ethylene π system [distance between the centroid of the ethylene group and the closest phenyl C atom = 3.267 (2) Å, Cg(phenyl)⋯Cg(ethylene) = 3.926 Å].

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Section: Related Literaturementioning

confidence: 99%

5-Benzylidene-3-phenyl-2-phenylimino-1,3-thiazolidin-4-one

et al. 2011

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Design, Synthesis and Cytotoxicity of Novel Chalcone Analogs Derived from 1‐Cyclohexylpyrrolidin‐2‐one and 2,3‐Dihydrobenzo[f]chromen‐1‐one

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et al. 2011

Archiv der Pharmazie

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Two divergent series of novel chalcone analogs, one derived from 1-cyclohexylpyrrolidin-2-one and the other derived from 1-benzo[f]chromanone, were designed, synthesized and evaluated for cytotoxicity against two murine cancer cell lines. Two 1-benzo[f]chromanone analogs, 4g and 4j yielded moderate toxicity against both melanoma B16 and lymphoma L1210 cell lines with IC(50) values between the range of 5 and 6 µM. With an IC(50) value of 3.4 µM, compound 4g was also active against human MDA-MB-435 melanoma cells. X-ray structures of the β-hydroxy ketone product (4a) and the α,β-unsaturated ketone (4h) were collected, and confirm the syn-configuration between the carbonyl moiety and the β-vinylic proton in 4h. X-ray structures of two 1-cyclohexylpyrrolidin-2-one derivatives were also obtained, and both showed an E-configuration for the double bond.

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