Wen-Liang Dong

Microwave-assisted synthesis, crystal structure of pyrazolo[1,5-a]pyrazin-4(5H)-ones and their selective effects on lung cancer cells.

A series of novel pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives with hydrophilic group was synthesized under general heating condition and microwave-assisted condition. The structures of compounds were determined by IR, 1H NMR and HRMS, moreover, representative crystal structures were characterized by using X-ray diffraction analysis. Preliminary biological evaluation showed that some compounds could inhibit the growth of A549, H322 and H1299 cells in dosage dependent manners. The compounds could inhibit growth of A549, H322 and H1299 cells in different mechanism. Compounds 3e-h inhibited growth of A549 cells by inducing a strong G1-phase arrest. Whereas these compounds inhibited growth of H1299 and H322 cells by inducing apoptosis.

N-Benzyl-2-(2,4-dichloro­phen­oxy)acetamide

In the title compound, C15H13Cl2NO2, the dihedral angle between the aromatic rings is 27.17u2005(11)°. In the crystal the molecules are linked by N—H⋯O hydrogen bonds.

1-(2-Hydr­oxy-5-methoxy­phen­yl)ethan-1-one N-[(E)-1-(2-hydr­oxy-5-methoxy­phen­yl)ethyl­idene]hydrazone

In the title molecule, C18H20N2O4, which resides on a crystallographic centre of inversion (at the centre of the N—N bond), all non-H atoms apart from the methoxy substituent are approximately coplanar. The structure displays intramolecular O—H⋯N hydrogen bonding.

(E)-2,4-Dichloro-6-{1-[(2-chloro-eth-yl)imino]-eth-yl}phenol.

The title Schiff base compound, C10H10Cl3NO, was prepared by the condensation of 1-(3,5-dichloro-2-hydroxyphenyl)ethanone with chloroethylamine. The imine adopts an E configuration with respect to the C=N bond. The H atom of the phenolic OH group is disordered over two positions with site occupation factors of 0.52u2005(7) and 0.48u2005(7), respectively, and the major occupancy component is involved in an intramolecular N—H⋯O hydrogen bond. The compound therefore exists in an iminium–phenolate as well as in the imino–phenol form. In the crystal, molecules are connected by C—H⋯O and C—H⋯Cl hydrogen bonds and Cl⋯Cl interactions [3.7864u2005(9)u2005Å] into a three-dimensional network. In addition, intermolecular π–π stacking interactions [centroid–centroid distance = 4.4312u2005(9)u2005Å] are observed.

1-[(6-Chloro-3-pyrid­yl)meth­yl]-N-(4-ethoxy­phen­yl)-3-phenyl-1H-pyrazole-5-carboxamide

In the title compound, C24H21ClN4O2, the pyrazole ring makes dihedral angles of 7.70u2005(11), 89.17u2005(11) and 40.68u2005(11)° with the phenyl, pyridine and ethoxyphenyl rings, respectively. There are some intramolecular C—H⋯O and C—H⋯π bonds giving rigidity to the molecule, while weak intermolecular N—H⋯N and C—H⋯π hydrogen bonds link the molecules into a two-dimensional structure.

7-Chloro-4-phenethyl-2H-1,4-benzoxazin-3(4H)-one.

In the crystal structure of title compound, C16H14ClNO2, the dihedral angle between the aromatic rings is 4.2u2005(2)°.

N-Cyclo­hexyl-2-(2,3-dichloro­phenyl­sulfan­yl)acetamide

In the crystal structure of title compound, C14H17Cl2NOS, the cyclohexyl ring has a chair conformation and connects with an equatorial N atom. Molecules are connected via N—H⋯O hydrogen bonds into chains.

8-Chloro-4-cyclo-hexyl-2H-1,4-benzoxazin-3(4H)-one.

In the crystal structure of title compound, C14H16ClNO2, the cyclohexyl ring is in a chair conformation. The molecules are connected into centrosymmetric dimers via weak C—H⋯O hydrogen bonds.

N-Cyclo­hexyl-2-(2,3-dichloro­phen­oxy)acetamide

In the crystal structure of title compound, C14H17Cl2NO2, the cyclohexyl ring is in a chair conformation and the molecules are connected via N—H⋯O hydrogen bonding into chains.

Ethyl 3‐(4‐chlorophenyl)‐5‐(ethoxycarbonyl)‐1H‐pyrazole‐1‐acetate

In the title compound, C16H17ClN2O4, all bond lengths and angles show normal values. The dihedral angle between the pyrazole ring and the benzene ring is 5.75u2005(8)°. The molxadecules are linked into a network by interxadmolecular C—Cl⋯π interxadactions.