Chun-Nian Xia

Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines.

Forty caffeate analogues were synthesized via a convenient method starting from vanillin with moderate to good yields. The testing of biological activity of these compounds against HIV-1 integrase indicates that four compounds: bornyl caffeate, bornyl 2-nitrocaffeate, 5-nitrocaffeic acid and 5-nitrocaffeic acid phenethyl ester (5-nitroCAPE) possess a good HIV integrase inhibitory activity, IC(50) 19.9, 26.8, 25.0 and 13.5 microM , respectively. Twelve caffeate analogues were tested by MTT assay on growth of human hepatocellular carcinoma BEL-7404, human breast MCF-7 adenocarcinoma, human lung A549 adenocarcinoma and human gastric cancer BCG823 cell lines, respectively. And the best result is IC(50) 5.5 microM for CAPE against BEL-7404.

Synthesis and antitumor activity of feruloyl and caffeoyl derivatives

We developed two efficient protocols for the synthesis of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde. Pharmacological activities were assessed against a panel of human cancer cell lines in vitro. Most synthesized compounds demonstrated attractive cytotoxicity. Several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. In particular, 5-nitro caffeic adamantyl ester showed broad spectrum of tumor inhibition in 10 cell lines, and reduced tumor weight by 36.7% in vivo when administered at a dose of 40 mg kg(-1).

The synthesis and biological evaluation of some caffeic acid amide derivatives: E-2-cyano-(3-substituted phenyl)acrylamides.

A series of caffeic acid amide derivatives 2-cyano-(3-substituted phenyl)acrylamides were synthesized via Knoevenogal condensation of substituted benzaldehydes with cyanoacetamides. The structure of compound 1f was determined as E-isomer by X-ray diffractive analysis. The biological screening tests in vitro showed that compound 1b has obvious inhibitory activities against human gastric carcinoma cell line BGC-823, human nasopharyngeal carcinoma cell line KB and human hepatoma cell line BEL-7402 with IC(50) values of 5.6 microg/mL, 13.1 microg/mL and 12.5 microg/mL, respectively. Some preliminary structure-activity relationships (SAR) were also proposed which may provide a direction for further study.

Methyl 17,17-ethyl­enedi­oxy-7-oxo-15β,16β-methyl­ene-5-androstene-3β-carboxyl­ate

The title compound, C24H32O5, has rings A and C in regular chair, ring B in a distorted half-chair and ring D in an envelope conformation. The dioxolane ring adopts a twist conformation.

Propyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

# 2005 International Union of Crystallography Printed in Great Britain – all rights reserved Crystals of the title compound, C13H15NO6, were obtained from the modified Knoevenagel condensation reaction of 3,4dihydroxybenzaldehyde and mono-2-methyl-2-nitropropyl malonate. The molecule is the E isomer with the usual bond lengths and angles. The crystal packing is stabilized by intermolecular O—H O and C—H O hydrogen bonds.

3-Diethyl­carbamoyl-2′,4′-difluoro­biphenyl-4-yl 2,6-dichloro-5-fluoro­pyridine-3-carboxyl­ate

In the title compound, C23H17Cl2F3N2O3, the molecular conformation is significantly strained: atoms O, C(=O) and C attached to the central benzene ring deviate from its plane by 0.118 (2), 0.139 (2) and 0.174 (2) Å, respectively. In the crystal, weak C—H⋯O interactions link the molecules into chains along [110]. The crystal packing exhibits short intermolecular Cl⋯F [2.9840 (16) Å] and Cl⋯Cl [3.2957 (12) Å] contacts.

(22E,24R)-5α-Ergosta-2,22-dien-6-one.

In the title molecule, C28H44O, two six-membered rings have regular chair conformations, while the six-membered ring containing the C=C double bond exhibits a distorted chair conformation. The five-membered ring adopts an envelope conformation. In the crystal, weak intermolecular C—H⋯O interactions link molecules into chains along the b axis. The absolute configuration was assigned to correspond with that of the known chiral centres in a precursor molecule.

(22E,24R)-3α,5-Cyclo-5α-ergosta-22-en-6-one.

In the title molecule, C28H44O, the two six-membered rings have a chair conformation and the two five-membered rings haveenvelope conformations. The crystal packing exhibits no short intermolecular contacts. The absolute configuration was assigned to correspond with that of the known chiral centres in a precursor molecule, which remained unchanged during the synthesis of the title compound.

3β,5α,15α‐Trihydroxy‐5‐androsten‐17‐one dihydrate

In the steroid skeleton of the title compound, C19H28O4 center dot 2H(2)O, ring A assumes a slightly twisted chair conformation, ring C adopts a regular chair conformation, ring B adopts a half-chair conformation and ring D has a somewhat twisted envelope conformation. The crystal packing exhibits an extensive three-dimensional hydrogen-bonding network, formed by intermolecular O-H center dot center dot center dot O hydrogen bonds between the steroid and water molecules.