SYNTHESIS AND IN-VITRO STUDY OF NOVEL (Z)-1-BENZHYDRYL-4-CINNAMYLPIPERAZINE DERIVATIVES AS POTENTIAL ANTICANCER AGENTS

Objective: The objective of this study was to synthesize Z- 1-benzhydryl-4-cinnamylpiperazines by novel stereo selective synthetic method and evaluation of their anticancer properties.Methods: A series of novel (Z)-1-benzhydryl-4-cinnamylpiperazine derivatives (9a-j) were synthesized, starting from benzophenones in six steps. Wittig condensation of appropriate benzyltriphenyl phosphonium halides with various 1-benzhydryl- 4-(2-ethanal) piperazines (3a-j), and column purification over silica gel afforded pure Z- 1-benzhydryl-4-cinnamylpiperazines.Results: The structures of newly synthesized compounds 9a-j were established by 1H & 13C NMR and mass spectral analysis. The anticancer potential (MTT assay) of synthesized compounds was tested against human cervical cancer (HeLa) and murine microglial (BV-2) cell lines. Results indicated that the most of the Z-derivatives exhibited moderate to good anticancer activity on both the cell lines over their E- antipodes.Conclusion: Compound 9i (cis- flunarizine) exhibited exceptionally superior activity against both HeLa and BV-2 cell lines with IC50 value of 13.23±3.51 µM and 23.1±4.12 µM respectively. Hence, this compound may be considered to be a potential lead molecule for further developmentÂ

Synthesis of <i>trans</i>-resveratrol using modified Julia olefination route

1035-1038Bioactive hydroxystilbinoid−trans-resveratrol [(E)-3,5,4ʹ-trihydroxy stilbene, 1] has been synthesized by modified Julia olefination method. The reaction between corresponding carbanion of benzothiazol-2-yl sulfone derivative and p-anisaldehyde dimethyl acetal with sodium hydride as a base, affords mainly cis-3,5,4ʹ-trimethoxystilbene 10b with minor quantity of trans-isomer. Both the isomers have been separated in pure form and confirmed by their NMR spectral data. Demethylation of cis-3,5,4ʹ-trimethoxystilbene either with AlCl3/pyridine or AlCl3/triethylamine results in the formation of trans-resveratrol

1-[Bis(4-fluorophenyl)methyl]-4-[(2Z)-3-phenylprop-2-en-1-yl]piperazine-1,4-diium dichloride hemihydrate

The asymmetric unit of the title monohydrated salt, 2C26H28F2N22+·4Cl−.H2O, consists of a 1-[bis(4-fluorophenyl)methyl]-4-[(2Z)-3-phenylprop-2-en-1-yl]piperazine-1,4-diium cation with a diprotonated piperizine ring in close proximity to two chloride anions and a single water molecule that lies on a twofold rotation axis. In the cation, the piperazine ring adopts a slightly distorted chair conformation. The dihedral angles between the phenyl ring and the 4-fluorophenyl rings are 89.3 (9) and 35.0 (5)°. The two fluorophenyl rings are inclined at 65.0 (5)° to one another. In the crystal, N—H...Cl hydrogen bonds and weak C—H...Cl intermolecular interactions link the molecules into chains along [010]. In addition, weak C—H...O interactions between the piperizine and prop-2-en-1-yl groups with the water molecule, along with weak C—H...Cl interactions between the prop-2en-1-yl and methyl groups with the chloride ions, weak C—H...F interactions between the two fluorophenyl groups and weak O—H...Cl interactions between the water molecule and chloride ions form a three-dimensional supramolecular network

(Z)-1-Diphenylmethyl-4-(3-phenylprop-2-enyl)piperazine

In the title compound, C26H28N2, the piperazine group adopts a chair conformation with the exocyclic N—C bonds in equatorial orientations. The dihedral angle between the geminal benzene rings is 80.46 (12)° and the C=C—C—N torsion angle is 145.9 (2)°. In the crystal, weak C—H...π interactions link the molecules into [100] chains

New water soluble glycosides of 11-keto-β-boswellic acid: A paradigm

<p>Though several glycosides of various triterpenes are known, but surprisingly no boswellic acid glycosides are reported so far. With a view to make water soluble boswellic acids, prepared glycosides of 11-keto boswellic acid for the first time. Naturally occurring boswellic acids which are anti-inflammatory agents are lipophylic in nature and thus, become a limiting factor in terms of their bioavailability. Among boswellic acids, 11-keto-β-boswellic acid is found to exhibit superior biological activity and hence successfully prepared its glucosyl and maltosyl derivatives viz., 11-keto-β-boswellic acid-24-O-β-D-glucopyranoside (<b>9</b>) and 11-keto-β-boswellic acid-24-O-α-D-glucopyranosyl-(1 → 4)-β-D-glucopyranoside (<b>15</b>) which are water soluble. Both these compounds are soluble in water to the extent of 10% (w/w) which is very significant.</p