Synthesis, Characterization, and Antimicrobial Activity of a Novel Trisazo Dye from 3-Amino-4H-thieno[3,4-c]benzopyran-4-one.
ABSTRACT: A new trisazo dye has been synthesized by coupling the diazonium ion of 3-amino-4H thieno[3,4-c]benzopyran-4-one with 2-tert-butyl-4-methoxyphenol. The newly prepared trisazo dye was characterized by its physical, elemental, and spectroscopic data. 2D-NMR (COSY, HSQC, and HMBC) techniques were used to secure the structural assignments. The new trisazo dye (compound 7) along with precursors 3, 4, and 6 was screened by microdilution susceptibility assay for antibacterial and antifungal activities towards eight bacterial strains and three yeasts selected on the basis of their relevance as human pathogens. The results showed that compound 7 (MIC = 2-128??g/mL) was the most active as compared with its precursors. The most resistant microorganisms were V. cholerae NB2 and V. cholerae SG24, whereas the most sensitive microorganism was C. neoformans. The overall results of this study indicated that compound 7 had the greatest potential value against both yeasts and multidrug-resistant bacteria, so further investigation is warranted.
Project description:The asymmetric unit of the title compound, C(26)H(12)ClNO(6), consists of two independent mol-ecules. The central pyran rings and both the 1-benzopyran ring systems are nearly planar in both mol-ecules [r.m.s. deviations of pyan rings = 0.0264?(1) and 0.0326?(1)?Å for molecules A and B, respectively; r.m.s. deviations of benzopyran rings = 0.0439?(1) and 0.0105?(1) for molecule A, 0.0146?(1) and 0.0262?(1)?Å for molecule B]. In the crystal, the molecules are linked by C-H?O, N-H?O and C-H?? inter-actions.
Project description:In the title compound, C(18)H(16)O(6), the dimethoxy-phenyl ring is rotated by 61.8?(1)° from the plane of the benzopyran system. The mol-ecule is stabilized by an intra-molecular O-H?O hydrogen bond.
Project description:Selagintamarlin A (1), a novel selaginellin analogue featuring the unique motif of 1H-2-benzopyran, a new selaginpulvilin E (2), together with eight known analogues were isolated from Selaginella tamariscina. Their structures were elucidated by extensive spectroscopic analyses. A plausible biosynthetic pathway of 1 was also postulated. Compound 1 showed remarkable inhibitory activity against phosphodiesterase-4 (PDE4D2), with an IC50 value of 40 nM, which is 20-fold higher than that of the positive control (rolipram). Furthermore, compound 1 significantly inhibited tubulin polymerization.
Project description:In the crystal structure of the title compound, C(19)H(17)Cl(2)NO, the indoline and benzopyran ring systems are approximately perpendicular to each other. The indoline ring is in an envelope conformation with the spiro C atom as the flap. The N atom of the indoline ring forms a pyramidal environment, the sum of the angles at this atom being 352.46°.
Project description: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.
Project description:In the title compound, C(19)H(18)O(6), also known as 3,4',5,7-tetra-methoxy-flavone, the dihedral angle between the benzopyran-4-one group and the attached benzene ring is 11.23?(8)°. An intra-molecular C-H?O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked into a two-dimensional network parallel to (01) by inter-molecular C-H?O hydrogen bonds, which generate R(4) (4)(20), R(4) (4)(12) and R(2) (2)(14) ring motifs. Adjacent networks interact by ?-? inter-actions between the pyran ring and its methoxy-phenyl substituent [centroid-centroid distance = 3.5267?(8)?Å].
Project description:In the title compound, C(26)H(12)FNO(6), the central pyran ring and both benzopyran systems are nonplanar, having total puckering amplitudes of 0.139?(2), 0.050?(1) and 0.112?(2)?Å, respectively. The central pyran ring adopts a boat conformation. The crystal structure is stabilized by C-H?O, N-H?O, N-H?F and C-H?? inter-actions.
Project description:An anti-fibrotic compound produced by Streptomycesn xiamenensis, found in mangrove sediments, was investigated for possible therapeutic effects against fibrosis. The compound, N-[[3,4-dihydro-3S-hydroxy-2S-methyl-2-(4'R-methyl-3'S-pentenyl)-2H-1-benzopyran-6-yl]carbonyl]-threonine (1), was isolated from crude extracts and its structure, including the absolute configuration was determined by extensive spectroscopic data analyses, Mosher's method, Marfey's reagent and quantum mechanical calculations. In terms of biological effects, this compound inhibits the proliferation of human lung fibroblasts (WI26), blocks adhesion of human acute monocytic leukemia cells (THP-1) to a monolayer of WI26 cells, and reduces the contractile capacity of WI26 cells in three-dimensional free-floating collagen gels. Altogether, these data indicate that we have identified a bioactive alkaloid (1) with multiple inhibitory biological effects on lung excessive fibrotic characteristics, that are likely involved in fibrosis, suggesting that this molecule might indeed have therapeutic potential against fibrosis.
Project description:The title compound, C(16)H(12)N(2)O(4)S, was obtained by the condensation of 3-acetyl-4-hy-droxy-coumarin with thien-2-ylcarbonyl hydrazide. The pyran ring adopts a 2,4-dione tautomeric form. The benzopyran ring system is almost coplanar with the thio-phene ring [dihedral angle 0.9?(2)°]. The exocyclic C=C double bond has an E geometry. The mol-ecular conformation is stabilized by an intra-molecular N-H?O hydrogen bond. In the crystal, inter-molecular N-H?O hydrogen bonds link the mol-ecules into chains along the a axis.
Project description:The benzopyran compound obtained by cultivating a mangrove-derived strain, Streptomyces xiamenensis strain 318, shows multiple biological effects, including anti-fibrotic and anti-hypertrophic scar properties. To increase the diversity in the structures of the available benzopyrans, by means of biosynthesis, the strain was screened for spontaneous rifampicin resistance (Rif), and a mutated rpsL gene to confer streptomycin resistance (Str), was introduced into the S. xiamenensis strain M1-94P that originated from deep-sea sediments. Two new benzopyran derivatives, named xiamenmycin C (1) and D (2), were isolated from the crude extracts of a selected Str-Rif double mutant (M6) of M1-94P. The structures of 1 and 2 were identified by analyzing extensive spectroscopic data. Compounds 1 and 2 both inhibit the proliferation of human lung fibroblasts (WI26), and 1 exhibits better anti-fibrotic activity than xiamenmycin. Our study presents the novel bioactive compounds isolated from S. xiamenensis mutant strain M6 constructed by ribosome engineering, which could be a useful approach in the discovery of new anti-fibrotic compounds.