3-(4-Iodo-phen-yl)-2,3-di-hydro-1H-benzo[f]chromen-1-one.

In the title compound, C19H13IO2, the dihedral angle between the naphthyl ring system and the pendant iodo-phenyl ring is 72.48 (11)°. In the crystal, C-H⋯π inter-actions and I⋯O [3.293 (2) Å] halogen bonds are observed, which combine to generate a herringbone packing motif.

Design, Synthesis, and Evaluation of (2-(Pyridinyl)methylene)-1-tetralone Chalcones for Anticancer and Antimicrobial Activity.

BACKGROUND: Chalcones, natural products produced by plants as a natural defense mechanisms against various pathogens, are molecules with structures that include two aromatic rings joined by an α, ß unsaturated carbonyl system. Previous research has demonstrated that chalcones exhibit a wide variety of biological activities, including anticancer, antifungal, and antibiotic properties. OBJECTIVE: Our goal is to synthesize novel heterocyclic-containing chalcones and have their biological activities evaluated. Methods Sixteen chalcones were synthesized by the crossed aldol condensation of substituted tetralones with substituted pyridinylaldehydes. The products were purified by recrystallization in MeOH/H2O and characterized by 1H NMR, 13C NMR, and HRMS. Anticancer assays were performed by NCI (National Cancer Institute) against the NCI-60 panel of 60 different human cancer cell lines, including leukemia, non-small-cell lung cancer, colon, central nervous system, melanoma, ovarian, renal, prostate, and breast cancer. Antimicrobial assays were performed by COADD (Community for Open Antimicrobial Drug Discovery) against Escherichia coli, Klebsiella pneumonia, Acinetobacter baumannii, Pseudomonas aeruginosa, Staphylococcus aureus, Cryptococcus neoformans var. grubii, and Candida albicans. RESULT: Chalcone 3d had demonstrated growth inhibition greater than 60% against a variety of cancers: leukemia (MOLT-4, SR), non-small cell lung cancer (NCI-H522), colon cancer (HCT- 116), prostate cancer (DU-145), and breast cancer (MCF7, MDA-MB-468) and was also cytotoxic to three different cell lines (CCRF-CEM, RPMI-8226, and KM12). 5c was active against leukemia (CCRF-CEM, RPMI-8226, SR) and breast cancer (MCF7) and 5e was active only against leukemia (RPMI-8226, SR). 5h was partially active and the best compound with growth inhibition of MRSA by 75%. 3b was the best compound against EC, KP, and PA and 3f had the greatest activity against AB. For fungi, 3f and 3e demonstrated the best growth inhibition. CONCLUSION: A small library of heterocyclic-containing chalcones was developed and initial screening demonstrates modest activity against cancers, bacteria, and fungi.

Design and synthesis of benzopyran-based inhibitors of the hypoxia-inducible factor-1 pathway with improved water solubility.

While progress has been made in treating cancer, cytotoxic chemotherapeutic agents are still the most widely used drugs and are associated with severe side-effects. Drugs that target unique molecular signalling pathways are needed for treating cancer with low or no intrinsic toxicity to normal cells. Our goal is to target hypoxic tumours and specifically the hypoxia inducible factor (HIF) pathway for the development of new cancer therapies. To this end, we have previously developed benzopyran-based HIF-1 inhibitors such as arylsulfonamide KCN1. However, KCN1 and its earlier analogs have poor water solubility, which hamper their applications. Herein, we describe a series of KCN1 analogs that incorporate a morpholine moiety at various positions. We found that replacing the benzopyran group of KCN1 with a phenyl group with a morpholinomethyl moiety at the para positions had minimal effect on potency and improved the water solubility of two new compounds by more than 10-fold compared to KCN1, the lead compound.

Crystal structure of (E)-2-[(2-bromopyridin-3-yl)methyl-idene]-6-meth-oxy-3,4-di-hydro-naphthalen-1(2H)-one and 3-[(E)-(6-meth-oxy-1-oxo-1,2,3,4-tetra-hydro-naphthalen-2-ylidene)meth-yl]pyridin-2(1H)-one.

The title compounds C17H14BrNO2, (I), and C17H15NO3, (II), were obtained from the reaction of 6-meth-oxy-3,4-di-hydro-2H-naphthalen-1-one and 2-bromo-nicotinaldehyde in ethanol. Compound (I) was the expected product and compound (II) was the oxidation product from air exposure. In the crystal structure of compound (I), there are no short contacts or hydrogen bonds. The structure does display π-π inter-actions between adjacent benzene rings and adjacent pyridyl rings. Compound (II) contains two independent mol-ecules, A and B, in the asymmetric unit; both are non-planar, the dihedral angles between the meth-oxy-benzene and 1H-pyridin-2-one mean planes being 35.07 (9)° in A and 35.28 (9)°in B. In each mol-ecule, the 1H-pyridin-2-one unit participates in inter-molecular N-H⋯O hydrogen bonding to another mol-ecule of the same type (A to A or B to B). The structure also displays π-π inter-actions between the pyridyl and the benzene rings of non-equivalent mol-ecules (viz., A to B and B to A).

Crystal structure of (E)-1-(3-chloro-phen-yl)-3-(furan-2-yl)prop-2-en-1-one.

The title compound, C13H9ClO2, exhibits a non-planar geometry; the furan ring being inclined to the benzene ring by 50.52 (16)°. In the crystal, mol-ecules stack along the a axis; however, there are no significant inter-molecular inter-actions present.