(±)-Pestalachloride D, an antibacterial racemate of chlorinated benzophenone derivative from a soft coral-derived fungus Pestalotiopsis sp.

A new antibacterial chlorinated benzophenone derivative, (±)-pestalachloride D (1), along with a related analog, (±)-pestalachloride C (2), was recently isolated from the marine-derived fungus Pestalotiopsis sp. isolated from a soft coral Sarcophyton sp. collected from Yongxing Island in the South China Sea. Both chiral HPLC analysis and single-crystal X-ray data indicated that 1 is a racemic mixture. Interestingly, 1 did not exhibit any effect in the zebrafish embryo teratogenicity assay, while 2 led to abnormal growth. The potential impact on zebrafish embryo growth is discussed based on their crystal structures. The main difference of crystal structures between 1 and 2 is that the six-member non-aromatic ring (O4, C10, C9, C8, C2', and C3') in 1 exhibits a distorted chair conformation, while 2 shows a distorted boat conformation. Moreover, compounds 1 and 2 both exhibited moderate antibacterial activity.

Bioactive hydroanthraquinones and anthraquinone dimers from a soft coral-derived Alternaria sp. fungus.

Five new hydroanthraquinone derivatives, tetrahydroaltersolanols C-F (1-4) and dihydroaltersolanol A (5), and five new alterporriol-type anthranoid dimers, alterporriols N-R (12-16), along with seven known analogues (6-11 and 17), were isolated from the culture broth and the mycelia of Alternaria sp. ZJ-2008003, a fungus obtained from a Sarcophyton sp. soft coral collected from the South China Sea. Their structures and the relative configurations were elucidated using comprehensive spectroscopic methods including 1D and 2D NOE spectra as well as single-crystal X-ray crystallography. Compound 13 represents the first isolated alterporriol dimer with a C-4-C-4' linkage, and the absolute configuration of 4 was determined using the modified Mosher's method. Compounds 1 and 15 exhibited antiviral activity against the porcine reproductive and respiratory syndrome virus (PRRSV), with IC50 values of 65 and 39 µM, respectively. Compound 14 showed cytotoxic activity against PC-3 and HCT-116 cell lines, with IC50 values of 6.4 and 8.6 µM, respectively.

Stereoselective Access to Spirooxindoles and Bisoxindoles Through Organocatalyzed Asymmetric Divergent Transformations of Isatin-derived MBH Carbonates.

An interesting ß-isoquinidine catalyzed divergent reaction was developed to produce either spirocyclopentene oxindoles, spirocyclopentadiene oxindoles or bisoxindoles in a high enantioselective fashion. The utility of this protocol was demonstrated by the versatile transformations of the products. This work not only represents the first highly stereoselective intermolecular catalytic asymmetric allylic alkylation reaction between two isatin-derived MBH carbonate molecules but also constitutes a rare example of isatin-derived MBH carbonate-based enantioselective and α-regioselective [3+2] cycloaddition reactions.

Penicinoline, a new pyrrolyl 4-quinolinone alkaloid with an unprecedented ring system from an endophytic fungus Penicillium sp.

A new pyrrolyl 4-quinolinone alkaloid with an unprecedented ring system, named penicinoline (1) was isolated from a mangrove endophytic fungus. The structure of 1 was elucidated by spectroscopic methods and comparison with its derivative, penicinotam (1a), an unexpected lactam that was obtained from 1 by intramolecular dehydration. The structure of 1a was unambiguously confirmed by single-crystal X-ray analysis. Penicinoline (1) showed potent in vitro cytotoxicity toward 95-D and HepG2 cell lines with IC(50) values of 0.57 and 6.5 microg/mL, respectively.

2,2'-Dimeth-oxy-6,6'-dinitro-biphen-yl.

In the title compound, C(14)H(12)N(2)O(6), the half mol-ecule in the asymmetric unit of the cell is completed by a crystallographic twofold rotation axis, and the two benzene rings of the complete mol-ecule make a dihedral angle of 60.5 (3)°. Furthermore, inter-molecular weak C-H⋯O hydrogen bonds link adjacent mol-ecules, forming a two-dimensional sheet. These sheets are stablized by face-to-face weak π-π contacts [centroid-centroid distance = 3.682 (1) Å] between the nearly parallel [dihedral angle = 0.12 (7)°] benzene rings of the neighboring mol-ecules, resulting in a three-dimensional network.

Tetra-aqua-diimidazole-nickel(II) naphthalene-1,5-disulfonate.

The triclinic unit cell of the title compound, [Ni(C(3)H(4)N(2))(2)(H(2)O)(4)](C(10)H(6)O(6)S(2)), contains one centrosymmetric cation and one centrosymmetric anion. In the cation, the Ni(II) ion is six-coordinated by two imidazole ligands [Ni-N = 2.0568 (14) Å] and four water mol-ecules [both independent Ni-O distances are 2.098 (1) Å] in a distorted octa-hedral geometry. Inter-molecular O-H⋯O and N-H⋯O hydrogen bonds form an extensive three-dimensional network, which consolidates the crystal packing.

Bis[bis(1H-imidazole-κN)silver(I)] naphthalene-1,5-disulfonate.

The title compound, [Ag(C(3)H(4)N(2))(2)](2)(C(10)H(6)O(6)S(2)), exists in the form of isolated cations and anions with electrostatic inter-action between them. The Ag atom is two-coordinated by the N atoms of two crystallographically independent imidazole mol-ecules. The naphthalene-1,5-disulfonate anion is located on a crystallographic center of symmetry. The cations and anions are connected through inter-molecular N-H⋯O hydrogen bonds.

Bis(3-meth-oxy-6-methyl-2-pyrid-yl) ether.

In the mol-ecule of the title compound, C(14)H(16)N(2)O(3), the dihedral angle between the pyridyl rings is 87.74 (3)°. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into infinite zigzag chains.

6,6'-Dimeth-oxy-2,2',3,3',5-penta-nitro-1,1'-biphen-yl.

In the axially chiral title compound, C(14)H(9)N(5)O(12), the dihedral angle between the two benzene rings is 86.0 (8)°. In the crystal structure, the mol-ecules display a two-dimensional framework formed by weak inter-molecular C-H⋯O hydrogen bonds.

A new copper-based metal-organic framework as a promising heterogeneous catalyst for chemo- and regio-selective enamination of ß-ketoesters.

Assembly of 5-nitro-1,2,3-benzenetricarboxylic acid (H3nbta) with Cu(II) in the presence of 1,3-bis(1,2,4-triazol-1-yl)propane (1,3-btp) leads to a new metal-organic framework, [Cu(Hnbta)(1,3-btp)]·2H2O (A1), which is shown to be an efficient and recyclable heterogeneous catalyst for enamination of ß-ketoesters with excellent product yields and selectivity.