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3,5-Bis(benzylidene)-1-[3-(2-hydroxyethylthio)propanoyl]piperidin-4-ones: a novel cluster of potent tumor-selective cytotoxins.

ABSTRACT: Novel 3,5-bis(benzylidene)-1-[3-(2-hydroxyethylthio)propanoyl]piperidin-4-ones (3a-e) display potent cytotoxicity and a preferential lethality toward various neoplasms compared to some normal cells. The corresponding sulfonic acid analogues 5a-e and an isostere 4 demonstrated substantially lower activity. The leads 3d and 3e possess very high activity against colon cancer and leukemia cell lines, caused DNA fragmentation, and activated caspase-3 in HL-60 cells. The enones 3b-e were well tolerated in a short-term toxicity screen in mice.

SUBMITTER: Das U

PROVIDER: S-EPMC3346748 | biostudies-literature | 2011 May

REPOSITORIES: biostudies-literature

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3,5-Bis(benzylidene)-1-[3-(2-hydroxyethylthio)propanoyl]piperidin-4-ones: a novel cluster of potent tumor-selective cytotoxins.

Das Umashankar U Pati Hari N HN Sakagami Hiroshi H Hashimoto Ken K Kawase Masami M Balzarini Jan J De Clercq Erik E Dimmock Jonathan R JR

Journal of medicinal chemistry 20110420 9

Novel 3,5-bis(benzylidene)-1-[3-(2-hydroxyethylthio)propanoyl]piperidin-4-ones (3a-e) display potent cytotoxicity and a preferential lethality toward various neoplasms compared to some normal cells. The corresponding sulfonic acid analogues 5a-e and an isostere 4 demonstrated substantially lower activity. The leads 3d and 3e possess very high activity against colon cancer and leukemia cell lines, caused DNA fragmentation, and activated caspase-3 in HL-60 cells. The enones 3b-e were well tolerate ...[more]

PMID: 21449610

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Novel 3,5-bis(bromohydroxybenzylidene)piperidin-4-ones as coactivator-associated arginine methyltransferase 1 inhibitors: enzyme selectivity and cellular activity.

Project description:Coactivator-associated arginine methyltransferase 1 (CARM1) represents a valuable target for hormone-dependent tumors such as prostate and breast cancers. Here we report the enzyme and cellular characterization of the 1-benzyl-3,5-bis(3-bromo-4-hydroxybenzylidene)piperidin-4-one (7g) and its analogues 8a-l. Among them, 7g, 8e, and 8l displayed high and selective CARM1 inhibition, with lower or no activity against a panel of different PRMTs or HKMTs. In human LNCaP cells, 7g showed a significant dose-dependent reduction of the PSA promoter activity.

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Project description:In the crystal structure of the title compound, C(22)H(21)Cl(2)NO(2), the piperidinone ring is in a boat conformation.

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Project description:The inversion-related mol-ecules of the title compound, C(26)H(21)F(2)NO, associate into closed dimeric subunits via co-operative C-H⋯π inter-actions. Two non-classical C-H⋯O and one C-H⋯N intra-molecular hydrogen bonds are also found in the crystal structure. The piperidin-4-one ring adopts a sofa conforamtion with the 1-benzyl group in the equatorial position, and the equiplanar fluoro-phenyl substituents in the 3- and 5-positions stretched out on either side. The 1-benzyl group is disposed towards the substituent in the 6th position of the piperidin-4-one ring. The 3,5-diene units possess E configurations.

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Project description:In the title compound, C(23)H(26)BrNO(4), the piperidinone ring adopts a boat conformation. The dihedral angle between the two benzene rings is 70.9?(1)°. The two meth-oxy groups are close to coplanar with the attached benzene rings [C-C-O-C torsion angles of 6.3?(5) and 16.4?(4)°]. A weak C-H?Br intra-molecular inter-action is observed. In the crystal structure, mol-ecules are linked into a chain along [101] by inter-molecular C-H?O hydrogen bonds. A short inter-molecular Br?O contact [3.063?(2)?Å] is observed.

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